Diethyl ether
765457
224675395
2008-07-09T22:36:09Z
24.184.90.191
/* Cultural references */ MASH
{{Chembox new
| Name = Diethyl ether
| ImageFileL1 = Diethyl-ether-2D-skeletal.png
| ImageSizeL1 = 120px
| ImageNameL1 = Diethyl ether
| ImageFileR1 = Diethyl-ether-3D-balls.png
| ImageSizeR1 = 120px
| ImageNameR1 = Diethyl ether
| IUPACName = ethoxyethane<br />3-oxapentane
| OtherNames = diethyl ether<br />ethyl ether<br />ethyl oxide
| Section1 = {{Chembox Identifiers
| SMILES = CCOCC
| CASNo = 60-29-7
| RTECS = KI5775000
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>4</sub>H<sub>10</sub>O<br />C<sub>2</sub>H<sub>5</sub>OC<sub>2</sub>H<sub>5</sub>
| MolarMass = 74.12 g/mol
| Appearance = clear, colorless liquid
| Density = 0.7134 g/cm³, liquid
| Solubility = 6.9 g/100 ml (20 °C)
| MeltingPt = −116.3 °C (156.85 K)
| BoilingPt = 34.6 °C (307.75 K)
| pKa =
| pKb =
| Viscosity = 0.224 [[Poise|cP]] at 25 °C
}}
| Section3 = {{Chembox Structure
| MolShape =
| Dipole = 1.15 [[Debye|D]] (gas)
}}
| Section7 = {{Chembox Hazards
| ExternalMSDS = [http://physchem.ox.ac.uk/MSDS/DI/diethyl_ether.html External MSDS]
| MainHazards = Extremely Flammable (F+),<br /> Harmful (Xn)
| NFPA-H = 2
| NFPA-F = 4 | Reactivity=1
| NFPA-R =
| FlashPt = -45 °C
| RPhrases = {{R12}} {{R19}} {{R22}} {{R66}} {{R67}}
| SPhrases = {{S9}} {{S16}} {{S29}} {{S33}}
}}
| Section8 = {{Chembox Related
| Function = [[Ether]]s
| OtherFunctn = [[Dimethyl ether]]<br />[[Methoxypropane]]
}}
}}
:''This article is about the chemical compound. For other uses, see [[aether]].''
'''Diethyl ether''', also known as '''ether''' and '''ethoxyethane''', is a clear, colorless, and highly [[flammable liquid]] with a low [[boiling point]] and a characteristic smell. It is the most common member of a class of chemical compounds known generically as [[ether]]s. It is an [[isomer]] of [[butanol]]. Diethyl ether has the formula CH<sub>3</sub>-CH<sub>2</sub>-O-CH<sub>2</sub>-CH<sub>3</sub>. It is used as a common [[solvent]] and has been used as a general [[anesthetic]]. Ether is sparingly [[soluble]] in [[Water (molecule)|water]] (6.9 g/100 ml).
==History==
[[Alchemy|Alchemist]] [[Ramon Llull|Raymundus Lullus]] is credited with discovering the compound in [[1275]] AD, although there is no contemporary evidence of this. It was first synthesized in [[1540]] by [[Valerius Cordus]], who called it "'''oil of sweet vitriol'''" ('''''oleum dulcis vitrioli''''')—the name was because it was originally discovered by distilling a mixture of [[ethanol]] and [[sulfuric acid]] (then known as oil of vitriol)—and noted some of its medicinal properties. At about the same time, Theophrastus Bombastus von Hohenheim, better known as [[Paracelsus]], discovered ether's [[analgesic]] properties. The name ''[[ether]]'' was given to the substance in [[1730]] by [[August Siegmund Frobenius]].
==Metabolism==
A putative [[cytochrome P450]] enzyme is believed to metabolize diethyl ether.<ref>[http://www.fgsc.net/asilomar1997/secmetab.html 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 </ref>
Diethyl ether inhibits [[alcohol dehydrogenase]], and thus slows down the metabolism of [[ethanol]].<ref>{{cite journal | author = P. T. Normann, A. Ripel and J. Morland | title = Diethyl Ether Inhibits Ethanol Metabolism in Vivo by Interaction with Alcohol Dehydrogenase | year = 1987 | journal = [[Alcoholism: Clinical and Experimental Research]] | volume = 11 | issue = 2 | pages = 163–166 | doi = 10.1111/j.1530-0277.1987.tb01282.x}}</ref> It also inhibits metabolism of other drugs requiring [[oxidative metabolism]].<ref>{{cite journal | title = Inhibition of N-Nitrosodimethylamine Metabolism in Rats by Ether Anesthesia | author = Larry K. Keefer, William A. Garland, Neil F. Oldfield, James E. Swagzdis, and Bruce A. Mico | journal = [[Cancer Research (journal)|Cancer Research]] | volume = 45 | pages = 5457–60 | year = 1985 | url = http://cancerres.aacrjournals.org/cgi/reprint/45/11_Part_1/5457.pdf}}</ref>
==Applications==
Diethyl ether is a common laboratory [[solvent]]. It has limited solubility in water, thus it is commonly used for [[liquid-liquid extraction]]. Being less dense than water, the ether layer is usually on top. Its counterpart is [[dichloromethane]], which is similarly insoluble in water, and is also used for liquid-liquid extraction (dichloromethane is usually the lower phase). Diethyl ether is a common solvent for the [[Grignard reaction]], and for many other reactions involving organometallic reagents. It is particularly important as a solvent in the production of cellulose plastics such as [[cellulose acetate]].<ref name="kirk">{{cite encyclopedia
| title =Ethers, by Lawrence Karas and W. J. Piel
| encyclopedia =Kirk‑Othmer Encyclopedia of Chemical Technology
| volume =
| pages =
| publisher =John Wiley & Sons, Inc
| date =2004
| id =
| accessdate =2007-09-05}}</ref> Diethyl ether has a high [[cetane number]] of 85 - 96 and is used as a starting fluid for diesel and gasoline engines<ref>{{cite web|url=http://www.valvoline.com/pages/products/product_detail.asp?product=38§ion=402 | title = Extra Strength Starting Fluid: How it Works | publisher = Valvovine | accessdate=2007-09-05}}</ref> because of its high volatility and low [[autoignition temperature]].
===Anesthetic use===
[[Image:Ether monument-Boston.JPG||thumb|300px|Panel from monument in Boston commemorating Morton's demonstration of ether's anesthetic use.]]
The American doctor [[Crawford Williamson Long]], M.D., was the first surgeon to use it as a [[general anesthetic]], on March 30, 1842.<ref name=hill>Hill, John W. and Kolb, Doris K. ''Chemistry for changing times: 10th edition''. Page 257. Pearson: Prentice Hall. Upper saddle river, New Jersey. 2004.</ref> [[William T.G. Morton]] was previously credited with the first public demonstration of ether anesthesia on [[October 16]], [[1846]] at the [[Ether Dome]] in [[Boston, Massachusetts]], although Dr. [[Crawford Long]] is now known to have demonstrated its use publicly to other officials in Georgia. Ether was sometimes used in place of [[chloroform]] because it had a higher [[therapeutic index]], a larger difference between the recommended dosage and a toxic overdose. Ether is still the preferred anesthetic in some [[developing nation]]s due to its high [[therapeutic index]] (~1.5-2.2) <ref> Calderone, F.A. ''J. Pharmacology Experimental Therapeutics'', '''1935''', ''55(1)'', 24-39, http://jpet.aspetjournals.org/cgi/reprint/55/1/24.pdf</ref> and low price.
Because of its associations with Boston, the use of ether became known as the "Yankee Dodge."
Today, ether is rarely used. The use of flammable ether waned as nonflammable anesthetic agents such as [[halothane]] became available. Additionally, ether had many undesirable side effects, such as postanesthetic nausea and vomiting. Modern anesthetic agents, such as [[methyl propyl ether]] (Neothyl) and [[methoxyflurane]] (Penthrane) reduce these side effects.<ref name=hill/>
Ether may be used to anesthetize [[tick]]s before removing them from an animal or a person's body. The anesthesia relaxes the tick and prevents it from maintaining its mouthpart under the skin.{{Fact|date=April 2007}}
===Recreational use===
The anesthetic effects of ether have made it a recreational drug, although not a popular one. Diethyl ether is not as [[toxic]] as other solvents used as recreational drugs.
Ether, mixed with [[ethanol]], was marketed in the 19th century as a cure-all and recreational drug, during one of Western society's [[temperance movement]]s. At the time, it was considered improper for women to consume alcoholic beverages at social functions, and sometimes ether-containing drugs would be consumed instead. A cough medicine called [[Hoffmann's Drops]] was marketed at the time as one of these drugs, and contained both ether and alcohol in its capsules.<ref>[http://www.erowid.org/chemicals/ether/ether_info1.shtml Erowid Ether Vaults : Hoffmann's Drops<!-- Bot generated title -->]</ref> Ether tends to be difficult to consume alone, and thus was often mixed with drugs like ethanol for recreational use. Ether may also be used as an [[inhalant]].
Due to its immiscibility with water and the fact that non-polar organic compounds are highly soluble in it, ether is also used in the production of [[Freebase (chemistry)|freebase]] cocaine, and is listed as a Table II precursor under the [[United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances]].<ref>[http://www.incb.org/pdf/e/list/red.pdf Microsoft Word - RedListE2007.doc<!-- Bot generated title -->]</ref>
==Production==
Diethyl ether is rarely prepared in laboratories because of the hazards involved and the easy availability to legitimate labs. Most diethyl ether is produced as a byproduct of the vapor-phase [[Hydration reaction|hydration]] of [[ethylene]] to make [[ethanol]]. This process uses solid-supported [[phosphoric acid]] [[Catalysis|catalysts]] and can be adjusted to make more ether if the need arises.<ref name="kirk"/> Vapor-phase [[Dehydration reaction|dehydration]] of ethanol over some [[Aluminium oxide|alumina]] catalysts can give diethyl ether yields of up to 95%<ref>{{cite book |last= |first= |authorlink= |coauthors= |title=Ethyl Ether, Chem. Economics Handbook |year=1991 |publisher=SRI International |location=Menlo Park, Calif |isbn= }}</ref> .
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]], H<sub>2</sub>SO<sub>4</sub>. The acid [[Dissociation (chemistry)|dissociates]] producing [[Hydron (chemistry)|hydrogen ions]], H<sup>+</sup>. A hydrogen ion [[Protonation|protonates]] the [[Electronegativity|electronegative]] oxygen atom of the ethanol, giving the ethanol molecule a positive charge:
:CH<sub>3</sub>CH<sub>2</sub>OH + H<sup>+</sup> → CH<sub>3</sub>CH<sub>2</sub>OH<sub>2</sub><sup>+</sup>
A [[nucleophilic]] oxygen atom of unprotonated ethanol [[Single displacement reaction|displaces]] a water molecule from the protonated ([[electrophilic]]) ethanol molecule, producing water, a hydrogen ion and diethyl ether.
:CH<sub>3</sub>CH<sub>2</sub>OH<sub>2</sub><sup>+</sup> + CH<sub>3</sub>CH<sub>2</sub>OH → H<sub>2</sub>O + H<sup>+</sup> + CH<sub>3</sub>CH<sub>2</sub>OCH<sub>2</sub>CH<sub>3</sub>
This reaction must be carried out at temperatures lower than 150°C in order to ensure that an elimination product ([[ethylene]]) is not product of the reaction. At higher temperatures, ethanol will dehydrate to form ethylene. The reaction to make diethyl ether is reversible, so eventually an [[Chemical equilibrium|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]].
==Safety==
Diethyl ether is prone to [[organic peroxide|peroxide]] formation, and can form explosive [[diethyl ether peroxide]]. Ether peroxides are higher boiling and are contact explosives when dry. Diethyl ether is typically supplied with trace amounts of the [[antioxidant]] [[BHT]] (2,6-di-tert-butyl-4-methylphenol), which reduces the formation of peroxides. Storage over NaOH 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]].<ref>{{cite book | author = W. L. F. Armarego and C. L. L. Chai | title = Purification of laboratory chemicals | year = 2003 | publisher = Butterworth-Heinemann | city = Boston | isbn = 978-0750675710}}</ref>
Ether is an extremely flammable material. Open flames and even electrically heated devices should be avoided when using ether since it is easily ignited by a flame or spark. Ether's autoignition temperature is only 170°C (338°F), so it can be ignited by a hot surface without a flame or spark. The most common practice in chemical labs is to use steam (thus limiting the temperature to 100°C (212°F) when ether must be heated or distilled.
==Cultural references==
Recreational use of diethyl ether was portrayed in the film ''[[Fear and Loathing in Las Vegas]]'', based on the book of the same name by [[Hunter S. Thompson]], and portrayed in the novel ''[[The Cider House Rules]]'' by [[John Irving]] and in the film adaptation of the same name. An example of ether being used as a drug in the 19th century is to be found in [[Italo Svevo]]'s novel ''[[Senilità]]'' (1898). One of the main characters, Amalia, a reticent spinster in her early thirties, has become addicted to ether, falls into delirium and dies. It is also mentioned in Raymond Chandler's novel "The Big Sleep", in which he describes one of the characters under the influence of it.
In a [[Simpsons]] episode, [[Mr. Burns]] gets high on ether and drills into the skull of [[Hans Moleman]].
At the end of [[Water, Water Every Hare]], a flask of ether is broken when the evil scientist is chasing [[Bugs Bunny]] which causes them to move and speak slowly and fall asleep.
In the television series [[M*A*S*H]], ether is occasionally used as an anesthesia for patients being treated.
==References==
{{reflist}}
==External links==
* [http://www.erowid.org/chemicals/ether/ether.shtml Erowid]
* [http://www.anesthesia-nursing.com/ether.html The unusual history of ether as an anesthetic]
* [http://www.worldwidewords.org/nl/fjdz.htm#content Etheromania]
{{General anesthetics}}
[[Category:Ethers]]
[[Category:Anesthetics]]
[[Category:Dissociatives]]
[[Category:Ether solvents]]
[[Category:DEA List II chemicals]]
[[ca:Dietilèter]]
[[cs:Diethylether]]
[[de:Diethylether]]
[[et:Dietüüleeter]]
[[es:Éter etílico]]
[[fa:دیاتیل اتر]]
[[fr:Éther diéthylique]]
[[it:Etere dietilico]]
[[he:דיאתיל אתר]]
[[lv:Dietilēteris]]
[[lt:Dietileteris]]
[[hu:Dietil-éter]]
[[nl:Diethylether]]
[[ja:ジエチルエーテル]]
[[pl:Eter dietylowy]]
[[pt:Éter etílico]]
[[ru:Диэтиловый эфир]]
[[simple:Diethyl ether]]
[[fi:Dietyylieetteri]]
[[tr:Dietil eter]]
[[uk:Діетиловий ефір]]
[[zh:乙醚]]