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{{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}} {{DISPLAYTITLE:Ethyl ''tert''-butyl ether}}
{{chembox {{chembox
| Watchedfields = changed
| verifiedrevid = 402115048 | verifiedrevid = 413513038
| Name=Ethyl ''tert''-butyl ether | Name =Ethyl ''tert''-butyl ether
| Reference = <ref>''Merck Index'', 11th Edition, '''3732'''.</ref> | Reference = <ref>''Merck Index'', 11th Edition, '''3732'''.</ref>
| ImageFile = Ethyl-tertiary-butyl-ether-chemical.png | ImageFile = Ethyl tert-butyl ether.svg
| ImageSize = 250px | ImageSize = 250px
| ImageFile1 = Ethyl-tert-butyl-ether-3D-balls.png | ImageFile1 = Ethyl-tert-butyl-ether-3D-balls.png
| ImageSize1 = 160px | ImageSize1 = 160px
| ImageName1 = Ball-and-stick model | ImageName1 = Ball-and-stick model
| IUPACName = 2-Ethoxy-2-methyl-propane | 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 | 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 |Section1={{Chembox Identifiers
| Abbreviations = ETBE | Abbreviations = ETBE
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 637-92-3 | CASNo = 637-92-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 3R9B16WR19
| EINECS = 211-309-7 | EINECS = 211-309-7
| PubChem = 12512 | PubChem = 12512
Line 28: Line 35:
| RTECS =KN4730200 | RTECS =KN4730200
| MeSHName = | MeSHName =
| ChEBI = | ChEBI = 141564
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = | KEGG =
}}
| ATCCode_prefix =
|Section2={{Chembox Properties
| ATCCode_suffix =
| C=6 | H=14 | O=1
| ATC_Supplemental =}}
| Section2 = {{Chembox Properties
| C=6|H=14|O=1
| MolarMass =102.18 | MolarMass =102.18
| Appearance =Clear colorless liquid | Appearance =Clear colorless liquid
| Density = 0.7364 g/cm<sup>3</sup> | Density = 0.7364 g/cm<sup>3</sup>
| MeltingPtC = -94 | MeltingPtC = -94
| Melting_notes = | MeltingPt_notes =
| BoilingPt = 69-71 °C | BoilingPtC = 69 to 71
| Boiling_notes = | BoilingPt_notes =
| Solubility = 1.2 g/100 g | Solubility = 1.2 g/100 g
| SolubleOther = | SolubleOther =
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| pKa = | pKa =
| pKb = }} | pKb = }}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
| EUClass =
| EUIndex =
| MainHazards = | MainHazards =
| NFPA-H = | NFPA-H =
| NFPA-F = | NFPA-F =
| NFPA-R = | NFPA-R =
| NFPA-O = | NFPA-S =
| RPhrases = {{R11}} {{R20}} | GHSPictograms = {{GHS02}}{{GHS07}}
| GHSSignalWord = Danger
| SPhrases = {{S16}}
| HPhrases = {{H-phrases|224|225|315|319|335|336}}
| RSPhrases =
| 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}}
| FlashPt = -19 °C
| Autoignition = | FlashPtC = -19
| AutoignitionPtC =
| ExploLimits = | ExploLimits =
| PEL = }} | PEL =
}}
}} }}


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


== Synthesis == == Production ==
Ethyl tert-butyl ether is manufactured industrially by the acidic etherification of ] with ] 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 ] as a ].<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>
It is synthesized by mixing ] and ] and reacting them with heat over a ].
]

Suitable reactors are fixed-bed reactors such as tube bundle or circulation reactors in which the reflux can be cooled optionally.<ref name="production" />
]


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


== See also == == See also ==
*] *] (MTBE)
*] *] (TAME)
*] (TEL)
*]


==References== ==References==
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==External links== ==External links==
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