WO2011100022A3 - Catalyseur de métathèse et procédé d'utilisation associé - Google Patents

Catalyseur de métathèse et procédé d'utilisation associé 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
English (en)
Other versions
WO2011100022A2 (fr
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 EP10845952.0A priority Critical patent/EP2533899A4/fr
Priority to BR112012020146-8A priority patent/BR112012020146A2/pt
Priority to CA2785897A priority patent/CA2785897C/fr
Priority to CN201080062860.8A priority patent/CN102781583B/zh
Publication of WO2011100022A2 publication Critical patent/WO2011100022A2/fr
Publication of WO2011100022A3 publication Critical patent/WO2011100022A3/fr

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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 Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Inorganic Chemistry (AREA)
  • Materials Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)

Abstract

La présente invention a pour objet un composé catalyseur pour la métathèse d'oléfines représenté par la formule : dans laquelle M est un métal du Groupe 8 ; X et X1 sont des ligands anioniques ; L est un donneur de deux électrons neutre ; L1 est N, O, P, ou S, de préférence N ou O ; R est un hydrocarbyle en C1 à C30 ou un hydrocarbyle en C1 à C30 substitué ; G* est choisi dans le groupe comprenant l'hydrogène, un hydrocarbyle en C1 à C30, et un hydrocarbyle en C1 à C30 substitué ; R1 est choisi dans le groupe comprenant l'hydrogène, un hydrocarbyle en C1 à C30, et un hydrocarbyle en C1 à C30 substitué ; et G est choisi indépendamment dans le groupe comprenant l'hydrogène, un halogène, les hydrocarbyles en C1 à C30 et les hydrocarbyles en C1 à C30 substitués. Cette invention concerne également un procédé pour fabriquer des alpha-oléfines comprenant la mise en contact d'une oléfine, telle que l'éthylène, avec une huile d'alimentation contenant un triacylglycéride (typiquement un ester d'acide gras (tel que l'oléate de méthyle)) avec le composé catalyseur décrit ci-dessus. L'ester d'acide gras peut être un ester méthylique d'acide gras dérivé d'un biodiesel.
PCT/US2010/059703 2010-02-12 2010-12-09 Catalyseur de métathèse et procédé d'utilisation associé WO2011100022A2 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP10845952.0A EP2533899A4 (fr) 2010-02-12 2010-12-09 Catalyseur de métathèse et procédé d'utilisation associé
BR112012020146-8A BR112012020146A2 (pt) 2010-02-12 2010-12-09 catalisador de metátese e processos para uso do mesmo.
CA2785897A CA2785897C (fr) 2010-02-12 2010-12-09 Catalyseur de metathese et procede d'utilisation associe
CN201080062860.8A CN102781583B (zh) 2010-02-12 2010-12-09 复分解催化剂和其应用方法

Applications Claiming Priority (4)

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

Publications (2)

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

Family

ID=42260291

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2010/059703 WO2011100022A2 (fr) 2010-02-12 2010-12-09 Catalyseur de métathèse et procédé d'utilisation associé

Country Status (5)

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

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014004089A1 (fr) * 2012-06-28 2014-01-03 Exxonmobil Chemical Patents Inc. Catalyseur de métathèse et son procédé d'utilisation
CN103936793B (zh) 2013-01-10 2017-02-08 光明创新（武汉）有限公司 含卡宾配体的催化剂及其制备方法与其在复分解反应中的应用
EP3129347B1 (fr) 2014-04-10 2021-10-06 California Institute of Technology Réactions en présence de complexes de ruthénium
RU2674471C2 (ru) 2014-07-03 2018-12-11 Гуан Мин Инновейшн Компани (Ухань) Катализаторы на основе переходного металла 8 группы, способ их получения и способ их применения в реакции метатезиса
EP3219778A1 (fr) * 2016-03-15 2017-09-20 Umicore AG & Co. KG Biocarburant et procédé de préparation par isomérisation de métathèse
FI128954B (en) 2019-09-26 2021-03-31 Neste Oyj Preparation of renewable base oil including metathesis
FI128952B (en) 2019-09-26 2021-03-31 Neste Oyj Preparation of renewable alkenes including metathesis
FI130917B1 (fi) * 2019-12-20 2024-05-28 Neste Oyj Joustava integroitu tuotantolaitosjärjestelmä ja menetelmä

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
CA2441980C (fr) * 2001-03-26 2011-07-19 Dow Global Technologies Inc. Metathese d'esters d'acides gras insatures ou d'acides gras insatures avec des olefines inferieures
GB0428172D0 (en) * 2004-12-23 2005-01-26 Ici Plc Olefin metathesis polymerisation
CA2655575C (fr) * 2006-06-30 2014-07-29 F.Hoffmann-La Roche Ag Nouveaux complexes du ruthenium comme catalyseurs pour des reactions de metathese
DE102006040569A1 (de) * 2006-08-30 2008-03-06 Lanxess Deutschland Gmbh Verfahren zum Metathese-Abbau von Nitrilkautschuken
DE102006043704A1 (de) * 2006-09-18 2008-03-27 Umicore Ag & Co. Kg Neue Metathesekatalysatoren
WO2008064223A1 (fr) * 2006-11-21 2008-05-29 California Institute Of Technology Initiateurs de métathèse d'oléfine portant des ligands thiazol-2-ylidène

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
CN102781583A (zh) 2012-11-14
CA2785897A1 (fr) 2011-08-18
BR112012020146A2 (pt) 2020-08-18
CA2785897C (fr) 2014-01-28
CN102781583B (zh) 2015-07-22
EP2533899A2 (fr) 2012-12-19
EP2533899A4 (fr) 2013-08-07
WO2011100022A2 (fr) 2011-08-18

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