WO2008016428A3 - Process for making butenes from dry isobutanol - Google Patents

Process for making butenes from dry isobutanol Download PDF

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Publication number
WO2008016428A3
WO2008016428A3 PCT/US2007/014205 US2007014205W WO2008016428A3 WO 2008016428 A3 WO2008016428 A3 WO 2008016428A3 US 2007014205 W US2007014205 W US 2007014205W WO 2008016428 A3 WO2008016428 A3 WO 2008016428A3
Authority
WO
WIPO (PCT)
Prior art keywords
butenes
dry isobutanol
making
making butenes
dry
Prior art date
Application number
PCT/US2007/014205
Other languages
French (fr)
Other versions
WO2008016428A2 (en
Inventor
Amore Michael B D
Leo Ernest Manzer
Jr Edward S Miller
Jeffrey P Knapp
Original Assignee
Du Pont
Amore Michael B D
Leo Ernest Manzer
Jr Edward S Miller
Jeffrey P Knapp
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 Du Pont, Amore Michael B D, Leo Ernest Manzer, Jr Edward S Miller, Jeffrey P Knapp filed Critical Du Pont
Priority to BRPI0711993-3A priority Critical patent/BRPI0711993A2/en
Priority to EP07835819A priority patent/EP2043971A2/en
Publication of WO2008016428A2 publication Critical patent/WO2008016428A2/en
Publication of WO2008016428A3 publication Critical patent/WO2008016428A3/en

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Classifications

    • 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
    • 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
    • C07C1/24—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 elimination of water
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
    • C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
    • C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
    • C07C2/08—Catalytic processes
    • C07C2/14—Catalytic processes with inorganic acids; with salts or anhydrides of acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
    • C07C2/56—Addition to acyclic hydrocarbons
    • C07C2/58—Catalytic processes
    • C07C2/62—Catalytic processes with acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
    • C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
    • C07C2/66—Catalytic processes
    • C07C2/70—Catalytic processes with acids
    • 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

Abstract

The present invention relates to a process for making butenes using dry isobutanol derived from fermentation broth. The butenes so produced may be converted to isoalkanes, alkyl-substituted aromatics, isooctanes, isooctanols, and octyl ethers, which are useful in transportation fuels.
PCT/US2007/014205 2006-06-16 2007-06-15 Process for making butenes from dry isobutanol WO2008016428A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
BRPI0711993-3A BRPI0711993A2 (en) 2006-06-16 2007-06-15 processes for the manufacture of at least one butene, at least one aromatic compound of at least one buitl alkyl ether, at least one isooctane and processes for the production of a reaction product
EP07835819A EP2043971A2 (en) 2006-06-16 2007-06-15 Process for making butenes from dry isobutanol

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US81413706P 2006-06-16 2006-06-16
US60/814,137 2006-06-16

Publications (2)

Publication Number Publication Date
WO2008016428A2 WO2008016428A2 (en) 2008-02-07
WO2008016428A3 true WO2008016428A3 (en) 2008-11-20

Family

ID=38930237

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2007/014205 WO2008016428A2 (en) 2006-06-16 2007-06-15 Process for making butenes from dry isobutanol

Country Status (5)

Country Link
US (1) US20080132741A1 (en)
EP (1) EP2043971A2 (en)
CN (1) CN101472858A (en)
BR (1) BRPI0711993A2 (en)
WO (1) WO2008016428A2 (en)

Families Citing this family (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090030239A1 (en) * 2006-06-16 2009-01-29 D Amore Michael B Process for making butenes from aqueous isobutanol
US20080015397A1 (en) * 2006-06-16 2008-01-17 D Amore Michael B Process for making isooctenes from aqueous 1-butanol
US20080009656A1 (en) * 2006-06-16 2008-01-10 D Amore Michael B Process for making isooctenes from dry isobutanol
US20080045754A1 (en) * 2006-06-16 2008-02-21 D Amore Michael B Process for making butenes from dry 1-butanol
US20080015395A1 (en) * 2006-06-16 2008-01-17 D Amore Michael B Process for making butenes from aqueous 1-butanol
US20080132732A1 (en) * 2006-12-01 2008-06-05 Leo Ernest Manzer Process for making butenes from aqueous 2-butanol
US20080234523A1 (en) * 2006-12-01 2008-09-25 Leo Ernest Manzer Process for making isooctenes from aqueous 2-butanol
US20080132730A1 (en) * 2006-12-01 2008-06-05 Leo Ernest Manzer Process for making butenes from dry 2-butanol
JP2011505490A (en) 2007-12-03 2011-02-24 ジーヴォ，インコーポレイテッド Renewable composition
US8193402B2 (en) * 2007-12-03 2012-06-05 Gevo, Inc. Renewable compositions
US8101808B2 (en) * 2007-12-27 2012-01-24 Gevo, Inc. Recovery of higher alcohols from dilute aqueous solutions
FR2940801B1 (en) * 2009-01-06 2012-08-17 Arkema France PROCESS FOR THE PRODUCTION OF A METHYL METHACRYLATE DERIVED FROM BIOMASS
WO2010099201A1 (en) * 2009-02-24 2010-09-02 Gevo, Inc. Methods of preparing renewable butadiene and renewable isoprene
KR20120104509A (en) * 2009-06-26 2012-09-21 게보 인코포레이티드 Recovery of higher alcohols from dilute aqueous solutions
US8968522B2 (en) * 2009-07-15 2015-03-03 Butamax Advanced Biofuels Llc Recovery of butanol isomers from a mixture of butanol isomers, water, and an organic extractant
US8968523B2 (en) * 2009-07-15 2015-03-03 Butamax Advanced Biofuels Llc Recovery of butanol isomers from a mixture of butanol isomers, water, and an organic extractant
US8373008B2 (en) * 2009-11-23 2013-02-12 Butamax (Tm) Advanced Biofuels Llc Recovery of butanol from a mixture of butanol, water, and an organic extractant
US8373009B2 (en) * 2009-11-23 2013-02-12 Butamax (Tm) Advanced Biofuels Llc Recovery of butanol from a mixture of butanol, water, and an organic extractant
EP2336340A1 (en) * 2009-12-21 2011-06-22 Philippe Marliere Method for producing an alkene comprising the step of converting an alcohol by an enzymatic dehydration step
EP2336341A1 (en) * 2009-12-21 2011-06-22 Philippe Marliere Method for producing an alkene comprising the step of converting an alcohol by an enzymatic dehydration step
SG182407A1 (en) * 2010-01-08 2012-08-30 Gevo Inc Integrated methods of preparing renewable chemicals
BR112012023261B1 (en) 2010-03-15 2018-09-18 Total Res & Technology Feluy propylene production by dehydration and simultaneous isomerization of the isobutanol backbone over acid catalysts followed by metathesis
EP2366682A1 (en) * 2010-03-15 2011-09-21 Total Petrochemicals Research Feluy Simultaneous dehydration and skeletal isomerisation of isobutanol on acid catalysts
EP2374780A1 (en) * 2010-04-09 2011-10-12 Total Petrochemicals Research Feluy Production of propylene via simultaneous dehydration and skeletal isomerisation of isobutanol on acid catalysts followed by metathesis
MY158968A (en) 2010-03-15 2016-11-30 Total Res & Technology Feluy Simultaneous dehydration and skeletal isomerisation of isobutanol on acid catalysts
EP2374781A1 (en) * 2010-04-09 2011-10-12 Total Petrochemicals Research Feluy Simultaneous dehydration and skeletal isomerisation of isobutanol on acid catalysts
US8373012B2 (en) 2010-05-07 2013-02-12 Gevo, Inc. Renewable jet fuel blendstock from isobutanol
CN103153921A (en) * 2010-08-03 2013-06-12 道达尔研究技术弗吕公司 Process to make olefins from methanol and isobutanol
CN103140458B (en) * 2010-08-03 2016-10-12 道达尔研究技术弗吕公司 The combined method of alkene is manufactured by isobutanol
US9115040B2 (en) * 2010-09-24 2015-08-25 Total Research & Technology Feluy Production of isoprene from iso-butanol
FR2969147B1 (en) 2010-12-21 2013-01-04 Total Raffinage Marketing PRODUCTION OF FUEL ADDITIVES BY DEHYDRATION AND SIMULTANEOUS SKELETAL ISOMERISATION OF ISOBUTANOL ON ACID CATALYSTS FOLLOWED BY ETHERIFICATION
US8742187B2 (en) 2011-04-19 2014-06-03 Gevo, Inc. Variations on prins-like chemistry to produce 2,5-dimethylhexadiene from isobutanol
EP2583957A1 (en) 2011-10-18 2013-04-24 LANXESS Deutschland GmbH Linear butene from isobutanol
JP2015517303A (en) 2012-05-04 2015-06-22 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 Method and system for the production and recovery of alcohol

Citations (10)

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Publication number Priority date Publication date Assignee Title
US2080034A (en) * 1935-02-09 1937-05-11 Shell Dev Mixed tertiary butyl ethers
US2322800A (en) * 1940-01-22 1943-06-29 Phillips Petroleum Co Conversion of hydrocarbons
DE890953C (en) * 1938-08-21 1953-10-29 Basf Ag Process for the preparation of butylene-isobutylene mixtures
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JPS6178898A (en) * 1984-09-26 1986-04-22 Eisaku Ando Raising octane value of gasoline
WO1997003932A1 (en) * 1995-07-21 1997-02-06 Shell Internationale Research Maatschappij B.V. Dehydration of primary alcohols
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WO2005040392A1 (en) * 2003-10-24 2005-05-06 Swedish Biofuels Ab Method for producing hydrocarbons and oxygen-containing compounds, from biomass
WO2005056503A1 (en) * 2003-12-12 2005-06-23 University Of Waterloo Composite catalyst for the selective oligomerization of lower alkenes and the production of high octane products

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IL132883A0 (en) * 1997-05-14 2001-03-19 Univ Illinois A method of producing butanol using a mutant strain of clostridium beijerinckii
US20080045754A1 (en) * 2006-06-16 2008-02-21 D Amore Michael B Process for making butenes from dry 1-butanol
US20080015395A1 (en) * 2006-06-16 2008-01-17 D Amore Michael B Process for making butenes from aqueous 1-butanol
US20090030239A1 (en) * 2006-06-16 2009-01-29 D Amore Michael B Process for making butenes from aqueous isobutanol
US20080015397A1 (en) * 2006-06-16 2008-01-17 D Amore Michael B Process for making isooctenes from aqueous 1-butanol
US20080009656A1 (en) * 2006-06-16 2008-01-10 D Amore Michael B Process for making isooctenes from dry 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
US20080132173A1 (en) * 2006-11-30 2008-06-05 Korea Advanced Institute Of Science And Technology Channel estimation apparatus and channel estimation method
US20080234523A1 (en) * 2006-12-01 2008-09-25 Leo Ernest Manzer Process for making isooctenes from aqueous 2-butanol
US20080131948A1 (en) * 2006-12-01 2008-06-05 Leo Ernest Manzer Process for making isooctenes from dry 2-butanol
US20080132732A1 (en) * 2006-12-01 2008-06-05 Leo Ernest Manzer Process for making butenes from aqueous 2-butanol

Patent Citations (10)

* Cited by examiner, † Cited by third party
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DE890953C (en) * 1938-08-21 1953-10-29 Basf Ag Process for the preparation of butylene-isobutylene mixtures
US2322800A (en) * 1940-01-22 1943-06-29 Phillips Petroleum Co Conversion of hydrocarbons
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JPS6178898A (en) * 1984-09-26 1986-04-22 Eisaku Ando Raising octane value of gasoline
WO1997003932A1 (en) * 1995-07-21 1997-02-06 Shell Internationale Research Maatschappij B.V. Dehydration of primary alcohols
US20020007100A1 (en) * 2000-03-16 2002-01-17 Manzer Leo E. Process for the preparation of p-xylene
WO2003031539A1 (en) * 2001-10-12 2003-04-17 Fortum Oyj An oxygenated gasoline component and a method of producing thereof
WO2005040392A1 (en) * 2003-10-24 2005-05-06 Swedish Biofuels Ab Method for producing hydrocarbons and oxygen-containing compounds, from biomass
WO2005056503A1 (en) * 2003-12-12 2005-06-23 University Of Waterloo Composite catalyst for the selective oligomerization of lower alkenes and the production of high octane products

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Also Published As

Publication number Publication date
BRPI0711993A2 (en) 2012-01-10
US20080132741A1 (en) 2008-06-05
EP2043971A2 (en) 2009-04-08
CN101472858A (en) 2009-07-01
WO2008016428A2 (en) 2008-02-07

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