'''Diethyl ether''', also known as '''ethoxyethane''', '''ethyl ether''', '''sulfuric ether''', or simply '''ether''', is an [[organic compound]] in the [[ether]] class with the formula {{chem|({{chem|C|2|H|5}})|2|O}}. It is a colorless, highly [[Volatility (chemistry)|volatile]] [[flammable liquid]]. It is commonly used as a [[solvent]] and was once used as a [[general anesthetic]]. It has narcotic properties and has been known to cause temporary dependence, the only symptom of which is the will to consume more, sometimes referred to as [[etheromania]].
==Overview==
== History ==
'''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).
The compound may have been created by either [[Jābir ibn Hayyān]] in the 8th century<ref name=Barash>{{cite book |author=Toski, Judith A; Bacon, Douglas R; Calverley, Rod K |title=The history of Anesthesiology |edition=4 |publisher=Lippincott Williams & Wilkins |year=2001 |isbn=978-0-7817-2268-1 |page=3 |work=In: Barash, Paul G; Cullen, Bruce F; Stoelting, Robert K. Clinical Anesthesia}}</ref> or [[Ramon Llull]] in 1275,<ref name=Barash/><ref name=Lullus>{{cite book |author=Hademenos, George J.; Murphree, Shaun; Zahler, Kathy; Warner, Jennifer M. |title=McGraw-Hill's PCAT |publisher=McGraw-Hill |page=39 |url=http://books.google.com/?id=8MwxkLP87IUC&pg=PA39&lpg=PA39&dq=Raymundus+Lullus+ether#v=onepage&q=Raymundus%20Lullus%20ether&f=false |accessdate=2011-05-25 |isbn=978-0-07-160045-3 |date=2008-11-12}}</ref> 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]].<ref name=Barash/> At about the same time, [[Paracelsus]] discovered ether's [[analgesic]] properties in chickens.<ref name=Barash/> The name ''ether'' was given to the substance in 1729 by [[August Sigmund Frobenius]].<ref>Dr. Frobenius (1729) [http://rstl.royalsocietypublishing.org/content/36/407-416/283.full.pdf+html "An account of a spiritus vini æthereus, together with several experiments tried therewith,"] ''Philosophical Transactions of the Royal Society'' (London), '''36''' : 283-289.</ref>
==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 dulci vitrioli''''')—the name was due to the fact that 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]].
== 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.
| year =2004
| id =}}</ref>
==Metabolism==
=== As a fuel ===
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 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<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 |archiveurl = http://web.archive.org/web/20070927222427/http://www.valvoline.com/pages/products/product_detail.asp?product=38§ion=402 <!-- Bot retrieved archive --> |archivedate = 2007-09-27}}</ref> because of its high volatility and low [[flash point]]. For the same reason it is also used as a component of the fuel mixture for [[carbureted compression ignition model engine]]s. In this way diethyl ether is very similar to one of its precursors, [[ethanol]].
Diethyl ether inhibits [[alcohol dehydrogenase]], and thus slows down the metabolism of [[ethanol]].<ref>[http://www.blackwell-synergy.com/doi/abs/10.1111/j.1530-0277.1987.tb01282.x?journalCode=acer blackwell-synergy.com]</ref> It also inhibits metabolism of other drugs requiring [[oxidative metabolism]] <ref> [http://cancerres.aacrjournals.org/cgi/reprint/45/11_Part_1/5457.pdf Inhibition of N-Nitrosodimethylamine Metabolism in Rats by Ether ...]</ref>
=== Laboratory uses ===
Diethyl ether is a common laboratory [[solvent]]. It has limited [[solubility]] in [[Water (molecule)|water]] (6.05 g/100 mL at 25 °C.) <ref>The Merck Index, 10th Edition, Martha Windholz, editor, Merck & Co., Inc, Rahway, NJ, 1983, page 551</ref> and dissolves 1.5 g/100 mL water at 25 °C.<ref name="water_in_ether">{{cite journal
| author = H. H. Rowley, Wm. R. Reed
| year = 1951
| title = Solubility of Water in Diethyl Ether at 25 °
}}</ref> Therefore, it is commonly used for [[liquid-liquid extraction]]. When used with an aqueous solution, the organic layer is on top as the diethyl ether has a lower density than the water. Please note that this is not an effective means of extracting diethyl ether as water is highly [[chemical polarity|polar]] while ether is non-polar. It is also a common solvent for the [[Grignard reaction]] in addition to other reactions involving organometallic reagents. Due to its application in the manufacturing of illicit substances, it is listed in the Table II precursor under the [[United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances]] as well as substances such as [[acetone]], [[toluene]] and [[sulphuric acid]].<ref>[http://www.incb.org/pdf/e/list/red.pdf Microsoft Word - RedListE2007.doc<!-- Bot generated title -->]</ref>
==Applications==
=== Anesthetic use ===
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
[[Image:Ether monument-Boston.JPG||thumb|300px|left|Panel from monument in Boston commemorating Morton's demonstration of ether's anesthetic use.]]
| title =Ethers, by Lawrence Karas and W. J. Piel
[[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 six occasions before the Boston demonstration.<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><ref name="newgeorgiaencylcopedia">{{cite web | url=http://www.georgiaencyclopedia.org/articles/science-medicine/crawford-long-1815-1878 | title=Crawford Long (1815-1878) | publisher=University of Georgia Press | work=New Georgia Encylcopedia | date=May 14, 2004 | accessdate=February 13, 2015 | author=Madden, M. Leslie}}</ref><ref name="southernmedicalassoc">{{cite web | url=http://sma.org/sma-alliance/doctors-day-2/crawford-w-long/ | title=Crawford W. Long | publisher=Southern Medical Association | work=Doctors' Day | accessdate=February 13, 2015}}</ref> British doctors were aware of the anesthetic properties of ether as early as 1840 where it was widely prescribed in conjunction with opium.<ref name= Grattan>Grattan, N. ''Treatment of Uterine Haemorrhage''. Provincial Medicine and Surgical Journal. Vol. 1, No. 6 (Nov. 7, 1840), p. 107.</ref>
| encyclopedia =Kirk‑Othmer Encyclopedia of Chemical Technology
Diethyl ether largely supplanted the use of [[chloroform]] as a general anesthetic due to ethers more favorable [[therapeutic index]], that is, a greater difference between an effective dose and a potentially toxic dose.<ref>{{cite journal | author = Calderone, F.A. | journal = J. Pharmacology Experimental Therapeutics | year = 1935 | volume = 55 | issue= 1 | pages = 24–39 | url = http://jpet.aspetjournals.org/cgi/reprint/55/1/24.pdf Jpet.aspetjournals.org}}</ref> Because of its associations with Boston, the use of ether became known as the "Yankee Dodge."
| 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===
Diethyl ether depresses the [[myocardium]] and increases tracheobronchial secretions.<ref>{{cite journal |title=Ether and its effects in Anesthesia |url=http://anesthesiageneral.com/ether-effects/}}</ref>
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 wider margin of [[therapeutic index]], a larger difference between the recommended dosage and a toxic overdose.
Diethyl ether could also be mixed with other anesthetic 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 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/>
Today, ether is rarely used. The use of flammable ether was displaced by nonflammable fluorinated hydrocarbon anesthetics. [[Halothane]] was the first such anesthetic developed and other currently used inhaled anesthetics, such as isoflurane, desflurane, and sevoflurane, are halogenated ethers.<ref name=morgan>Morgan, G. Edward, Jr. et al. "Clinical Anesthesiology" 3rd Ed, p. 3. New York: Mc Graw-Hill. 2002</ref> Diethyl ether was found to have undesirable side effects, such as post-anesthetic nausea and vomiting. Modern anesthetic agents 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}}
=== Medical use ===
It was once used in pharmaceuticals. A mixture of alcohol and ether was known as "Spirit of ether" or Hoffman's Drops. In the United States, it was removed from [[United States Pharmacopeia|Pharmacopeia]] prior to June 1917.<ref>The National druggist, Volume 47, June 1917, pp.220</ref>
===Recreational use===
=== Recreational use ===
{{See also|Addiction to ether consumption}}
The anesthetic 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. 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 15-20ml of ether, depending on body weight and physical condition. Ether causes a very long excitation stage prior to blacking out.
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.
In the 19th century and early 20th century ether drinking was popular among Polish peasants.<ref>{{Cite journal
| last = Zandberg | first = Adrian
| title = Short Article "Villages … Reek of Ether Vapours": Ether Drinking in Silesia before 1939
| journal = Medical History
| volume = 54
| issue = 3
| pages = 387–396
| year = 2010
| pmid = 20592886
| pmc = 2890321
| doi =10.1017/s002572730000466x}}</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]].
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</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]].
== 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>
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]] 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</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 | pmid=3296835}}</ref> It also inhibits metabolism of other drugs requiring [[oxidative metabolism]].
For example [[diazepam]] requires hepatic oxidization whereas its oxidized metabolite [[oxazepam]] does not.<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 | pmid=4053020 | issue = 11 Pt 1}}</ref>
==Production==
== 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> .
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 dehydrating 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:
Diethyl ether can be prepared both in laboratories and on an industrial scale by the acid ether synthesis.<ref>{{cite book|last=Cohen|first=Julius Berend|title=A Class-book of Organic Chemistry, Volume 1|year=1920|publisher=Macmillan and Co.|location=London|page=39|url=http://books.google.com/books?id=jyZIAAAAIAAJ&pg=PA37&dq=the+structure+of+ethyl+alcohol+cohen+julius+diethyl+ether&hl=en&sa=X&ei=fA2qUselPM_koATuhoCgAw&ved=0CEIQ6AEwAA#v=onepage&q=the%20structure%20of%20ethyl%20alcohol%20cohen%20julius%20diethyl%20ether&f=false}}</ref> [[Ethanol]] is mixed with a strong acid, typically [[sulfuric acid]], H<sub>2</sub>SO<sub>4</sub>. The acid [[Dissociation (chemistry)|dissociates]] in the aqueous environment producing [[hydronium]] ions, H<sub>3</sub>O<sup>+</sup>. A hydrogen ion [[Protonation|protonates]] the [[Electronegativity|electronegative]] oxygen atom of the [[ethanol]], giving the ethanol molecule a positive charge:
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.
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.
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]].
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]].
==Safety==
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]].
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.
== Safety and stability ==
Diethyl ether is extremely flammable and may be explosive.<ref name=msds01>http://www.chem.purdue.edu/chemsafety/safetyclass/SDS/GHS-Et2O.pdf</ref>
==Cultural references==
Since ether is heavier than air it can collect low to the ground and the vapour may travel considerable distances to ignition sources, which need not be an open flame, but may be a hot plate, steam pipe, heater etc.{{r|msds01}} 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 {{convert|160|C|F}}. A common practice in chemical labs is to use steam (thus limiting the temperature to {{convert|100|C|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).{{Citation needed|date=August 2011}}
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.
Ether is sensitive to light and air, tending to form explosive [[diethyl ether peroxide|peroxides]].{{r|msds01}} Ether peroxides are higher boiling than ether and are contact explosives when dry.{{r|msds01}} 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]].<ref>{{cite book | author = W. L. F. Armarego and C. L. L. Chai | title = Purification of laboratory chemicals | year = 2003 | publisher = Butterworth-Heinemann | location = Boston | isbn = 978-0-7506-7571-0}}</ref>
* [http://www.anesthesia-nursing.com/ether.html The unusual history of ether as an anesthetic]
* [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]
Diethyl ether, also known as ethoxyethane, ethyl ether, sulfuric ether, or simply ether, is an organic compound in the ether class with the formula (C 2H 5) 2O. It is a colorless, highly volatileflammable liquid. It is commonly used as a solvent and was once used as a general anesthetic. It has narcotic properties and has been known to cause temporary dependence, the only symptom of which is the will to consume more, sometimes referred to as etheromania.
History
The compound may have been created by either Jābir ibn Hayyān in the 8th century[4] or Ramon Llull in 1275,[4][5] 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.[4] At about the same time, Paracelsus discovered ether's analgesic properties in chickens.[4] The name ether was given to the substance in 1729 by August Sigmund Frobenius.[6]
Applications
It is particularly important as a solvent in the production of cellulose plastics such as cellulose acetate.[7]
As a fuel
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[8] because of its high volatility and low flash point. 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.
Laboratory uses
Diethyl ether is a common laboratory solvent. It has limited solubility in water (6.05 g/100 mL at 25 °C.) [9] and dissolves 1.5 g/100 mL water at 25 °C.[10] Therefore, it is commonly used for liquid-liquid extraction. When used with an aqueous solution, the organic layer is on top as the diethyl ether has a lower density than the water. Please note that this is not an effective means of extracting diethyl ether as water is highly polar while ether is non-polar. It is also a common solvent for the Grignard reaction in addition to other reactions involving organometallic reagents. Due to its application in the manufacturing of illicit substances, it is listed in the Table II precursor under the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances as well as substances such as acetone, toluene and sulphuric acid.[11]
Anesthetic use
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 six occasions before the Boston demonstration.[12][13][14] British doctors were aware of the anesthetic properties of ether as early as 1840 where it was widely prescribed in conjunction with opium.[15]
Diethyl ether largely supplanted the use of chloroform as a general anesthetic due to ethers more favorable therapeutic index, that is, a greater difference between an effective dose and a potentially toxic dose.[16] Because of its associations with Boston, the use of ether became known as the "Yankee Dodge."
Diethyl ether depresses the myocardium and increases tracheobronchial secretions.[17]
Today, ether is rarely used. The use of flammable ether was displaced by nonflammable fluorinated hydrocarbon anesthetics. Halothane was the first such anesthetic developed and other currently used inhaled anesthetics, such as isoflurane, desflurane, and sevoflurane, are halogenated ethers.[18] Diethyl ether was found to have undesirable side effects, such as post-anesthetic nausea and vomiting. Modern anesthetic agents reduce these side effects.[12]
Medical use
It was once used in pharmaceuticals. A mixture of alcohol and ether was known as "Spirit of ether" or Hoffman's Drops. In the United States, it was removed from Pharmacopeia prior to June 1917.[19]
The anesthetic 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. 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 15-20ml of ether, depending on body weight and physical condition. Ether causes a very long excitation stage prior to blacking out.
In the 19th century and early 20th century ether drinking was popular among Polish peasants.[20] It is a traditional and still relatively popular recreational drug among Lemkos.[21] It is usually consumed in a small quantity (kropka, or "dot") poured over milk, water with sugar or orange juice in a shot glass.
Most diethyl ether is produced as a byproduct of the vapor-phase hydration of ethylene to make ethanol. This process uses solid-supported phosphoric acidcatalysts and can be adjusted to make more ether if the need arises.[7] Vapor-phase dehydration of ethanol over some alumina catalysts can give diethyl ether yields of up to 95%.[25]
Diethyl ether can be prepared both in laboratories and on an industrial scale by the acid ether synthesis.[26]Ethanol is mixed with a strong acid, typically sulfuric acid, H2SO4. 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. 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.
Diethyl ether is extremely flammable and may be explosive.[27]
Since ether is heavier than air it can collect low to the ground and the vapour may travel considerable distances to ignition sources, which need not be an open flame, but may be a hot plate, steam pipe, heater etc.[27] 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 160 °C (320 °F). 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 0.918·10−5 m2/s (298K, 101.325 kPa).[citation needed]
Ether is sensitive to light and air, tending to form explosive peroxides.[27] Ether peroxides are higher boiling than ether and are contact explosives when dry.[27] Commercial diethyl ether is typically supplied with trace amounts of the antioxidantbutylated 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.[28]
↑ 4.04.14.24.3Toski, Judith A; Bacon, Douglas R; Calverley, Rod K (2001). The history of Anesthesiology. In: Barash, Paul G; Cullen, Bruce F; Stoelting, Robert K. Clinical Anesthesia (4 ed.). Lippincott Williams & Wilkins. p. 3. ISBN978-0-7817-2268-1.CS1 maint: Multiple names: authors list (link)
↑Hademenos, George J.; Murphree, Shaun; Zahler, Kathy; Warner, Jennifer M. (2008-11-12). McGraw-Hill's PCAT. McGraw-Hill. p. 39. ISBN978-0-07-160045-3. Retrieved 2011-05-25.CS1 maint: Multiple names: authors list (link)
↑ 12.012.1Hill, John W. and Kolb, Doris K. Chemistry for changing times: 10th edition. Page 257. Pearson: Prentice Hall. Upper saddle river, New Jersey. 2004.
↑Madden, M. Leslie (May 14, 2004). "Crawford Long (1815-1878)". New Georgia Encylcopedia. University of Georgia Press. Retrieved February 13, 2015.
↑"Crawford W. Long". Doctors' Day. Southern Medical Association. Retrieved February 13, 2015.
↑Grattan, N. Treatment of Uterine Haemorrhage. Provincial Medicine and Surgical Journal. Vol. 1, No. 6 (Nov. 7, 1840), p. 107.
↑Kaszycki, Nestor (2006-08-30). "Łemkowska Watra w Żdyni 2006 – pilnowanie ognia pamięci". Histmag.org – historia od podszewki (in Polish). Kraków, Poland: i-Press. Retrieved 2009-11-25. 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”.CS1 maint: Unrecognized language (link)
↑W. L. F. Armarego and C. L. L. Chai (2003). Purification of laboratory chemicals. Boston: Butterworth-Heinemann. ISBN978-0-7506-7571-0.
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