Ethyl tert-butyl ether: Difference between revisions

Ethyl *tert*-butyl ether^[1]
Names
	Preferred IUPAC name 2-Ethoxy-2-methylpropane
	Other names Ethyl tert-butyl ether; Ethyl tertiary butyl ether; Ethyl tert-butyl oxide; tert-Butyl ethyl ether; Ethyl t-butyl ether
Identifiers
CAS Number	637-92-3 ;
3D model (JSmol)	Interactive image;
Abbreviations	ETBE
ChEBI	CHEBI:141564;
ChemSpider	11996 ;
ECHA InfoCard	100.010.282
EC Number	211-309-7;
PubChem CID	12512;
RTECS number	KN4730200;
UNII	3R9B16WR19 ;
CompTox Dashboard (EPA)	DTXSID601024578 DTXSID0025604, DTXSID601024578 ;
	InChI InChI=1S/C6H14O/c1-5-7-6(2,3)4/h5H2,1-4H3 Key: NUMQCACRALPSHD-UHFFFAOYSA-N ; InChI=1/C6H14O/c1-5-7-6(2,3)4/h5H2,1-4H3 Key: NUMQCACRALPSHD-UHFFFAOYAB;
	SMILES O(C(C)(C)C)CC;
Properties
Chemical formula	C6H14O
Molar mass	102.18
Appearance	Clear colorless liquid
Density	0.7364 g/cm3
Melting point	−94 °C (−137 °F; 179 K)
Boiling point	69 to 71 °C (156 to 160 °F; 342 to 344 K)
Solubility in water	1.2 g/100 g
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H224, H225, H315, H319, H335, H336
Precautionary statements	P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, P501
Flash point	−19 °C (−2 °F; 254 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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Latest revision as of 20:33, 9 April 2022

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.^[2]

Suitable reactors are fixed-bed reactors such as tube bundle or circulation reactors in which the reflux can be cooled optionally.^[2]

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.

References

^ Merck Index, 11th Edition, 3732.
^ ^a ^b Grömping, Matthias; Höper, Frank; Leistner, Jörg; Nierlich, Franz; Peters, Udo; Praefke, Jochen; Rix, Armin; Röttger, Dirk; Santiago Fernandez, Silvia. "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". Google Patents. Evonik Degussa GmbH. Retrieved 5 March 2019.

External links

[1] Merck Index, 11th Edition, 3732.

[production-2] Grömping, Matthias; Höper, Frank; Leistner, Jörg; Nierlich, Franz; Peters, Udo; Praefke, Jochen; Rix, Armin; Röttger, Dirk; Santiago Fernandez, Silvia. "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". Google Patents. Evonik Degussa GmbH. Retrieved 5 March 2019.

[1]

[2]

@@ Line 1: / Line 1: @@
+{{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
@@ Line 5: / Line 9: @@
 | Name =Ethyl ''tert''-butyl ether
 | Reference = <ref>''Merck Index'', 11th Edition, '''3732'''.</ref>
-| ImageFile = Ethyl-tertiary-butyl-ether-chemical.png
+| ImageFile = Ethyl tert-butyl ether.svg
 | ImageSize = 250px
 | ImageFile1 = Ethyl-tert-butyl-ether-3D-balls.png
 | ImageSize1 = 160px
 | 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
 |Section1={{Chembox Identifiers
@@ Line 23: / Line 27: @@
 | CASNo_Ref = {{cascite|correct|CAS}}
 | CASNo = 637-92-3
+| UNII_Ref = {{fdacite|correct|FDA}}
+| UNII = 3R9B16WR19
 | EINECS = 211-309-7
 | PubChem = 12512
@@ Line 29: / Line 35: @@
 | RTECS =KN4730200
 | MeSHName =
+| ChEBI = 141564
-| ChEBI_Ref = {{ebicite|correct|EBI}}
-| ChEBI =
 | KEGG_Ref = {{keggcite|correct|kegg}}
 | KEGG =
+}}
-| ATCCode_prefix =
-| ATCCode_suffix =
-| ATC_Supplemental =}}
 |Section2={{Chembox Properties
-| C =6|H=14|O=1
+| C=6 | H=14 | O=1
 | MolarMass =102.18
 | Appearance =Clear colorless liquid
 | Density = 0.7364 g/cm<sup>3</sup>
 | MeltingPtC = -94
-| Melting_notes =
+| MeltingPt_notes =
 | BoilingPtC = 69 to 71
-| Boiling_notes =
+| BoilingPt_notes =
 | Solubility = 1.2 g/100 g
 | SolubleOther =
@@ Line 51: / Line 54: @@
 | pKb = }}
 |Section7={{Chembox Hazards
-| EUClass =
-| EUIndex =
 | MainHazards =
 | NFPA-H =
 | NFPA-F =
 | 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}}
 | FlashPtC = -19
 | AutoignitionPtC =
@@ Line 68: / Line 70: @@
 }}
-'''Ethyl ''tert''-butyl ether''' ('''ETBE''') 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.
+'''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.
-== Synthesis ==
+== 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>
-It is synthesized by mixing [[ethanol]] and [[isobutylene]] and reacting them with heat over a [[catalyst]].
+[[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" />
-[[Image:ETBE-Synthese (Reaktionsgleichung).png|400px]]
 [[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.
@@ Line 80: / Line 82: @@
 *[[Methyl tert-butyl ether|Methyl ''tert''-butyl ether]] (MTBE)
 *[[tert-Amyl methyl ether|''tert''-Amyl methyl ether]] (TAME)
-*[[Tetraethyl lead]] (TEL)
+*[[Tetraethyllead]] (TEL)
+*[[List of gasoline additives]]
 ==References==
@@ Line 86: / Line 89: @@
 ==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://www.efoa.org/docs/ETBE_PRODUCT_BULLETTIN_JUN_2006.PDF ETBE Product Bulletin]
-* [http://ecb.jrc.it/classlab/8306_FIN_ETBE.doc EC Joint Research Centre ETBE risk assessment report]
 * [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]
-* [http://circa.europa.eu/Public/irc/env/fuel_quality/library?l=/stakeholder_october/presentations/copert_brusselsppt/_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]
+* [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:Biofuels technology]]
 [[Category:Commodity chemicals]]
-[[Category:Ethers]]
+[[Category:Dialkyl ethers]]
 [[Category:Ether solvents]]
 [[Category:Oxygenates]]
 [[Category:Pollutants]]
+[[Category:Tert-butyl compounds]]

Latest revision as of 20:33, 9 April 2022

Production

See also

References

External links