WO2007149373A3 - Process for making isooctenes from aqueous isobutanol - Google Patents

Process for making isooctenes from aqueous isobutanol Download PDF

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Publication number
WO2007149373A3
WO2007149373A3 PCT/US2007/014169 US2007014169W WO2007149373A3 WO 2007149373 A3 WO2007149373 A3 WO 2007149373A3 US 2007014169 W US2007014169 W US 2007014169W WO 2007149373 A3 WO2007149373 A3 WO 2007149373A3
Authority
WO
WIPO (PCT)
Prior art keywords
isooctenes
making
aqueous isobutanol
isobutanol
making isooctenes
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2007/014169
Other languages
French (fr)
Other versions
WO2007149373A2 (en
Inventor
Amore Michael B D
Leo Ernest Manzer
Edward S Miller Jr
Jeffrey P Knapp
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Priority to EP07796216.5A priority Critical patent/EP2043975B1/en
Priority to BRPI0712272-1A priority patent/BRPI0712272A2/en
Publication of WO2007149373A2 publication Critical patent/WO2007149373A2/en
Publication of WO2007149373A3 publication Critical patent/WO2007149373A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
    • C07C1/22—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by reduction
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/03—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2
    • C07C29/04—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2 by hydration of carbon-to-carbon double bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
    • C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
    • C07C5/03—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of non-aromatic carbon-to-carbon double bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C9/00—Aliphatic saturated hydrocarbons
    • C07C9/14—Aliphatic saturated hydrocarbons with five to fifteen carbon atoms
    • C07C9/16—Branched-chain hydrocarbons
    • C07C9/21—2, 2, 4-Trimethylpentane
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/16—Hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/16—Hydrocarbons
    • C10L1/1608—Well defined compounds, e.g. hexane, benzene
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
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    • C10L1/18—Organic compounds containing oxygen
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    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
    • C10L1/1822—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms
    • C10L1/1824—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms mono-hydroxy
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    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
    • C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P5/00—Preparation of hydrocarbons or halogenated hydrocarbons
    • C12P5/02—Preparation of hydrocarbons or halogenated hydrocarbons acyclic
    • C12P5/026—Unsaturated compounds, i.e. alkenes, alkynes or allenes
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
    • C07C2521/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
    • C07C2521/08—Silica
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/02—Sulfur, selenium or tellurium; Compounds thereof
    • C07C2527/053—Sulfates or other compounds comprising the anion (SnO3n+1)2-
    • C07C2527/054—Sulfuric acid or other acids with the formula H2Sn03n+1
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2529/00—Catalysts comprising molecular sieves
    • C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
    • C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • C07C2529/18—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the mordenite type
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2529/00—Catalysts comprising molecular sieves
    • C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
    • C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • C07C2529/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • C07C2531/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
    • C07C2531/08—Ion-exchange resins
    • C07C2531/10—Ion-exchange resins sulfonated
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/40—Characteristics of the process deviating from typical ways of processing
    • C10G2300/4006—Temperature
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/40—Characteristics of the process deviating from typical ways of processing
    • C10G2300/4012—Pressure
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    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/80—Additives
    • C10G2300/805—Water
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    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
    • C10G2400/22—Higher olefins
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    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L2200/00—Components of fuel compositions
    • C10L2200/04—Organic compounds
    • C10L2200/0461—Fractions defined by their origin
    • C10L2200/0469—Renewables or materials of biological origin
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    • C10L2270/00—Specifically adapted fuels
    • C10L2270/02—Specifically adapted fuels for internal combustion engines
    • C10L2270/023—Specifically adapted fuels for internal combustion engines for gasoline engines
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    • C10L2270/00—Specifically adapted fuels
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    • C10L2270/00—Specifically adapted fuels
    • C10L2270/04—Specifically adapted fuels for turbines, planes, power generation
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    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L2290/00—Fuel preparation or upgrading, processes or apparatus therefore, comprising specific process steps or apparatus units
    • C10L2290/26—Composting, fermenting or anaerobic digestion fuel components or materials from which fuels are prepared

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Zoology (AREA)
  • Microbiology (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

The present invention relates to a catalytic process for making isooctenes using a reactant comprising isobutanol and water. The isooctenes so produced are useful for the production of fuel additives.
PCT/US2007/014169 2006-06-16 2007-06-15 Process for making isooctenes from aqueous isobutanol Ceased WO2007149373A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP07796216.5A EP2043975B1 (en) 2006-06-16 2007-06-15 Process for making isooctenes from aqueous isobutanol
BRPI0712272-1A BRPI0712272A2 (en) 2006-06-16 2007-06-15 PROCESSES FOR MANUFACTURING AT LEAST ONE ISOOCTENE, REACTION PRODUCTS, AT LEAST ONE ISOOCTAN AND AT LEAST ONE ISOOCTANOL

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US81415306P 2006-06-16 2006-06-16
US60/814,153 2006-06-16

Publications (2)

Publication Number Publication Date
WO2007149373A2 WO2007149373A2 (en) 2007-12-27
WO2007149373A3 true WO2007149373A3 (en) 2008-04-03

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PCT/US2007/014169 Ceased WO2007149373A2 (en) 2006-06-16 2007-06-15 Process for making isooctenes from aqueous isobutanol

Country Status (5)

Country Link
US (4) US20090099401A1 (en)
EP (1) EP2043975B1 (en)
CN (1) CN101472863A (en)
BR (1) BRPI0712272A2 (en)
WO (1) WO2007149373A2 (en)

Families Citing this family (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BRPI0614026A2 (en) * 2005-01-25 2012-12-25 Bp Corp North America Inc petrol composition and rvp reduction methods of a hydrogen peroxide and rvp construction over in gasoline mixture stock in the production of peroxide having a predetermined maximum limit of rvp
US20090099401A1 (en) 2006-06-16 2009-04-16 D Amore Michael B Process for making isooctenes from aqueous isobutanol
US20080131948A1 (en) * 2006-12-01 2008-06-05 Leo Ernest Manzer Process for making isooctenes from dry 2-butanol
WO2009079213A2 (en) * 2007-12-03 2009-06-25 Gevo, Inc. Renewable compositions
US8193402B2 (en) * 2007-12-03 2012-06-05 Gevo, Inc. Renewable compositions
US8734543B2 (en) 2008-05-08 2014-05-27 Butamax Advanced Biofuels Llc Oxygenated gasoline composition having good driveability performance
US10192038B2 (en) 2008-05-22 2019-01-29 Butamax Advanced Biofuels Llc Process for determining the distillation characteristics of a liquid petroleum product containing an azeotropic mixture
BRPI1008287A2 (en) * 2009-02-24 2016-03-15 Gevo Inc renewable butadiene and isoprene preparation methods
TWI434921B (en) * 2009-06-17 2014-04-21 Danisco Us Inc Methods and systems for producing fuel constituents from bioisoprene compositions
SG10201408071TA (en) * 2009-10-06 2015-01-29 Gevo Inc Integrated process to selectively convert renewable isobutanol to p-xylene
US9272965B2 (en) * 2009-12-22 2016-03-01 Catalytic Distillation Technologies Process for the conversion of alcohols to olefins
BR112012016883A2 (en) 2010-01-08 2018-06-05 Gevo Inc integrated methods of preparing renewable chemical produsot
US8373012B2 (en) 2010-05-07 2013-02-12 Gevo, Inc. Renewable jet fuel blendstock from isobutanol
WO2011143215A2 (en) 2010-05-10 2011-11-17 Catalytic Distillation Technologies Production of jet and other heavy fuels from isobutanol
WO2011159901A1 (en) 2010-06-16 2011-12-22 Butamax(Tm) Advanced Biofuels Llc Oxygenated butanol gasoline composition having good driveability performance
CN102947425B (en) 2010-06-16 2015-10-21 布特马斯先进生物燃料有限责任公司 Oxygenated butanol gasoline composition with good running properties
CN103025688A (en) 2010-06-17 2013-04-03 丹尼斯科美国公司 Fuel compositions comprising isoprene derivatives
CA2811394A1 (en) 2010-09-20 2012-03-29 Butamax (Tm) Advanced Biofuels Llc Multimedia evaluation of butanol-containing fuels
WO2012145495A2 (en) 2011-04-19 2012-10-26 Gevo, Inc. Variations on prins-like chemistry to produce 2,5-dimethylhexadiene from isobutanol
JP6100785B2 (en) 2011-09-23 2017-03-22 ビュータマックス・アドバンスド・バイオフューエルズ・エルエルシー Systems and processes for producing fuels and fuel blends
US8968429B2 (en) 2011-09-23 2015-03-03 Butamax Advanced Biofuels Llc Butanol compositions for fuel blending and methods for the production thereof
KR20140116175A (en) 2011-12-30 2014-10-01 부타맥스 어드밴스드 바이오퓨얼스 엘엘씨 Corrosion inhibitor compositions for oxygenated gasolines
US9914672B2 (en) 2012-10-19 2018-03-13 Lummus Technology Inc. Conversion of alcohols to distillate fuels
CN106660904B (en) * 2014-07-11 2020-01-07 阿彻丹尼尔斯米德兰德公司 System and method for extracting ethanol from fermentation media
CN107056576B (en) * 2017-01-16 2020-04-28 重庆邮电大学 Preparation method of 2,4,4-trimethyl-1-pentene
CN116472718A (en) * 2020-09-10 2023-07-21 特励达数字成像有限公司 A method and device for high-speed charge-coupled CMOS TDI imaging
WO2025038806A1 (en) * 2023-08-17 2025-02-20 ExxonMobil Technology and Engineering Company Process to make sustainable aviation fuel

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0088602A2 (en) * 1982-03-08 1983-09-14 Exxon Research And Engineering Company Microbiological oxidation process
EP0263403A2 (en) * 1986-10-03 1988-04-13 Idemitsu Kosan Company Limited Novel microorganism and method for producing oxygenous compounds with said microorganism
US5288924A (en) * 1992-09-18 1994-02-22 Mobil Oil Corporation Process for starting up an olefin hydration reactor
WO1997003932A1 (en) * 1995-07-21 1997-02-06 Shell Internationale Research Maatschappij B.V. Dehydration of primary alcohols
WO2003031539A1 (en) * 2001-10-12 2003-04-17 Fortum Oyj An oxygenated gasoline component and a method of producing thereof

Family Cites Families (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2228662A (en) * 1939-05-31 1941-01-14 Standard Oil Co Motor fuel
GB576480A (en) 1942-10-31 1946-04-05 Universal Oil Prod Co Process for producing olefinic hydrocarbons
US3481718A (en) * 1969-01-15 1969-12-02 Sinclair Research Inc Gasoline fuel composition
GB1287443A (en) * 1969-06-06 1972-08-31 Exxon Research Engineering Co Gasoline compositions
US4338469A (en) * 1976-08-23 1982-07-06 Suntech, Inc. 8-Methoxy-p-menthane
US4292219A (en) * 1977-12-22 1981-09-29 Suntech, Inc. Latex-base paint containing 2-methoxy-2-phenyl propane or 8-methoxy-p-menthane
US4374859A (en) * 1980-07-07 1983-02-22 The Regents Of The University Of California Method for reducing fusel oil in alcoholic beverages and yeast strain useful in that method
US4450294A (en) 1981-11-27 1984-05-22 National Distillers And Chemical Corporation Process for recovering oxygenated organic compounds from dilute aqueous solutions employing solid sorbent
US4628116A (en) 1986-01-08 1986-12-09 Cenedella Richard J Vinyl bromide extraction of butyric acid and butanol from microbial fermentation broth
US5755967A (en) 1996-05-22 1998-05-26 Meagher; Michael M. Silicalite membrane and method for the selective recovery and concentration of acetone and butanol from model ABE solutions and fermentation broth
IL132883A0 (en) * 1997-05-14 2001-03-19 Univ Illinois A method of producing butanol using a mutant strain of clostridium beijerinckii
US6716258B2 (en) * 1999-12-21 2004-04-06 Exxonmobil Research And Engineering Company Fuel composition
DE60103335T2 (en) 2000-08-29 2006-03-30 Bp Fuels Deutschland Gmbh A process for the selective production of di-isobutene from an i-butene-containing C4 feed
ES2282488T3 (en) * 2001-07-02 2007-10-16 Exxonmobil Chemical Patents Inc. INHIBITION OF THE COKE FORMATION IN A CATALYST IN THE MANUFACTURE OF AN OLEFINA.
US7199275B2 (en) * 2003-03-24 2007-04-03 Exxonmobil Chemical Patents Inc. Feed pretreating
US7030249B2 (en) 2003-09-10 2006-04-18 E. I. Upont De Nemours And Company Process for converting α-angelica lactone to 5-methyl-N-alkyl-2-pyrrolidone using alkyl amines
US20050089979A1 (en) 2003-09-18 2005-04-28 Ezeji Thaddeus C. Process for continuous solvent production
SE526429C2 (en) * 2003-10-24 2005-09-13 Swedish Biofuels Ab Intensifying fermentation of carbohydrate substrate for, e.g. producing one to five carbon alcohols, involves using amino acid leucine, isoleucine, and/or valine as source of nitrogen
US7413882B2 (en) * 2004-03-25 2008-08-19 Novozymes, Inc. Methods for degrading or converting plant cell wall polysaccharides
MX359740B (en) 2005-10-26 2018-10-09 Du Pont Fermentive production of four carbon alcohols.
US7659104B2 (en) 2006-05-05 2010-02-09 E.I. Du Pont De Nemours And Company Solvent tolerant microorganisms and methods of isolation
US20090099401A1 (en) 2006-06-16 2009-04-16 D Amore Michael B Process for making isooctenes from aqueous isobutanol
US8975047B2 (en) * 2006-06-16 2015-03-10 E I Du Pont De Nemours And Company Process for making isooctenes from dry 1-butanol
US20080131948A1 (en) * 2006-12-01 2008-06-05 Leo Ernest Manzer Process for making isooctenes from dry 2-butanol

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0088602A2 (en) * 1982-03-08 1983-09-14 Exxon Research And Engineering Company Microbiological oxidation process
EP0263403A2 (en) * 1986-10-03 1988-04-13 Idemitsu Kosan Company Limited Novel microorganism and method for producing oxygenous compounds with said microorganism
US5288924A (en) * 1992-09-18 1994-02-22 Mobil Oil Corporation Process for starting up an olefin hydration reactor
WO1997003932A1 (en) * 1995-07-21 1997-02-06 Shell Internationale Research Maatschappij B.V. Dehydration of primary alcohols
WO2003031539A1 (en) * 2001-10-12 2003-04-17 Fortum Oyj An oxygenated gasoline component and a method of producing thereof

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
ADKINS, PERKINS: "Dehydration of alcohols over alumina", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 47, 1925, pages 1163 - 1167, XP002465130 *
FRITSCH D ET AL: "Application of a forced-flow catalytic membrane reactor for the dimerisation of isobutene", CATALYSIS TODAY, ELSEVIER, vol. 98, no. 1-2, 24 November 2004 (2004-11-24), pages 295 - 308, XP004640277, ISSN: 0920-5861 *
IPATIEFF V N ET AL: "The dehydration of the lower aliphatic alcohols in the presence of dilute aqueous solutions of acids and salts", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 66, 1944, pages 1627 - 1631, XP002458829, ISSN: 0002-7863 *
JEAN BAPTISTE SENDERENS: "Chimique Organique. Déshydratation catalytique, en phase gazeuse, des alcools forméniques en présence des bisulfates alcalins", COMPTES RENDUS HEBDOMADAIRES DES SEANCES DE L'ACADEMIE DES SCIENCES, GAUTHIER-VILLARS, PARIS,, FR, vol. 190, 1930, pages 1167 - 1170, XP009092311, ISSN: 0001-4036 *
PÉTROFF A D ET AL: "De la structure du di-isobutylène de Malbot", BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, MASSON, PARIS, FR, vol. 53, 1933, pages 327 - 330, XP009092312, ISSN: 0037-8968 *

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