But for the amateur scientist, breaking your mother's heart* involves diethyl ether and the family pool.
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Diethyl ether hydroperoxide, upon heating in water, decomposes to acetaldehyde: :C2H5OCH(OOH)CH3 → CH3CHO + C2H5OH + H2O2 → Diethyl ether hydroperoxide forms polymers known as diethyl ether peroxide, or ethylidene peroxide: Formation of diethyl ether peroxide The peroxide is a colorless oil that is an extremely brisant and friction sensitive explosive material, however the polymeric materials are solid making them more dangerous as evaporation of the volatile diethyl ether can leave thin films of pure explosive.
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Diethyl ether hydroperoxide is the organic compound with the formula C2H5OCH(OOH)CH3. It is a colorless, distillable liquid. Diethyl ether hydroperoxide and its condensation products are blamed for the explosive organic peroxides that slowly form upon exposure of diethyl ether to ambient air and temperature conditions.
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It is very soluble in acetone, benzene, diethyl ether and ethanol.
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The reaction mixture is then rotary evaporated to dryness and the residue is dissolved in methanol. Undissolved cisplatin is filtered out and diethyl ether is added to the filtrate to precipitate out phenanthriplatin crystals. Phenanthriplatin is then collected by filtration, washed twice with diethyl ether before dissolving it in methanol. The drug is precipitated by adding it dropwise to a vigorously stirred solution of diethyl ether.
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This method was shown to be unsuitable in diethyl ether or isoamyl alcohol.
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It is a crystalline solid that is slightly soluble in water, but very soluble in ethanol and diethyl ether.
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Most diethyl ether is produced as a byproduct of the vapor- phase hydration of ethylene to make ethanol. This process uses solid-supported phosphoric acid catalysts and can be adjusted to make more ether if the need arises. Vapor-phase dehydration of ethanol over some alumina catalysts can give diethyl ether yields of up to 95%. Diethyl ether can be prepared both in laboratories and on an industrial scale by the acid ether synthesis. Ethanol is mixed with a strong acid, typically sulfuric acid, H2SO4.
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A cytochrome P450 enzyme is proposed to metabolize diethyl ether.109\. Aspergillus flavus mutant strain 241, blocked in aflatoxin biosynthesis, does not accumulate aflR transcript. Matthew P. Brown and Gary A. Payne, North Carolina State University, Raleigh, NC 27695 fgsc.net Diethyl ether inhibits alcohol dehydrogenase, and thus slows the metabolism of ethanol.
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Conversely, if the reaction is conducted in diethyl ether at -10 °C, (Zn2(η5-C5Me5)2) is the major product.
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The book Fear and Loathing in Las Vegas describes how the two main characters inhale diethyl ether and amyl nitrite.
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Many solvents can lead to a sudden loss of consciousness if inhaled in large amounts. Solvents like diethyl ether and chloroform have been used in medicine as anesthetics, sedatives, and hypnotics for a long time. Ethanol (grain alcohol) is a widely used and abused psychoactive drug. Diethyl ether, chloroform, and many other solvents e.g.
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The sodium salt is the starting point for most BARF derivatives. It is prepared by treating Grignard reagents derived from XC6H3-3,5-(CF3)2 (X = Br, I) with NaBF4. A popular method is summarized in the following equation: :NaBF4 \+ 4 ArFMgBr → 4 MgBrF + NaBArF4 Brookhart's acid is the salt of the BARF anion with the diethyl ether oxonium cation, [(Et2O)2H]BArF4. It can be formed from the sodium salt in diethyl ether in the presence of hydrogen chloride as sodium chloride is insoluble in diethyl ether, facilitating cation exchange.
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It can be prepared by absorbing ethylene into concentrated sulfuric acid or by fuming sulfuric acid into diethyl ether or ethanol.
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The filtrate can then made basic with NH4OH and extracted with diethyl ether. Shaking the extract with 5% sodium hydroxide and retaining the organic layer removes the phenolic content of the extract. The hydrogen chloride salt is then obtained by mixing with hydrochloric acid and recrystallized from diethyl ether. The free base can then be obtained.
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Other relatives of ethanol with similar effects include chloral hydrate, paraldehyde, and many volatile and inhalational anesthetics (e.g., chloroform, diethyl ether, and isoflurane).
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Historically, Diethyl ether, with a small amount of oil, a trace amount of a stabilizer and a hydrocarbon propellant has been used to help start internal combustion engines because of its low autoignition temperature. Diethyl ether is distinct from petroleum ether (a crude oil distillate consisting mostly of pentane and other alkanes) which has also been used for starting engines.
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Lithium chloride precipitates from the diethyl ether since it does not form a strong complex with methyllithium. The filtrate consists of fairly pure methyllithium.
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It also reacts with other chloride salts to give the yellow tetrahedral ion. Salts of in hydrochloric acid can be extracted into diethyl ether.
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It is also soluble in ethanol, acetone, acetic acid, glycerine, pyridine, aldehydes; slightly soluble in diethyl ether; and insoluble in oil, fat and most hydrocarbons.
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Diethyl ether hydroperoxide can be formed by the photooxygenation of diethyl ether. This is a radical process, driven by UV excitation of molecular oxygen into a more reactive form. Its formation is usually undesirable due to the associated risk of explosion. For this reason commercial samples of diethyl ether will usually contain antioxidants such as BHT and be contained in a material able to block UV rays, such as amber glass. :400px It can be intentionally prepared in high yield by the acid-catalyzed addition of hydrogen peroxide to ethyl vinyl ether: :C2H5OCH=CH2 \+ H2O2 → C2H5OCH(OOH)CH3 Related hydroperoxides can be produced similarly.
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It is used for treating leprosy. It crystallises as pale yellow needles from diethyl ether, and as leaflets from dilute ethanol. It is slightly soluble in water.
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As late as 1913, Webster's Dictionary states without further comment, "'common gin' is usually flavoured with turpentine". Another common variation was to distill in the presence of sulphuric acid. Although the acid itself does not distil, it imparts the additional aroma of diethyl ether to the resulting gin. Sulphuric acid subtracts one water molecule from two ethanol molecules to create diethyl ether, which also forms an azeotrope with ethanol, and therefore distils with it.
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MTBE is extensively used in industry as a safer alternative to diethyl ether (which is commonly used in academic research) as the tert- butyl group prevents MTBE from forming potentially explosive peroxides. It also is used as a solvent in academic research, although it is used less commonly than diethyl ether. Although an ether, MTBE is a poor Lewis base and does not support formation of Grignard reagents. It is also unstable toward strong acids.
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The convulsant properties of flurothyl pose a challenge to unifying theories of general anesthetics such as the Meyer- Overton hypothesis (see Theories of general anaesthetic action). A variety of halogenated ethers (e.g., isoflurane, sevoflurane) and diethyl ether itself are general anesthetics, and flurothyl is a substituted diethyl ether. Even more strikingly, a structural isomer of flurothyl known as ‘iso-flurothyl’ (1,1,1,3,3,3-hexafluoro-2-methoxypropane) induces general anesthesia and not convulsions in mice and dogs.
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Ethers like diethyl ether and tetrahydrofuran (THF) can form highly explosive organic peroxides upon exposure to oxygen and light. THF is normally more likely to form such peroxides than diethyl ether. One of the most susceptible solvents is diisopropyl ether, but all ethers are considered to be potential peroxide sources. The heteroatom (oxygen) stabilizes the formation of a free radical which is formed by the abstraction of a hydrogen atom by another free radical.
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Chlorophyll c2 is the most common form of chlorophyll c. Its absorption maxima are around 447, 580, 627 nm and 450, 581, 629 nm in diethyl ether and acetone respectively.
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Ethanol is an important industrial ingredient. It has widespread use as a precursor for other organic compounds such as ethyl halides, ethyl esters, diethyl ether, acetic acid, and ethyl amines.
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Nitromethane is a popular solvent in organic and electroanalytical chemistry. It can be purified by cooling below its freezing point, washing the solid with cold diethyl ether, followed by distillation.
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Guanosine is a white, crystalline powder with no odor and mild saline taste. It is very soluble in acetic acid, slightly soluble in water, insoluble in ethanol, diethyl ether, benzene and chloroform.
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Ethers serve as Lewis bases and Bronsted bases. Strong acids protonate the oxygen to give "oxonium ions". For instance, diethyl ether forms a complex with boron trifluoride, i.e. diethyl etherate (BF3·OEt2).
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Diazodiphenylmethane can be synthesized via the oxidation of benzophenone hydrazone with mercury(II) oxide in diethyl ether and the presence of a basic catalyst. An improved procedure involves dehydrogenation with oxalyl chloride.
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Japan Acad., volume 43, pages 41--44. Online version accessed on 2010-02-01. It is soluble in diethyl ether and crystallizes as brownish red needles that sublime at 285−295 °C.
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Alchemist Ramon Llull has been credited with discovering diethyl ether in 1275. Aureolus Theophrastus Bombastus von Hohenheim (1493–1541), better known as Paracelsus, discovered the analgesic properties of diethyl ether around 1525. It was first synthesized in 1540 by Valerius Cordus, who noted some of its medicinal properties. He called it oleum dulce vitrioli, a name that reflects the fact that it is synthesized by distilling a mixture of ethanol and sulfuric acid (known at that time as oil of vitriol).
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Diethyl ether is extremely flammable and may form explosive vapour/air mixtures. Since ether is heavier than air it can collect low to the ground and the vapour may travel considerable distances to ignition sources, which does not need to be an open flame, but may be a hot plate, steam pipe, heater etc. Vapour may be ignited by the static electricity which can build up when ether is being poured from one vessel into another. The autoignition temperature of diethyl ether is .
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They are miscible with ethanol and diethyl ether and slightly soluble in water. Xylidines are used in production of pigments and dyestuffs, and various antioxidants, agrochemicals, pharmaceuticals, hypergolic propellants, and many other organic chemicals.
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In 1950 a research group led by Glenn D. Barbaras, synthesized cadmium hydride for the first time. This reaction sequence consisted of demethylation of dimethylcadmium in diethyl ether at −78 °C, to cadmium hydride.
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Benzyl alcohol has moderate solubility in water (4 g/100 mL) and is miscible in alcohols and diethyl ether. The anion produced by deprotonation of the alcohol group is known as benzylate or benzyloxide.
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Oxamide is the organic compound with the formula (CONH2)2. This white crystalline solid is soluble in ethanol, slightly soluble in water and insoluble in diethyl ether. Oxamide is the diamide derived from oxalic acid.
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Chlorophyll c3 is a form of chlorophyll c found in microalga Emiliania huxleyi, identified in 1989. Its absorption maxima are around 452, 585, 625 nm and 452, 585, 627 nm in diethyl ether and acetone respectively.
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Diethyl selenide is an organoselenium compound with the formula . First reported in 1836, it was the first organoselenium compound to be discovered. It is the selenium analogue of diethyl ether. It has a strong and unpleasant smell.
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Allylmagnesium bromide is a Grignard reagent used for introducing the allyl group. It is commonly available as a solution in diethyl ether. If desired, it may be synthesized in the normal method from magnesium and allyl bromide.
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Baeyer and Villiger prepared the dimer by combining potassium persulfate in diethyl ether with acetone, under cooling. After separating the ether layer, the product was purified and found to melt at .(Baeyer and Villiger, 1899), p. 3632.
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Diethyl ether is a hard Lewis base that reacts with a variety of Lewis acids such as I2, phenol, and Al(CH3)3, and its base parameters in the ECW model are EB = 1.80 and CB = 1.63. Diethyl ether is a common laboratory aprotic solvent. It has limited solubility in water (6.05 g/100 ml at 25 °C) and dissolves 1.5 g/100 g (1.0 g/100 ml) water at 25 °C. This, coupled with its high volatility, makes it ideal for use as the non- polar solvent in liquid-liquid extraction.
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The synthesis of 2,2-diethoxytetrahydrofuran via γ-butyrolactone and the Meerwein salt (triethyloxonium tetrafluoroborate) in diethyl ether was first described by Hans Meerwein and co-workers. In the reaction the electrophilic ethyl cation attackes the carbonyl oxygen and forms the stable but extraordinarily hygroscopic O-ethyl-γ-butyrolactonium tetrafluoroborate (melting point 42 °C). The compound dissolves in dichloromethane, chloroform and 1,2-dichloroethane but is insoluble in diethyl ether, benzene and tetrachloromethane. The onium salt reacts practically quantitatively with an ethanolate anion from sodium ethoxide in ethanol forming 2,2-diethoxytetrahydrofuran.
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Acetic formic anhydride can be produced by reacting sodium formate with acetyl chloride in anhydrous diethyl ether between 23–27 °C. It can also be prepared by the reaction of acetic anhydride and formic acid at 0 °C.
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Phenylhydrazine forms monoclinic prisms that melt to an oil around room temperature which may turn yellow to dark red upon exposure to air. Phenylhydrazine is miscible with ethanol, diethyl ether, chloroform and benzene. It is sparingly soluble in water.
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The extraction of trimyristin can also be done with diethyl ether at room temperature, due to its high solubility in the ether. The experiment is frequently included in curricula, both for its relative ease and to provide instruction in these techniques.
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Dimethoxyethane is often used as a higher boiling alternative to diethyl ether and THF. Dimethoxyethane acts as a bidentate ligand for some metal cations. It is therefore often used in organometallic chemistry. Grignard reactions and hydride reductions are typical application.
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Appearance of blood red color indicates presence of peroxides. The dangerous properties of ether peroxides are the reason that diethyl ether and other peroxide forming ethers like tetrahydrofuran (THF) or ethylene glycol dimethyl ether (1,2-dimethoxyethane) are avoided in industrial processes.
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Mixtures with acetic acid or acetic anhydride can explode if not kept cold. Explosions can occur when mixtures of calcium permanganate and sulfuric acid come into contact with benzene, carbon disulfide, diethyl ether, ethyl alcohol, petroleum, or other organic matter.
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Thiosalicylic acid is an organosulfur compound containing carboxyl and sulfhydryl functional groups. Its molecular formula is C6H4(SH)(CO2H). it is a yellow solid that is slightly soluble in water, ethanol and diethyl ether, and alkanes, but more soluble in DMSO.
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The compound is prepared in a tube furnace by the reaction of bromine vapor and chromium powder at 1000 °C. It is purified by extracting with absolute diethyl ether to remove any CrBr2, and is subsequently washed with absolute diethyl ether and absolute ethanol. Analogous to the behavior of related chromium(III) halides, the tribromide dissolves in water to give CrBr3(H2O)3 only upon the addition of catalytic amounts of a reducing agent, which generates CrBr2. The reducing agent generates chromous bromide on the surface of the solid, which dissolves and re-oxidizes to Cr(III).
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Solvent effects and the epimerization of a chiral Grignard reagent. The cis form of the reagent is stabilized, and so more strongly favored, in the reaction solvent THF, over diethyl ether; a larger equilibrium constant is observed in THF. A modern example of the study of solvent effects on chemical equilibrium can be seen in a study of the epimerization of chiral cyclopropylnitrile Grignard reagents. This study reports that the equilibrium constant for the cis to trans isomerization of the Grignard reagent is much greater—the preference for the cis form is enhanced—in THF as a reaction solvent, over diethyl ether.
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Diethyl ether has a high cetane number of 85–96 and is used as a starting fluid, in combination with petroleum distillates for gasoline and Diesel engines because of its high volatility and low flash point. Ether starting fluid is sold and used in countries with cold climates, as it can help with cold starting an engine at sub-zero temperatures. For the same reason it is also used as a component of the fuel mixture for carbureted compression ignition model engines. In this way diethyl ether is very similar to one of its precursors, ethanol.
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Whereas at 20 °C, diethyl ether will dissolve 1% by weight water, DIPE only dissolves 0.88%. It is used as a specialized solvent to remove or extract polar organic compounds from aqueous solutions, e.g. phenols, ethanol, acetic acid. DIPE was used as an antiknock agent.
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Compound spirit of ether, also called Hoffmann's anodyne, Hoffmann's drops, or aetheris spiritus compositus, is a solution of one part diethyl ether in three parts alcohol.Werner Gerabek: Enzyklopädie Medizingeschichte. Berlin 2005, p. 610\. It is used traditionally as an anodyne or as a hypnotic.
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Ethers can be prepared by numerous routes. In general alkyl ethers form more readily than aryl ethers, with the later species often requiring metal catalysts. The synthesis of diethyl ether by a reaction between ethanol and sulfuric acid has been known since the 13th century.
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About 200,000 tonnes of tetrahydrofuran are produced annually. The most widely used industrial process involves the acid-catalyzed dehydration of 1,4-butanediol. Ashland/ISP is one the biggest producers of this chemical route. The method is similar to the production of diethyl ether from ethanol.
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Phenylmagnesium bromide, with the simplified formula , is a magnesium- containing organometallic compound. It is commercially available as a solution in diethyl ether or tetrahydrofuran (THF). Phenylmagnesium bromide is a Grignard reagent. It is often used as a synthetic equivalent for the phenyl "Ph−" synthon.
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Merck Index, 11th edition, 6031. Marketed under the trade names Metopryl and Neothyl, methoxypropane was used as an alternative to diethyl ether because of its greater potency. Its use as an anaesthetic has since been supplanted by modern halogenated ethers which are much less flammable.
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Several medical anesthetics are used as recreational drugs, including diethyl ether (a drug that is no longer used medically, due to its high flammability and the development of safer alternatives) and nitrous oxide, which is widely used in the 2010s by dentists as an anti-anxiety drug during dental procedures. Diethyl ether has a long history of use as a recreational drug. The effects of ether intoxication are similar to those of alcohol intoxication, but more potent. Also, due to NMDA antagonism, the user may experience all the psychedelic effects present in classical dissociatives such as ketamine in forms of thought loops and feeling of mind being disconnected from one's body.
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It does not oxidize on exposure to the air and is not readily acted on by chemical reagents. It is insoluble in water. It is soluble in dichloromethane, chloroform, benzene, diethyl ether, carbon disulfide and turpentine.Vaseline (Petroleum Jelly) Material Safety Data Sheet (MSDS) (June 15, 2007). MakingCosmetics.
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Electrophilic alkylating agents deliver the equivalent of an alkyl cation. Alkyl halides are typical alkylating agents. Trimethyloxonium tetrafluoroborate and triethyloxonium tetrafluoroborate are particularly strong electrophiles due to their overt positive charge and an inert leaving group (dimethyl or diethyl ether). Dimethyl sulfate is intermediate in electrophilicity.
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TMG is prepared by the reaction of gallium trichloride with various methylating agents. These include methyl lithium,, dimethylzinc, and trimethylaluminium. The less volatile diethyl ether adduct can be prepared by using methylmagnesium iodide in ether. The ether ligands may be displaced with liquid ammonia as well.
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In the direct synthesis, methyl bromide is treated with a suspension of lithium in diethyl ether. :2 Li + MeBr → LiMe + LiBr The lithium bromide forms a complex with the methyllithium. Most commercially available methyllithium consists of this complex. "Halide-free" methyllithium is prepared from methyl chloride.
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176 in the 1678 edition. The history of artificial refrigeration began when Scottish professor William Cullen designed a small refrigerating machine in 1755. Cullen used a pump to create a partial vacuum over a container of diethyl ether, which then boiled, absorbing heat from the surrounding air.
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In this process copper(I) and tetrahydroaluminate react to produce molecular copper hydride and triiodoaluminium adducts. The molecular copper hydride is precipitated into amorphous copper hydride with the addition of diethyl ether. Amorphous copper hydride is converted into the Wurtz phase by annealing, accompanied by some decomposition.
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Azeotropes consisting of two constituents are called binary azeotropes such as diethyl ether (33%) / halothane (66%) a mixture once commonly used in anesthesia. For example, benzene and hexafluorobenzene form a double binary azeotrope. Azeotropes consisting of three constituents are called ternary azeotropes, e.g. acetone / methanol / chloroform.
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As for other organic compounds, very common ethers acquired names before rules for nomenclature were formalized. Diethyl ether is simply called "ether", but was once called sweet oil of vitriol. Methyl phenyl ether is anisole, because it was originally found in aniseed. The aromatic ethers include furans.
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The six hydrogens of that core are removed at a later metabolic stage by the enzyme protoporphyrinogen oxidase. Because of this connection, the compound is also called (unsubstituted) porphyrinogen. The compound is a colorless solid, soluble in dichloromethane, acetone, and diethyl ether. It decomposes at 185°C.
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Most Grignard reactions are conducted in ethereal solvents, especially diethyl ether and THF. With the chelating diether dioxane, some Grignard reagents undergo a redistribution reaction to give diorganomagnesium compounds (R = organic group, X = halide): :2 RMgX + dioxane R2Mg + MgX2(dioxane) This reaction is known as the Schlenk equilibrium.
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Octachloropropane treated with aluminum in diethyl ether affords several unsaturated perchlorocarbons, by way of hexachloropropene (, ). For instance, : + 2/3 2/3 + : 2 + 4/3 4/3 + (three isomers) : 2 + 2 2 + (two isomers) The products were identified as : α-: colorless, m. p. 148 °C. : β-: red, m. p.
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It can be prepared by reacting ethylmagnesium bromide with methyl acetate in the so-called Grignard reaction using dried diethyl ether or tetrahydrofuran as solvent. Synthesis of 3-Methyl-3-pentanol It can be prepared also by reacting ethylmagnesium bromide with butanone in the same conditions already mentioned.
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Mixtures containing hexaethyl tetraphosphate are produced by heating diethyl ether and phosphorus pentoxide. The reaction entails cleavage of the C-O bond of the ether. The molecule contains three pyrophosphate bonds, which are the sites of high reactivity. The compound exists as two diastereomers, the meso- and dl-isomers.
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Butanol, with a four-carbon chain, is moderately soluble. Because of hydrogen bonding, alcohols tend to have higher boiling points than comparable hydrocarbons and ethers. The boiling point of the alcohol ethanol is 78.29 °C, compared to 69 °C for the hydrocarbon hexane, and 34.6 °C for diethyl ether.
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The substance is a white crystalline powder. It is freely soluble in methanol and acetone; soluble in water, ethanol, 0.01 M hydrochloric acid, and 0.01 M sodium hydroxide; sparingly soluble in isopropyl alcohol and acetonitrile; slightly soluble in diethyl ether; and very slightly soluble in isopropyl ether. on Lonsurf.
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Butyl butyrate, or butyl butanoate, is an organic compound that is an ester formed by the condensation of butyric acid and n-butanol. It is a clear, colorless liquid that is insoluble in water, but miscible with ethanol and diethyl ether. Its refractive index is 1.406 at 20 °C.
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Crawford W. Long was a physician and pharmacist practicing in Jefferson, Georgia in the mid-19th century. During his time as a student at the University of Pennsylvania School of Medicine in the late 1830s, he had observed and probably participated in the ether frolics that had become popular at that time. At these gatherings, Long observed that some participants experienced bumps and bruises, but afterward had no recall of what had happened. He postulated that diethyl ether produced pharmacologic effects similar to those of nitrous oxide. On 30 March 1842, he administered diethyl ether by inhalation to a man named James Venable, in order to remove a tumor from the man's neck.
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2-MeTHF has solvating properties that are intermediate between diethyl ether and THF, has limited water miscibility, and forms an azeotrope with water on distillation. Its lower melting point makes it useful for lower temperature reactions, and its higher boiling point allows procedures under reflux at higher temperatures (relative to THF).
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Fluoroboric acid is corrosive and attacks the skin. It is available commercially as a solution in water and other solvents such as diethyl ether. It is a strong acid with a weakly coordinating, non-oxidizing conjugate base. It is structurally similar to perchloric acid, but lacks the hazards associated with oxidants.
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Victory V lozenges are available in specialist shops and online, but no longer contain chloroform or ether. However, their scent and flavour is still vividly reminiscent of diethyl ether - presumably recreated via artificial means to preserve the original flavour. Today they are manufactured by Ernest Jackson & Co. Ltd. in Crediton, Devon.
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General anesthetic propofol and inhaled anesthetics xeon, chloroform, isoflurane, diethyl ether disrupt lipid raft function including palmitate mediated localization of PLD2 to lipid rafts. Activation of PLD then activates TREK-1 channels. The membrane mediated PLD2 activation could be transferred to an anesthetic insensitive homolog TRAAK, rending the channel anesthetic sensitive.
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Diethyl ether peroxides can be detected with a potassium iodide (KI) solution in acetic acid or potassium iodide / starch paper. A positive test results in the formation of iodine (I2) that causes a yellow or brown color of the ether phase or a dark bluish spot on the paper strip.
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The first reported syntheses of ferrocene were nearly simultaneous. Pauson and Kealy synthesised ferrocene using iron(III) chloride and a Grignard reagent, cyclopentadienyl magnesium bromide. Iron(III) chloride is suspended in anhydrous diethyl ether and added to the Grignard reagent. A redox reaction occurs, forming the cyclopentadienyl radical and iron(II) ions.
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A pKa does not seem to have been recorded for MLA, but it is considered to be a weak base because it can be readily extracted into diethyl ether from an aqueous solution at pH 7.5-8. The optical rotation of the free base, [α]D was found to be +49° in alcohol.
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Lithium tetrahydridogallate is easily dissolved in diethyl ether with which it forms a stable complex, making removal of the solvent difficult. Ethereal solutions of LiGaH4 are indefinitely stable if sealed in glass vessels at 0 °C. Lithium tetrahydridogallate can also be dissolved in tetrahydrofuran and diglyme. Lithium tetrahydridogallate slowly decomposes at room temperature.
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Commercial diethyl ether is typically supplied with trace amounts of the antioxidant butylated hydroxytoluene (BHT), which reduces the formation of peroxides. Storage over sodium hydroxide precipitates the intermediate ether hydroperoxides. Water and peroxides can be removed by either distillation from sodium and benzophenone, or by passing through a column of activated alumina.
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Butyramide is the amide of butyric acid. It has the molecular formula C3H7CONH2. It is a white solid that freely soluble in water and ethanol, but slightly soluble in diethyl ether. At room temperature, butyramide is a crystalline solid and in contrast to butyric acid, it is devoid of unpleasant, rancid smell.
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The county is named after Crawford Long (1815–1878), American surgeon and pharmacist, first to use diethyl ether as an anaesthetic. As of the 2010 census, the population was 14,464. With a per-capita income of $22,599, Long County is #10 on the list of lowest-income counties in the United States.
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Phenymagnesium bromide is prepared by reaction of bromobenzene with magnesium metal. Phenylmagnesium bromide is commercially available as solutions of diethyl ether or THF. Laboratory preparation involves treating bromobenzene with magnesium metal, usually in the form of turnings. A small amount of iodine may be used to activate the magnesium to initiate the reaction.
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Morton arranged for Wells to demonstrate his technique for dental extraction under nitrous oxide general anesthesia at Massachusetts General Hospital, in conjunction with the prominent surgeon John Collins Warren. This demonstration, which took place on 20 January 1845, ended in failure when the patient cried out in pain in the middle of the operation. On 30 September 1846, Morton administered diethyl ether to Eben Frost, a music teacher from Boston, for a dental extraction. Two weeks later, Morton became the first to publicly demonstrate the use of diethyl ether as a general anesthetic at Massachusetts General Hospital, in what is known today as the Ether Dome. On 16 October 1846, John Collins Warren removed a tumor from the neck of a local printer, Edward Gilbert Abbott.
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The mechanism of the formation of ethyl sulfate, diethyl ether, and ethylene is based on the reaction between ethanol and sulfuric acid, which involves protonation of the ethanolic oxygen to form the oxonium ion. Ethyl sulfate accumulates in hair after chronic alcohol consumption and its detection can be used as a biomarker for alcohol consumption.
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Ethyl 2-methylacetoacetate and campholenic aldehyde react in an Aldol condensation. The synthetic procedureEthyl 2-methylacetoacetate (2) is added to a stirred solution of sodium hydride in dioxane. Then campholenic aldehyde (1) is added and the mixture refluxed for 15 h. Then 2N hydrochloric acid is added and the mixture extracted with diethyl ether.
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The crystalline metal carbonyls often are sublimable in vacuum, although this process is often accompanied by degradation. Metal carbonyls are soluble in nonpolar and polar organic solvents such as benzene, diethyl ether, acetone, glacial acetic acid, and carbon tetrachloride. Some salts of cationic and anionic metal carbonyls are soluble in water or lower alcohols.
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Formic anhydride is a liquid with boiling point 24 °C at 20 mmHg. It is stable in diethyl ether solution. It can be isolated by low-temperature, low-pressure distillation, but decomposes on heating above room temperature. At room temperature and higher, it decomposes through a decarbonylation reaction into formic acid and carbon monoxide.
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Transition metal complexes of isodiazomethane have been prepared. In bulk form isodiazomethane is a liquid which decomposes when the temperature exceeds 15 °C. If it is heated to 40 °C, the substance explodes. A solution of isodiazomethane in diethyl ether at –30 °C gradually isomerizes to diazomethane upon exposure to sodium hydroxide for 20 min.
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Pentoxyverine dihydrogen citrate, the salt that is commonly used for oral preparations, is a white to off-white, crystalline powder. It dissolves easily in water or chloroform, but not in benzene, diethyl ether, or petroleum ether. It melts at . Other orally available salts are the hydrochloride and the tannate; suppositories contain the free base.
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Dipyrrin is unstable above −40 °C. However, its acts as a base, and its chloride [] [] is sufficiently stable in solution. The so-called BODIPY dyes can be obtained by reacting 2,2'-dipyrromethene or its derivatives with boron trifluoride-diethyl ether complex (·) in the presence of triethylamine or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).
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Acetylenedicarboxylic acid or butynedioic acid is an organic compound (a dicarboxylic acid) with the formula C4H2O4 or . It is a crystalline solid that is soluble in diethyl ether. The removal of two protons yields the acetylenedicarboxylate dianion , which consists only of carbon and oxygen, making it an oxocarbon anion. Partial ionization yields the monovalent hydrogenacetylenedicarboxylate anion .
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SEM image of LAH powder LAH is a colorless solid, but commercial samples are usually gray due to contamination. This material can be purified by recrystallization from diethyl ether. Large-scale purifications employ a Soxhlet extractor. Commonly, the impure gray material is used in synthesis, since the impurities are innocuous and can be easily separated from the organic products.
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Tipiracil is used in form of the hydrochloride, which is a white crystalline powder. Solubility in water is 5 mg/mL; it is also soluble in 0.01 M hydrochloric acid and 0.01 M sodium hydroxide; slightly soluble in methanol; very slightly soluble in ethanol; and practically insoluble in acetonitrile, isopropyl alcohol, acetone, diisopropyl ether, and diethyl ether. on Lonsurf.
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Lithium borohydride is a stronger reducing agent than sodium borohydride. In mixtures of methanol and diethyl ether, lithium borohydride is able to reduce esters to alcohols and primary amides to amines. In contrast, these substrates are unaffected by sodium borohydride. The enhanced reactivity is attributed to the polarization of the carbonyl substrate by complexation to the lithium cation.
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Chlorophyll c1 is a common form of chlorophyll c. It differs from chlorophyll c2 in its C8 group, having an ethyl group instead of vinyl group (C-C single bond instead of C=C double bond). Its absorption maxima are around 444, 577, 626 nm and 447, 579, 629 nm in diethyl ether and acetone respectively.
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2-Aminothiazole is a heterocyclic amine featuring a thiazole core. It can also be considered a cyclic isothiourea. It possesses an odor similar to pyridine and is soluble in water, alcohols and diethyl ether. It is commonly used as a starting point for the synthesis of many compounds including sulfur drugs, biocides, fungicides, dyes and chemical reaction accelerators.
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Structure of the polymeric diethyl ether peroxide The C-O bonds that comprise simple ethers are strong. They are unreactive toward all but the strongest bases. Although generally of low chemical reactivity, they are more reactive than alkanes. Specialized ethers such as epoxides, ketals, and acetals are unrepresentative classes of ethers and are discussed in separate articles.
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Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 \- often abbreviated to PPh3 or Ph3P. It is widely used in the synthesis of organic and organometallic compounds. PPh3 exists as relatively air stable, colorless crystals at room temperature. It dissolves in non-polar organic solvents such as benzene and diethyl ether.
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Other solvents for producing tinctures include vinegar, glycerol (also called glycerine), diethyl ether and propylene glycol, not all of which can be used for internal consumption. Ethanol has the advantage of being an excellent solvent for both acidic and basic (alkaline) constituents. A tincture using glycerine is called a glycerite. Glycerine is generally a poorer solvent than ethanol.
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InCl3 is a Lewis acid and forms complexes with donor ligands, L, InCl3L, InCl3L2, InCl3L3. For example, with the chloride ion it forms tetrahedral InCl4−, trigonal bipyramidal InCl52−, and octahedral InCl63−. In diethyl ether solution, InCl3 reacts with lithium hydride, LiH, to form LiInH4. This unstable compound decomposes below 0 °C, and is reacted in situ in organic synthesis as a reducing agentMain Group Metals in Organic Synthesis vol 1, ed. Hisashi Yamamoto, Koichiro Oshima, Wiley VCH, 2004, and to prepare tertiary amine and phosphine complexes of InH3.The Group 13 Metals Aluminium, Gallium, Indium and Thallium: Chemical Patterns and Peculiarities, Simon Aldridge, Anthony J. Downs, Wiley, 2011, Trimethylindium, InMe3, can be produced by reacting InCl3 in diethyl ether solution either with the Grignard reagent MeMgI or methyllithium, LiMe.
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He showed that dormancy could be broken by various anesthetic compounds, such as diethyl ether and chloroform. In 1892, he was appointed lecturer at Royal Veterinary and Agricultural University and later became professor of botany and plant physiology. He taught plant physiology.Warming, Eug. & W. Johannsen (1895) Den almindelige Botanik (General Botany): En Lærebog, nærmest til Brug for Studerende og Lærere. 3rd edn, Kjøbenhavn.
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In 1923, the famous radical chemist Moses Gomberg proposed a production method of chlorine tetroxide. He claimed that treating iodine and silver perchlorate in anhydrous diethyl ether produced it. :I2 \+ 2 AgClO4 → 2 AgI + (ClO4)2 However, later researchers claimed that the product was iodine perchlorate. So far, however, there is no certain evidence for the existence of iodine perchlorate either.
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Schematic of a separatory funnel showing two immiscible liquids, where 1 is any phase less dense than 2. Phase 1 is typically an organic solvent and 2 an aqueous phase. Laboratory-scale liquid-liquid extraction. Photograph of a separatory funnel in a laboratory scale extraction of 2 immiscible liquids: liquids are a diethyl ether upper phase, and a lower aqueous phase.
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Acetic oxalic anhydride is an unstable colorless crystalline solid, soluble in diethyl ether, that decomposes at about −3 °C into acetic anhydride (-(C=O)-)2O, carbon dioxide () and carbon monoxide (CO). It is hydrolyzed by water into acetic and oxalic acids. Acetic oxalic anhydride was conjectured to be an intermediate in the decomposition of anhydrous oxalic acid by acetic anhydride.
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Benzenesulfonic acid (conjugate base benzenesulfonate) is an organosulfur compound with the formula C6H6O3S. It is the simplest aromatic sulfonic acid. It forms white deliquescent sheet crystals or a white waxy solid that is soluble in water and ethanol, slightly soluble in benzene and insoluble in nonpolar solvents like diethyl ether. It is often stored in the form of alkali metal salts.
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These "diesels" run on a mixture of kerosene, ethanol, ether, castor oil or vegetable oil, and cetane or amyl nitrite booster. The fuel used contains Diethyl ether, which is highly volatile and has an extremely low flash point, combined with kerosene and a lubricant plus a very small proportion (typically 2%) of ignition improver such as Amyl nitrite or preferably Isopropyl nitrate nowadays.
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Monobenzone, also called 4-(Benzyloxy)phenol and monobenzyl ether of hydroquinone (MBEH) is an organic chemical in the phenol family with chemical formula C6H5CH2OC6H4OH. It is used as a topical drug for medical depigmentation. It is a colourless solid that is classified as the monobenzyl ether of hydroquinone. Monobenzone is soluble in alcohol, benzene, and diethyl ether, and practically insoluble in water.
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A common practice in chemical labs is to use steam (thus limiting the temperature to ) when ether must be heated or distilled. The diffusion of diethyl ether in air is (298 K, 101.325 kPa). Ether is sensitive to light and air, tending to form explosive peroxides. Ether peroxides have a higher boiling point than ether and are contact explosives when dry.
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Oxygen is more electronegative than carbon, thus the hydrogens alpha to ethers are more acidic than in simple hydrocarbons. They are far less acidic than hydrogens alpha to carbonyl groups (such as in ketones or aldehydes), however. Ethers can be symmetrical of the type ROR or unsymmetrical of the type ROR'. Examples of the former are diethyl ether, dimethyl ether, dipropyl ether etc.
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The tendency of TaF5 to form clusters in the solid state indicates the Lewis acidity of the monomer. Indeed, TaF5 reacts with fluoride sources to give the ions , , and . With neutral Lewis bases, such as diethyl ether TaF5 forms adducts. is used in combination with HF as a catalyst for the alkylation of alkanes and alkenes and for the protonation of aromatic compounds.
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Structure of tetrabenzylzirconium as determined by X-ray crystallography, with H atoms omitted for clarity. X-ray crystallography demonstrates that the benzyl ligands are highly flexible: one polymorph features four η2-ligands, whereas another has two η1\- and two η2-benzyl ligands. The compound is prepared by combining benzylmagnesium chloride and zirconium tetrachloride in diethyl ether. It readily undergoes protonolysis, e.g.
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Decamethyldizincocene is an organozinc compound with the formula [Zn2(η5–C5Me5)2]. It is the first and an unusual example of a compound with a Zn-Zn bond. Decamethyldizincocene is a colorless crystalline solid that burns spontaneously in the presence of oxygen and reacts with water. It is stable at room temperature and especially soluble in diethyl ether, benzene, pentane, or tetrahydrofuran.
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Upon heating to 300 °C, it decomposes to sodium sulfate and sodium polysulfide: : Thiosulfate salts characteristically decompose upon treatment with acids. Initial protonation occurs at sulfur. When the protonation is conducted in diethyl ether at −78 °C, H2S2O3 (thiosulfuric acid) can be obtained. It is a somewhat strong acid with pKas of 0.6 and 1.7 for the first and second dissociations, respectively.
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Chemical compounds with boron to boron double bonds are rare. In 2007 the first neutral diborene (RHB=BHR) was presented by Gregory Robinson of the University of Georgia.Neutral Diborene Is A First Ron Dagani Chemical & Engineering News October 1, 2007 Volume 85, Number 40 p. 10 The boron precursor is boron tribromide and the reducing agent is KC8 which abstracts the required protons from diethyl ether solvent.
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Gallium trichloride is a common starting reagent for the formation of organogallium compounds, such as in carbogallation reactions. Gallium trichloride reacts with lithium cyclopentadienide in diethyl ether to form the trigonal planar gallium cyclopentadienyl complex GaCp3. Gallium(I) forms complexes with arene ligands such as hexamethylbenzene. Because this ligand is quite bulky, the structure of the [Ga(η6-C6Me6)]+ is that of a half-sandwich.
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Adrenalone is a derivative of epinephrine, having the alcohol function replaced with a ketone. As a consequence, it is not optically active any more. Solubility in water, ethanol and diethyl ether is low. The substance is typically used in form of the hydrochloride, a white crystalline powder which tastes bitter and slightly acidic, and is soluble in water (1:8) and 94% ethanol (1:45).
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Isoquinoline is a colorless hygroscopic liquid at temperatures above its melting point with a penetrating, unpleasant odor. Impure samples can appear brownish, as is typical for nitrogen heterocycles. It crystallizes in platelets that have a low solubility in water but dissolve well in ethanol, acetone, diethyl ether, carbon disulfide, and other common organic solvents. It is also soluble in dilute acids as the protonated derivative.
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Tetraethyltin or tetraethyl tin is a chemical compound with the formula and molecular structure (CH3CH2)4Sn, that is, a tin atom attached to four ethyl groups. It is an important example of an organotin compound, often abbreviated as TET. Tetraethyltin is a colourless flammable liquid, soluble in diethyl ether and insoluble in water, that freezes at -112 °C and boils at 181 °C.SAFC corp, tetraethyltin catalog page.
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BODIPY and its derivatives can be obtained by reacting the corresponding 2,2'-dipyrromethene derivatives with boron trifluoride-diethyl ether complex (·) in the presence of triethylamine or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The difficulty of the synthesis was due to instability of the usual dipyrromethene precursor, rather than of BODIPY itself. The dipyrromethene precursors are accessed from a suitable pyrrole derivatives by several methods.
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3-Hydroxypropionic acid is a carboxylic acid, specifically a beta hydroxy acid. It is an acidic viscous liquid with a pKa of 4.5. It is very soluble in water, soluble in ethanol and diethyl ether. Upon distillation, it dehydrates to form acrylic acid, and is occasionally called hydracrylic acid 3-Hydroxypropionic acid is used in the industrial production of various chemicals such as acrylates.
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Ipomoea purga resin can be dissolved in either alcohol or diethyl ether. The resin that is insoluble in ether is odorless while the resin insoluble in alcohol does have an odor and is typically a brownish color. The convolvulinolic acid (C28H52O14)that is produced in Ipomoea purga can be broken down into a sugar molecule (C6H12O6) and a form of crystallized convolvulinolic acid (C16H30O3) when diluted.
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1-Hexanol is an organic alcohol with a six-carbon chain and a condensed structural formula of CH3(CH2)5OH. This colorless liquid is slightly soluble in water, but miscible with diethyl ether and ethanol. Two additional straight chain isomers of 1-hexanol, 2-hexanol and 3-hexanol, exist, both of which differing by the location of the hydroxyl group. Many isomeric alcohols have the formula C6H13OH.
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Potassium tert-butoxide crystallises from tetrahydrofuran/pentane at −20 °C as [tBuOK·tBuOH]∞, which consists of infinite one-dimensional chains linked by hydrogen bonding. Sublimation of [tBuOK·tBuOH]∞ affords the tetramer [tBuOK]4, which adopts a cubane-like structure. Mild Lewis basic solvents such as THF and diethyl ether do not break up the tetrameric structure, which persists in the solid, in solution and even in the gas phase.
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Grinkevich, p. 132 Plants are thoroughly ground before extraction.Grinkevich, p. 5 Most alkaloids are present in the raw plants in the form of salts of organic acids. The extracted alkaloids may remain salts or change into bases. Base extraction is achieved by processing the raw material with alkaline solutions and extracting the alkaloid bases with organic solvents, such as 1,2-dichloroethane, chloroform, diethyl ether or benzene.
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The reagent can be prepared (scheme 1) by reaction of triphenylphosphine 1 with chloromethyl methyl ether 2 in diethyl ether to the phosphonium salt 3. 3 can also be prepared from triphenylphosphine, methylal and acetyl chloride, a reaction avoiding the costly and carcinogenic chloroalkyl ether and especially useful for large batches. This salt is deprotonated to the phosphonium ylide Methoxymethylenetriphenylphosphine 4 by phenyllithium. Scheme 1.
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The oxygen atom at this point has three bonds and carries a positive charge (i.e., the molecule is an oxonium). Another water molecule comes along and takes up the extra proton. This reaction tends to yield many undesirable side products, (for example diethyl ether in the process of creating ethanol) and in its simple form described here is not considered very useful for the production of alcohol.
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This organic compound is a white powdered solid with a slight aromatic, phenolic odor. Categorized as a polychloro phenoxy phenol, triclosan is a chlorinated aromatic compound that has functional groups representative of both ethers and phenols. Phenols often demonstrate antibacterial properties. Triclosan is soluble in ethanol, methanol, diethyl ether, and strongly basic solutions such as a 1M sodium hydroxide solution, but only slightly soluble in water.
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Urushiol in its pure form is a pale-yellow liquid with a specific gravity of 0.968 and a boiling point of . It is soluble in diethyl ether, acetone, ethanol, carbon tetrachloride, and benzene. Urushiol is a mixture of several closely related organic compounds. Each consists of a catechol substituted in the 3 position with a hydrocarbon chain that has 15 or 17 carbon atoms.
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Hexachlorophene, also known as Nabac, is an organochlorine compound that was once widely used as a disinfectant. The compound occurs as a white odorless solid, although commercial samples can be off-white and possess a slightly phenolic odor. It is insoluble in water but dissolves in acetone, ethanol, diethyl ether, and chloroform. In medicine, hexachlorophene is useful as a topical anti-infective, anti-bacterial agent, often used in soaps and toothpaste.
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Deltic acid or dihydroxycyclopropenone is a chemical substance with the chemical formula C3O(OH)2. It can be viewed as a ketone and double alcohol of cyclopropene. At room temperature, it is a stable white solid, soluble in diethyl ether, that decomposes (sometimes explosively) between 140 °C and 180 °C, and reacts slowly with water. The synthesis of deltic acid was first described in 1975 by David Eggerding and Robert West.
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Benzvalene is an organic compound and one of several isomers of benzene. It was first synthesized in 1971 by Thomas J. Katz et al. The 1971 synthesis consisted of treating cyclopentadiene with methyllithium in dimethyl ether and then with dichloromethane and methyllithium in diethyl ether at −45 °C. It can also be formed in low yield (along with fulvene and Dewar benzene) by irradiation of benzene at 237 to 254 nm.
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Boyle promoted intratracheal insufflation techniques using nitrous oxide, oxygen and ether, replacing open- drop anaesthesia. Initially he used imported Gwathmey machines from the USA, but finding them unreliable, he developed his own continuous-flow machines. His design included cylinders for the gases and a "Boyle's Bottle" to vaporize diethyl ether. Until recently, an anaesthetic machine was often referred to as a "Boyle's Machine" in honour of his contribution.
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His most famous research was his efforts to use diethyl ether in the treatment of phthisis. In 1870 he published Method and Medicine, a defence of scientific research in medicine. This was his last major piece of medical work; in the 1870s he became involved the public health and the social applications of medicine. In 1873 he was elected a Fellow of the Royal College of Physicians (FRCP).
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A general synthetic route to organomercury compounds entails alkylation with Grignard reagents and organolithium compounds. Diethylmercury results from the reaction of mercury chloride with two equivalents of ethylmagnesium bromide, a conversion that would typically be conducted in diethyl ether solution. The resulting (CH3CH2)2Hg is a dense liquid (2.466 g/cm3) that boils at 57 °C at 16 torr. The compound is slightly soluble in ethanol and soluble in ether.
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The order of addition of the reagents of the Mitsunobu reaction can be important. Typically, one dissolves the alcohol, the carboxylic acid, and triphenylphosphine in tetrahydrofuran or other suitable solvent (e.g. diethyl ether), cool to 0 °C using an ice-bath, slowly add the DEAD dissolved in THF, then stir at room temperature for several hours. If this is unsuccessful, then preforming the betaine may give better results.
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A common historical example of azeotropic distillation is its use in dehydrating ethanol and water mixtures. For this, a near azeotropic mixture is sent to the final column where azeotropic distillation takes place. Several entrainers can be used for this specific process: benzene, pentane, cyclohexane, hexane, heptane, isooctane, acetone, and diethyl ether are all options as the mixture. Of these benzene and cyclohexane have been used the most extensively.
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IUPAC Provisional Recommendations 2004, Rule P-53.2.2, Chapter5 Substitutive nomenclature (replacement of hydrogen atoms in the parent structure) is used most extensively, for example "ethoxyethane" instead of diethyl ether and "tetrachloromethane" instead of carbon tetrachloride. Functional class nomenclature (also known as radicofunctional nomenclature) is used for acid anhydrides, esters, acyl halides and pseudohalides and salts. Also skeletal replacement operations, additive and subtractive operations and conjunctive operations are applied.
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Alkyl magnesium chlorides in ether are present as dimers.J. March Advanced Organic Chemistry 3rd Ed. The position of the equilibrium is influenced by solvent, temperature, and the nature of the various substituents. It is known that magnesium center in Grignard reagents typically coordinates two molecules of ether such as diethyl ether or tetrahydrofuran (THF). Thus they are more precisely described as having the formula RMgXL2 where L = an ether.
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Diethyl ether, or simply ether, is an organic compound in the ether class with the formula , sometimes abbreviated as (see Pseudoelement symbols). It is a colorless, highly volatile, sweet-smelling ("Ethereal odour") flammable liquid. It is commonly used as a solvent in laboratories and as a starting fluid for some engines. It was formerly used as a general anesthetic, until non-flammable drugs were developed, such as halothane.
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The anesthetic and intoxicating effects of ether have made it a recreational drug. Diethyl ether in anesthetic dosage is an inhalant which has a long history of recreational use. One disadvantage is the high flammability, especially in conjunction with oxygen. One advantage is a well-defined margin between therapeutic and toxic doses, which means one would lose consciousness before dangerous levels of dissolved ether in blood would be reached.
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The dehydration of alcohols affords ethers: : 2 R–OH → R–O–R + H2O at high temperature center This direct nucleophilic substitution reaction requires elevated temperatures (about 125 °C). The reaction is catalyzed by acids, usually sulfuric acid. The method is effective for generating symmetrical ethers, but not unsymmetrical ethers, since either OH can be protonated, which would give a mixture of products. Diethyl ether is produced from ethanol by this method.
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The purpose of completing the hydrolysis of dichlorosilane is to collect the concentrated hydrolysis products, distill the solution, and retrieve a solution of [H2SiO]n oligomers in dichloromethane. These methods were used to obtain cyclic polysiloxanes. Another purpose for hydrolyzing dichlorosilane is to obtain linear polysiloxanes, and can be done by many different complex methods. The hydrolysis of dichlorosilane in diethyl ether, dichloromethane, or pentane gives cyclic and linear polysiloxanes.
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Preparation of high purity solutions is possible using the methytrioxorhenium(VII) catalyst. In acetone-d6 at –20 °C, the characteristic 1H NMR signal of trioxidane could be observed at a chemical shift of 13.1 ppm. Solutions of hydrogen trioxide in diethyl ether can be safely stored at -20 °C for as long as a week. The reaction of ozone with hydrogen peroxide is known as the "peroxone process".
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For example, consider three compounds of similar chemical composition: sodium n-butoxide (C4H9ONa), diethyl ether (C4H10O), and n-butanol (C4H9OH). Figure 8. Boiling points of 4-carbon compounds The predominant non-covalent interactions associated with each species in solution are listed in the above figure. As previously discussed, ionic interactions require considerably more energy to break than hydrogen bonds, which in turn are require more energy than dipole–dipole interactions.
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The trends observed in their boiling points (figure 8) shows exactly the correlation expected, where sodium n-butoxide requires significantly more heat energy (higher temperature) to boil than n-butanol, which boils at a much higher temperature than diethyl ether. The heat energy required for a compound to change from liquid to gas is associated with the energy required to break the intermolecular forces each molecule experiences in its liquid state.
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Antoine Balard, one of the discoverers of bromine Bromine was discovered independently by two chemists, Carl Jacob Löwig and Antoine Balard, in 1825 and 1826, respectively. Löwig isolated bromine from a mineral water spring from his hometown Bad Kreuznach in 1825. Löwig used a solution of the mineral salt saturated with chlorine and extracted the bromine with diethyl ether. After evaporation of the ether a brown liquid remained.
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Dexpanthenol Panthenol is an odourless, slightly bitter, highly viscous, transparent and colourless liquid at room temperature, but salts of pantothenic acid (for example sodium pantothenate) are powders (typically white). It is easily soluble in water and alcohol, moderately soluble in diethyl ether, soluble in chloroform (1:100), in propylene glycol, and slightly soluble in glycerin. Panthenol's expanded chemical formula is HO–CH2–C(CH3)2–CH(OH)–CONH–CH2CH2CH2–OH.
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The reaction was originally carried out in diethyl ether and routinely generated high yields due to the inherent irreversibly of the reaction caused by the formation of nitrogen gas. Though these reactions can be carried out at room temperature, the rate does increase at higher temperatures. Typically, the reaction is carried out at less than refluxing temperatures. The optimal reaction temperature is determined by the specific diazoalkane used.
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At standard ambient temperature and pressure, trifluoroperacetic acid is a colourless liquid with a boiling point of 162 °C. It is soluble in acetonitrile, dichloromethane, diethyl ether, and sulfolane, and readily reacts with water. Like all peroxy acids, it is potentially explosive and requires careful handling. It is not commercially available, but can be made in the lab and stored for up to several weeks at −20 °C.
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Swiss scientist Nicolas-Théodore de Saussure also studied it in 1807.Théodore de Saussure (1807) "Mémoire sur la composition de l'alcohol et de l'éther sulfurique," Journal de physique, de chimie, d'histoire naturelle et des arts, 64 : 316–354. In 1827, French chemist and pharmacist Félix- Polydore Boullay (1806-1835) along with Jean-Baptiste André Dumas noted the role of ethyl sulfate in the preparation of diethyl ether from sulfuric acid and ethanol.
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They are normally handled as solutions in solvents such as diethyl ether or tetrahydrofuran; which are relatively stable as long as water is excluded. In such a medium, a Grignard reagent is invariably present as a complex with the magnesium atom connected to the two ether oxygens by coordination bonds. The discovery of the Grignard reaction in 1900 was awarded with the Nobel prize in 1912. For more details on the history see Victor Grignard.
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W Pötsch. Lexikon bedeutender Chemiker (VEB Bibliographisches Institut Leipzig, 1989) ()M B Smith, J March. March's Advanced Organic Chemistry (Wiley, 2001) () The name "Schotten–Baumann reaction conditions" often indicate the use of a two-phase solvent system, consisting of water and an organic solvent. The base within the water phase neutralizes the acid, generated in the reaction, while the starting materials and product remain in the organic phase, often dichloromethane or diethyl ether.
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The potassium salt of dinitromethanide, KCH(NO2)2, was first prepared by Villiers in 1884 by reduction of bromodinitromethane. Hydrogen fluoride and the potassium salt of dinitromethane react in diethyl ether to form dinitromethane. Free dinitromethane was previously understood to be a pale, yellow oil that decomposed rapidly at ambient temperatures. Dinitromethane should not be confused with methylene dinitrate (CH2(ONO2)2), which is produced as a byproduct in the production of the explosive RDX.
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Cummings, p. 54; Shachtman, p. 57. Various methods had been invented to do this, including Jacob Perkins's diethyl ether vapor- compression refrigeration engine, invented in 1834; engines that used pre- compressed air; John Gorrie's air cycle engines; and ammonia-based approaches such as those championed by Ferdinand Carré and Charles Tellier.Cummings, p. 55; Blain, p. 26. The resulting product was variously called plant or artificial ice, but there were numerous obstacles to manufacturing it commercially.
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For edible oils, the tolerated limit of unsaponifiable matter is 1.5 % (olive, refined soybean), while inferior quality crude or pomace oil could reach 3 %. Determination of unsaponifiables involves a saponification step of the sample followed by extraction of the unsaponifiable using an organic solvent (i.e. diethyl ether). Official methods for animal and vegetable fats and oils are described by ASTM D1065 - 18, ISO 3596: 2000 or 18609: 2000, AOCS method Ca 6a-40.
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Unlike some other anhydrides, Acetic oxalic anhydride cannot be obtained directly from the acids. It was synthesized in 1953 by W. Edwards and W. M. Henley, by reacting silver oxalate () suspended in diethyl ether with acetyl chloride at temperatures below −5 °C and distilling off the solvent under low pressure. It can also be obtained by reacting anhydrous oxalic acid with ketene (=C=O).W. R. Edwards and Walter M. Henley (1953), Acetic Oxalic Anhydride.
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Additionally, the complex is highly stable in benzene retaining its reactivity after a month of storage. Phenyllithium can also be used to modify the properties of phenylsodium. Ordinarily, phenylsodium reacts violently with diethyl ether, but Georg Wittig showed that by synthesizing PhNa with PhLi in ether, the complex (C6H5Li)(C6H5Na)n was formed. The phenylsodium component of the complex reacts before the phenyllithium, making it an effective compound to stabilize the highly reactive sodium compound.
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Pyrophosphoric acid, also known as diphosphoric acid, is the inorganic compound with the formula H4P2O7 or, more descriptively, [(HO)2P(O)]2O. Colorless and odorless, it is soluble in water, diethyl ether, and ethyl alcohol. The anhydrous acid crystallizes in two polymorphs, which melt at 54.3 °C and 71.5 °C. The compound is not particularly useful, except that it is a component of polyphosphoric acid and the conjugate acid of the pyrophosphate anion.
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1090 Similarly, Co2+ gives a blue complex with thiocyanate. Both the iron and cobalt complexes can be extracted into organic solvents like diethyl ether or amyl alcohol. This allows the determination of these ions even in strongly coloured solutions. The determination of Co(II) in the presence of Fe(III) is possible by adding KF to the solution, which forms uncoloured, very stable complexes with Fe(III), which no longer react with SCN−.
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One strategy involves degradation of five-carbon building blocks. For example, the oxidative decarboxylation of cyclobutanecarboxylic acid was improved by the use of other reagents and methods. A newer, more efficient preparation of cyclobutanone was found by P. Lipp and R. Köster in which a solution of diazomethane in diethyl ether is reacted with ketene. This reaction is based on a ring expansion of the cyclopropanone intermediate initially formed, wherein molecular nitrogen is split off.
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2-Ethoxyethanol, also known by the trademark Cellosolve or ethyl cellosolve, is a solvent used widely in commercial and industrial applications. It is a clear, colorless, nearly odorless liquid that is miscible with water, ethanol, diethyl ether, acetone, and ethyl acetate. 2-Ethoxyethanol is manufactured by the reaction of ethylene oxide with ethanol. As with other glycol ethers, 2-ethoxyethanol has the useful property of being able to dissolve chemically diverse compounds.
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Diazomethane is the chemical compound CH2N2, discovered by German chemist Hans von Pechmann in 1894. It is the simplest diazo compound. In the pure form at room temperature, it is an extremely sensitive explosive yellow gas; thus, it is almost universally used as a solution in diethyl ether. The compound is a popular methylating agent in the laboratory, but it is too hazardous to be employed on an industrial scale without special precautions.
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Magnesium iodide is stable at high heat under a hydrogen atmosphere, but decomposes in air at normal temperatures, turning brown from the release of elemental iodine. When heated in air, it decomposes completely to magnesium oxide. Another method to prepare MgI2 is mixing powdered elemental iodine and magnesium metal. In order to obtain anhydrous MgI2, the reaction should be conducted in a strictly anhydrous atmosphere; dry-diethyl ether can be used as a solvent.
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Transactions of the American Electrochemical Society, volume 45, page 161.D. Hibert and C. Duval (1937): Comptes rendues, volume 204, page 780. however, those results do not seem to have been reproduced, or have been attributed to other substances like the hexachlorocobaltate(III) anion . Those earlier reports claim that it gives green solutions in anhydrous solvents such as ethanol and diethyl ether, and that it is stable only a very low temperatures (below −60 °C).
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In terms of mechanism, the oxidative polymerization using ferric chloride, a radical pathway has been proposed. Proposed mechanisms for ferric chloride oxidative polymerizations of thiophenes. Polymerization was only observed in solvents where the catalyst was either partially or completely insoluble (chloroform, toluene, carbon tetrachloride, pentane, and hexane, and not diethyl ether, xylene, acetone, or formic acid). The polymerization may occur at the surface of solid ferric chloride.. Quantum mechanical calculations also point to a radical mechanism.
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Other oxygen- donor ligands include phosphine oxides and phosphate esters. Uranyl nitrate, UO2(NO3)2, can be extracted from aqueous solution into diethyl ether. The complex that is extracted has two nitrato ligands bound to the uranyl ion, making a complex with no electrical charge and also the water molecules are replaced by ether molecules, giving the whole complex notable hydrophobic character. Electroneutrality is the most important factor in making the complex soluble in organic solvents.
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Biodiesel from vegetable oil sources have been recorded as having a cetane number range of 46 to 52, and animal-fat based biodiesels cetane numbers range from 56 to 60. Dimethyl ether is a potential diesel fuel as it has a high cetane rating (55-60) and can be produced as a biofuel. Most simple ethers, including liquid ones, such as diethyl ether can be used as diesel fuels, although the lubricity can be of concern.
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1,4-Dioxane () is a heterocyclic organic compound, classified as an ether. It is a colorless liquid with a faint sweet odor similar to that of diethyl ether. The compound is often called simply dioxane because the other dioxane isomers (1,2- and 1,3-) are rarely encountered. Dioxane is used as a solvent for a variety of practical applications as well as in the laboratory, and also as a stabilizer for the transport of chlorinated hydrocarbons in aluminum containers.
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In addition the four copper atoms form a planar Cu4 ring based on three-center two-electron bonds. The copper to copper bond length is 242 pm compared to 256 pm in bulk copper. In pentamesitylpentacopper a 5-membered copper ring is formed, similar to (2,4,6-trimethylphenyl)gold, and pentafluorophenylcopper is a tetramer. :Organocopper aggregates Lithium dimethylcuprate is a dimer in diethyl ether, forming an 8-membered ring with two lithium atoms linking two methyl groups.
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These alkoxy radicals are susceptible to C—C fragmentation reactions, which explains the formation of a mixture of products.Sheldon B. Markofsky “Nitro Compounds, Aliphatic” in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. . Alternatively, nitroethane can be produced by the Victor Meyer reaction of haloethanes such as chloroethane, bromoethane, or iodoethane with silver nitrite in diethyl ether or THF. The Kornblum modification of this reaction uses sodium nitrite in either a dimethyl sulfoxide or dimethylformamide solvent.
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Thiocyanogen, (SCN)2, is a pseudohalogen derived from the pseudohalide thiocyanate, [SCN]−. This hexatomic compound exhibits C2 point group symmetry and has the connectivity NCS-SCN. The oxidation ability is greater than bromine. It reacts with water: 3(SCN)2 \+ 4H2O → H2SO4 \+ HCN + 5SCN− \+ 5H+ Thiocyanogen was originally prepared by the reaction of iodine with a suspension of silver thiocyanate in diethyl ether, but this reaction suffers from competing equilibria attributed to the weak oxidizing power of iodine.
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Space-filling model of dimethylcadmium The first organocadmium compounds, dimethylcadmium, CH3-Cd-CH3, and diethylcadmium, CH3CH2-Cd-CH2CH3, were prepared in 1917 by Erich Krause. In general, they are prepared by transmetalation or by an exchange reaction between an organometallic reagent and a cadmium salt. One procedure for the synthesis of diethylcadmium is by the reaction of cadmium bromide with two equivalents of the Grignard reagent ethylmagnesium bromide in diethyl ether. A byproduct is magnesium bromide.
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Sodium aluminium hydride or sodium alanate is an inorganic compound with the chemical formula NaAlH4. It is a white pyrophoric solid that dissolves in tetrahydrofuran (THF), but not in diethyl ether or hydrocarbons. It has been evaluated as an agent for the reversible storage of hydrogen and it is used as a reagent for the chemical synthesis of organic compounds. Similar to lithium aluminium hydride, it is a salt consisting of separated sodium cations and tetrahedral AlH anions.
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For one method of isolating amygdalin, the stones are removed from the fruit and cracked to obtain the kernels, which are dried in the sun or in ovens. The kernels are boiled in ethanol; on evaporation of the solution and the addition of diethyl ether, amygdalin is precipitated as minute white crystals. Natural amygdalin has the (R)-configuration at the chiral phenyl center. Under mild basic conditions, this stereogenic center isomerizes; the (S)-epimer is called neoamygdalin.
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Niobium(III) chloride, in the form of Nb2Cl6 with ligands, is also a metal cluster compound with a double bond between the two niobium atoms. Some known complexes have the following formulae: Nb2Cl6(Me2S)3, Nb2Cl6(PPhMe2)4, Nb2Cl6[o-(AsMe2)2C6H4]2 (diars), Nb2Cl6[MeC(CH2AsMe2)3]2 (triars), Nb2Cl6[Ph2PCH2CH2PPh2]4 (diphos), Nb2Cl6[PhPMe2]4, and yet other ligands such as 1,4-dioxane, diethyl ether, or the crown thioether (SC4H8)3 (which is violet).
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57, p.50. Online version :Et2NSiMe3 \+ SF4 → Et2NSF3 \+ Me3SiF The original paper calls for trichlorofluoromethane (Freon-11) as a solvent, a compound that has been banned under the Montreal Protocol and is no longer available as a commodity chemical. diethyl ether is a green alternative that can be used with no decrease in yield. Because of the dangers involved in the preparation of DAST (glass etching, possibility of exothermic events), it is often purchased from a commercial source.
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Lunn, J.N. (1982) Lecture Notes on Anaesthetics, 2nd edn. Blackwell Scientific Publications, Oxford.Guedel AE. Inhalation anesthesia, Ed 2, New York, 1951, Macmillan This classification was designed for use of a sole inhalational anesthetic agent, diethyl ether (commonly referred to as simply "ether"), in patients who were usually premedicated with morphine and atropine. At that time, intravenous anesthetic agents were not yet in common use, and neuromuscular-blocking drugs were not used at all during general anesthesia.
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At the time of Suckling's original research, the main anaesthetic gases in use were chloroform and diethyl ether, both of which had several serious drawbacks. Ether was highly flammable, which was particularly dangerous in operating theatres as electrical equipment such as diathermy became more common. Chloroform was toxic to the liver. The halogenated alkanes (alkyl halides, also known as haloalkanes) in general, and in particular the fluorinated compounds were promising because they were volatile but not flammable.
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Masters of Medicine. Web. 2017. This practice revealed the pain-annulling properties of ether inhalation during surgery. Pioneers of obstetric anesthesia extended these findings to cases of parturition or childbirth, notably including James Young Simpson of Scotland (1811-1870), John Snow of London (1813-1858) and Walter Channing of the United States of America (1786-1876). Prior to the anesthetizing of Queen Victoria in 1853, the use of diethyl ether and chloroform as obstetric anesthetics faced social, religious, and medical opposition.
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Halothane was first synthesized by C. W. Suckling of Imperial Chemical Industries in 1951 in Widnes and was first used clinically by M. Johnstone in Manchester in 1956. It became popular as a nonflammable general anesthetic replacing other volatile anesthetics such as trichloroethylene, diethyl ether and cyclopropane. In many parts of the world it has been largely replaced by newer agents since the 1980s but is still widely used in developing countries because of its lower cost. A meter for measuring halothane.
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Usually, the mixture is dissolved in a suitable solvent such as dichloromethane or diethyl ether (ether), and poured into a separating funnel. An aqueous solution of the acid or base is added, and the pH of the aqueous phase is adjusted to bring the compound of interest into its required form. After shaking and allowing for phase separation, the phase containing the compound of interest is collected. The procedure is then repeated with this phase at the opposite pH range.
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When freshly prepared, it reverts rapidly to the monomer in solution. :Conversion of dihydroxyacetone dimer to monomer The monomer is very soluble in water, ethanol, diethyl ether, acetone and toluene. DHA may be prepared, along with glyceraldehyde, by the mild oxidation of glycerol, for example with hydrogen peroxide and a ferrous salt as catalyst. It can also be prepared in high yield and selectivity at room temperature from glycerol using cationic palladium-based catalysts with oxygen, air or benzoquinone acting as co-oxidants.
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Another type of entrainer is one that has a strong chemical affinity for one of the constituents. Using again the example of the water/ethanol azeotrope, the liquid can be shaken with calcium oxide, which reacts strongly with water to form the nonvolatile compound, calcium hydroxide. Nearly all of the calcium hydroxide can be separated by filtration and the filtrate redistilled to obtain 100% pure ethanol. A more extreme example is the azeotrope of 1.2% water with 98.8% diethyl ether.
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The mesoionic structure of molsidomine Molsidomine and linsidomine are sydnone imines, a class of mesoionic heterocyclic aromatic chemical compounds. Molsidomine melts at , is freely soluble in chloroform, soluble in aqueous hydrochloric acid, ethanol, ethyl acetate and methanol, sparingly soluble in water and acetone, and very slightly soluble in diethyl ether and petroleum ether. It is stable in aqueous solutions at pH 5–7, but not in alkaline solutions. Its absorption maximum is in the near ultraviolet, at 326 nm, in chloroform.
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It is a colorless or white oil that is virtually insoluble in water but very soluble in acetone, benzene, diethyl ether and ethanol. It typically occurs in nature as a triglyceride (ester of glycerin) rather than as a free fatty acid. It is one of two essential fatty acids for humans, who must obtain it through their diet. The word "linoleic" derives from the Latin linum "flax" + oleum "oil", reflecting the fact that it was first isolated from linseed oil.
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Strongly acidic ion exchange resin is then added. The resin is filtered and the opiates are recovered with the addition of ammonia water. The resulting liquid is evaporated using a chemical condenser, then when dry (it is then called glazura - glaze) it is acetylated using acetic anhydride in an anhydrous environment of a non-polar solvent, for example toluene, diethyl ether, chloroform, or most commonly acetone. After acetylation, the solvent is evaporated to remove the acetic anhydride, and finally water is added.
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Elaterium has been produced in light, thin, friable, flat or slightly incurved opaque cakes, of a greyish-green color, bitter taste and tea-like smell. The extract is soluble in ethanol, but insoluble in water and diethyl ether. The official dose used to be grain, and the British pharmacopeia at the beginning of the 20th century directs that the drug is to contain from 20 to 25% of the active principle elaterinum or elaterin. A resin in the natural product aids its action.
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G. A. Spiller Caffeine, CRC Press, 1997 Many alkaloids dissolve poorly in water but readily dissolve in organic solvents, such as diethyl ether, chloroform or 1,2-dichloroethane. Caffeine, cocaine, codeine and nicotine are slightly soluble in water (with a solubility of ≥1g/L), whereas others, including morphine and yohimbine are very slightly water-soluble (0.1–1 g/L). Alkaloids and acids form salts of various strengths. These salts are usually freely soluble in water and ethanol and poorly soluble in most organic solvents.
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If the chromic acid oxidation is performed with stoichiometric oxidant in the presence of diethyl ether as co-solvent, a method introduced by H.C. Brown, the epimerization of l-menthone to d-isomenthone is largely avoided. If menthone and isomenthone are equilibrated at room temperature, the isomenthone content will reach 29%. Pure l-menthone has an intensely minty clean aroma. By contrast, d-isomenthone has a "green" note, increasing levels of which are perceived to detract from the odor quality of l-menthone.
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Dr. Wilbur Larch, in John Irving's novel The Cider House Rules, is an ether addict. Dr. Foster—Ruth’s father, and Milkman Dead’s grandfather—is described as an ether addict in Toni Morrison’s novel Song of Solomon. In the second season of the television series Borgia, Rodrigo Borgia, named Pope Alexander VI, and his mistress become addicted to sweet oil of vitriol (a sixteenth century name for diethyl ether). Delusions, paranoia, and hallucinations plague the pope as he falls deeper into his addiction.
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Cyclo-hexasulfur, cyclo-S6 This allotrope was first prepared by M. R. Engel in 1891 by treating thiosulfate with HCl. Cyclo-S6 is orange-red and forms a rhombohedral crystal.Greenwood, 656 It is called ρ-sulfur, ε-sulfur, Engel's sulfur and Aten's sulfur. Another method of preparation involves the reaction of a polysulfane with sulfur monochloride: :H2S4 \+ S2Cl2 → cyclo-S6 \+ 2 HCl (dilute solution in diethyl ether) The sulfur ring in cyclo-S6 has a "chair" conformation, reminiscent of the chair form of cyclohexane.
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Reduction may typically be carried out in a round-bottom flask equipped with a drying-tube-capped reflux condenser, a mercury-sealed mechanical stirrer, a thermometer, a nitrogen inlet, and an additional funnel with a pressure-equalizing side arm. The most common solvents used are tetrahydrofuran and diethyl ether. Whatever solvent is used should be anhydrous and pure. Alkoxyaluminium hydrides should be kept as dry as possible and represent a significant fire hazard, particularly when an excess of hydride is used (hydrogen evolves during workup).
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LiClO4 is highly soluble in organic solvents, even diethyl ether. Such solutions are employed in Diels-Alder reactions, where it is proposed that the Lewis acidic Li+ binds to Lewis basic sites on the dienophile, thereby accelerating the reaction.Charette, A. B. "Lithium Perchlorate" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. . Lithium perchlorate is also used as a co-catalyst in the coupling of α,β-unsaturated carbonyls with aldehydes, also known as the Baylis-Hillman reaction.
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However, in 1799, British chemist and inventor Humphry Davy decided to find out by experimenting on himself. To his astonishment he found that nitrous oxide made him laugh, so he nicknamed it "laughing gas". In 1800 Davy wrote about the potential anesthetic properties of nitrous oxide in relieving pain during surgery, but nobody at that time pursued the matter any further. American physician Crawford W. Long noticed that his friends felt no pain when they injured themselves while staggering around under the influence of diethyl ether.
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Diphenyl ketene is at room temperature an orange-colored to red oil (with the color of concentrated potassium dichromate solution) which is miscible with nonpolar organic solvents (such as diethyl ether, acetone, benzene, tetrahydrofuran, chloroform) and solidifies in the cold forming yellow crystals. The compound is easily oxidized by air but can be stored in tightly closed containers at 0 °C for several weeks without decomposition or in a nitrogen atmosphere with the addition of a small amount of hydroquinone as a polymerization inhibitor.
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It can be prepared by homolysis of triphenylmethyl chloride 1 by a metal like silver or zinc in benzene or diethyl ether. The radical 2 forms a chemical equilibrium with the quinoid- type dimer 3 (Gomberg's dimer). In benzene the concentration of the radical is 2%. Triphenylmethyl radical Solutions containing the radical are yellow; when the temperature of the solution is raised, the yellow color becomes more intense as the equilibrium is shifted in favor of the radical (in accordance with Le Châtelier's principle).
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The Curtisite variety is only slightly soluble in hot acetone, amyl acetate, butanol, petroleum ether. The solubility is 0.5% or less in hot carbon bisulfide, carbon tetrachloride, chloroform, diethyl ether, or boiling benzene; about 1.5% in toluene, about 2.5% in xylene, and over 10% in hot aniline. The material purified by repeated recrystallization melts at 360-370 C while turning very black. It sublimes giving very thin iridescent colors. Raman spectroscopy studies indicate that it may be a mixture of complex hydrocarbons including benzonaphthothiophenes (chemical formula: C16H10S) and dinaphthothiophenes (chemical formula: C20H12S).
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The Schimmelbusch mask The Schimmelbusch mask is an open breathing system for delivering an anesthetic. The device was invented by Curt Schimmelbusch in 1889, and was used until the 1950s (though it is still applied in some developing countries). The device consists of a wire frame which is covered with several beds of gauze and applied to the patient's face over the mouth and nose. Then high-volatility anesthetic (usually diethyl ether or halothane, and historically chloroform) is dripped on it, allowing the patient to inhale a mix of the evaporated anesthetic and air.
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The hydroxide anion of the salt reacts with the carbonyl group of the ester. The immediate product is called an orthoester. :Saponification part I Expulsion of the alkoxide generates a carboxylic acid: :Saponification part II The alkoxide ion is a strong base so that the proton is transferred from the carboxylic acid to the alkoxide ion creating an alcohol: :saponification part III In a classic laboratory procedure, the triglyceride trimyristin is obtained by extracting it from nutmeg with diethyl ether. Saponification to the soap sodium myristate takes place using NaOH in water.
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It produces around the same degree of respiratory depression as morphine, but less inhibition of gastrointestinal motility. Animal studies show it to be a potent analgesic which produces significant analgesic effects even at low doses while inducing comparatively few side effects, however it has never been developed for medical use in humans. 6-Methylenedihydrodesoxymorphine is synthesised in two steps; first a Wittig reaction is used, reacting hydrocodone with methylenetriphenylphosphorane and an alkyl lithium reagent in diethyl ether to form 6-Methylenedihydrodesoxycodeine. The 3-methoxy group is then cleaved to hydroxy, by reaction with pyridine.
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Passing gaseous S4N4 over silver metal wool at 250–300 °C at low pressure (1mm Hg) yields cyclic S2N2. The silver reacts with the sulfur produced by the thermal decomposition of the S4N4 to form Ag2S, and the resulting Ag2S catalyzes the conversion of the remaining S4N4 into the four-membered ring S2N2, :S4N4 \+ 8 Ag → 4 Ag2S + 2 N2 :S4N4 → 2S2N2 An alternative uses the less explosive S4N3Cl. S2N2 decomposes explosively above 30°C, and is shock sensitive. It readily sublimes, and is soluble in diethyl ether.
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Pristane is a natural saturated terpenoid alkane obtained primarily from shark liver oil, from which its name is derived (Latin pristis, "shark"). It is also found in the stomach oil of birds in the order Procellariiformes and in mineral oil and some foods. Pristane and phytane are used in the fields of geology and environmental science as biomarkers to characterize origins and evolution of petroleum hydrocarbons and coal. It is a transparent oily liquid that is immiscible with water, but soluble in diethyl ether, benzene, chloroform and carbon tetrachloride.
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At the end of the synthesis, the crude peptide is cleaved from the solid support while simultaneously removing all protecting groups using a reagent strong acids like trifluoroacetic acid or a nucleophile. The crude peptide can be precipitated from a non-polar solvent like diethyl ether in order to remove organic soluble by products. The crude peptide can be purified using reversed-phase HPLC. The purification process, especially of longer peptides can be challenging, because small amounts of several byproducts, which are very similar to the product, have to be removed.
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The effects of methoxyflurane on the circulatory system resemble those of diethyl ether. In dogs, methoxyflurane anesthesia causes a moderate decrease in blood pressure with minimal changes in heart rate, and no significant effect on blood sugar, epinephrine, or norepinephrine. Bleeding and increased arterial partial pressure of carbon dioxide (PaCO2) both induce further decreases in blood pressure, as well as increases in blood glucose, epinephrine and norepinephrine. In humans, methoxyflurane produces some decrease in blood pressure, but cardiac output, stroke volume, and total peripheral resistance are only minimally depressed.
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Triethylamine is prepared by the alkylation of ammonia with ethanol: :NH3 \+ 3 C2H5OH → N(C2H5)3 \+ 3 H2O The pKa of protonated triethylamine is 10.75,David Evans Research Group and it can be used to prepare buffer solutions at that pH. The hydrochloride salt, triethylamine hydrochloride (triethylammonium chloride), is a colorless, odorless, and hygroscopic powder, which decomposes when heated to 261 °C. Triethylamine is soluble in water to the extent of 112.4 g/L at 20 °C. It is also miscible in common organic solvents, such as acetone, ethanol, and diethyl ether.
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3,4-Diaminopyridine is a pale yellow to pale brown crystalline powder that melts at about under decomposition. It is readily soluble in methanol, ethanol and hot water, but only slightly in diethyl ether.. Index page: FDA Docket 98N-0812: Bulk Drug Substances to be Used in Pharmacy Compounding Solubility in water at is 25 g/L. The drug formulation amifampridine phosphate contains the phosphate salt, more specifically 4-aminopyridine-3-ylammonium dihydrogen phosphate. This salt forms prismatic, monoclinic crystals (space group C2/c) and is readily soluble in water.
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A specific example of a M-Z bond wherein other L-ligands are present in the complex Both uncharged transition metal complexes and anionic complexes lead to the required adducts with acidic boranes. On the right is a typical reaction of a Z-ligand where the electron deficit BPh3 adds to the anionic Fe complex. The presence of Cp and CO ligands further stabilize the Fe-BPh3 bond. More specific examples include [NEt4][CpFe(CO)2] which gives the anionic borane iron complex as an amorphous solid from reaction with BPh3 in diethyl ether.
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The order of strength/weakness depends on the coating (stationary phase) of the TLC plate. For silica gel-coated TLC plates, the eluent strength increases in the following order: perfluoroalkane (weakest), hexane, pentane, carbon tetrachloride, benzene/toluene, dichloromethane, diethyl ether, ethyl acetate, acetonitrile, acetone, 2-propanol/n-butanol, water, methanol, triethylamine, acetic acid, formic acid (strongest). For C18-coated plates the order is reverse. In other words, when the stationary phase is polar and the mobile phase is nonpolar, the method is normal-phase as opposed to reverse- phase.
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The first method is by the addition of diborane to a solution of hydrazoic acid in diethyl ether at a temperature range between −20 °C and −10 °C. This synthesis proceeds via the intermediates monoazidoborane, BH2N3, and diazidoborane, BH(N3)2. : B2H6 \+ 6 HN3 → 2 B(N3)3 \+ 6 H2 The compound can also be obtained by passing boron tribromide vapor over solid silver azide in high vacuum. : BBr3 \+ 3 AgN3 → B(N3)3 \+ 3 AgBr A similar gas-phase synthesis uses the spontaneous reaction of boron trichloride with hydrazoic acid.
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Coordination polymers can also show color changes upon the change of solvent molecules incorporated into the structure. An example of this would be the two Co coordination polymers of the [Re6S8(CN)6]4− cluster that contains water ligands that coordinate to the cobalt atoms. This originally orange solution turns either purple or green with the replacement of water with tetrahydrofuran, and blue upon the addition of diethyl ether. The polymer can thus act as a solvent sensor that physically changes color in the presence of certain solvents.
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The acid dissociates in the aqueous environment producing hydronium ions, H3O+. A hydrogen ion protonates the electronegative oxygen atom of the ethanol, giving the ethanol molecule a positive charge: :CH3CH2OH + H3O+ → CH3CH2OH2+ \+ H2O A nucleophilic oxygen atom of unprotonated ethanol displaces a water molecule from the protonated (electrophilic) ethanol molecule, producing water, a hydrogen ion and diethyl ether. : CH3CH2OH2+ \+ CH3CH2OH → H2O + H+ \+ CH3CH2OCH2CH3 This reaction must be carried out at temperatures lower than 150 °C in order to ensure that an elimination product (ethylene) is not a product of the reaction.
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At higher temperatures, ethanol will dehydrate to form ethylene. The reaction to make diethyl ether is reversible, so eventually an equilibrium between reactants and products is achieved. Getting a good yield of ether requires that ether be distilled out of the reaction mixture before it reverts to ethanol, taking advantage of Le Chatelier's principle. Another reaction that can be used for the preparation of ethers is the Williamson ether synthesis, in which an alkoxide (produced by dissolving an alkali metal in the alcohol to be used) performs a nucleophilic substitution upon an alkyl halide.
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The process is relevant to many phenomena including aging, paint, spoilage of foods, degradation of petrochemicals, and the industrial production of chemicals. Autoxidation is important because it is a useful reaction for converting compounds to oxygenated derivatives, and also because it occurs in situations where it is not desired (as in the destructive cracking of the rubber in automobile tires or in rancidification). A classic example of autoxidation involves the conversion of diethyl ether to its hydroperoxide. It can be considered to be a slow, flameless combustion of materials by reaction with oxygen.
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Matrix isolation spectroscopy prevents disproportionation of aluminium monohalides and thus allows for the measuring of transitional vibrations as well as reactivity with molecules such as O2. Analysis by 27Al NMR spectroscopy of AlCl, AlBr, and AlI in toluene/diethyl ether at room temperature reveal two signals: one very broad signal at δ = 100-130 ppm (regardless of the halogen), and one at higher field strength (AlCl: δ = + 30, AlBr: δ = + 50, AlI: δ = + 80). The first signal corresponds to a donor-stabilized four-coordinate aluminium species, while the identity of the latter is inconclusive.
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Ethanol is a versatile solvent, miscible with water and with many organic solvents, including acetic acid, acetone, benzene, carbon tetrachloride, chloroform, diethyl ether, ethylene glycol, glycerol, nitromethane, pyridine, and toluene. Its main use as a solvent is in making tincture of iodine,cough syrups etc. It is also miscible with light aliphatic hydrocarbons, such as pentane and hexane, and with aliphatic chlorides such as trichloroethane and tetrachloroethylene. Ethanol's miscibility with water contrasts with the immiscibility of longer-chain alcohols (five or more carbon atoms), whose water miscibility decreases sharply as the number of carbons increases.
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Methyl cyanoformate is the organic compound with the formula CH3OC(O)CN. It is used as a reagent in organic synthesis as a source of the methoxycarbonyl group,Simon R. Crabtree, W. L. Alex Chu, Lewis N. Mander "C-Acylation of Enolates by Methyl Cyanoformate: An Examination of Site- and Stereoselectivity"Synlett 1990; 1990: 169–170. in which context it is also known as Mander's reagent. When a lithium enolate is generated in diethyl ether or methyl t-butyl ether (but not THF), treatment with Mander's reagent will selectively afford the C-acylation product.
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Dioxane tetraketone (or 1,4-dioxane-2,3,5,6-tetrone) is an organic compound with the formula C4O6. It is an oxide of carbon (an oxocarbon), which can be viewed as the fourfold ketone of dioxane. It can also be viewed as the cyclic dimer of oxiranedione (C2O3), the hypothetical anhydride of oxalic acid. In 1998, Paolo Strazzolini and others synthesized this compound by reacting oxalyl chloride (COCl)2 or the bromide (COBr)2 with a suspension of silver oxalate (Ag2C2O4) in diethyl ether at −15 °C, followed by evaporation of the solvent at low temperature and pressure.
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The drawover vaporizer is driven by negative pressure developed by the patient, and must therefore have a low resistance to gas flow. Its performance depends on the minute volume of the patient: its output drops with increasing minute ventilation. The design of the drawover vaporizer is much simpler: in general it is a simple glass reservoir mounted in the breathing attachment. Drawover vaporizers may be used with any liquid volatile agent (including older agents such as diethyl ether or chloroform, although it would be dangerous to use desflurane).
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August Sigmund Frobenius (1727 (first mentioned) – 1741?), FRS,Royal Society Selected Fellows' details also known as Sigismond Augustus Frobenius, Joannes Sigismundus Augustus Frobenius, and Johann Sigismund August Froben, was a German-born chemist in the 18th century who is known for the first detailed description of the properties of diethyl ether and the naming of this substance (Spiritus Vini Æthereus). Not much is known about his life. He worked in Paris, Germany, and Italy. In the laboratory or Ambrose Godfrey in London he produced ether, following a method of Isaac Newton.
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Cocaine freebase ("white tornado") is prepared from cocaine hydrochloride by extracting the cocaine with an alkaline solution (sodium hydroxide or ammonia) and adding a non-polar solvent such as diethyl ether or benzene. The mixture separates into two layers, the top solvent layer containing the dissolved cocaine. The solvent is then evaporated leaving almost pure cocaine crystals, white and crumbly like feta cheese. A solution of cocaine hydrochloride can also be heated ("cooked") in a pan with baking soda added until a solid "rock" is formed, pieces of which can be smoked directly (crack cocaine).
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However, most inhalant abuse takes place when people inhale solvents by themselves or in groups of people who are intoxicated. Certain solvents are more hazardous than others, such as gasoline. In contrast, a few inhalants like amyl nitrate and diethyl ether have medical applications and are not toxic in the same sense as solvents, though they can still be dangerous when used recreationally. Nitrous oxide is thought to be particularly non-toxic, though heavy long-term use can lead to a variety of serious health problems linked to destruction of vitamin B12 and folic acid.
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With one molar equivalent of anhydrous HCl, the simple addition product 6a can be formed at low temperature in the presence of diethyl ether, but it is very unstable. At normal temperatures, or if no ether is present, the major product is bornyl chloride 6b, along with a small amount of fenchyl chloride 6c. For many years 6b (also called "artificial camphor") was referred to as "pinene hydrochloride", until it was confirmed as identical with bornyl chloride made from camphene. If more HCl is used, achiral 7 (dipentene hydrochloride) is the major product along with some 6b.
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Wandering lecturers would hold public gatherings, referred to as "ether frolics", where members of the audience were encouraged to inhale diethyl ether or nitrous oxide to demonstrate the mind-altering properties of these agents while providing much entertainment to onlookers. Four notable men participated in these events and witnessed the use of ether in this manner. They were William Edward Clarke (1819–1898), Crawford W. Long (1815–1878), Horace Wells (1815–1848), and William T. G. Morton (1819–1868). While attending undergraduate school in Rochester, New York, in 1839, classmates Clarke and Morton apparently participated in ether frolics with some regularity.
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Unlike diethyl ether, methoxyflurane is a significant respiratory depressant. In dogs, methoxyflurane causes a dose-dependent decrease in respiratory rate and a marked decrease in respiratory minute volume, with a relatively mild decrease in tidal volume. In humans, methoxyflurane causes a dose-dependent decrease in tidal volume and minute volume, with respiratory rate relatively constant. The net effect of these changes is profound respiratory depression, as evidenced by CO2 retention with a concomitant decrease in arterial pH (this is referred to as a respiratory acidosis) when anesthetized subjects are allowed to breathe spontaneously for any length of time.
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Triethyloxonium tetrafluoroborate is prepared from boron trifluoride, diethyl ether and epichlorohydrin: : 4 Et2O·BF3 \+ 2 Et2O + 3 C2H3(O)CH2Cl -> 3 Et3O+ \+ B[(OCH(CH2Cl)CH2OEt]3 The trimethyloxonium salt is available from dimethyl ether via an analogous route. These salts do not have long shelf-lives at room temperature. They degrade by hydrolysis: :[(CH3CH2)3O]+ \+ H2O → (CH3CH2)2O + CH3CH2OH + HBF4 The propensity of trialkyloxonium salts for alkyl-exchange can be advantageous. For example, trimethyloxonium tetrafluoroborate, which reacts sluggishly due to it low solubility in most compatible solvents may be converted in situ to higher alkyl/more soluble oxoniums, thereby accelerating alkylation reactions.
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William Cullen, the first to conduct experiments into artificial refrigeration. The history of artificial refrigeration began when Scottish professor William Cullen designed a small refrigerating machine in 1755. Cullen used a pump to create a partial vacuum over a container of diethyl ether, which then boiled, absorbing heat from the surrounding air. The experiment even created a small amount of ice, but had no practical application at that time. In 1758, Benjamin Franklin and John Hadley, professor of chemistry, collaborated on a project investigating the principle of evaporation as a means to rapidly cool an object at Cambridge University, England.
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Located on River Street Columbus, OH, the Organic manufacturing facility as a location is a relatively new facility. GFS has always performed organic chemistries, however after the acquisition period more space was needed to further develop the business and to explore the future scientific opportunities which could be advanced. These newer developments have at times crossed over with the Inorganic side with anhydrous Lithium Perchlorate in the form of Lithium Perchlorate-Diethyl Ether to promote synthetic organic chemical synthesis in bulk, as an example. They added a Kilo lab and a Distillation lab as well in the proceeding years.
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Although anesthesia had very recently become available and used experimentally, Sims did not use any anesthetic during his procedures on these three women. According to Sims, anesthesia was not yet fully accepted into surgical practice, and he was unaware of the use of diethyl ether. Experimental use of ether as an anesthetic was performed as early as 1842, however it was not published or demonstrated until 1846. A 2006 review of Sims' work in the Journal of Medical Ethics said that ether anesthesia was first publicly demonstrated in Boston in 1846, a year after Sims began his experimental surgery.
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2-Butanol is manufactured industrially by the hydration of 1-butene or 2-butene: :300px Sulfuric acid is used as a catalyst for this conversion.. In the laboratory it can be prepared via Grignard reaction by reacting ethylmagnesium bromide with acetaldehyde in dried diethyl ether or tetrahydrofuran. Although some 2-butanol is used as a solvent, it is mainly converted to butanone (methyl ethyl ketone, MEK), which is an important industrial solvent and found in many domestic cleaning agents and paint removers. Volatile esters of 2-butanol have pleasant aromas and are used in small amounts as perfumes or in artificial flavors.
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An example of this procedure is the reaction of 2,2,6-trimethylcyclohexanone to the hydrazone by reaction with hydrazine and triethylamine in ethanol at reflux followed by reaction of the hydrazone with iodine in the presence of 2-tert-butyl-1,1,3,3-tetramethylguanidine (cheaper than DBU) in diethyl ether at room temperature.Preparation and reactions of 2-tert-butyl-1,1,3,3-tetramethylguanidine: 2,2,6-trimethylcyclohexen-1-yl iodide Derek H. R. Barton, Mi Chen, Joseph Cs. Jászberényi, and Dennis K. Taylor Organic Syntheses, Coll. Vol. 9, p.147 (1998); Vol. 74, p.101 (1997) Article Another example can be found in the Danishefsky Taxol total synthesis.
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Ether was once used in pharmaceutical formulations. A mixture of alcohol and ether, one part of diethyl ether and three parts of ethanol, was known as "Spirit of ether", Hoffman's Anodyne or Hoffman's Drops. In the United States this concoction was removed from the Pharmacopeia at some point prior to June 1917,The National druggist, Volume 47, June 1917, pp.220 as a study published by William Procter, Jr. in the American Journal of Pharmacy as early as 1852 showed that there were differences in formulation to be found between commercial manufacturers, between international pharmacopoeia, and from Hoffman's original recipe.
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Ethylene oxide readily reacts with aqueous solutions of hydrochloric, hydrobromic and hydroiodic acids to form halohydrins. The reaction occurs easier with the last two acids: : (CH2CH2)O + HCl → HO–CH2CH2–Cl The reaction with these acids competes with the acid-catalyzed hydration of ethylene oxide; therefore, there is always a by-product of ethylene glycol with an admixture of diethylene glycol. For a cleaner product, the reaction is conducted in the gas phase or in an organic solvent. Ethylene fluorohydrin is obtained differently, by boiling hydrogen fluoride with a 5–6% solution of ethylene oxide in diethyl ether.
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They have the general formula R–O–R′, where R and R′ represent the alkyl or aryl groups. Ethers can again be classified into two varieties: if the alkyl groups are the same on both sides of the oxygen atom, then it is a simple or symmetrical ether, whereas if they are different, the ethers are called mixed or unsymmetrical ethers. A typical example of the first group is the solvent and anesthetic diethyl ether, commonly referred to simply as "ether" (). Ethers are common in organic chemistry and even more prevalent in biochemistry, as they are common linkages in carbohydrates and lignin.
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In 1755 he was enticed by Lord Kames to become Professor of Chemistry and Medicine at the University of Edinburgh. It was in Edinburgh, in 1756, that he gave the first documented public demonstration of artificial refrigeration.William Cullen, Of the Cold Produced by Evaporating Fluids and of Some Other Means of Producing Cold, in Essays and Observations Physical and Literary Read Before a Society in Edinburgh and Published by Them, II, (Edinburgh 1756) Cullen used a pump to create a partial vacuum over a container of diethyl ether, which then boiled, absorbing heat from the surroundings. This created a small amount of ice, but the process found no commercial application.
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Ph3PO is a byproduct of many useful reactions in organic synthesis including the Wittig, Staudinger, and Mitsunobu reactions. It is also formed when PPh3Cl2 is employed to convert alcohols into alkyl chlorides: :Ph3PCl2 \+ ROH -> Ph3PO + HCl + RCl Triphenylphosphine can be regenerated from the oxide by treatment with a variety of deoxygenation agents, such as phosgene or trichlorosilane/triethylamine: :Ph3PO + SiHCl3 -> PPh3 \+ 1/n (OSiCl2)n \+ HCl Triphenylphosphine oxide can be difficult to remove from reaction mixtures by means of chromatography. It is poorly soluble in hexane and cold diethyl ether. Trituration or chromatography of crude products with these solvents often leads to a good separation of triphenylphosphine oxide.
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Duke becomes irrational and believes that they are in the middle of a battlefield, so he fires Lacerda and returns to the hotel. After consuming more mescaline, as well as huffing diethyl ether, Duke and Gonzo arrive at the Bazooko Circus casino but leave shortly afterwards, the chaotic atmosphere frightening Gonzo. Back in the hotel room, Duke leaves Gonzo unattended, and tries his luck at Big Six. When Duke returns he finds that Gonzo, high on LSD, has trashed the room, and is in the bathtub clothed, attempting to pull the tape player in with him as he wants to hear the song better.
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Unlike the aluminium and gallium trihalides, the boron trihalides are all monomeric. They undergo rapid halide exchange reactions: :BF3 \+ BCl3 → BF2Cl + BCl2F Because of the facility of this exchange process, the mixed halides cannot be obtained in pure form. Boron trifluoride is a versatile Lewis acid that forms adducts with such Lewis bases as fluoride and ethers: :CsF + BF3 → CsBF4 :O(C2H5)2 \+ BF3 → BF3O(C2H5)2 Tetrafluoroborate salts are commonly employed as non- coordinating anions. The adduct with diethyl ether, boron trifluoride diethyl etherate, or just boron trifluoride etherate, (BF3·O(Et)2) is a conveniently handled liquid and consequently is widely encountered as a laboratory source of BF3.
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With a strong, dense smell, ether causes irritation to respiratory mucosa and is uncomfortable to breathe, and in overdose triggering salivation, vomiting, coughing or spasms. In concentrations of 3–5% in air, an anesthetic effect can slowly be achieved in 15–20 minutes of breathing approximately 15–20 ml of ether, depending on body weight and physical condition. Ether causes a very long excitation stage prior to blacking out. The recreational use of ether also took place at organised parties in the 19th century called ether frolics, where guests were encouraged to inhale therapeutic amounts of diethyl ether or nitrous oxide, producing a state of excitation.
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When stored in the presence of air or oxygen, ethers tend to form explosive peroxides, such as diethyl ether hydroperoxide. The reaction is accelerated by light, metal catalysts, and aldehydes. In addition to avoiding storage conditions likely to form peroxides, it is recommended, when an ether is used as a solvent, not to distill it to dryness, as any peroxides that may have formed, being less volatile than the original ether, will become concentrated in the last few drops of liquid. The presence of peroxide in old samples of ethers may be detected by shaking them with freshly prepared solution of a ferrous sulfate followed by addition of KSCN.
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Florida State Sedation Permits for General Anesthesia In the specialty's infancy, dental and oral surgeons were plenary in the introduction of anesthesia to modern medicine and the development of modern surgery. In 1844, at Harvard Medical School's Massachusetts General Hospital, dentist, Dr. Horace Wells was the first to use anesthesia, but with limited success. On 16 October 1846, Boston oral surgeon, Dr. William Thomas Green Morton gave a successful demonstration using diethyl ether to Harvard medical students at the same venue. In one of the most important and well documented events in American medical history, Morton was invited to Massachusetts General Hospital to demonstrate his technique for painless surgery.
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Marble bust of Mitscherlich by Elisabet Ney at the Museum für Naturkunde in Berlin In 1833 Mitscherlich made a series of careful determinations of the vapor densities of a large number of volatile substances, confirming the law of Gay-Lussac. In 1833-34, Mitscherlich investigated the synthesis of diethyl ether from ethanol and sulfuric acid.E. Mitscherlich (1834) "Ueber die Aetherbildung" (On the formation of ether), Annalen der Physik und Chemie, 31 (18) : 273-282. Through his careful studies, he realized that the acid was not being consumed during the production of the ether, although the reaction would not proceed unless the acid was present.
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Flurothyl (Indoklon) (IUPAC names: 1,1,1-trifluoro-2-(2,2,2-trifluoroethoxy)ethane or bis(2,2,2-trifluoroethyl) ether) is a volatile liquid drug from the halogenated ether family, related to inhaled anaesthetic agents such as diethyl ether, but having the opposite effects, acting as a stimulant and convulsant. A clear and stable liquid, it has a mild ethereal odor whose vapors are non-flammable. It is excreted from the body by the lungs in an unchanged state. Several compounds related to the halogenated ether anesthetics have similar convulsant effects rather than producing sedation, and this has been helpful in studying the mechanism of action of these drugs.
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In carbon tetrachloride and alkane solvents phenol hydrogen bonds with a wide range of Lewis bases such as pyridine, diethyl ether, and diethyl sulfide. The enthalpies of adduct formation and the –OH IR frequency shifts accompanying adduct formation have been studied. Drago, R S. Physical Methods For Chemists, (Saunders College Publishing 1992), IBSN 0-03-075176-4 Phenol is classified as a hard acid which is compatible with the C/E ratio of the ECW model with EA = 2.27 and CA = 1.07. The relative acceptor strength of phenol toward a series of bases, versus other Lewis acids, can be illustrated by C-B plots.
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Starting fluid is a volatile, flammable liquid which is used to aid the starting of internal combustion engines, especially during cold weather or in engines that are difficult to start using conventional starting procedures. It is typically available in an aerosol spray can, and may sometimes be used for starting direct injected diesel engines or lean burn spark engines running on alcohol fuel. Some modern starting fluid products contain mostly volatile hydrocarbons such as heptane, (the main component of natural gasoline) with a small portion of diethyl ether, and carbon dioxide (as a propellant). Some formulations contain butane or propane as both propellant and starting fuel.
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Solvent vapors can also be found in supposedly empty drums and cans, posing a flash fire hazard; hence empty containers of volatile solvents should be stored open and upside down. Both diethyl ether and carbon disulfide have exceptionally low autoignition temperatures which increase greatly the fire risk associated with these solvents. The autoignition temperature of carbon disulfide is below 100 °C (212 °F), so objects such as steam pipes, light bulbs, hotplates, and recently extinguished bunsen burners are able to ignite its vapours. In addition some solvents, such as methanol, can burn with a very hot flame which can be nearly invisible under some lighting conditions.
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Instead, diethyl ether, being a stronger and more potent anaesthetic, was demonstrated and accepted for use in October 1846, along with chloroform in 1847. When Joseph Thomas Clover invented the "gas-ether inhaler" in 1876, however, it became a common practice at hospitals to initiate all anaesthetic treatments with a mild flow of nitrous oxide, and then gradually increase the anaesthesia with the stronger ether or chloroform. Clover's gas-ether inhaler was designed to supply the patient with nitrous oxide and ether at the same time, with the exact mixture being controlled by the operator of the device. It remained in use by many hospitals until the 1930s.
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Ethanol was produced primarily by the sulfuric acid hydration process in which ethylene is reacted with sulfuric acid to produce ethyl sulfate followed by hydrolysis, but this method has been mostly replaced by direct hydration of ethylene. Ethyl sulfate can be produced in a laboratory setting by reacting ethanol with sulfuric acid under a gentle boil, while keeping the reaction below 140 °C. The sulfuric acid must be added dropwise or the reaction must be actively cooled because the reaction itself is highly exothermic. :CH3CH2OH + H2SO4 → CH3-CH2-O-SO3H + H2O If the temperature exceeds 140 °C, the ethyl sulfate product tends to react with residual ethanol starting material, producing diethyl ether.
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For example, at any given temperature, methyl chloride has the highest vapor pressure of any of the liquids in the chart. It also has the lowest normal boiling point (−24.2 °C), which is where the vapor pressure curve of methyl chloride (the blue line) intersects the horizontal pressure line of one atmosphere (atm) of absolute vapor pressure. Note that at higher altitudes, the atmospheric pressure is less than that at sea level, so boiling points of liquids are reduced. At the top of Mount Everest, the atmospheric pressure is approximately 0.333 atm, so by using the graph, the boiling point of diethyl ether would be approximately 7.5 °C versus 34.6 °C at sea level (1 atm).
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It is a clear colorless method and can be converted to the amine hydrochloride etherate which is recrystallized four times from diethyl ether at -30 °C. Neutralization of this salt regenerates the free amine which distilled under high vacuum. It has melting point of −34 °C; boiling point of 164-168 °C at 0.7 mmHg and 365-367 °C at 1 atm; density of 0.810 g/mL at 20 °C; refractive index of n20/D 1.449; flash point of >230 °F; storage temperature is below 30 °C. It can easily soluble in chloroform; it has a form of low melting crystalline mass, and it has the color of white to off-white.
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Similar to n-butyllithium, tert-butyllithium can be used for the exchange of lithium with halogens and for the deprotonation of amines and activated C—H compounds. This compound and other alkyllithium compounds are known to react with ether solvents; the half-life of tert-butyllithium is 60 minutes at 0 °C in diethyl ether, 40 minutes at −20 °C in tetrahydrofuran (THF), and about 11 minutes at −70 °C in dimethoxyethane. In this example, the reaction of tert-butyllithium with (THF) is shown: :450px :250px To minimize degradation by these solvents, reactions involving tert-butyllithium are often conducted at very low temperatures in special solvents, such as the Trapp solvent mixture.
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For example, a mixture of salt (sodium chloride) and silica may be separated by dissolving the salt in water, and filtering off the undissolved silica. The synthesis of chemical compounds, by the milligram in a laboratory, or by the ton in industry, both make use of the relative solubilities of the desired product, as well as unreacted starting materials, byproducts, and side products to achieve separation. Another example of this is the synthesis of benzoic acid from phenylmagnesium bromide and dry ice. Benzoic acid is more soluble in an organic solvent such as dichloromethane or diethyl ether, and when shaken with this organic solvent in a separatory funnel, will preferentially dissolve in the organic layer.
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The classic 1964 synthesis starts with the conversion of 2-cyclopentenone to 2-bromocyclopentadienone: :500px Allylic bromination with N-bromosuccinimide in carbon tetrachloride followed by addition of molecular bromine to the alkene gives a 2,3,4-tribromocyclopentanone. Treating this compound with diethylamine in diethyl ether causes elimination of two equivalents of hydrogen bromide to give the diene product. :Eaton's 1964 synthesis of cubane The construction of the eight-carbon cubane framework begins when 2-bromocyclopentadienone undergoes a spontaneous Diels-Alder dimerization, analogous to the dimerization of cyclopentadiene to dicyclopentadiene—two molecules of 1 react to form 2. For the subsequent steps to succeed, only the endo isomer is useful, and this is the predominant isomer formed in this reaction.
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However, this was a more delicate surgery, and Abbot had to be tied to his chair so that he would not choke on his own blood. Morton used a newly developed apparatus, later called the Morton Etherizer, to deliver the diethyl-ether vapors, holding the mouthpiece to Abbott's lips and instructing him to breathe deeply and slowly. Abbott fell into an unconscious, sleeplike state within three to four minutes, and did not react when Morton made the first incision in his neck for the surgery. During the surgery, Warren noted that the blood of the patient was very dark, and thought that the anesthesia might be producing its effect through carbonization of the blood, a remark which was met with a burst of applause.
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The solution structure of organocerium reagents remains unclear, although there is agreement that it depends heavily on the manner in which it is prepared. In particular, those derived from organolithium reagents likely are believed to form something similar to a 'true' organocerium structure, "R-CeCl2," while those derived from Grignard reagents are more appropriately characterized as -ate complexes of the form "R-MgX•CeCl3". Furthermore, the solvent seems to alter the solution structure of the complex, with differences noted between reagents prepared in diethyl ether and tetrahydrofuran. There is evidence that the parent chloride forms a polymeric species in THF solution, of the form [Ce(μ-Cl)2(H2O)(THF)2]n, but whether this type of polymer exists once the organometallic reagent is formed is unknown.
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The TASF reagent or tris(dimethylamino)sulfonium difluorotrimethylsilicate is a reagent in organic chemistry with structural formula [((CH3)2N)3S]+[F2Si(CH3)3]−. It is an anhydrous source of fluoride and is used to cleave silyl ether protective groups. Many other fluoride reagents are known, but few are truly anhydrous, because of the extraordinary basicity of "naked" F−. In TASF, the fluoride is masked as an adduct with the weak Lewis acid trimethylsilylfluoride (FSi(CH3)3). The sulfonium cation ((CH3)2N)3S+ is unusually non-electrophilic due to the electron-donating properties of the three (CH3)2N substituents. This compound is prepared from sulfur tetrafluoride: :3 (CH3)2NSi(CH3)3 \+ SF4 -> 2 (CH3)3SiF + [((CH3)2N)3S]+[F2Si(CH3)3]− The colorless salt precipitates from the reaction solvent, diethyl ether.
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2,2,5,5-tetramethyltetrahydrofuran (TMTHF) or 2,2,5,5-tetramethyloxolane (TMO) is a heterocyclic compound with the formula , or (CH3)2(C(CH2)2OC)(CH3)2. It can be seen as derivative of tetrahydrofuran (oxolane) with four methyl groups replacing four hydrogen atoms on each of the carbon atoms in the ring that are adjacent to the oxygen. The absence of hydrogen atoms adjacent to the oxygen means that TMTHF (TMO) does not form peroxides, unlike other common ethers such as tetrahydrofuran, diethyl ether and CPME. The compound has been demonstrated as a non-polar solvent in research chemistry, having similar properties to tolueneFergal Byrne, Bart Forier, Greet Bossaert, Charly Hoebers, Thomas J Farmer, James H Clark, Andrew J Hunt (2017) 2, 2, 5, 5-Tetramethyltetrahydrofuran (TMTHF): a non-polar, non-peroxide forming ether replacement for hazardous hydrocarbon solvents.
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Illustration of a lipid bilayer, typical of a cell membrane, showing the alt=Representation of tall molecules lined up in two rows, one above the other. The top ends of the molecules in the upper row coloured red, as are the bottom ends of those in the bottom row The precise mechanism is not well understood, but it appears to be the direct effect of gas dissolving into nerve membranes and causing temporary disruption in nerve transmissions. While the effect was first observed with air, other gases including argon, krypton and hydrogen cause very similar effects at higher than atmospheric pressure. Some of these effects may be due to antagonism at NMDA receptors and potentiation of GABAA receptors, similar to the mechanism of nonpolar anesthetics such diethyl ether or ethylene.
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The industrial synthesis of alkylated ketenedimers (at that time still called ketoethenones) was patented in 1945 from long-chain carboxylic acid chlorides in inert solvents (such as diethyl ether or benzene) with triethylamine as tertiary amine under anhydrous conditions. After filtration of the insoluble triethylamine hydrochloride and evaporation of the solvent, long-chain alkyl chain dimers are obtained in yields of more than 90%. Synthese von C18-AKD aus Stearoylchlorid The use of other solvents, such as carboxylic acid esters or ketones for easier separation of trialkylamine hydrochlorides or other amines, such as N,N,N',N'-tetramethyl-hexane-1,6-diamine does not provide any significant advantages. Also processes without the solvent use are described, in which the resulting amine hydrochloride is either filtered off or extracted with diluted aqueous acids.
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In 1961, Eddy showed that an extract of rhesus monkey kidney cells (RMKC), notable because of its use as a growth medium in the creation of the polio vaccine, caused tumors in newborn hamsters. In 1962 she presented evidence that the oncological agent present in the RMKC serum was capable of inducing histologically similar tumors under the same conditions as SV40, and that these tumors showed different properties than the SE polyoma virus, which was the only other biological material known to be capable of inducing tumors in almost all hamsters injected as newborns. Similar to SV40, RMKC extracts remained infectious after passage through filters, and similar levels of exposure to diethyl ether, heat, and storage at -70 °C. Eddy also provided evidence that the RMKC extracts were inhibited (tumors would not develop) under conditions that also inhibited SV40 tumor development.
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He immediately thought of its potential in surgery. Conveniently, a participant in one of those "ether frolics", a student named James Venable, had two small tumors he wanted excised. But fearing the pain of surgery, Venable kept putting the operation off. Hence, Long suggested that he have his operation while under the influence of ether. Venable agreed, and on 30 March 1842 he underwent a painless operation. However, Long did not announce his discovery until 1849. ether operation; daguerrotype by Southworth & Hawes Morton's ether inhaler Horace Wells conducted the first public demonstration of the inhalational anesthetic at the Massachusetts General Hospital in Boston in 1845. However, the nitrous oxide was improperly administered and the patient cried out in pain. On 16 October 1846, Boston dentist William Thomas Green Morton gave a successful demonstration using diethyl ether to medical students at the same venue.
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Following the passage of the second International Opium Convention in 1925, which specifically banned morphine and the diacetyl ester of morphine, heroin, a number of alternative esters of morphine quickly started to be manufactured and sold. The most notable of these were dibenzoylmorphine and acetylpropionylmorphine, which have virtually identical effects to heroin but were not covered by the Opium Convention. This then led the Health Committee of the League of Nations to pass several resolutions attempting to bring these new drugs under control, ultimately leading in 1930 to the first broad analogues provisions extending legal control to all esters of morphine, oxycodone, and hydromorphone. Another early example of what could loosely be termed designer drug use, was during the Prohibition era in the 1930s, when diethyl ether was sold and used as an alternative to illegal alcoholic beverages in a number of countries.
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Piperazine is freely soluble in water and ethylene glycol, but insoluble in diethyl ether. It is a weak base with two pKbs of 5.35 and 9.73 at 25 °C.; the pH of a 10% aqueous solution of piperazine is 10.8–11.8. Piperazine readily absorbs water and carbon dioxide from the air. Although many piperazine derivatives occur naturally, piperazine itself can be synthesized by reacting alcoholic ammonia with 1,2-dichloroethane, by the action of sodium and ethylene glycol on ethylene diamine hydrochloride, or by reduction of pyrazine with sodium in ethanol. A form in which piperazine is commonly available industrially is as the hexahydrate, C4H10N2. 6H2O, which melts at 44 °C and boils at 125–130 °C.The Merck index, 10th Ed. (1983), p. 1076, Rahway:Merck & Co. Two common salts in the form of which piperazine is usually prepared for pharmaceutical or veterinary purposes are the citrate, 3C4H10N2.2C6H8O7 (i.e.
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Granadaene contains a conjugated system made up of a linear chain of 12 conjugated double bonds which is connected to the amino acid ornithine at one end and the sugar rhamnose at the other. Granadaene is dark red, odorless, insoluble in water, methanol, ethanol, diethyl ether, acetone, hexane, dimethyl sulfoxide (DMSO), acetonitrile, tetrahydrofuran, chloroform, and in most solvents, it is soluble in DMSO–0.1% trifluoroacetic acid (TFA). Granadaene, can be extracted from cultures of S.agalactiae in granada broth (granada medium without agar) with 0.1 M potassium hydroxide (KOH) and purified by size-exclusion chromatography on Sephadex LH using DMSO–0.1%TFA. Streptococcus agalactiae in granada broth Ultraviolet/visible spectrum of granadaene, in DMSO+TFA Proposed metabolic pathway for granadaene biosynthesis The ultraviolet-visible absorption spectrum of the granadaene (in DMSO/TFA) is almost identical to that of a carotene with a similar conjugated system of double bonds (e.g.
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It is barely soluble in water, but very soluble in organic solvents such as chloroform or diethyl ether. Aconitine is also soluble in mixtures of alcohol and water if the concentration of alcohol is high enough. Like many other alkaloids, the basic nitrogen atom in one of the six-membered ring structure of aconitine can easily form salts and ions, giving it affinity for both polar and lipophilic structures (such as cell membranes and receptors) and making it possible for the molecule to pass the blood-brain barrier. The acetoxyl group at the c8 position can readily be replaced by a methoxy group, by heating aconitine in methanol, to produce a 8-deacetyl-8-O-methyl derivatives. If aconitine is heated in its dry state, it undergoes a pyrolysis to form pyroaconitine ((1α,3α,6α,14α,16β)-20-ethyl-3,13-dihydroxy-1,6,16-trimethoxy-4-(methoxymethyl)-15-oxoaconitan-14-yl benzoate) with the chemical formula C32H43NO9.
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Diazald (N-methyl-N-nitroso-p-toluenesulfonamide) is used as a relatively safe and easily handled precursor to diazomethane, which is toxic and unstable.Diazald in Chemical Synthesis, Sigma Aldrich Diazald has become the favored commercially available precursor for the synthesis of diazomethane, compared to reagents like N-methyl-N-nitrosourea and N-methyl-N'-nitro-N- nitrosoguanidine, which are less thermally stable and more toxic and mutagenic, respectively. Upon the addition of a base such as sodium hydroxide or potassium hydroxide and mild heating (65–70 °C) in a mixture of water, diethyl ether, and a high boiling polar cosolvent (e.g., diethylene glycol monomethyl ether), the N-nitrososulfonamide undergoes successive elimination reactions to produce diazomethane (which is codistilled as an ethereal solution) as well as a p-toluenesulfonate salt as a byproduct, according to the following mechanism: 500x500pxLike other nitroso compounds, it is thermally sensitive, as a result of its weak N–NO bond whose bond dissociation energy was measured to be 33.4 kcal/mol.
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Tautomerisation of the sodium salt of pyrithione (thione form on the left, thiolate form on the right) Pyrithione exists as a pair of prototropes, a form of tautomerism whereby the rapid interconversion of constitutional isomers involves the shift of a single proton, in this case between the sulfur and oxygen atoms (shown in the infobox). Salts of the conjugate base of pyrithione can also be considered to exhibit tautomerism by notionally associating the sodium ion with whichever heteroatom bears the negative charge of the anion (as opposed to the formal charges associated with the N-oxide); however, considering the anion alone, this could also be described as an example of resonance. Pyrithione is a weak acid with pKa values of −1.95 and +4.6 (thiol proton), but is a markedly stronger acid than either of its parent compounds (pyridine-N-oxide and pyridine-2-thiol), both of which have pKa > 8. It is only slightly soluble in water (2.5 g L−1) but is soluble in many organic solvents (including benzene, chloroform, dichloromethane, dimethylformamide, dimethylsulfoxide, and ethyl acetate) and slight solubility in others (diethyl ether, ethanol, methyl tert-butyl ether, and tetrahydrofuran).
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Diborane also reacts readily with alkynes to form substituted alkene products which will readily undergo further addition reactions. As a pyrophoric substance, diborane reacts exothermically with oxygen to form boron trioxide and water, so much that it was considered as a possible rocket or ramjet propellant but discarded because back then it was too expensive and dangerous to handle: : 2 B2H6 \+ 6 O2 → 2 B2O3 \+ 6 H2O (ΔHr = –2035 kJ/mol = –73.47 kJ/g) Diborane also reacts violently with water to form hydrogen and boric acid: : B2H6 \+ 6 H2O → 2 B(OH)3 \+ 6 H2 (ΔHr = –466 kJ/mol = –16.82 kJ/g) Diborane also reacts with methanol to give hydrogen and trimethoxyborate ester: : B2H6 \+ 6 MeOH → 2 B(OMe)3 \+ 6 H2 Treating diborane with sodium amalgam gives NaBH4 and Na[B3H8] When diborane is treated with lithium hydride in diethyl ether, Lithium borohydride is formed: : B2H6 \+ 2 LiH → 2 LiBH4 Diborane reacts with anhydrous hydrogen chloride or hydrogen bromide gas to give a boron halohydride: : B2H6 \+ HX → B2H5X + H2 (X = Cl, Br) Treating diborane with carbon monoxide at 470 K and 20 bar gives H3BCO.
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Two distinct expansions of benzene can be called carbo-benzene (C18H6): :carbo-benzene One (above right) expands each C-H bond to C-C≡C-H, making hexaethynylbenzene, a substituted benzene derivative.Hexaethynylbenzene Rainer Diercks, James C. Armstrong, Roland Boese, K. Peter C. Vollhardt. Hexaethynylbenzene. Angewandte Chemie International. 1986; 25(3):268-269. One (above left) expands each C=C and C≡C bond of the benzene core, making 1,2,4,5,7,8,10,11,13,14,16,17-dodecadehydro[18]annulene. An analog of this molecule, with the hydrogen atoms replaced by phenyl groups, 3,6,9,12,15,18-hexaphenyl-1,2,4,5,7,8,10,11,13,14,16,17-dodecadehydro[18]annulene, is stable.Synthesis of the first 3,6,9,15,18,18-hexa- substituted-1,2,4,5,7,8,10,11,13,14,16,17-dodecadehydro[18]annulenes with D6h-symmetry Yoshiyuki Kuwatani, Naoto Watanabe and Ikuo Ueda Tetrahedron Letters Volume 36, Issue 1, 2 January 1995, Pages 119-122 Its proton NMR spectrum shows that the phenyl protons are shifted downfield compared to a proton position in benzene itself (chemical shift position for the ortho proton is 9.49 ppm), suggesting the presence of a diamagnetic ring current and thus aromaticity. The final step in its organic synthesis is reaction of the triol with stannous chloride and hydrochloric acid in diethyl ether: :carbo- benzene synthesis With both core and periphery expanded, the total carbo-mer of benzene (C30H6) only exists in silico (computer simulation).
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