Diethyl ether: Difference between revisions

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{{short description|Organic chemical compound}}

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"

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! {{chembox header}} | Diethyl ether <!-- replace if not identical with the article name -->

{{Chembox

|-

| Watchedfields = changed

| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Diethylether_chemical_structure.png|Chemical structure of diethyl ether]] <!-- replace if not identical with the pagename -->

| verifiedrevid = 477163372

|-

| Name = Diethyl ether

! {{chembox header}} | General

| ImageFile1 = Diethyl-ether-2D-skeletal.svg

|-

| ImageName1 = Skeletal formula

| [[IUPAC nomenclature|Systematic name]]

| ImageClass1 = skin-invert

| ethoxyethane <!-- e.g. Iron(II) chloride -->

| ImageFile2 = Diethyl-ether-3D-balls.png

|-

| ImageClass2 = bg-transparent

| Other names

| ImageName2 = Ball-and-stick model

| diethyl ether<br/>ethyl ether<br/>ethyl oxide <!-- e.g. Ferrous chloride etc, + linked mineral names -->

| ImageFile3 = Dietil eter.png

|-

| ImageName3 = Sample of diethyl ether

| [[Chemical formula|Molecular formula]]

| PIN = Ethoxyethane

| C₄H₁₀O<br/>C₂H₅OC₂H₅ <!-- e.g. Na₂CO₃ -->

| OtherNames = {{ubl|3-Oxapentane|Dether|Diethyl ether|Diethyl oxide|Ether|Ethyl ether|Ethyl oxide|Solvent ether|Sulfuric ether|Sulphuric ether|Sweet oil of vitriol|Vitriolic ether}}

|-

| Section1 = {{Chembox Identifiers

| [[Simplified molecular input line entry specification|SMILES]] <!-- mostly for organic compounds, omit otherwise -->

|ChEBI_Ref = {{ebicite|correct|EBI}}

| CCOCC

|ChEBI = 35702

|-

|Beilstein = 1696894

| [[Molar mass]]

|Gmelin = 25444

| 74.12 g/mol

|EINECS = 200-467-2

|-

|UNNumber = 1155

| Appearance

|SMILES = CCOCC

| clear, colorless liquid <!-- e.g. pale yellow solid, [[hygroscopic]] -->

|UNII_Ref = {{fdacite|correct|FDA}}

|-

|UNII = 0F5N573A2Y

| [[CAS registry number|CAS number]]

|KEGG_Ref = {{keggcite|correct|kegg}}

| [60-29-7]

|KEGG = D01772

|-

|InChI = 1/C4H10O/c1-3-5-4-2/h3-4H2,1-2H3

! {{chembox header}} | Properties

|InChIKey = RTZKZFJDLAIYFH-UHFFFAOYAB

|-

|ChEMBL_Ref = {{ebicite|correct|EBI}}

| [[Density]] and [[Phase (matter)|phase]]

|ChEMBL = 16264

| 0.7134 g/cm³, liquid <!-- ? g/cm³, solid / ? g/ml, liquid / ? g/l, gas -->

|StdInChI_Ref = {{stdinchicite|correct|chemspider}}

|-

|StdInChI = 1S/C4H10O/c1-3-5-4-2/h3-4H2,1-2H3

| [[Soluble|Solubility]] in [[Water (molecule)|water]]

|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| 6.9 g/100 ml (20 °C) <!-- at least put miscible with, not soluble in -->

|StdInChIKey = RTZKZFJDLAIYFH-UHFFFAOYSA-N

|-

|CASNo = 60-29-7

<!-- | Other solvents e.g. [[ethanol]], [[acetone]] -->

|CASNo_Ref = {{cascite|correct|CAS}}

<!-- | solubility info on other solvents -->

|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

<!-- |- -->

|ChemSpiderID = 3168

| [[Melting point]]

|PubChem = 3283

| &minus;116.3 °C (156.85 K) <!-- (mention any decomposition) -->

|RTECS = KI5775000

|-

}}

| [[Boiling point]]

| Section2 = {{Chembox Properties

| 34.6 °C (307.75 K)

|C=4|H=10|O=1

|-

|Appearance = Colorless liquid

| [[Acid dissociation constant|Acidity]] (p''K''_a) <!-- omit if not an acid or a base. If several values, be clear -->

|Odor = Dry, rum-like, sweetish odor<ref name=PGCH/>

| ?

|Density = 0.7134 g/cm³, liquid

|-

|Solubility = 6.05&nbsp;g/(100&nbsp;mL)<ref name=merckindex>''[[Merck Index]]'', 10th ed., Martha Windholz, editor, Merck & Co., Inc, Rahway, NJ, 1983, p. 551</ref>

| [[Acid dissociation constant|Basicity]] (p''K''_b) <!-- omit if not a base. If several values, be clear -->

|MeltingPtC = −116.3

| ?

|BoilingPtC = 34.6

|-

|BoilingPt_ref =<ref>{{cite web|title=Diethyl ether|url=http://www.chemspider.com/Chemical-Structure.3168.html|publisher=ChemSpider|access-date=19 January 2017}}</ref>

| [[Viscosity]]

|RefractIndex = 1.353 (20&nbsp;°C)

| 0.224 [[Poise|cP]] at 25 °C <!-- Liquids only, omit if data unavailable. You may use [[Pascal second|Pa.s]] if you prefer -->

|Viscosity = 0.224 [[Poise (unit)|cP]] (25&nbsp;°C)

|-

|VaporPressure = 440 mmHg (58.66 kPa) at 20&nbsp;°C<ref name=PGCH/>

! {{chembox header}} | Structure

|MagSus = −55.1·10⁻⁶ cm³/mol

|-

|LogP =0.98<ref name="chemsrc">{{Cite web|url=https://www.chemsrc.com/en/cas/60-29-7_667780.html|title= Diethyl ether_msds}}</ref>

| [[Orbital hybridisation#Molecule shape|Molecular shape]] <!-- for simple covalent molecules (omit for most large molecules, ionics and complexes) -->

}}

| ? <!-- e.g. trigonal bipyramidal -->

| Section3 = {{Chembox Structure

|-

|Dipole = 1.15 [[Debye|D]] (gas)

| [[Dipole#Molecular dipoles|Dipole moment]]

}}

| 1.15 [[Debye|D]] (gas)

| Section4 = {{Chembox Thermochemistry

|-

|DeltaHc = −2732.1 ± 1.9 kJ/mol

! {{chembox header}} | Hazards <!-- Summary only- MSDS entry provides more complete information -->

|DeltaHf = −271.2 ± 1.9 kJ/mol

|-

|Entropy = 253.5 J/(mol·K)

| [[Material safety data sheet|MSDS]]

|HeatCapacity = 172.5 J/(mol·K)

| [[Diethyl ether (data page)#Material Safety Data Sheet|External MSDS]] <!-- please replace with proper link-->

}}

|-

| Section5 = {{Chembox Pharmacology

| Main [[Worker safety and health|hazard]]s

|ATCCode_prefix = N01

| Extremely Flammable (F+),<br> Irritant (Xi) <!-- e.g. highly toxic, explosive, flammable, corrosive -->

|ATCCode_suffix = AA01

|-

}}

| [[NFPA 704]]

| Section6 = {{Chembox Hazards

| {{NFPA 704 | Health=2 | Flammability=4 | Reactivity=1 }}

|ExternalSDS = [http://www.sciencelab.com/msds.php?msdsId=9927164 External MSDS]

|-

|MainHazards = Extremely flammable, harmful to skin, decomposes to explosive [[diethyl ether peroxide|peroxides]] in [[air]] and [[light]], may cause dizziness in a less ventilated place or if ingested.<ref name=PGCH/>

| [[Flash point]]

| NFPA-45H = °C2

|NFPA-F = 4

|-

|NFPA-R = 1

| [[Autoignition temperature|Autoignition<br>temperature]]

|AutoignitionPtC = 160

| 170 °C

|AutoignitionPt_ref =<ref name="MSDS">{{cite web | url = http://hazard.com/msds/mf/baker/baker/files/e2340.htm | title = Ethyl Ether MSDS | publisher = J.T. Baker |access-date = 2010-06-24 | archive-url = https://web.archive.org/web/20120328181719/http://hazard.com/msds/mf/baker/baker/files/e2340.htm | archive-date = 2012-03-28 | url-status = dead}}</ref>

|-

|FlashPtC = −45

| [[Risk and Safety Statements|R/S statement]]

|FlashPt_ref =<ref name="MSDS"/>

| {{R12}} {{R19}} {{R22}} {{R66}} {{R67}} <br> {{S9}} {{S16}} {{S29}} {{S33}}

|ExploLimits = 1.85–48.0%<ref name = "Yaws">Carl L. Yaws, ''Chemical Properties Handbook'', McGraw-Hill, New York, 1999, p. 567</ref>

|-

|GHSPictograms = {{GHS flame}}{{GHS07}}

| [[RTECS]] number

|GHSSignalWord = Danger

| KI5775000

|HPhrases = {{H-phrases|224|302|336}}

|-

|PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|270|271|280|301+312|303+361+353|304+340|312|330|370+378|403+233|403+235|405|501}}

! {{chembox header}} | [[Diethyl ether (data page)|Supplementary data page]]

|PEL = TWA 400 ppm (1200 mg/m³)<ref name=PGCH>{{PGCH|0277}}</ref>

|-

|IDLH = 1900 ppm<ref name=PGCH/>

| [[Diethyl ether (data page)#Structure and properties|Structure and<br/>properties]]

|REL = No established REL<ref name=PGCH/>

| [[Refractive index|''n'']], [[Dielectric constant|ε_r]], etc.

|LCLo = 106,000 ppm (rabbit)<br />76,000 ppm (dog)<ref name=IDLH>{{IDLH|60297|Ethyl ether}}</ref>

|-

|LC50 = 73,000 ppm (rat, 2 hr)<br />6500 ppm (mouse, 1.65 hr)<ref name=IDLH />

| [[Diethyl ether (data page)#Thermodynamic properties|Thermodynamic<br/>data]]

}}

| Phase behaviour<br>Solid, liquid, gas

| Section7 = {{Chembox Related

|-

|OtherFunction_label = [[ether]]s

| [[Diethyl ether (data page)#Spectral data|Spectral data]]

|OtherFunction = {{ubl|[[Dimethyl ether]]|[[Ethyl methyl ether]]|[[Methyl propyl ether]]|[[Dipropyl ether]]|[[Diisopropyl ether]]|[[Dibutyl ether]]|[[Divinyl ether]]|[[Diphenyl ether]]|[[1,4-Dioxane]]|[[Furan]]}}

| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[NMR spectroscopy|NMR]], [[Mass spectrometry|MS]]

|OtherCompounds = {{ubl|[[Diethyl sulfide]]|[[Diethyl selenide]]|[[Ethanol]]|[[Butanol]]s ([[isomer]])|[[2-Ethoxyethanol]]|[[Diethylene glycol]]|[[Polyethylene glycol]]|[[Diethyl ether hydroperoxide]]|[[Diethylamine]]|[[Triethylamine]]}}

|-

}}

! {{chembox header}} | Related compounds

}}

|-

| Related [[ether|Ethers]] <!-- PLEASE INSERT FUNCTIONAL GROUP (e.g. [[aldehyde]]) FOR ORGANICS, please omit if not applicable -->

| [[dimethyl ether]] <!-- Insert related organics e.g. on formaldehyde page put [[acetaldehyde]] -->

|-

| {{chembox header}} | <small>Except where noted otherwise, data are given for<br> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br/>[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>

|-

|}

'''Diethyl ether''', or simply '''ether''' (abbreviated as '''eth.'''<ref name="LoganAbbrev"/> or {{chem2|Et2O}}){{efn|"Et" stands for monovalent [[ethyl group]] {{chem2|CH3CH2}} (see [[pseudoelement symbol]])}}<ref name="LoganAbbrev">{{Cite book |title=Logan's Medical and Scientific Abbreviations |vauthors=Logan CM, Rice MK |publisher=[[J. B. Lippincott & Co.|J. B. Lippincott]] |year=1987 |isbn=0-397-54589-4 |page=182 |type=Hardbound book}}</ref> is an [[organic compound]] with the [[chemical formula]] {{chem2|(CH3CH2)2O}}, belonging to the [[ether]] class. It is a colourless, highly [[Volatility (chemistry)|volatile]], sweet-smelling (termed "ethereal odour"), extremely [[flammable liquid]]. It is a common [[solvent]] and was formerly used as a [[general anesthetic]].<ref>{{cite book |doi=10.1002/14356007.a10_023.pub2 |chapter=Ethers, Aliphatic |title=Ullmann's Encyclopedia of Industrial Chemistry |date=2010 |last1=Sakuth |first1=Michael |last2=Mensing |first2=Thomas |last3=Schuler |first3=Joachim |last4=Heitmann |first4=Wilhelm |last5=Strehlke |first5=Günther |last6=Mayer |first6=Dieter |isbn=978-3-527-30385-4 }}</ref>

'''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. Diethyl ether has the formula CH₃-CH₂-O-CH₂-CH₃. It is used as a common [[solvent]] and has been used as a general [[anesthetic]]. Diethyl ether has a high [[cetane number]] of 85 - 96 and is used as a [[starting fluid]] for [[diesel engine|diesel]] and [[gasoline engine]]s. Ether is sparingly [[soluble]] in [[Water (molecule)|water]] (7 g/100 ml).

== 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 |title=Ethyl Ether, Chem. Economics Handbook |year=1991 |publisher=SRI International |___location=Menlo Park, Calif}}</ref>

:{{chem2|2 CH3CH2OH → (CH3CH2)2O + H2O}}

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=[https://archive.org/details/aclassbookorgan00cohegoog/page/n53 39]|url=https://archive.org/details/aclassbookorgan00cohegoog|quote=the structure of ethyl alcohol cohen julius diethyl ether.}}</ref>

== Uses ==

The dominant use of diethyl ether is as a solvent. One particular application is 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

| publisher =John Wiley & Sons, Inc.

| year =2004

}}</ref>

===Laboratory solvent===

It is a common solvent for the [[Grignard reaction]] in addition to other reactions involving organometallic reagents.<ref>{{cite journal |doi=10.15227/orgsyn.011.0098 |first1=W. W.|last1=Moyer|first2= C. S.|last2=Marveltitle=Triethyl Carbinol |title=Triethyl Carbinol |journal=Organic Syntheses |date=1931 |volume=11 |page=98 }}</ref> These uses exploit its basicity. Diethyl ether is a popular non-polar solvent in [[liquid-liquid extraction]]. As an extractant, it is immiscible with and less [[density|dense]] than water.

Although immiscible, it has significant [[solubility]] in [[Water (molecule)|water]] (6.05&nbsp;g/(100&nbsp;ml) at 25&nbsp;°C<ref name=merckindex/>) and dissolves 1.5&nbsp;g/(100&nbsp;g) (1.0&nbsp;g/(100&nbsp;ml)) water at 25&nbsp;°C.<ref name="water_in_ether">{{cite journal

|author1=H. H. Rowley |author2=Wm. R. Reed | year = 1951

| title = Solubility of Water in Diethyl Ether at 25 °

| journal = J. Am. Chem. Soc.

| volume = 73

| issue = 6

| pages = 2960

| doi = 10.1021/ja01150a531

|bibcode=1951JAChS..73.2960R }}</ref>

=== Fuel ===

Diethyl ether has a high [[cetane number]] of 85–96 and, 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&section=402 | title = Extra Strength Starting Fluid: How it Works | publisher = Valvovine | access-date=2007-09-05 |archive-url = https://web.archive.org/web/20070927222427/http://www.valvoline.com/pages/products/product_detail.asp?product=38&section=402 <!-- Bot retrieved archive --> |archive-date = 2007-09-27}}</ref> is used as a [[starting fluid]] 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 engine]]s.

==Chemical reactions==

[[Triethyloxonium tetrafluoroborate]] is prepared from [[boron trifluoride]], diethyl ether, and [[epichlorohydrin]]:<ref>{{OrgSynth | author = H. Meerwein | volume = 46 | year = 1966| page = 113 | doi = 10.15227/orgsyn.046.0113| title = Triethyloxonium fluoroborate}}</ref>

:{{chem2|4 Et2O*BF3 + 2 Et2O + 3 C2H3OCH2Cl → 3 [Et3O]+[BF4]− + B(OCH(CH2Cl)CH2OEt)3}}

Diethyl ether is a common laboratory [[Polar_aprotic_solvent|aprotic solvent]]. It is susceptible to the formation of [[hydroperoxide]]s.

== 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.] {{Webarchive|url=https://web.archive.org/web/20170917080739/http://www.fgsc.net/asilomar1997/secmetab.html |date=2017-09-17 }} Matthew P. Brown and Gary A. Payne, [[North Carolina State University]], Raleigh, NC, fgsc.net</ref>

Diethyl ether inhibits [[alcohol dehydrogenase]], and thus slows the metabolism of [[ethanol]].<ref>{{cite journal |author1=P. T. Normann |author2=A. Ripel |author3=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 |author1=Larry K. Keefer |author2=William A. Garland |author3=Neil F. Oldfield |author4=James E. Swagzdis |author5=Bruce A. Mico | journal = [[Cancer Research (journal)|Cancer Research]] | volume = 45 | pages = 5457–5460 | year = 1985 | url = http://cancerres.aacrjournals.org/cgi/reprint/45/11_Part_1/5457.pdf | pmid=4053020 | issue = 11 Pt 1}}</ref>

== Safety, stability, regulations ==

Diethyl ether is extremely flammable and may form explosive vapour/air mixtures.<ref name=msds01>{{cite web |url=http://www.chem.purdue.edu/chemsafety/safetyclass/SDS/GHS-Et2O.pdf |title=Archived copy |access-date=2014-02-15 |url-status=dead |archive-url=https://web.archive.org/web/20141113221658/http://www.chem.purdue.edu/chemsafety/safetyclass/SDS/GHS-Et2O.pdf |archive-date=2014-11-13}}</ref>

Since ether is heavier than air it can collect low to the ground and the vapour may travel considerable distances to ignition sources. Ether will ignite if exposed to an open flame, though due to its high flammability, an open flame is not required for ignition. Other possible ignition sources include – but are not limited to – hot plates, steam pipes, heaters, and electrical arcs created by switches or outlets.{{r|msds01}} Vapour may also 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}}. The diffusion of diethyl ether in air is {{nowrap|9.18 × 10⁻⁶ m²/s}} (298 K, 101.325 kPa).{{Citation needed|date=August 2011}}

Ether is sensitive to light and air, tending to form explosive [[diethyl ether peroxide|peroxides]].{{r|msds01}} Ether peroxides have a higher boiling point 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 |author1=W. L. F. Armarego |author2=C. L. L. Chai | title = Purification of laboratory chemicals | year = 2003 | publisher = Butterworth-Heinemann | ___location = Boston | isbn = 978-0-7506-7571-0}}</ref>

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 [[sulfuric acid]].<ref>[http://www.incb.org/pdf/e/list/red.pdf Microsoft Word – RedListE2007.doc<!-- Bot generated title -->] {{webarchive |url=https://web.archive.org/web/20080227224025/http://www.incb.org/pdf/e/list/red.pdf |date=February 27, 2008}}</ref>

== History ==

The compound may have been synthesised by either [[Jābir ibn Hayyān]] in the 8th century<ref name=Barash>{{cite book |author1=Toski, Judith A |author2=Bacon, Douglas R |author3=Calverley, Rod K |title=The history of Anesthesiology |edition=4th |publisher=Lippincott Williams & Wilkins |year=2001 |isbn=978-0-7817-2268-1 |page=3 |series=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 |author1=Hademenos, George J. |author2=Murphree, Shaun |author3=Zahler, Kathy |author4=Warner, Jennifer M. |title=McGraw-Hill's PCAT |publisher=McGraw-Hill |page=39 |url=https://books.google.com/books?id=8MwxkLP87IUC&pg=PA39 |access-date=2011-05-25 |isbn=978-0-07-160045-3 |date=2008}}</ref> It was synthesised 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 the [[analgesic]] properties of the molecule in dogs.<ref name=Barash/> The name ''ether'' was given to the substance in 1729 by [[August Sigmund Frobenius]].<ref>{{cite journal | doi = 10.1098/rstl.1729.0045 | title = VIII. An account of a spiritus vini æthereus, together with several experiments tried therewith | journal = Philosophical Transactions of the Royal Society of London | volume = 36 | issue = 413 | pages = 283–289 | year = 1730 | s2cid = 186207852}}</ref>

It was considered to be a sulfur compound until the idea was disproved in about 1800.<ref name="EB1911">{{Cite EB1911|wstitle=Ether|volume=9|page=806}}</ref>

[[Alchemy|Alchemist]] [[Ramon Llull|Raymundus Lullus]] is credited with discovering the compound in [[1275]], 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 [[A.S.Frobenius]].

The synthesis of diethyl ether by a reaction between [[ethanol]] and [[sulfuric acid]] has been known since the 13th century.<ref name="EB1911">{{Cite EB1911|wstitle=Ether|volume=9|page=806}}</ref>

== Anesthetic use ==

=== Anesthesia ===

The American doctor [[Crawford Williamson Long]], M.D., was the first surgeon to use it as a [[general anesthetic]], on March 30, 1842. Its first use is normally associated with the [[Ether Dome]] in [[Boston, Massachusetts]]. Ether is no longer used as an anesthetic when other, safer substances are available; ether is flammable, and is an irritant to some patients.

[[File:The first use of ether in dental surgery, 1846. Ernest Board. Wellcome V0018140.jpg|thumb|left|The first use of ether in dental surgery, by [[Ernest Board]].]]

[[File:Ether monument-Boston.JPG|thumb|250px|left|Panel from [[Ether 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]]. Morton had called his ether preparation, with aromatic oils to conceal its smell, "''Letheon''" after the [[Lethe|Lethe River]] (Λήθη, meaning "forgetfulness, oblivion").<ref>{{Cite book|url=https://books.google.com/books?id=YcPvV893aXgC&pg=PA1129|page=1129|title=Inventors and Inventions, Volume 4|year=2008|isbn=978-0-7614-7767-9|first=Marshall|last=Cavendish|publisher=Marshall Cavendish }}</ref> However, [[Crawford Williamson Long]] 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''. p. 257. Pearson: Prentice Hall. Upper Saddle River, New Jersey. 2004.</ref><ref name="newgeorgiaencylcopedia">{{cite encyclopedia | url=http://www.georgiaencyclopedia.org/articles/science-medicine/crawford-long-1815-1878 | title=Crawford Long (1815–1878) | publisher=University of Georgia Press | encyclopedia=New Georgia Encyclopedia | date=May 14, 2004 | access-date=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 | access-date=February 13, 2015 | url-status=dead | archive-url=https://web.archive.org/web/20150213210340/http://sma.org/sma-alliance/doctors-day-2/crawford-w-long/ | archive-date=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">{{Cite journal |last=Gratian |first=N. |date=1840-11-07 |title=Dr. Grattan on the Treatment of Uterine Haemorrhage |journal=BMJ |language=en |volume=s1-1 |issue=6 |pages=107 |doi=10.1136/bmj.s1-1.6.107 |issn=0959-8138 |pmc=2488546 |pmid=21372908}}</ref> Diethyl ether was preferred by some practitioners over [[chloroform]] as a general anesthetic due to ether's 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 = Journal of Pharmacology and Experimental Therapeutics | year = 1935 | volume = 55 | issue= 1 | pages = 24–39 | url = http://jpet.aspetjournals.org/cgi/reprint/55/1/24.pdf | title = Studies on Ether Dosage After Pre-Anesthetic Medication with Narcotics (Barbiturates, Magnesium Sulphate and Morphine)}}</ref>

Owing to these reasons, plus its high [[volatility]] and low ignition point, diethyl ether is considered as one of the risk factors in laboratories.

Diethyl ether does not depress the [[myocardium]] but rather it stimulates the sympathetic nervous system leading to hypertension and tachycardia. It is safely used in patients with shock as it preserves the [[Baroreflex|baroreceptor reflex]].<ref>{{Cite web|url=https://anesthesiageneral.com/ether-effects/|title = Ether effects|date = 31 October 2010}}</ref> Its minimal effect on myocardial depression and respiratory drive, as well as its low cost and high therapeutic index allows it to see continued use in developing countries.<ref>{{cite journal |date=2010-10-31 |title=Ether and its effects in Anesthesia |url=http://anesthesiageneral.com/ether-effects/ |journal=Anesthesia General}}</ref> 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]]. In the 21st century, 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. (2002). ''Clinical Anesthesiology'' 3rd Ed. New York: McGraw-Hill. p. 3.</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.

[[File:Ether Dreams.jpg|thumb|left|An illustration depicting ether's effects, 1840s–1870s]]

Prior to 2005, it was on the [[World Health Organization's List of Essential Medicines]] for use as an anesthetic.<ref>{{cite web|title=Essential Medicines WHO Model List (revised April 2003)|___location=Geneva, Switzerland|publisher=World Health Organization|website=apps.who.int|date=April 2003|access-date=6 September 2017|url=http://apps.who.int/iris/bitstream/10665/68168/1/a80290.pdf|edition=13th}}</ref><ref>{{cite web|title=Essential Medicines WHO Model List (revised March 2005)|___location=Geneva, Switzerland|publisher=World Health Organization|website=apps.who.int|date=March 2005|access-date=6 September 2017|archive-url=https://web.archive.org/web/20050805200129/http://whqlibdoc.who.int/hq/2005/a87017.pdf|archive-date=5 August 2005|url=http://whqlibdoc.who.int/hq/2005/a87017.pdf|edition=14th}}</ref>

=== Recreational useMedicine ===

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 [[Compound spirit of ether|"Spirit of ether"]], Hoffman's [[Anodyne]] or Hoffman's Drops. In the United States this concoction was removed from the [[United States Pharmacopeia|Pharmacopeia]] at some point prior to June 1917,<ref>The National Druggist, Volume 47, June 1917, pp. 220</ref> 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.<ref>{{Cite journal|last=Procter|first=William Jr.|date=1852|title=On Hoffman's Anodyne Liquor|url=https://recipes.hypotheses.org/tag/hoffmans-anodyne#_ftnref1|journal=American Journal of Pharmacy|volume=28}}</ref> It is also used to treat [[hiccups]] through instillation into the nasal cavity.<ref>[https://www.ncbi.nlm.nih.gov/m/pubmed/5534411/ ncbi, Treatment of hiccups with instillation of ether into the nasal cavity.]</ref>

=== 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 (see [[volatile substance abuse]]).

{{See also|Ether addiction}}

The recreational use of ether also took place at organised parties in the 19th century called [[History of general anesthesia#Western world|ether frolics]], where guests were encouraged to inhale therapeutic amounts of diethyl ether or [[nitrous oxide]], producing a state of excitation. Long, as well as fellow dentists [[Horace Wells]], William Edward Clarke, and [[William T. G. Morton]], observed that during these gatherings, people would often experience minor injuries but appear to show no reaction to them, nor memory that it had happened, demonstrating ether's anaesthetic effects.<ref>{{Cite web|title=How Ether Went from a Recreational 'Frolic' Drug to the First Surgery Anesthetic|url=https://www.smithsonianmag.com/science-nature/ether-went-from-recreational-frolic-drug-first-surgery-anesthetic-180971820/|access-date=2020-10-11|website=Smithsonian Magazine}}</ref>

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. [http://www.erowid.org/chemicals/ether/ether_info1.shtml] Ether tends to be difficult to consume alone, and thus was often mixed with drugs like ethanol for recreational use.

Ethyl ether is listed as a Table II precursor under the [[United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances]][http://www.incb.org/pdf/e/list/red.pdf].

In the 19th and early 20th centuries, 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 = pl| access-date = 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".

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.

}}</ref> It is usually consumed in a small quantity (''[[wikt:kropka|kropka]]'', or "dot") poured over milk, sugar water, or orange juice in a [[shot glass]]. As a drug, it has been known to cause [[psychological dependence]], sometimes referred to as [[etheromania]].<ref>{{cite journal |last1=Krenz |first1=Sonia |last2=Zimmermann |first2=Grégoire |last3=Kolly |first3=Stéphane |last4=Zullino |first4=Daniele Fabio |title=Ether: a forgotten addiction |journal=Addiction |date=August 2003 |volume=98 |issue=8 |pages=1167–1168 |doi=10.1046/j.1360-0443.2003.00439.x |pmid=12873252 |url=https://www.researchgate.net/publication/10652053}}</ref>{{medcn|date=April 2020}}

Ether intoxication is referenced in [[Hunter S. Thompson]]'s ''[[Fear and Loathing in Las Vegas]]'', where in one of the book's most famous quotes, protagonist Raoul Duke declares that "There is nothing in the world more helpless and irresponsible and depraved than a man in the depths of an ether binge."<ref>{{Cite web | url=http://www.goodreads.com/author/quotes/5237.Hunter_S_Thompson | title=Hunter S. Thompson Quotes (Author of Fear and Loathing in las Vegas)}}</ref>

== Precautions ==

==See also==

Diethyl ether is highly flammable. Its vapors are denser than air and will accumulate if proper ventilation is not present. Simple [[static electricity]] will ignite ether vapors. Diethyl ether vapors ignite explosively, and should only be used inside a [[fume hood]].

* [[The Great Moment (1944 film)|''The Great Moment'']] – film about William T.G. Morton and ether

* [[Flurothyl]] – fluorinated derivative

== Explanatory notes ==

Additionally, 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. Ether should never be distilled to dryness, as the risk of explosion increases dramatically. Diethyl ether is typically supplied with [[BHT]] (2,6-di-tert-butyl-4-methylphenol), which reduces the formation of peroxides. Bottles older than 3 months should be routinely tested for peroxides. An iron wire, releasing Fe(III) ions catalyzing the peroxide decomposition, was often added to bottles with diethyl ether as a preventive measure, however, Fe(III) ions also strongly enhance peroxide formation. Storage over NaOH precipitates the intermediate ether hydroperoxides.

{{Notelist}}

== See also References==

{{reflist|30em}}

*[[Fictional applications of real materials]]

== External links ==

{{Commons category}}

* [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] {{Webarchive|url=https://web.archive.org/web/20110522040512/http://journals.lww.com/anesthesiology/Abstract/1992/10000/Michael_Faraday_and_His_Contribution_to_Anesthesia.27.aspx |date=2011-05-22}}

* [http://www.erowid.org/chemicals/ether/ether.shtml Erowid]

* [httphttps://www.anesthesia-nursingcdc.comgov/etherniosh/npg/npgd0277.html TheCDC unusual– historyNIOSH ofPocket etherGuide asto anChemical anesthetic.Hazards]

* [http://www.welsch.com/e/index.php?chap=6_1&modulekey=wpmoleculeviewer&specialmol=60-29-7 diethyl ether 3D view and pdb-file]

{{General anesthetics}}

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