50:
315:
220:
518:
514:
41:
517:
589:
519:
865:
MTBE is used in organic chemistry as a relatively inexpensive solvent with properties comparable to diethyl ether, but with a higher boiling point and less solubility in water. As a solvent, MTBE has one distinct advantage over most ethers - it has a much lower tendency to form explosive organic
897:
produced from coconut shells and optimized for MTBE adsorption may reduce MTBE to undetectable levels, although this level of reduction is likely to occur only in the most ideal circumstances. There are currently no known published cases of any in-situ treatment method that has been capable of
866:
peroxides. It is widely used as a solvent in industry where, for safety and regulatory reasons, handling diethyl ether or other ethers is much more difficult and expensive. MTBE as a solvent is used in the oil refining industry as a method for dewaxing waxy petroleum fractions.
699:
converts the various light hydrocarbons in natural gas (primarily methane) into carbon monoxide and hydrogen. The resulting gases then further react in the presence of a catalyst to form methanol. Isobutylene can be produced through a variety of methods.
1079:
952:, $ 2 billion in transition assistance while MTBE was phased out over the following nine years. Due to opposition in the Senate, the conference report dropped all MTBE provisions. The final bill was signed into law by President
745:
is now considered to be the world's largest producer with an estimated production capacity of 2.37 million metric tons per year (mt/yr). Worldwide production capacity of MTBE in 2018 was estimated to be 35 million metric tons.
812:
An alternative to ethanol is ETBE, which is manufactured from ethanol and isobutene. Its performance as an additive is similar to MTBE, but due to the higher price of ethanol compared to methanol, it is more expensive.
1524:
VopiÄka, OndĆej; PilnĂĄÄek, KryĆĄtof; ÄĂhal, Petr; Friess, Karel (2016-03-01). "Sorption of methanol, dimethyl carbonate, methyl acetate, and acetone vapors in CTA and PTMSP: General findings from the GAB Analysis".
976:, including removing the compound from aquifers and municipal water supplies and replacing leaky underground oil tanks. In one case, the cost to oil companies to clean up the MTBE in wells belonging to the city of
882:(USTs) at gasoline stations or spills of gasoline. The higher water solubility and persistence of MTBE cause it to travel faster and farther than many other components of gasoline when released into an aquifer.
1842:
Charles
Babington, House Again Passes GOP Energy Measures, Washington Post, June 16, 2004, at A4 (House passes Energy Bill, but Senate opponents of MTBE provision in House Bill have the votes to prevent its
809:
Ethanol has been advertised as a safe alternative by agricultural and other interest groups in the U.S. and Europe. In 2003, California was the first U.S. state to start replacing MTBE with ethanol.
737:
MTBE production in the U.S. peaked in 1999 at 260,000 barrels per day before dropping down to about 50,000 barrels per day and holding steady, mostly for the export market. After the purchase of
1570:
VopiÄka, OndĆej; RadotĂnskĂœ, Daniel; Friess, Karel (2016-02-01). "Sorption of vapour mixtures of methanol and dimethyl carbonate in PTMSP: Cooperative and competitive sorption in one system".
535:
1351:
602:
1527:
1209:
520:
1165:"Hydrogen production via natural gas steam reforming in a Pd-Au membrane reactor. Investigation of reaction temperature and GHSV effects and long-term stability"
528:
364:
1630:
902:
1728:
1281:
847:
with water (52.6 °C; 96.5% MTBE) and methanol (51.3 °C; 68.6% MTBE). The solubility of water in MTBE is reported to be 1.5 g/100g at 23 °C.
1234:"The United States continues to export MTBE, mainly to Mexico, Chile, and Venezuela - Today in Energy - U.S. Energy Information Administration (EIA)"
1424:
850:
In an investigational medical procedure called contact dissolution therapy, MTBE is injected directly into the gallbladder to dissolve cholesterol
655:. MTBE is a volatile, flammable, and colorless liquid that is sparingly soluble in water. Primarily used as a fuel additive, MTBE is blended into
542:
1446:
1646:
2084:
1966:
1807:
790:). Before the introduction of other oxygenates and octane enhancers, refiners chose MTBE for its blending characteristics and low cost.
2343:
948:, then chairman of the Energy and Commerce Committee. This bill did include a provision that gave MTBE makers, including some major
329:
1257:
2208:
1115:
828:
MTBE is sometimes used as a solvent, although it is used less commonly than diethyl ether. Although an ether, MTBE is a poor
1878:
2373:
1477:
1762:
Fischer A, Oehm C, Selle M, Werner P (2005). "Biotic and abiotic transformations of methyl tertiary butyl ether (MTBE)".
609:
2279:
2213:
1746:
783:
272:
2363:
936:, as approved by the U.S. House of Representatives, did not include a provision for shielding MTBE manufacturers from
293:
1331:
1599:
2203:
2175:
1900:
1853:
1038:
956:. The lack of MTBE liability protection is resulting in a switchover to the use of ethanol as a gasoline additive.
1091:
854:. Due to concerns of MTBE toxicity and potentially serious side effects in the event of solvent draining into the
1627:
1376:
1075:
1004:
933:
906:
2036:
2188:
2077:
1725:
1572:
1027:
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565:
2022:
898:
reducing contaminant concentrations to baseline (pre-development) conditions within the aquifer soil matrix.
2353:
2348:
2294:
2218:
1011:
in 2022 but has not announced whether it will develop an MCL. EPA uses toxicity data in developing MCLs for
1008:
995:
Many lawsuits are still pending regarding MTBE contamination of public and private drinking water supplies.
874:
MTBE gives water an unpleasant taste at very low concentrations. MTBE often is introduced into water-supply
215:
157:
2145:
1696:
1043:
1865:
1885:. Fairfax, VA: Society of Independent Gasoline Marketers of America (SIGMA). 2005-05-23. Archived from
1536:
1306:
940:
lawsuits. This provision was first proposed in 2003 and had been thought by some to be a priority of
859:
62:
2368:
2358:
2070:
1726:
San
Francisco Bay Area Regional Water Quality Control Board Integrated Basin Management Plan (2004)
1450:
1432:
1033:
1012:
969:
937:
310:
123:
49:
2198:
1862:
1787:
965:
724:
1941:
1352:"Saudi Aramco's MTBE trading volume likely to rise after Sabic purchase | S&P Global Platts"
1282:"Aramco completes its acquisition of a 70% stake in SABIC from the Public Investment Fund (PIF)"
816:
Higher quality gasoline is also an alternative, so that additives such as MTBE are unnecessary.
2253:
2233:
2193:
1804:
1779:
1678:
1552:
1506:
680:
1922:
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2135:
2007:
1988:
1771:
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1544:
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894:
893:
bioreactor, MTBE may be removed rapidly and economically from water to undetectable levels.
833:
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17:
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2010:
1991:
1501:
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953:
820:
itself is used. MTBE plants can be retrofitted to produce iso-octane from isobutylene.
775:
580:
475:
1674:
1258:"United States | Methyl Tertiary Butyl Ether (MTBE): Production | Economic Indicators"
1068:
2337:
2093:
1018:
California established a state-level MCL for MTBE, 13 micrograms per liter, in 2000.
989:
981:
890:
660:
453:
443:
208:
1791:
1585:
2243:
2183:
2160:
1983:
EPA (1998-03-02). "Announcement of the
Drinking Water Contaminant Candidate List."
1662:
1471:
Matyash, V.; Liebisch, G.; Kurzchalia, T. V.; Shevchenko, A.; Schwudke, D. (2008).
984:
estimated a $ 250 million cost for cleanup of a single wellfield in the borough of
949:
799:
742:
786:. Oxygenates also dilute or displace gasoline components such as aromatics (e.g.,
261:
1886:
1400:
2284:
2125:
2115:
1139:
692:
688:
668:
554:
1660:
Schoenfield LJ, Marks JW (1993). "Oral and contact dissolution of gallstones".
1491:
774:
In the U.S. MTBE has been used in gasoline at low levels since 1979, replacing
2274:
1185:
945:
910:
886:
851:
829:
817:
412:
188:
2039:. Sacramento, CA: California State Water Resources Control Board. 2014-08-04.
1743:
1556:
992:$ 236 million in damages in order to treat groundwater contaminated by MTBE.
913:. MTBE may be tasted in water at concentrations of 5â15 ÎŒg/L (5-15ppb).
2312:
2269:
2120:
1775:
1473:"Lipid extraction by methyl-tert-butyl ether for high-throughput lipidomics"
941:
844:
759:
716:
708:
485:
1783:
1510:
1003:
EPA first listed MTBE in 1998 as a candidate for development of a national
1682:
2289:
2150:
2140:
2130:
2110:
1828:
1823:
1603:
1210:"Methyl Tertiary Butyl Ether (MTBE) Production and Manufacturing Process"
855:
684:
656:
541:
534:
527:
500:
1908:
715:-Butyl hydroperoxide derived from isobutane oxygenation is treated with
2223:
2155:
2002:
EPA (2022-11-14). "Drinking Water
Contaminant Candidate List 5âFinal."
1548:
973:
875:
837:
787:
433:
248:
1307:"Saudi Aramco buys SABIC shares on market as it completes acquisition"
836:. It is also unstable toward strong acids. It reacts dangerously with
885:
MTBE is biodegraded by the action of bacteria. In the proper type of
763:
755:
701:
1332:"Saudi Aramco to have largest MTBE capacity in Middle East and Asia"
579:
Except where otherwise noted, data are given for materials in their
798:
Other oxygenates are available as additives for gasoline including
711:
which can be dehydrogenated to isobutylene. In the Halcon process,
236:
40:
738:
168:
156:
146:
2096:
1007:(MCL) standard in drinking water. The agency listed MTBE on its
803:
227:
2066:
2062:
758:
engines. It is one of a group of chemicals commonly known as
1907:. New York, NY: Napoli Bern, LLP. 2004-03-16. Archived from
1092:"Methyl tertiary butyl ether prices, markets & analysis"
298:
2057:
1805:
http://www.cnn.com/2005/POLITICS/04/21/energy.bill.mtbe.ap/
1967:"Exxon Mobil is Found Negligent in New Hampshire MTBE Use"
1186:"methanol | Properties, Production, Uses, & Poisoning"
778:(TEL) as an antiknock (octane rating) additive to prevent
2037:"MTBE: Regulations and Drinking Water Monitoring Results"
1901:"Long Island Utility Fighting to Defeat MTBE Safe Harbor"
1600:"Interaction between bromine and tert-butyl methyl ether"
512:
1714:
https://www.aetna.com/cpb/medical/data/500_599/0509.html
1401:"Overview | Methyl Tertiary Butyl Ether (MTBE) | US EPA"
980:
was estimated to exceed $ 200 million. In another case,
597:
2052:
782:. Oxygenates also help gasoline burn more completely,
1602:. UK Chemical Reaction Hazards Forum. Archived from
862:techniques, this procedure is considered obsolete.
2303:
2262:
2174:
2103:
1942:"City Awarded $ 105 Million in Exxon Mobil Lawsuit"
1923:"Oil Companies Pay Santa Monica MTBE Cleanup Costs"
1163:Anzelmo, Bryce; Wilcox, Jennifer; Liguori, Simona.
1854:
1528:Journal of Polymer Science Part B: Polymer Physics
870:Persistence and pervasiveness in the environment
260:
2023:"How EPA Regulates Drinking Water Contaminants"
1377:"MTBE annual production capacity globally 2023"
559:â32.78 °C (â27.00 °F; 240.37 K)
516:
132:
448:â108.6 °C (â163.5 °F; 164.6 K)
2078:
988:in 2009. In 2013 a jury awarded the State of
754:MTBE is used as a fuel component in fuel for
8:
1824:"House approves $ 12 billion energy package"
1080:Institute for Occupational Safety and Health
968:in the U.S. was estimated to cost from $ 1
903:International Agency for Research on Cancer
794:Alternatives to MTBE as an anti-knock agent
734:-butanol can be dehydrated to isobutylene.
458:55.5 °C (131.9 °F; 328.6 K)
2085:
2071:
2063:
1852:United States. Energy Policy Act of 2005.
928:Restrictions on MTBE manufacturing and use
313:
218:
196:
26:
1500:
1490:
280:
1064:
1062:
1929:. Ecology Prime Media, Inc. 2005-02-17.
1058:
369:
334:
309:
573:435 °C (815 °F; 708 K)
209:
1647:CRC Handbook of Chemistry and Physics
1623:
1621:
917:Regulation and litigation in the U.S.
691:. Methanol is primarily derived from
341:Key: BZLVMXJERCGZMT-UHFFFAOYSA-N
176:
7:
909:, MTBE is not classified as a human
351:Key: BZLVMXJERCGZMT-UHFFFAOYAA
338:InChI=1S/C5H12O/c1-5(2,3)6-4/h1-4H3
251:
235:
1859:Tooltip Public Law (United States)
964:MTBE removal from groundwater and
832:and does not support formation of
348:InChI=1/C5H12O/c1-5(2,3)6-4/h1-4H3
25:
587:
399:
48:
39:
2209:2,4-Dimethyl-6-tert-butylphenol
1586:10.1016/j.eurpolymj.2015.12.015
583:(at 25 °C , 100 kPa).
1940:Navarro, Mireya (2009-10-20).
405:
393:
1:
1675:10.1016/S0002-9610(05)80934-1
1478:The Journal of Lipid Research
679:MTBE is manufactured via the
643:with a structural formula (CH
2280:Automatic transmission fluid
2214:Dinonylnaphthylsulfonic acid
2166:Racing fuel (Tetraethyllead)
1716:| access-date = June 3, 2024
960:Cleanup costs and litigation
1965:Earle, Sarah (2013-04-09).
1425:"NExOCTANEâą - Neste Jacobs"
1172:Journal of Membrane Science
784:reducing tailpipe emissions
18:Methyl tertiary butyl ether
2390:
2204:Dimethyl methylphosphonate
1764:Environ Sci Pollut Res Int
1697:"Health Guide: Gallstones"
1492:10.1194/jlr.D700041-JLR200
1140:"How is Methanol Produced"
1039:List of gasoline additives
1009:Contaminant Candidate List
999:Drinking water regulations
920:
2058:MTBE webpage from the EPA
1076:GESTIS Substance Database
1005:Maximum Contaminant Level
934:Energy Policy Act of 2005
907:World Health Organization
880:underground storage tanks
802:and other ethers such as
675:Production and properties
577:
494:
380:
360:
325:
116:
73:
67:2-Methoxy-2-methylpropane
61:
56:
47:
38:
2344:Hazardous air pollutants
2189:Butylated hydroxytoluene
1927:Environment News Service
1879:"MTBE Cleanup Estimates"
1573:European Polymer Journal
1429:www.nesteengineering.com
1028:Cyclopentyl methyl ether
978:Santa Monica, California
905:(IARC), a branch of the
707:can be isomerized into
2295:Windshield washer fluid
2239:Methyl tert-butyl ether
2219:2,6-Di-tert-butylphenol
2131:Lead Replacement Petrol
1776:10.1065/espr2005.08.277
1190:Encyclopedia Britannica
1071:Methyl tert-butyl ether
762:because they raise the
2146:Compressed natural gas
1868:. Approved 2005-08-08.
770:As anti-knocking agent
667:, and reduce unwanted
523:
490:3.4·10 Pa·s (at 25ÂșC)
766:content of gasoline.
522:
2374:Tert-butyl compounds
1013:public water systems
860:laparoscopic surgery
858:, and the advent of
505:(fire diamond)
63:Preferred IUPAC name
1905:The MTBE e-Resource
1883:SIGMA Weekly Report
1541:2016JPoSB..54..561V
1435:on January 6, 2006.
1286:www.saudiaramco.com
1034:Di-tert-butyl ether
938:water contamination
637:-butyl methyl ether
465:Solubility in water
420: g·mol
99:-Butyl methyl ether
35:
2364:Soil contamination
2199:1,2-Dichloroethane
2025:. EPA. 2017-05-03.
1946:The New York Times
1810:2005-04-22 at the
1749:2011-07-28 at the
1731:2008-02-29 at the
1633:2011-07-22 at the
1549:10.1002/polb.23945
1447:"KBR - NExOCTANEâą"
1144:METHANOL INSTITUTE
1047:-Amyl methyl ether
966:soil contamination
610:Infobox references
524:
428:colourless liquid
27:
2331:
2330:
2254:Tetranitromethane
2234:Metal deactivator
2194:1,2-Dibromoethane
2004:Federal Register,
901:According to the
834:Grignard reagents
681:chemical reaction
632:), also known as
618:Chemical compound
616:
615:
294:CompTox Dashboard
158:Interactive image
16:(Redirected from
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2318:MTBE controversy
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1606:on 13 March 2011
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1485:(5): 1137â1146.
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1449:. Archived from
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1431:. Archived from
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923:MTBE controversy
895:Activated carbon
665:knock resistance
659:to increase its
641:organic compound
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388:Chemical formula
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2323:Pay at the pump
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2229:Ethylenediamine
2170:
2111:Gasoline/petrol
2099:
2091:
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780:engine knocking
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721:propylene oxide
697:steam reforming
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470:26 g/L (20 °C)
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2176:Fuel additives
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2055:
2053:MTBE in Europe
2048:
2047:External links
2045:
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2014:
1995:
1976:
1957:
1932:
1914:
1911:on 2007-10-20.
1892:
1889:on 2009-10-09.
1870:
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1754:
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1701:New York Times
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1650:, 90th edition
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1535:(5): 561â569.
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1863:109â58 (text)
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1832:. 2005-04-22.
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1669:(4): 427â30.
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1453:on 2006-01-06
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891:fluidized bed
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661:octane rating
658:
642:
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631:
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569:
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531:
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484:
483:
480:27kPa (20ÂșC)
479:
477:
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457:
455:
454:Boiling point
452:
451:
447:
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444:Melting point
442:
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311:DTXSID3020833
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225:
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212:
210:ECHA InfoCard
207:
206:
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195:
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187:
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179:
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135:
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125:
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115:
107:
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101:
98:
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92:
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85:
82:
78:
77:
72:
64:
60:
55:
51:
46:
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32:
19:
2244:Nitromethane
2238:
2184:Butyl rubber
2161:Butanol fuel
2031:
2017:
2003:
1998:
1984:
1979:
1970:
1960:
1949:. Retrieved
1945:
1935:
1926:
1917:
1909:the original
1904:
1895:
1887:the original
1882:
1873:
1848:
1838:
1827:
1818:
1800:
1770:(6): 381â6.
1767:
1763:
1757:
1739:
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1709:
1700:
1691:
1666:
1663:Am. J. Surg.
1661:
1655:
1645:
1641:
1608:. Retrieved
1604:the original
1594:
1577:
1571:
1565:
1532:
1526:
1519:
1482:
1476:
1466:
1455:. Retrieved
1451:the original
1441:
1433:the original
1428:
1419:
1408:. Retrieved
1404:
1395:
1384:. Retrieved
1380:
1371:
1360:. Retrieved
1358:. 2019-04-09
1355:
1346:
1335:. Retrieved
1326:
1315:. Retrieved
1313:. 2020-06-14
1310:
1301:
1290:. Retrieved
1285:
1276:
1265:. Retrieved
1261:
1252:
1241:. Retrieved
1237:
1228:
1217:. Retrieved
1214:ICIS Explore
1213:
1204:
1193:. Retrieved
1189:
1180:
1171:
1158:
1147:. Retrieved
1143:
1134:
1123:. Retrieved
1119:
1116:"Oxygenates"
1110:
1099:. Retrieved
1096:ICIS Explore
1095:
1086:
1070:
1044:
1017:
1002:
994:
963:
931:
900:
889:, such as a
884:
873:
864:
849:
842:
827:
824:As a solvent
815:
811:
808:
797:
773:
753:
743:Saudi Aramco
741:, oil giant
736:
731:
725:
712:
702:
678:
634:
633:
629:
626:-butyl ether
623:
621:
620:
566:Autoignition
501:
438:0.7404 g/cm
372:O(C(C)(C)C)C
117:Identifiers
105:
96:
90:-butyl ether
87:
83:-butyl ether
80:
74:Other names
33:-butyl ether
30:
2285:Brake fluid
2136:Electricity
2126:Biogasoline
1843:enactment).
1580:: 243â250.
1238:www.eia.gov
1120:www.api.org
878:by leaking
843:MTBE forms
719:to produce
693:natural gas
689:isobutylene
568:temperature
555:Flash point
425:Appearance
381:Properties
216:100.015.140
178:CHEBI:27642
2369:Oxygenates
2359:Pollutants
2338:Categories
2275:Antifreeze
2104:Fuel types
1951:2010-05-12
1457:2006-01-31
1410:2021-04-07
1386:2020-06-28
1362:2020-06-29
1337:2020-06-29
1317:2020-06-29
1292:2020-06-29
1267:2020-06-28
1243:2020-06-28
1219:2020-06-29
1195:2020-06-29
1149:2020-06-29
1125:2020-06-28
1101:2020-06-28
1069:Record of
1054:References
972:to US$ 30
946:Joe Barton
911:carcinogen
887:bioreactor
852:gallstones
845:azeotropes
830:Lewis base
818:Iso-octane
760:oxygenates
413:Molar mass
282:29I4YB3S89
189:ChemSpider
145:3D model (
124:CAS Number
2313:Fuel card
2270:Motor oil
2121:Biodiesel
1971:Bloomberg
1744:link text
1557:1099-0488
944:and Rep.
942:Tom DeLay
717:propylene
709:isobutane
669:emissions
486:Viscosity
134:1634-04-4
2290:Gear oil
2151:Hydrogen
2141:Kerosene
1829:NBC News
1808:Archived
1792:97168152
1784:16305145
1747:Archived
1729:Archived
1631:Archived
1511:18281723
1381:Statista
1174:: 25â32.
1022:See also
876:aquifers
856:duodenum
756:gasoline
728:-butanol
695:, where
685:methanol
657:gasoline
639:, is an
502:NFPA 704
495:Hazards
81:tertiary
2224:Ecalene
2156:Ethanol
1855:Pub. L.
1683:8480875
1537:Bibcode
1502:2311442
1311:Reuters
1078:of the
1074:in the
974:billion
970:billion
838:bromine
800:ethanol
788:benzene
705:-butane
622:Methyl
603:what is
601: (
434:Density
249:PubChem
86:Methyl
79:Methyl
29:Methyl
2305:Retail
2263:Fluids
2116:Diesel
1861:
1790:
1782:
1681:
1610:13 May
1555:
1509:
1499:
1049:(TAME)
1030:(CPME)
986:Queens
764:oxygen
730:. The
598:verify
595:
418:88.150
365:SMILES
237:C11344
108:-BuOMe
57:Names
2097:fuels
2094:Motor
2011:68060
1992:10274
1987:, 63
1866:(PDF)
1788:S2CID
1168:(PDF)
739:SABIC
330:InChI
262:15413
198:14672
169:ChEBI
147:JSmol
1780:PMID
1679:PMID
1612:2010
1553:ISSN
1507:PMID
1045:tert
932:The
804:ETBE
750:Uses
723:and
687:and
663:and
651:COCH
635:tert
630:MTBE
624:tert
273:UNII
228:KEGG
106:tert
102:tBME
97:tert
93:MTBE
31:tert
2006:87
1772:doi
1671:doi
1667:165
1582:doi
1545:doi
1497:PMC
1487:doi
683:of
299:EPA
252:CID
2340::
2008:FR
1989:FR
1969:.
1944:.
1925:.
1903:.
1881:.
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1786:.
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1768:12
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1677:.
1620:^
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1379:.
1354:.
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1061:^
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840:.
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403:12
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1954:.
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529:2
406:O
400:H
397:5
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297:(
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88:t
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