WO2007149371A3 - Process for making isooctenes from dry isobutanol - Google Patents

Process for making isooctenes from dry isobutanol Download PDF

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Publication number
WO2007149371A3
WO2007149371A3 PCT/US2007/014166 US2007014166W WO2007149371A3 WO 2007149371 A3 WO2007149371 A3 WO 2007149371A3 US 2007014166 W US2007014166 W US 2007014166W WO 2007149371 A3 WO2007149371 A3 WO 2007149371A3
Authority
WO
WIPO (PCT)
Prior art keywords
isooctenes
dry isobutanol
making
making isooctenes
dry
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/US2007/014166
Other languages
French (fr)
Other versions
WO2007149371A2 (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 BRPI0712271-3A priority Critical patent/BRPI0712271A2/en
Priority to EP07796213A priority patent/EP2043973A2/en
Publication of WO2007149371A2 publication Critical patent/WO2007149371A2/en
Publication of WO2007149371A3 publication Critical patent/WO2007149371A3/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
    • 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
    • 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
    • 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
    • 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
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • C07C2523/24—Chromium, molybdenum or tungsten
    • C07C2523/30—Tungsten
    • 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-
    • 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
    • C10G2300/40—Characteristics of the process deviating from typical ways of processing
    • C10G2300/44—Solvents
    • 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 process for making isooctenes using dry isobutanol derived from fermentation broth. The isooctenes so produced are useful for the production of fuel additives.
PCT/US2007/014166 2006-06-16 2007-06-15 Process for making isooctenes from dry isobutanol Ceased WO2007149371A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
BRPI0712271-3A BRPI0712271A2 (en) 2006-06-16 2007-06-15 processes for the manufacture of at least one isooctene, at least one isooctane, at least one isooctanol and a reaction product
EP07796213A EP2043973A2 (en) 2006-06-16 2007-06-15 Process for making isooctenes from dry isobutanol

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US81466306P 2006-06-16 2006-06-16
US60/814,663 2006-06-16

Publications (2)

Publication Number Publication Date
WO2007149371A2 WO2007149371A2 (en) 2007-12-27
WO2007149371A3 true WO2007149371A3 (en) 2008-02-28

Family

ID=38666966

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2007/014166 Ceased WO2007149371A2 (en) 2006-06-16 2007-06-15 Process for making isooctenes from dry isobutanol

Country Status (5)

Country Link
US (1) US20080009656A1 (en)
EP (1) EP2043973A2 (en)
CN (1) CN101472861A (en)
BR (1) BRPI0712271A2 (en)
WO (1) WO2007149371A2 (en)

Families Citing this family (21)

* 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
US20080015395A1 (en) * 2006-06-16 2008-01-17 D Amore Michael B Process for making butenes from aqueous 1-butanol
US20080015397A1 (en) * 2006-06-16 2008-01-17 D Amore Michael B Process for making isooctenes from aqueous 1-butanol
US20080045754A1 (en) * 2006-06-16 2008-02-21 D Amore Michael B Process for making butenes from dry 1-butanol
US20080132741A1 (en) * 2006-06-16 2008-06-05 D Amore Michael B Process for making butenes from dry isobutanol
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
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
TWI434921B (en) * 2009-06-17 2014-04-21 Danisco Us Inc Methods and systems for producing fuel constituents from bioisoprene compositions
US20130197279A1 (en) * 2009-07-29 2013-08-01 Michael E. Wright Water and Contaminants Removal from Butanol Fermentation Solutions and/or Broths Using a Brine Solution
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
CN103025688A (en) 2010-06-17 2013-04-03 丹尼斯科美国公司 Fuel compositions comprising isoprene derivatives
WO2012145495A2 (en) 2011-04-19 2012-10-26 Gevo, Inc. Variations on prins-like chemistry to produce 2,5-dimethylhexadiene from isobutanol
US9914672B2 (en) 2012-10-19 2018-03-13 Lummus Technology Inc. Conversion of alcohols to distillate fuels
MY192923A (en) 2014-10-08 2022-09-15 Ericsson Telefon Ab L M Mobility synchronization measurements
CN107056576B (en) * 2017-01-16 2020-04-28 重庆邮电大学 Preparation method of 2,4,4-trimethyl-1-pentene

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
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 (12)

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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
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
US20080045754A1 (en) * 2006-06-16 2008-02-21 D Amore Michael B Process for making butenes from dry 1-butanol
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
US20080015395A1 (en) * 2006-06-16 2008-01-17 D Amore Michael B Process for making butenes from aqueous 1-butanol
US20080132741A1 (en) * 2006-06-16 2008-06-05 D Amore Michael B Process for making butenes from dry isobutanol
US20080015397A1 (en) * 2006-06-16 2008-01-17 D Amore Michael B Process for making isooctenes from aqueous 1-butanol
US20080132732A1 (en) * 2006-12-01 2008-06-05 Leo Ernest Manzer Process for making butenes from aqueous 2-butanol
US20080132730A1 (en) * 2006-12-01 2008-06-05 Leo Ernest Manzer Process for making butenes from dry 2-butanol
US20080131948A1 (en) * 2006-12-01 2008-06-05 Leo Ernest Manzer Process for making isooctenes from dry 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
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)

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Title
DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; 1944, IPATIEFF, MONROE: "The dehydratation of the lower aliphatic alcohols in the presence of dilute aqueous solutions of acids and salts" *
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, MONROE: "The dehydration of the lower aliphatic alcohols in the presence of dilute aqueous solutions of acids and salts", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 66, 1944, pages 1627 - 1631, XP002458829 *
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 *

Also Published As

Publication number Publication date
CN101472861A (en) 2009-07-01
US20080009656A1 (en) 2008-01-10
EP2043973A2 (en) 2009-04-08
WO2007149371A2 (en) 2007-12-27
BRPI0712271A2 (en) 2012-01-17

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