View source for Diethyl ether

{{chembox
| Watchedfields = changed
| verifiedrevid = 351361413
|   Name = Diethyl ether
|   ImageFile1 = Diethyl-ether-2D-skeletal.png
|   ImageSize1 = 200px
|   ImageName1 = Skeletal formula
|   ImageFile2 = Diethyl-ether-3D-balls.png
|   ImageSize2 = 200px
|   ImageName2 = Ball-and-stick model
|   IUPACName = Ethoxyethane
|   OtherNames = Diethyl ether; Ethyl ether; Ethyl oxide; 3-Oxapentane; Ethoxyethane
| Section1 = {{Chembox Identifiers
|   SMILES = O(CC)CC
|   InChI = 1/C4H10O/c1-3-5-4-2/h3-4H2,1-2H3
| InChIKey = RTZKZFJDLAIYFH-UHFFFAOYAB
| CASNo = 60-29-7
|    CASNo_Ref = {{cascite}}
|   ChemSpiderID = 3168
|   PubChem = 3283
|   RTECS = KI5775000
  }}
| Section2 = {{Chembox Properties
|   C=4|H=10|O=1
|   Appearance = Colorless liquid
|   Density = 0.7134 g/cm<sup>3</sup>, liquid
|   Solubility = 6.9 g/100 ml (20 °C)
|   MeltingPtC = -116.3
|   BoilingPtC = 34.6
|   pKa =
|   pKb =
|   Viscosity = 0.224 [[Poise|cP]] (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
|   NFPA-R = 1
|   Autoignition = 160 °C<ref name="MSDS">{{cite web | url = http://www.jtbaker.com/msds/englishhtml/e2340.htm | title = Ethyl Ether MSDS | publisher = J.T. Baker | accessdate = 2010-06-24}}</ref>
|   FlashPt = -45 °C<ref name="MSDS"/>
|   RPhrases = {{R12}} {{R19}} {{R20}} {{R22}} {{R66}} {{R67}}
|   SPhrases = {{S9}} {{S16}} {{S29}} {{S33}}
  }}
| Section8 = {{Chembox Related
|   Function = [[Ether]]s
|   OtherFunctn = [[Dimethyl ether]]<br />[[Methoxypropane]]
|   OtherCpds = [[Diethyl sulfide]]
  }}
}}

'''Diethyl ether''', also known simply as ether, is the [[organic compound]] with the formula {{chem|({{chem|C|2|H|5}})|2|O}}.  It is a colorless and highly [[flammable liquid]] with a low [[boiling point]] and a characteristic odor. It is the most common member of a class of chemical compounds known generically as [[ether]]s.  It is a common [[solvent]] and was once 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 AD [[1275]], although there is no contemporary evidence of this. It was first synthesized in [[1540]] by [[Valerius Cordus]], who called it "sweet oil of vitriol" (''oleum dulce vitrioli'') — the name reflects the fact that it is obtained 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 [[cytochrome P450]] enzyme is proposed 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 fgsc.net</ref>

Diethyl ether inhibits [[alcohol dehydrogenase]], and thus slows 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==
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>

===As a fuel===
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&section=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]]. For the same reason it is also used as a component of the fuel mixture for [[carbureted compression ignition model engines]].
===Laboratory uses===
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. Diethyl ether is a common solvent for the [[Grignard reaction]], and for many other reactions involving organometallic reagents. Due to its [[wikt:immiscibility|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> However, for that purpose it has been largely replaced by cheaper, safer, uncontrolled hydrocarbons.

===Anesthetic use===
[[Image:Ether monument-Boston.JPG||thumb|300px|left|Panel from monument in Boston commemorating Morton's demonstration of ether's anesthetic use.]]
[[William T.G. Morton]] participated in a public demonstration of ether anesthesia on October 16, 1846 at the [[Ether Dome]] in [[Boston, Massachusetts]].  However, [[Crawford Williamson Long]], M.D., is now known to have demonstrated its use privately as a [[general anesthetic]] in surgery to officials in Georgia, as early as March 30, 1842, and  Long publicly demonstrated ether's use as a surgical anesthetic on numerous occasions before 1846.<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>

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 Jpet.aspetjournals.org]</ref>{{Dubious|date=August 2009}} and low price. Because of its associations with Boston, the use of ether became known as the "Yankee Dodge."

Ether could also be mixed with other anaesthetic agents such as [[chloroform]] to make [[C.E. mixture]], or chloroform and [[Ethanol|alcohol]] to make [[A.C.E. mixture]].

Today, ether is rarely used.  The use of flammable ether was displaced by nonflammable anesthetics such as [[halothane]].  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/>

===Recreational use===
{{See also|Addiction to ether consumption}}

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.{{Citation needed|date=September 2010}}

Ether, mixed with [[ethanol]], was marketed in the 19th century as a cure-all and recreational drug{{Citation needed|date=August 2008}}, 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.{{Citation needed|date=August 2008}} 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]].

In the 19th century and early 20th century ether drinking was popular among Polish peasants<ref>{{Cite journal
  | last = Zandberg  | first = Adrian
  | title = “Villages… Reek of Ether Vapours”: Ether Drinking in Silesia before 1939
  | journal = Medical History
  | volume = 54
  | issue = 3
  | pages = 387–396
  | year = 2010
  | url = http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2890321
  | pmid = 20592886
  | pmc = 2890321}}</ref>
. It is a traditional and still relatively popular recreational drug among [[Lemkos]].<ref>
{{Cite web
  | url = http://histmag.org/?id=349
  | title = Łemkowska Watra w Żdyni 2006 – pilnowanie ognia pamięci
  | last = Kaszycki
  | first = Nestor
  | date = 2006-08-30
  | work = Histmag.org – historia od podszewki
  | publisher = i-Press
  | location = Kraków, Poland
  | language = Polish
  | accessdate = 2009-11-25
  | quote = Dawniej eteru używało się w lecznictwie do narkozy, ponieważ ma właściwości halucynogenne, a już kilka kropel inhalacji wystarczyło do silnego znieczulenia pacjenta. Jednak eter, jak każda ciecz, może teoretycznie być napojem. Łemkowie tę teorię praktykują. Mimo to, nazywanie skroplonego eteru – „kropki” – ich „napojem narodowym” byłoby przesadą. Chociaż stanowi to pewną część mitu „bycia Łemkiem”.
}}</ref>  It is usually consumed in a small quantity (''[[wikt:kropka|kropka]]'', or “dot”) poured over [[milk]], water with sugar or [[orange juice]] in a [[shot glass]].

==Production==
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 a 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]] [[Butylated hydroxytoluene|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 extremely flammable.  The autoignition temperature of ether is only 170 °C (338°F), so it can be ignited by a hot surface without a flame or spark.  A 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.   The diffusion of diethyl ether in air is 0.918·10<sup>−5</sup> m<sup>2</sup>/s (298K 101.325 kPa).

==References==
{{Reflist}}

==External links==
* [http://www.erowid.org/chemicals/ether/ether.shtml Erowid.org]
* [http://journals.lww.com/anesthesiology/Abstract/1992/10000/Michael_Faraday_and_His_Contribution_to_Anesthesia.27.aspx Michael Faraday's announcement of ether as an anesthetic in 1818]
* [http://www.anesthesia-nursing.com/ether.html The unusual history of ether as an anesthetic], anesthesia-nursing.com
* [http://www.worldwidewords.org/nl/fjdz.htm#content Etheromania], worldwidewords.org
* Calculation of [http://ddbonline.ddbst.de/AntoineCalculation/AntoineCalculationCGI.exe?component=Diethyl%20ether vapor pressure], [http://ddbonline.ddbst.de/DIPPR105DensityCalculation/DIPPR105CalculationCGI.exe?component=Diethyl%20ether liquid density], [http://ddbonline.ddbst.de/VogelCalculation/VogelCalculationCGI.exe?component=Diethyl%20ether dynamic liquid viscosity], [http://ddbonline.ddbst.de/DIPPR106SFTCalculation/DIPPR106SFTCalculationCGI.exe?component=Diethyl%20ether surface tension] of diethyl ether, ddbonline.ddbst.de

{{General anesthetics}}

{{DEFAULTSORT:Diethyl Ether}}
[[Category:Ethers]]
[[Category:General anesthetics]]
[[Category:Dissociative drugs]]
[[Category:Ether solvents]]
[[Category:DEA List II chemicals]]

[[ar:ثنائي إيثيل الإيثر]]
[[bs:Dietil eter]]
[[ca:Dietilèter]]
[[cs:Diethylether]]
[[de:Diethylether]]
[[et:Dietüüleeter]]
[[el:Διαιθυλαιθέρας]]
[[es:Éter etílico]]
[[fa:دی‌اتیل اتر]]
[[fr:Éther diéthylique]]
[[ko:다이에틸 에테르]]
[[id:Dietil eter]]
[[it:Etere dietilico]]
[[he:דיאתיל אתר]]
[[lv:Dietilēteris]]
[[lt:Dietileteris]]
[[lmo:Eter dietilich]]
[[hu:Dietil-éter]]
[[mk:Диетил етер]]
[[nl:Diethylether]]
[[ja:ジエチルエーテル]]
[[pl:Eter dietylowy]]
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[[ru:Диэтиловый эфир]]
[[simple:Diethyl ether]]
[[sl:Dietil eter]]
[[fi:Dietyylieetteri]]
[[sv:Dietyleter]]
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[[uk:Діетиловий ефір]]
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[[Category:2Fix]]