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{{Short description|Oxygenate gasoline additive in the production of gasoline from crude oil}} |
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{{Use American English|date=March 2021}} |
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{{Use dmy dates|date=March 2021}} |
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{{More citations needed|date=November 2019}} |
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{{DISPLAYTITLE:Ethyl ''tert''-butyl ether}} |
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{{DISPLAYTITLE:Ethyl ''tert''-butyl ether}} |
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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 402115048 |
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| verifiedrevid = 413513038 |
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| Name=Ethyl ''tert''-butyl ether |
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| Name =Ethyl ''tert''-butyl ether |
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| Reference = <ref>''Merck Index'', 11th Edition, '''3732'''.</ref> |
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| Reference = <ref>''Merck Index'', 11th Edition, '''3732'''.</ref> |
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| ImageFile = Ethyl-tertiary-butyl-ether-chemical.png |
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| ImageFile = Ethyl tert-butyl ether.svg |
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| ImageSize = 250px |
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| ImageSize = 250px |
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| ImageFile1 = Ethyl-tert-butyl-ether-3D-balls.png |
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| ImageFile1 = Ethyl-tert-butyl-ether-3D-balls.png |
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| ImageSize1 = 160px |
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| ImageSize1 = 160px |
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| ImageName1 = Ball-and-stick model |
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| ImageName1 = Ball-and-stick model |
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| IUPACName = 2-Ethoxy-2-methyl-propane |
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| PIN = 2-Ethoxy-2-methylpropane |
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| 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 |
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| 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 |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| Abbreviations = ETBE |
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| Abbreviations = ETBE |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 637-92-3 |
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| CASNo = 637-92-3 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 3R9B16WR19 |
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| EINECS = 211-309-7 |
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| EINECS = 211-309-7 |
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| PubChem = 12512 |
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| PubChem = 12512 |
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| RTECS =KN4730200 |
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| RTECS =KN4730200 |
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| MeSHName = |
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| MeSHName = |
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| ChEBI = |
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| ChEBI = 141564 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = |
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| KEGG = |
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}} |
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| ATCCode_prefix = |
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|Section2={{Chembox Properties |
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| ATCCode_suffix = |
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| C=6 | H=14 | O=1 |
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| ATC_Supplemental =}} |
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| Section2 = {{Chembox Properties |
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| C=6|H=14|O=1 |
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| MolarMass =102.18 |
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| MolarMass =102.18 |
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| Appearance =Clear colorless liquid |
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| Appearance =Clear colorless liquid |
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| Density = 0.7364 g/cm<sup>3</sup> |
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| Density = 0.7364 g/cm<sup>3</sup> |
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| MeltingPtC = -94 |
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| MeltingPtC = -94 |
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| Melting_notes = |
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| MeltingPt_notes = |
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| BoilingPt = 69-71 °C |
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| BoilingPtC = 69 to 71 |
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| Boiling_notes = |
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| BoilingPt_notes = |
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| Solubility = 1.2 g/100 g |
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| Solubility = 1.2 g/100 g |
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| SolubleOther = |
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| SolubleOther = |
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| pKa = |
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| pKa = |
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| pKb = }} |
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| pKb = }} |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| EUClass = |
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| EUIndex = |
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| MainHazards = |
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| MainHazards = |
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| NFPA-H = |
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| NFPA-H = |
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| NFPA-F = |
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| NFPA-F = |
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| NFPA-R = |
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| NFPA-R = |
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| NFPA-O = |
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| NFPA-S = |
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| RPhrases = {{R11}} {{R20}} |
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| GHSPictograms = {{GHS02}}{{GHS07}} |
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| GHSSignalWord = Danger |
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| SPhrases = {{S16}} |
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| HPhrases = {{H-phrases|224|225|315|319|335|336}} |
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| RSPhrases = |
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| 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}} |
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| FlashPt = -19 °C |
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| Autoignition = |
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| FlashPtC = -19 |
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| AutoignitionPtC = |
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| ExploLimits = |
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| ExploLimits = |
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| PEL = }} |
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| PEL = |
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}} |
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}} |
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}} |
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'''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. |
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'''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. |
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== Synthesis == |
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== Production == |
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Ethyl tert-butyl ether is manufactured industrially by the acidic etherification of ] with ] at a temperature of 30–110 °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> |
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It is synthesized by mixing ] and ] and reacting them with heat over a ]. |
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] |
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Suitable reactors are fixed-bed reactors such as tube bundle or circulation reactors in which the reflux can be cooled optionally.<ref name="production" /> |
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], 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. |
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], 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. |
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== See also == |
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== See also == |
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*] |
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*] (MTBE) |
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*] |
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*] (TAME) |
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*] (TEL) |
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*] |
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==References== |
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==References== |
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==External links== |
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==External links== |
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