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Methyl tert-butyl ether

February 09, 2023

Methyl tertiary-butyl ether (MTBE), also known as methyl tert-butyl ether and tert-butyl methyl ether, is an organic compound with a structural formula (CH3)3COCH3. MTBE is a volatile, flammable, and colorless liquid that is sparingly soluble[1] in water. Primarily used as a fuel additive, MTBE is blended into gasoline to increase its octane rating and knock resistance, and reduce unwanted emissions.[2][3]

Methyl tert-butyl ether
Names
Preferred IUPAC name
2-Methoxy-2-methylpropane
Other names
Methyl tertiary-butyl ether; Methyl tert-butyl ether; Methyl t-butyl ether; MTBE; tert-Butyl methyl ether; tBME; tert-BuOMe
Identifiers
  • 1634-04-4 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:27642 Y
ChemSpider
  • 14672 Y
ECHA InfoCard 100.015.140
KEGG
  • C11344 Y
  • 15413
UNII
  • 29I4YB3S89 Y
  • DTXSID3020833
  • InChI=1S/C5H12O/c1-5(2,3)6-4/h1-4H3 Y
    Key: BZLVMXJERCGZMT-UHFFFAOYSA-N Y
  • InChI=1/C5H12O/c1-5(2,3)6-4/h1-4H3
    Key: BZLVMXJERCGZMT-UHFFFAOYAA
  • O(C(C)(C)C)C
Properties
C5H12O
Molar mass 88.150 g·mol−1
Appearance colourless liquid
Density 0.7404 g/cm3
Melting point −109 °C (−164 °F; 164 K)
Boiling point 55.2 °C (131.4 °F; 328.3 K)
26 g/L (20 °C)[1]
Viscosity 0.36 cP at 25 °C
Hazards
NFPA 704 (fire diamond)
1
3
Flash point −33.0 °C (−27.4 °F; 240.2 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)

Production and properties

MTBE is manufactured via the chemical reaction of methanol and isobutylene. Methanol is primarily derived from natural gas,[4] where steam reforming converts the various light hydrocarbons in natural gas (primarily methane) into carbon monoxide and hydrogen.[5] The resulting gases then further react in the presence of a catalyst to form methanol.[6] Isobutylene can be produced through a variety of methods. One process the isomerization of n-butane into isobutane, which then undergoes dehydrogenation to form the isobutylene.[7] In the Halcon process, t-Butyl hydroperoxide derived from isobutane oxygenation is reacted with propylene to produce propylene oxide and t-butanol. The t-butanol can be dehydrated to isobutylene.

MTBE production in the U.S. peaked in 1999 at 260,000 barrels per day[8] before dropping down to about 50,000 barrels per day and holding steady,[9] mostly for the export market. After the purchase of SABIC,[10][11] oil giant Saudi Aramco is now considered to be the world's largest producer[12] with an estimated production capacity of 2.37 million metric tons per year (mt/yr).[13] Worldwide production capacity of MTBE in 2018 was estimated to be 35 million metric tons.[14]

Uses

MTBE is used as a fuel component in fuel for gasoline engines. It is one of a group of chemicals commonly known as oxygenates because they raise the oxygen content of gasoline.

As anti-knocking agent

In the U.S. MTBE has been used in gasoline at low levels since 1979, replacing tetraethyllead (TEL) as an antiknock (octane rating) additive to prevent engine knocking.[15] Oxygenates also help gasoline burn more completely, reducing tailpipe emissions and dilute or displace gasoline components such as aromatics (e.g., benzene). Before the introduction of other oxygenates and octane enhancers, refiners chose MTBE for its blending characteristics and low cost.

Alternatives to MTBE as an anti-knock agent

Other oxygenates are available as additives for gasoline including ethanol and other ethers such as ETBE.

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.

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.

Higher quality gasoline is also an alternative, so that additives such as MTBE are unnecessary. Iso-octane itself is used. MTBE plants can be retrofitted to produce iso-octane from isobutylene.[16][17]

As a solvent

MTBE is extensively used in industry as a safer alternative to diethyl ether (which is commonly used in academic research) as the tert-butyl group prevents MTBE from forming potentially explosive peroxides. It also is used as a solvent in academic research,[18][19][20] although it is used less commonly than diethyl ether. Although an ether, MTBE is a poor Lewis base and does not support formation of Grignard reagents. It is also unstable toward strong acids. It reacts dangerously with bromine.[21]

MTBE forms azeotropes with water (52.6 °C; 96.5% MTBE)[22] and methanol (51.3 °C; 68.6% MTBE).[23]

In a medical procedure called contact dissolution therapy, MTBE is injected directly into the gallbladder to dissolve gallstones.[24][25]

Persistence and pervasiveness in the environment

MTBE gives water an unpleasant taste at very low concentrations. MTBE often is introduced into water-supply aquifers by leaking underground storage tanks (USTs) at gasoline stations or by gasoline containing MTBE being spilled onto the ground. 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.[26]

MTBE is biodegraded by the action of bacteria. In the proper type of bioreactor, such as a fluidized bed bioreactor, MTBE may be removed rapidly and economically from water to undetectable levels. Activated carbon produced from coconut shells and optimized for MTBE adsorption may reduce MTBE to undetectable levels,[27] 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 reducing contaminant concentrations to baseline (pre-development) conditions within the aquifer soil matrix.

According to the International Agency for Research on Cancer (IARC), a cancer research agency of the World Health Organization, MTBE is not classified as a human carcinogen. MTBE may be tasted in water at concentrations of 5–15 µg/L (5-15ppb).[28]

As of 2007, researchers have limited data about the health effects of ingestion of MTBE. The United States Environmental Protection Agency (EPA) has concluded that available data are inadequate to quantify health risks of MTBE at low exposure levels in drinking water, but the data support the conclusion that MTBE is a potential human carcinogen at high doses.[29]

Regulation and litigation in the U.S.

Main article: MTBE controversy

Restrictions on MTBE manufacturing and use

In 2000, EPA drafted plans to phase out the use of MTBE nationwide over four years.[citation needed] Some states enacted MTBE prohibitions without waiting for federal restrictions. California banned MTBE as a gasoline additive in 2002.[30] The State of New York banned the use of MTBE as a "fuel additive", effective in 2004.[31] However, MTBE is still legal in the state for other industrial uses.[32]

The Energy Policy Act of 2005, as approved by the U.S. House of Representatives, did not include a provision for shielding MTBE manufacturers from water contamination lawsuits. This provision was first proposed in 2003 and had been thought by some to be a priority of Tom DeLay and Rep. Joe Barton, then chairman of the Energy and Commerce Committee.[33] This bill did include a provision that gave MTBE makers, including some major oil companies, $2 billion in transition assistance while MTBE was phased out over the following nine years.[34] Due to opposition in the Senate,[35] the conference report dropped all MTBE provisions. The final bill was signed into law by President George W. Bush.[36] The lack of MTBE liability protection is resulting in a switchover to the use of ethanol as a gasoline additive.

Cleanup costs and litigation

MTBE removal from groundwater and soil contamination in the U.S. was estimated to cost from $1 billion[37] to US$30 billion,[38] 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 Santa Monica, California was estimated to exceed $200 million.[39] In another case, New York City estimated a $250 million cost for cleanup of a single wellfield in the borough of Queens in 2009.[40] In 2013 a jury awarded the State of New Hampshire $236 million in damages in order to treat groundwater contaminated by MTBE.[41]

As of 2016, hundreds of lawsuits are still pending regarding MTBE contamination of public and private drinking water supplies.[citation needed]

Drinking water regulations

EPA first listed MTBE in 1998 as a candidate for development of a national Maximum Contaminant Level (MCL) standard in drinking water.[42] As of 2020 the agency has not announced whether it will develop an MCL.[43] EPA uses toxicity data in developing MCLs for public water systems.[44]

California established a state-level MCL for MTBE, 13 micrograms per liter, in 2000.[45]

See also

References

  1. ^ a b Record of Methyl tert-butyl ether in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. ^ "Methyl tertiary butyl ether prices, markets & analysis". ICIS Explore. Retrieved 2020-06-28.
  3. ^ "Oxygenates". www.api.org. Retrieved 2020-06-28.
  4. ^ "How is Methanol Produced". METHANOL INSTITUTE. Retrieved 2020-06-29.
  5. ^ Anzelmo, Bryce; Wilcox, Jennifer; Liguori, Simona. "Hydrogen production via natural gas steam reforming in a Pd-Au membrane reactor. Investigation of reaction temperature and GHSV effects and long-term stability" (PDF). Journal of Membrane Science: 25–32.
  6. ^ "methanol | Properties, Production, Uses, & Poisoning". Encyclopedia Britannica. Retrieved 2020-06-29.
  7. ^ "Methyl Tertiary Butyl Ether (MTBE) Production and Manufacturing Process". ICIS Explore. Retrieved 2020-06-29.
  8. ^ "The United States continues to export MTBE, mainly to Mexico, Chile, and Venezuela - Today in Energy - U.S. Energy Information Administration (EIA)". www.eia.gov. Retrieved 2020-06-28.
  9. ^ "United States | Methyl Tertiary Butyl Ether (MTBE): Production | Economic Indicators". www.ceicdata.com. Retrieved 2020-06-28.
  10. ^ "Aramco completes its acquisition of a 70% stake in SABIC from the Public Investment Fund (PIF)". www.saudiaramco.com. Retrieved 2020-06-29.
  11. ^ "Saudi Aramco buys SABIC shares on market as it completes acquisition". Reuters. 2020-06-14. Retrieved 2020-06-29.
  12. ^ "Saudi Aramco to have largest MTBE capacity in Middle East and Asia". Retrieved 2020-06-29.
  13. ^ "Saudi Aramco's MTBE trading volume likely to rise after Sabic purchase | S&P Global Platts". www.spglobal.com. 2019-04-09. Retrieved 2020-06-29.
  14. ^ "MTBE annual production capacity globally 2023". Statista. Retrieved 2020-06-28.
  15. ^ "Overview | Methyl Tertiary Butyl Ether (MTBE) | US EPA". archive.epa.gov. Retrieved 2021-04-07.
  16. ^ . www.nesteengineering.com. Archived from the original on January 6, 2006.
  17. ^ . Archived from the original on 2006-01-06. Retrieved 2006-01-31.
  18. ^ Matyash, V.; Liebisch, G.; Kurzchalia, T. V.; Shevchenko, A.; Schwudke, D. (2008). "Lipid extraction by methyl-tert-butyl ether for high-throughput lipidomics". The Journal of Lipid Research. 49 (5): 1137–1146. doi:10.1194/jlr.D700041-JLR200. PMC 2311442. PMID 18281723.
  19. ^ Vopička, Ondřej; Pilnáček, Kryštof; Číhal, 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". Journal of Polymer Science Part B: Polymer Physics. 54 (5): 561–569. Bibcode:2016JPoSB..54..561V. doi:10.1002/polb.23945. ISSN 1099-0488.
  20. ^ Vopička, Ondřej; Radotínský, Daniel; Friess, Karel (2016-02-01). "Sorption of vapour mixtures of methanol and dimethyl carbonate in PTMSP: Cooperative and competitive sorption in one system". European Polymer Journal. 75: 243–250. doi:10.1016/j.eurpolymj.2015.12.015.
  21. ^ . UK Chemical Reaction Hazards Forum. Archived from the original on 13 March 2011. Retrieved 13 May 2010.
  22. ^ Zeon Corporation 2011-07-22 at the Wayback Machine
  23. ^ CRC Handbook of Chemistry and Physics, 90th edition
  24. ^ Schoenfield LJ, Marks JW (1993). "Oral and contact dissolution of gallstones". Am. J. Surg. 165 (4): 427–30. doi:10.1016/S0002-9610(05)80934-1. PMID 8480875.
  25. ^ "Health Guide: Gallstones". New York Times.
  26. ^ San Francisco Bay Area Regional Water Quality Control Board Integrated Basin Management Plan (2004) 2008-02-29 at the Wayback Machine
  27. ^ link text 2011-07-28 at the Wayback Machine
  28. ^ Fischer A, Oehm C, Selle M, Werner P (2005). "Biotic and abiotic transformations of methyl tertiary butyl ether (MTBE)". Environ Sci Pollut Res Int. 12 (6): 381–6. doi:10.1065/espr2005.08.277. PMID 16305145. S2CID 97168152.
  29. ^ "Methyl Tertiary Butyl Ether (MTBE) | US EPA".
  30. ^ "California Reformulated Gasoline Phase 3". Sacramento, CA: California Air Resources Board. 2015-07-24.
  31. ^ "Spill Response & Remediation FAQ". Chemical and Pollution Control. Albany, NY: New York State Department of Environmental Conservation. Retrieved 2018-04-06.
  32. ^ State of New York. New York Consolidated Laws, Agriculture and Markets Law. "AGM § 192-g. Methyl tertiary butyl ether; prohibited."
  33. ^ http://www.cnn.com/2005/POLITICS/04/21/energy.bill.mtbe.ap/ 2005-04-22 at the Wayback Machine
  34. ^ "House approves $12 billion energy package". NBC News. 2005-04-22.
  35. ^ 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 enactment).
  36. ^ United States. Energy Policy Act of 2005. Pub. L. 109–58 (text) (PDF). Approved 2005-08-08.
  37. ^ . SIGMA Weekly Report. Fairfax, VA: Society of Independent Gasoline Marketers of America (SIGMA). 2005-05-23. Archived from the original on 2009-10-09.
  38. ^ . The MTBE e-Resource. New York, NY: Napoli Bern, LLP. 2004-03-16. Archived from the original on 2007-10-20.
  39. ^ "Oil Companies Pay Santa Monica MTBE Cleanup Costs". Environment News Service. Ecology Prime Media, Inc. 2005-02-17.
  40. ^ Navarro, Mireya (2009-10-20). "City Awarded $105 Million in Exxon Mobil Lawsuit". The New York Times. Retrieved 2010-05-12.
  41. ^ Earle, Sarah (2013-04-09). "Exxon Mobil is Found Negligent in New Hampshire MTBE Use". Bloomberg.
  42. ^ EPA (1998-03-02). "Announcement of the Drinking Water Contaminant Candidate List." Federal Register, 63 FR 10274
  43. ^ "Drinking Water Regulations Under Development or Review". EPA. 2020-01-27.
  44. ^ "How EPA Regulates Drinking Water Contaminants". EPA. 2017-05-03.
  45. ^ "MTBE: Regulations and Drinking Water Monitoring Results". Sacramento, CA: California State Water Resources Control Board. 2014-08-04.

External links

  • MTBE in Europe
  • MTBE webpage from the EPA
  • Summary of health effects data from IACR

February 09, 2023
methyl, tert, butyl, ether, methyl, tertiary, butyl, ether, mtbe, also, known, methyl, tert, butyl, ether, tert, butyl, methyl, ether, organic, compound, with, structural, formula, 3coch3, mtbe, volatile, flammable, colorless, liquid, that, sparingly, soluble,. Methyl tertiary butyl ether MTBE also known as methyl tert butyl ether and tert butyl methyl ether is an organic compound with a structural formula CH3 3COCH3 MTBE is a volatile flammable and colorless liquid that is sparingly soluble 1 in water Primarily used as a fuel additive MTBE is blended into gasoline to increase its octane rating and knock resistance and reduce unwanted emissions 2 3 Methyl tert butyl ether NamesPreferred IUPAC name 2 Methoxy 2 methylpropaneOther names Methyl tertiary butyl ether Methyl tert butyl ether Methyl t butyl ether MTBE tert Butyl methyl ether tBME tert BuOMeIdentifiersCAS Number 1634 04 4 Y3D model JSmol Interactive imageChEBI CHEBI 27642 YChemSpider 14672 YECHA InfoCard 100 015 140KEGG C11344 YPubChem CID 15413UNII 29I4YB3S89 YCompTox Dashboard EPA DTXSID3020833InChI InChI 1S C5H12O c1 5 2 3 6 4 h1 4H3 YKey BZLVMXJERCGZMT UHFFFAOYSA N YInChI 1 C5H12O c1 5 2 3 6 4 h1 4H3Key BZLVMXJERCGZMT UHFFFAOYAASMILES O C C C C CPropertiesChemical formula C 5H 12OMolar mass 88 150 g mol 1Appearance colourless liquidDensity 0 7404 g cm3Melting point 109 C 164 F 164 K Boiling point 55 2 C 131 4 F 328 3 K Solubility in water 26 g L 20 C 1 Viscosity 0 36 cP at 25 CHazardsNFPA 704 fire diamond 13Flash point 33 0 C 27 4 F 240 2 K Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Contents 1 Production and properties 2 Uses 2 1 As anti knocking agent 2 2 Alternatives to MTBE as an anti knock agent 2 3 As a solvent 3 Persistence and pervasiveness in the environment 4 Regulation and litigation in the U S 4 1 Restrictions on MTBE manufacturing and use 4 2 Cleanup costs and litigation 4 3 Drinking water regulations 5 See also 6 References 7 External linksProduction and properties EditMTBE is manufactured via the chemical reaction of methanol and isobutylene Methanol is primarily derived from natural gas 4 where steam reforming converts the various light hydrocarbons in natural gas primarily methane into carbon monoxide and hydrogen 5 The resulting gases then further react in the presence of a catalyst to form methanol 6 Isobutylene can be produced through a variety of methods One process the isomerization of n butane into isobutane which then undergoes dehydrogenation to form the isobutylene 7 In the Halcon process t Butyl hydroperoxide derived from isobutane oxygenation is reacted with propylene to produce propylene oxide and t butanol The t butanol can be dehydrated to isobutylene MTBE production in the U S peaked in 1999 at 260 000 barrels per day 8 before dropping down to about 50 000 barrels per day and holding steady 9 mostly for the export market After the purchase of SABIC 10 11 oil giant Saudi Aramco is now considered to be the world s largest producer 12 with an estimated production capacity of 2 37 million metric tons per year mt yr 13 Worldwide production capacity of MTBE in 2018 was estimated to be 35 million metric tons 14 Uses EditMTBE is used as a fuel component in fuel for gasoline engines It is one of a group of chemicals commonly known as oxygenates because they raise the oxygen content of gasoline As anti knocking agent Edit In the U S MTBE has been used in gasoline at low levels since 1979 replacing tetraethyllead TEL as an antiknock octane rating additive to prevent engine knocking 15 Oxygenates also help gasoline burn more completely reducing tailpipe emissions and dilute or displace gasoline components such as aromatics e g benzene Before the introduction of other oxygenates and octane enhancers refiners chose MTBE for its blending characteristics and low cost Alternatives to MTBE as an anti knock agent Edit Other oxygenates are available as additives for gasoline including ethanol and other ethers such as ETBE 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 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 Higher quality gasoline is also an alternative so that additives such as MTBE are unnecessary Iso octane itself is used MTBE plants can be retrofitted to produce iso octane from isobutylene 16 17 As a solvent Edit MTBE is extensively used in industry as a safer alternative to diethyl ether which is commonly used in academic research as the tert butyl group prevents MTBE from forming potentially explosive peroxides It also is used as a solvent in academic research 18 19 20 although it is used less commonly than diethyl ether Although an ether MTBE is a poor Lewis base and does not support formation of Grignard reagents It is also unstable toward strong acids It reacts dangerously with bromine 21 MTBE forms azeotropes with water 52 6 C 96 5 MTBE 22 and methanol 51 3 C 68 6 MTBE 23 In a medical procedure called contact dissolution therapy MTBE is injected directly into the gallbladder to dissolve gallstones 24 25 Persistence and pervasiveness in the environment EditMTBE gives water an unpleasant taste at very low concentrations MTBE often is introduced into water supply aquifers by leaking underground storage tanks USTs at gasoline stations or by gasoline containing MTBE being spilled onto the ground 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 26 MTBE is biodegraded by the action of bacteria In the proper type of bioreactor such as a fluidized bed bioreactor MTBE may be removed rapidly and economically from water to undetectable levels Activated carbon produced from coconut shells and optimized for MTBE adsorption may reduce MTBE to undetectable levels 27 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 reducing contaminant concentrations to baseline pre development conditions within the aquifer soil matrix According to the International Agency for Research on Cancer IARC a cancer research agency of the World Health Organization MTBE is not classified as a human carcinogen MTBE may be tasted in water at concentrations of 5 15 µg L 5 15ppb 28 As of 2007 researchers have limited data about the health effects of ingestion of MTBE The United States Environmental Protection Agency EPA has concluded that available data are inadequate to quantify health risks of MTBE at low exposure levels in drinking water but the data support the conclusion that MTBE is a potential human carcinogen at high doses 29 Regulation and litigation in the U S EditMain article MTBE controversy Restrictions on MTBE manufacturing and use Edit In 2000 EPA drafted plans to phase out the use of MTBE nationwide over four years citation needed Some states enacted MTBE prohibitions without waiting for federal restrictions California banned MTBE as a gasoline additive in 2002 30 The State of New York banned the use of MTBE as a fuel additive effective in 2004 31 However MTBE is still legal in the state for other industrial uses 32 The Energy Policy Act of 2005 as approved by the U S House of Representatives did not include a provision for shielding MTBE manufacturers from water contamination lawsuits This provision was first proposed in 2003 and had been thought by some to be a priority of Tom DeLay and Rep Joe Barton then chairman of the Energy and Commerce Committee 33 This bill did include a provision that gave MTBE makers including some major oil companies 2 billion in transition assistance while MTBE was phased out over the following nine years 34 Due to opposition in the Senate 35 the conference report dropped all MTBE provisions The final bill was signed into law by President George W Bush 36 The lack of MTBE liability protection is resulting in a switchover to the use of ethanol as a gasoline additive Cleanup costs and litigation Edit MTBE removal from groundwater and soil contamination in the U S was estimated to cost from 1 billion 37 to US 30 billion 38 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 Santa Monica California was estimated to exceed 200 million 39 In another case New York City estimated a 250 million cost for cleanup of a single wellfield in the borough of Queens in 2009 40 In 2013 a jury awarded the State of New Hampshire 236 million in damages in order to treat groundwater contaminated by MTBE 41 As of 2016 hundreds of lawsuits are still pending regarding MTBE contamination of public and private drinking water supplies citation needed Drinking water regulations Edit EPA first listed MTBE in 1998 as a candidate for development of a national Maximum Contaminant Level MCL standard in drinking water 42 As of 2020 the agency has not announced whether it will develop an MCL 43 EPA uses toxicity data in developing MCLs for public water systems 44 California established a state level MCL for MTBE 13 micrograms per liter in 2000 45 See also EditCyclopentyl methyl ether CPME Di tert butyl ether List of gasoline additives tert Amyl methyl ether TAME References Edit a b Record of Methyl tert butyl ether in the GESTIS Substance Database of the Institute for Occupational Safety and Health Methyl tertiary butyl ether prices markets amp analysis ICIS Explore Retrieved 2020 06 28 Oxygenates www api org Retrieved 2020 06 28 How is Methanol Produced METHANOL INSTITUTE Retrieved 2020 06 29 Anzelmo Bryce Wilcox Jennifer Liguori Simona Hydrogen production via natural gas steam reforming in a Pd Au membrane reactor Investigation of reaction temperature and GHSV effects and long term stability PDF Journal of Membrane Science 25 32 methanol Properties Production Uses amp Poisoning Encyclopedia Britannica Retrieved 2020 06 29 Methyl Tertiary Butyl Ether MTBE Production and Manufacturing Process ICIS Explore Retrieved 2020 06 29 The United States continues to export MTBE mainly to Mexico Chile and Venezuela Today in Energy U S Energy Information Administration EIA www eia gov Retrieved 2020 06 28 United States Methyl Tertiary Butyl Ether MTBE Production Economic Indicators www ceicdata com Retrieved 2020 06 28 Aramco completes its acquisition of a 70 stake in SABIC from the Public Investment Fund PIF www saudiaramco com Retrieved 2020 06 29 Saudi Aramco buys SABIC shares on market as it completes acquisition Reuters 2020 06 14 Retrieved 2020 06 29 Saudi Aramco to have largest MTBE capacity in Middle East and Asia Retrieved 2020 06 29 Saudi Aramco s MTBE trading volume likely to rise after Sabic purchase S amp P Global Platts www spglobal com 2019 04 09 Retrieved 2020 06 29 MTBE annual production capacity globally 2023 Statista Retrieved 2020 06 28 Overview Methyl Tertiary Butyl Ether MTBE US EPA archive epa gov Retrieved 2021 04 07 NExOCTANE Neste Jacobs www nesteengineering com Archived from the original on January 6 2006 KBR NExOCTANE Archived from the original on 2006 01 06 Retrieved 2006 01 31 Matyash V Liebisch G Kurzchalia T V Shevchenko A Schwudke D 2008 Lipid extraction by methyl tert butyl ether for high throughput lipidomics The Journal of Lipid Research 49 5 1137 1146 doi 10 1194 jlr D700041 JLR200 PMC 2311442 PMID 18281723 Vopicka Ondrej Pilnacek Krystof Cihal 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 Journal of Polymer Science Part B Polymer Physics 54 5 561 569 Bibcode 2016JPoSB 54 561V doi 10 1002 polb 23945 ISSN 1099 0488 Vopicka Ondrej Radotinsky Daniel Friess Karel 2016 02 01 Sorption of vapour mixtures of methanol and dimethyl carbonate in PTMSP Cooperative and competitive sorption in one system European Polymer Journal 75 243 250 doi 10 1016 j eurpolymj 2015 12 015 Interaction between bromine and tert butyl methyl ether UK Chemical Reaction Hazards Forum Archived from the original on 13 March 2011 Retrieved 13 May 2010 Zeon Corporation Archived 2011 07 22 at the Wayback Machine CRC Handbook of Chemistry and Physics 90th edition Schoenfield LJ Marks JW 1993 Oral and contact dissolution of gallstones Am J Surg 165 4 427 30 doi 10 1016 S0002 9610 05 80934 1 PMID 8480875 Health Guide Gallstones New York Times San Francisco Bay Area Regional Water Quality Control Board Integrated Basin Management Plan 2004 Archived 2008 02 29 at the Wayback Machine link text Archived 2011 07 28 at the Wayback Machine Fischer A Oehm C Selle M Werner P 2005 Biotic and abiotic transformations of methyl tertiary butyl ether MTBE Environ Sci Pollut Res Int 12 6 381 6 doi 10 1065 espr2005 08 277 PMID 16305145 S2CID 97168152 Methyl Tertiary Butyl Ether MTBE US EPA California Reformulated Gasoline Phase 3 Sacramento CA California Air Resources Board 2015 07 24 Spill Response amp Remediation FAQ Chemical and Pollution Control Albany NY New York State Department of Environmental Conservation Retrieved 2018 04 06 State of New York New York Consolidated Laws Agriculture and Markets Law AGM 192 g Methyl tertiary butyl ether prohibited http www cnn com 2005 POLITICS 04 21 energy bill mtbe ap Archived 2005 04 22 at the Wayback Machine House approves 12 billion energy package NBC News 2005 04 22 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 enactment United States Energy Policy Act of 2005 Pub L 109 58 text PDF Approved 2005 08 08 MTBE Cleanup Estimates SIGMA Weekly Report Fairfax VA Society of Independent Gasoline Marketers of America SIGMA 2005 05 23 Archived from the original on 2009 10 09 Long Island Utility Fighting to Defeat MTBE Safe Harbor The MTBE e Resource New York NY Napoli Bern LLP 2004 03 16 Archived from the original on 2007 10 20 Oil Companies Pay Santa Monica MTBE Cleanup Costs Environment News Service Ecology Prime Media Inc 2005 02 17 Navarro Mireya 2009 10 20 City Awarded 105 Million in Exxon Mobil Lawsuit The New York Times Retrieved 2010 05 12 Earle Sarah 2013 04 09 Exxon Mobil is Found Negligent in New Hampshire MTBE Use Bloomberg EPA 1998 03 02 Announcement of the Drinking Water Contaminant Candidate List Federal Register 63 FR 10274 Drinking Water Regulations Under Development or Review EPA 2020 01 27 How EPA Regulates Drinking Water Contaminants EPA 2017 05 03 MTBE Regulations and Drinking Water Monitoring Results Sacramento CA California State Water Resources Control Board 2014 08 04 External links EditMTBE in Europe MTBE webpage from the EPA Summary of health effects data from IACR Retrieved from https en wikipedia org w index php title Methyl tert butyl ether amp oldid 1122464534, wikipedia, wiki, book, books, library,

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