WO2007149372A3 - Process for making isooctenes from aqueous 1-butanol - Google Patents

Process for making isooctenes from aqueous 1-butanol Download PDF

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Publication number
WO2007149372A3
WO2007149372A3 PCT/US2007/014168 US2007014168W WO2007149372A3 WO 2007149372 A3 WO2007149372 A3 WO 2007149372A3 US 2007014168 W US2007014168 W US 2007014168W WO 2007149372 A3 WO2007149372 A3 WO 2007149372A3
Authority
WO
WIPO (PCT)
Prior art keywords
butanol
aqueous
isooctenes
making
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/US2007/014168
Other languages
French (fr)
Other versions
WO2007149372A2 (en
Inventor
Amore Michael B D
Leo Ernest Manzer
Jr Edward S Miller
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 EP07796215A priority Critical patent/EP2043974A2/en
Priority to BRPI0711991-7A priority patent/BRPI0711991A2/en
Publication of WO2007149372A2 publication Critical patent/WO2007149372A2/en
Publication of WO2007149372A3 publication Critical patent/WO2007149372A3/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
    • 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
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • 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
    • 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
    • C07C2529/40—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
    • 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
    • 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
    • C10G2300/80—Additives
    • C10G2300/805—Water
    • 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
    • C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
    • C10G2400/22—Higher olefins
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E50/00—Technologies for the production of fuel of non-fossil origin
    • Y02E50/30—Fuel from waste, e.g. synthetic alcohol or diesel

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (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 1-butanol and water. The isooctenes so produced are useful for the production of fuel additives.
PCT/US2007/014168 2006-06-16 2007-06-15 Process for making isooctenes from aqueous 1-butanol Ceased WO2007149372A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP07796215A EP2043974A2 (en) 2006-06-16 2007-06-15 Process for making isooctenes from aqueous 1-butanol
BRPI0711991-7A BRPI0711991A2 (en) 2006-06-16 2007-06-15 PROCESSES FOR MANUFACTURING AT LEAST ONE ISOOCTENE AND AN REACTION PRODUCT

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US81413606P 2006-06-16 2006-06-16
US60/814,136 2006-06-16

Publications (2)

Publication Number Publication Date
WO2007149372A2 WO2007149372A2 (en) 2007-12-27
WO2007149372A3 true WO2007149372A3 (en) 2008-02-28

Family

ID=38662799

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2007/014168 Ceased WO2007149372A2 (en) 2006-06-16 2007-06-15 Process for making isooctenes from aqueous 1-butanol

Country Status (5)

Country Link
US (1) US20080015397A1 (en)
EP (1) EP2043974A2 (en)
CN (1) CN101472862A (en)
BR (1) BRPI0711991A2 (en)
WO (1) WO2007149372A2 (en)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080015395A1 (en) * 2006-06-16 2008-01-17 D Amore Michael B Process for making butenes from aqueous 1-butanol
US20080009656A1 (en) * 2006-06-16 2008-01-10 D Amore Michael B Process for making isooctenes from dry isobutanol
US20080132741A1 (en) * 2006-06-16 2008-06-05 D Amore Michael B Process for making butenes from dry isobutanol
US20090030239A1 (en) * 2006-06-16 2009-01-29 D Amore Michael B Process for making butenes from aqueous isobutanol
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
US8193402B2 (en) * 2007-12-03 2012-06-05 Gevo, Inc. Renewable compositions
WO2009079213A2 (en) 2007-12-03 2009-06-25 Gevo, Inc. Renewable compositions
BRPI1008287A2 (en) * 2009-02-24 2016-03-15 Gevo Inc renewable butadiene and isoprene preparation methods
BR112012000659A2 (en) * 2009-06-26 2019-09-24 Gevo Inc recovery of higher alcohols from dilute aqueous solutions
SG10201408071TA (en) * 2009-10-06 2015-01-29 Gevo Inc Integrated process to selectively convert renewable isobutanol to p-xylene
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
WO2012145495A2 (en) 2011-04-19 2012-10-26 Gevo, Inc. Variations on prins-like chemistry to produce 2,5-dimethylhexadiene from isobutanol
MX2013013555A (en) 2011-05-27 2014-02-27 Bp Corp North America Inc Method to convert fermentation mixture into fuels.
US8999013B2 (en) 2011-11-01 2015-04-07 Saudi Arabian Oil Company Method for contemporaneously dimerizing and hydrating a feed having butene
US9914672B2 (en) 2012-10-19 2018-03-13 Lummus Technology Inc. Conversion of alcohols to distillate fuels
US9790444B2 (en) 2013-04-26 2017-10-17 The Regents Of The University Of California Methods to produce fuels
EA034595B1 (en) 2014-03-24 2020-02-25 Дзе Риджентс Оф Дзе Юниверсити Оф Калифорния Methods for producing cyclic ketones
BR112017008899A2 (en) 2014-10-29 2017-12-19 Bp Corp North America Inc methods for producing fuels, gasoline additives and lubricants using amine catalysts
EP3212602A1 (en) 2014-10-29 2017-09-06 The Regents of the University of California Methods for producing fuels, gasoline additives, and lubricants using amine catalysts

Citations (5)

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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
WO2003031539A1 (en) * 2001-10-12 2003-04-17 Fortum Oyj An oxygenated gasoline component and a method of producing thereof
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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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
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US20080009656A1 (en) * 2006-06-16 2008-01-10 D Amore Michael B Process for making isooctenes from dry isobutanol
US20090030239A1 (en) * 2006-06-16 2009-01-29 D Amore Michael B Process for making butenes 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
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
US20080131948A1 (en) * 2006-12-01 2008-06-05 Leo Ernest Manzer Process for making isooctenes from dry 2-butanol
US20080132730A1 (en) * 2006-12-01 2008-06-05 Leo Ernest Manzer Process for making butenes from dry 2-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

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
WO2003031539A1 (en) * 2001-10-12 2003-04-17 Fortum Oyj An oxygenated gasoline component and a method of producing thereof
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
EP2043974A2 (en) 2009-04-08
CN101472862A (en) 2009-07-01
US20080015397A1 (en) 2008-01-17
BRPI0711991A2 (en) 2012-03-06
WO2007149372A2 (en) 2007-12-27

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