WO2011100022A3 - Metathesis catalyst and process for use thereof - Google Patents

Metathesis catalyst and process for use thereof Download PDF

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Publication number
WO2011100022A3
WO2011100022A3 PCT/US2010/059703 US2010059703W WO2011100022A3 WO 2011100022 A3 WO2011100022 A3 WO 2011100022A3 US 2010059703 W US2010059703 W US 2010059703W WO 2011100022 A3 WO2011100022 A3 WO 2011100022A3
Authority
WO
WIPO (PCT)
Prior art keywords
hydrocarbyl
group
hydrogen
fatty acid
substituted
Prior art date
Application number
PCT/US2010/059703
Other languages
French (fr)
Other versions
WO2011100022A2 (en
Inventor
Matthew W. Holtcamp
Catherine A. Faler
Caol P. Huff
Matthew S. Bedoya
John R. Hagadorn
Original Assignee
Exxonmobil Chemical Patents Inc.
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
Priority claimed from US12/705,136 external-priority patent/US8237003B2/en
Application filed by Exxonmobil Chemical Patents Inc. filed Critical Exxonmobil Chemical Patents Inc.
Priority to BR112012020146-8A priority Critical patent/BR112012020146A2/en
Priority to EP10845952.0A priority patent/EP2533899A4/en
Priority to CA2785897A priority patent/CA2785897C/en
Priority to CN201080062860.8A priority patent/CN102781583B/en
Publication of WO2011100022A2 publication Critical patent/WO2011100022A2/en
Publication of WO2011100022A3 publication Critical patent/WO2011100022A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/0046—Ruthenium compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2265—Carbenes or carbynes, i.e.(image)
    • B01J31/2269—Heterocyclic carbenes
    • B01J31/2273—Heterocyclic carbenes with only nitrogen as heteroatomic ring members, e.g. 1,3-diarylimidazoline-2-ylidenes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2265—Carbenes or carbynes, i.e.(image)
    • B01J31/2278—Complexes comprising two carbene ligands differing from each other, e.g. Grubbs second generation catalysts
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
    • C07C6/02—Metathesis reactions at an unsaturated carbon-to-carbon bond
    • C07C6/04—Metathesis reactions at an unsaturated carbon-to-carbon bond at a carbon-to-carbon double bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/50—Redistribution or isomerisation reactions of C-C, C=C or C-C triple bonds
    • B01J2231/54—Metathesis reactions, e.g. olefin metathesis
    • B01J2231/543—Metathesis reactions, e.g. olefin metathesis alkene metathesis
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/821—Ruthenium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2540/00—Compositional aspects of coordination complexes or ligands in catalyst systems
    • B01J2540/20—Non-coordinating groups comprising halogens
    • B01J2540/22—Non-coordinating groups comprising halogens comprising fluorine, e.g. trifluoroacetate
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/2252—Sulfonate ligands
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • C07C2531/24—Phosphines
    • 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
    • Y02E50/10—Biofuels, e.g. bio-diesel

Abstract

This invention relates to a catalyst compound for the metathesis of olefins represented by the formula (I): wherein M is a Group 8 metal; X and X1 are anionic ligands; L is a neutral two electron donor; L1 is N, O, P, or S, preferably N or O; R is a C1 to C30 hydrocarbyl or a C1 to C30 substituted hydrocarbyl; G* is selected from the group consisting of hydrogen, a C1 to C30 hydrocarbyl, and a C1 to C30 substituted hydrocarbyl; R1 is selected from the group consisting of hydrogen, a C1 to C30 hydrocarbyl, and a C1 to C30 substituted hydrocarbyl; and G is independently selected from the group consisting of hydrogen, halogen, C1 to C30 hydrocarbyls and C1 to C30 substituted hydrocarbyls. This invention also relates to process to make alphaolefms comprising contacting an olefin, such as ethylene, with a feed oil containing a triacylglyceride (typically a fatty acid ester (such as methyl oleate)) with the catalyst compound described above. The fatty acid ester may be a fatty acid methyl ester derived from biodiesel.
PCT/US2010/059703 2010-02-12 2010-12-09 Metathesis catalyst and process for use thereof WO2011100022A2 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
BR112012020146-8A BR112012020146A2 (en) 2010-02-12 2010-12-09 metathesis catalyst and processes for its use.
EP10845952.0A EP2533899A4 (en) 2010-02-12 2010-12-09 Metathesis catalyst and process for use thereof
CA2785897A CA2785897C (en) 2010-02-12 2010-12-09 Metathesis catalyst and process for use thereof
CN201080062860.8A CN102781583B (en) 2010-02-12 2010-12-09 Metathesis catalyst and process for use thereof

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US12/705,136 2010-02-12
US12/705,136 US8237003B2 (en) 2009-11-09 2010-02-12 Metathesis catalyst and process for use thereof
EP10159428.1 2010-04-08
EP10159428 2010-04-08

Publications (2)

Publication Number Publication Date
WO2011100022A2 WO2011100022A2 (en) 2011-08-18
WO2011100022A3 true WO2011100022A3 (en) 2011-11-17

Family

ID=42260291

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2010/059703 WO2011100022A2 (en) 2010-02-12 2010-12-09 Metathesis catalyst and process for use thereof

Country Status (5)

Country Link
EP (1) EP2533899A4 (en)
CN (1) CN102781583B (en)
BR (1) BR112012020146A2 (en)
CA (1) CA2785897C (en)
WO (1) WO2011100022A2 (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014004089A1 (en) * 2012-06-28 2014-01-03 Exxonmobil Chemical Patents Inc. Metathesis catalyst and process for use thereof
CN103936793B (en) 2013-01-10 2017-02-08 光明创新（武汉）有限公司 Catalyst containing carbene ligand, its preparation method and its application in double decomposition reaction
EP3129347B1 (en) 2014-04-10 2021-10-06 California Institute of Technology Reactions in the presence of ruthenium complexes
RU2674471C2 (en) 2014-07-03 2018-12-11 Гуан Мин Инновейшн Компани (Ухань) Group 8 transition metal catalysts and method for making same and process for use of same in metathesis reaction
EP3219778A1 (en) * 2016-03-15 2017-09-20 Umicore AG & Co. KG Biofuel and method for preparation by isomerizing metathesis
FI128952B (en) * 2019-09-26 2021-03-31 Neste Oyj Renewable alkene production engaging metathesis
FI128954B (en) 2019-09-26 2021-03-31 Neste Oyj Renewable base oil production engaging metathesis
FI20196122A1 (en) * 2019-12-20 2021-06-21 Neste Oyj Flexible production plant system and method

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4545941A (en) * 1983-06-20 1985-10-08 A. E. Staley Manufacturing Company Co-metathesis of triglycerides and ethylene
US7205424B2 (en) * 2003-06-19 2007-04-17 University Of New Orleans Research And Technology Foundation, Inc. Preparation of ruthenium-based olefin metathesis catalysts
US20090069516A1 (en) * 2007-08-21 2009-03-12 Lanxess Deutschland Gmbh Catalyst systems and their use for metathesis reactions
US20100022789A1 (en) * 2008-07-25 2010-01-28 Rhodia Operations Catalytic compositions for the metathesis of unsaturated fatty bodies with olefins and metathesis methods using catalytic compositions

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102146031B (en) * 2001-03-26 2014-08-06 陶氏环球技术有限责任公司 Metathesis of unsaturated fatty acid esters or unsaturated fatty acids with lower olefins
GB0428172D0 (en) * 2004-12-23 2005-01-26 Ici Plc Olefin metathesis polymerisation
WO2008000644A1 (en) * 2006-06-30 2008-01-03 F. Hoffmann-La Roche Ag New ruthenium complexes as catalysts for metahesis reactions
DE102006040569A1 (en) * 2006-08-30 2008-03-06 Lanxess Deutschland Gmbh Process for the metathesis degradation of nitrile rubbers
DE102006043704A1 (en) * 2006-09-18 2008-03-27 Umicore Ag & Co. Kg New metathesis catalysts
EP2104566B1 (en) * 2006-11-21 2016-01-27 California Institute Of Technology Olefin metathesis initiators bearing thiazol-2-ylidene ligands

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4545941A (en) * 1983-06-20 1985-10-08 A. E. Staley Manufacturing Company Co-metathesis of triglycerides and ethylene
US7205424B2 (en) * 2003-06-19 2007-04-17 University Of New Orleans Research And Technology Foundation, Inc. Preparation of ruthenium-based olefin metathesis catalysts
US20090069516A1 (en) * 2007-08-21 2009-03-12 Lanxess Deutschland Gmbh Catalyst systems and their use for metathesis reactions
US20100022789A1 (en) * 2008-07-25 2010-01-28 Rhodia Operations Catalytic compositions for the metathesis of unsaturated fatty bodies with olefins and metathesis methods using catalytic compositions

Also Published As

Publication number Publication date
EP2533899A4 (en) 2013-08-07
EP2533899A2 (en) 2012-12-19
CA2785897A1 (en) 2011-08-18
CN102781583B (en) 2015-07-22
BR112012020146A2 (en) 2020-08-18
WO2011100022A2 (en) 2011-08-18
CN102781583A (en) 2012-11-14
CA2785897C (en) 2014-01-28

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