View source for Ethyl tert-butyl ether

{{Short description|Oxygenate gasoline additive in the production of gasoline from crude oil}}
{{Use American English|date=March 2021}}
{{Use dmy dates|date=March 2021}}
{{More citations needed|date=November 2019}}
{{DISPLAYTITLE:Ethyl ''tert''-butyl ether}}
{{chembox
| Watchedfields = changed
| verifiedrevid = 413513038
| Name =Ethyl ''tert''-butyl ether
| Reference = <ref>''Merck Index'', 11th Edition, '''3732'''.</ref>
| ImageFile = Ethyl tert-butyl ether.svg
| ImageSize = 250px
| ImageFile1 = Ethyl-tert-butyl-ether-3D-balls.png
| ImageSize1 = 160px
| ImageName1 = Ball-and-stick model
| PIN = 2-Ethoxy-2-methylpropane
| OtherNames = Ethyl ''tert''-butyl ether<br>Ethyl tertiary butyl ether<br>Ethyl ''tert''-butyl oxide<br>''tert''-Butyl ethyl ether<br>Ethyl ''t''-butyl ether
|Section1={{Chembox Identifiers
| Abbreviations = ETBE
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 11996
| InChIKey = NUMQCACRALPSHD-UHFFFAOYAB
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C6H14O/c1-5-7-6(2,3)4/h5H2,1-4H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = NUMQCACRALPSHD-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 637-92-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 3R9B16WR19
| EINECS = 211-309-7
| PubChem = 12512
| SMILES = O(C(C)(C)C)CC
| InChI = 1/C6H14O/c1-5-7-6(2,3)4/h5H2,1-4H3
| RTECS =KN4730200
| MeSHName =
| ChEBI = 141564
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = 
}}
|Section2={{Chembox Properties
| C=6 | H=14 | O=1
| MolarMass =102.18
| Appearance =Clear colorless liquid
| Density = 0.7364 g/cm<sup>3</sup>
| MeltingPtC = -94
| MeltingPt_notes =
| BoilingPtC = 69 to 71
| BoilingPt_notes = 
| Solubility = 1.2 g/100 g
| SolubleOther = 
| Solvent = 
| pKa = 
| pKb = }}
|Section7={{Chembox Hazards
| MainHazards = 
| NFPA-H = 
| NFPA-F = 
| NFPA-R = 
| NFPA-S =
| GHSPictograms = {{GHS02}}{{GHS07}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|224|225|315|319|335|336}}
| PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|271|280|302+352|303+361+353|304+340|305+351+338|312|321|332+313|337+313|362|370+378|403+233|403+235|405|501}}
| FlashPtC = -19
| AutoignitionPtC = 
| ExploLimits = 
| PEL = 
 }}
}}

'''Ethyl ''tertiary''-butyl ether''' ('''ETBE'''), also known as '''ethyl ''tert''-butyl ether''', is commonly used as an [[oxygenate]] [[gasoline additive]] in the production of [[gasoline]] from [[crude oil]].  ETBE offers equal or greater air quality benefits than [[ethanol]], while being technically and logistically less challenging. Unlike ethanol, ETBE does not induce evaporation of gasoline, which is one of the causes of [[smog]], and does not [[hygroscopic|absorb moisture]] from the atmosphere.

== Production ==
Ethyl tert-butyl ether is manufactured industrially by the acidic etherification of [[isobutylene]] with [[ethanol]] at a temperature of 30–110&nbsp;°C and a pressure of 0,8–1,3 MPa. The reaction is carried out with an acidic [[ion-exchange resin]] as a [[catalyst]].<ref name=production>{{cite web |last1=Grömping |first1=Matthias |last2=Höper |first2=Frank |last3=Leistner |first3=Jörg |last4=Nierlich |first4=Franz |last5=Peters |first5=Udo |last6=Praefke |first6=Jochen |last7=Rix |first7=Armin |last8=Röttger |first8=Dirk |last9=Santiago Fernandez  |first9=Silvia |title=Preparing ethyl tertiary butylether from hydrocarbon mixture, useful as fuel additive, comprises reacting isobutene with ethanol, separating the hydrocarbon, reacting separated isobutene with ethanol and separating unconverted hydrocarbon |url=https://patents.google.com/patent/DE102005062722A1/en?q=verfahren+zur+herstellung+von&q=etbe&oq=verfahren+zur+herstellung+von+etbe |website=Google Patents |publisher=Evonik Degussa GmbH |access-date=5 March 2019 |ref=production method}}</ref>
[[File:Synthese von Ethyl-tert-butylether.svg|frameless|upright=3.5|center|Synthesis of Ethyl tert-butyl ether]]
Suitable reactors are fixed-bed reactors such as tube bundle or circulation reactors in which the reflux can be cooled optionally.<ref name="production" />

[[Ethanol]], produced by fermentation and distillation, is more expensive than [[methanol]], which is derived from natural gas. Therefore, [[MTBE]], made from methanol is cheaper than ETBE, made from ethanol.

== See also ==
*[[Methyl tert-butyl ether|Methyl ''tert''-butyl ether]] (MTBE) 
*[[tert-Amyl methyl ether|''tert''-Amyl methyl ether]] (TAME) 
*[[Tetraethyllead]] (TEL)
*[[List of gasoline additives]]

==References==
<references/>

==External links==
* [http://ecb.jrc.it/classlab/8306_FIN_ETBE.doc EC Joint Research Centre ETBE risk assessment report]{{Dead link|date=August 2019 |bot=InternetArchiveBot |fix-attempted=yes }}
* [http://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=CELEX:31998L0070:EN:NOT Directive 98/70/EC of the European Parliament and of the Council of 13 October 1998 relating to the quality of petrol and diesel fuels and amending Council Directive 93/12/EEC]
* [https://web.archive.org/web/20110930011745/http://circa.europa.eu/Public/irc/env/fuel_quality/library?l=%2Fstakeholder_october%2Fpresentations%2Fcopert_brusselsppt%2F_EN_1.0_&a=d An assessment of the impact of ethanol-blended petrol on the total NMVOC emission from road transport in selected countries]

{{Authority control}}

[[Category:Commodity chemicals]]
[[Category:Dialkyl ethers]]
[[Category:Ether solvents]]
[[Category:Oxygenates]]
[[Category:Pollutants]]
[[Category:Tert-butyl compounds]]