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 = Merck Index, 11th Edition, 3732.

| 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
Ethyl tertiary butyl ether
Ethyl tert-butyl oxide
tert-Butyl ethyl ether
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/cm3

| 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 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 °C and a pressure of 0,8–1,3 MPa. The reaction is carried out with an acidic ion-exchange resin as a catalyst.{{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}}

File:Synthese von Ethyl-tert-butylether.svg

Suitable reactors are fixed-bed reactors such as tube bundle or circulation reactors in which the reflux can be cooled optionally.

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

References