CA2777176C - Catalyseurs de metathese et leurs procedes d'utilisation - Google Patents

Catalyseurs de metathese et leurs procedes d'utilisation Download PDF

Info

Publication number
CA2777176C
CA2777176C CA2777176A CA2777176A CA2777176C CA 2777176 C CA2777176 C CA 2777176C CA 2777176 A CA2777176 A CA 2777176A CA 2777176 A CA2777176 A CA 2777176A CA 2777176 C CA2777176 C CA 2777176C
Authority
CA
Canada
Prior art keywords
fatty acid
oil
olefin
alpha
catalyst
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.)
Expired - Fee Related
Application number
CA2777176A
Other languages
English (en)
Other versions
CA2777176A1 (fr
Inventor
Matthew W. Holtcamp
Matthew S. Bedoya
Catherine A. Faler
Caol P. Huff
John R. Hagadorn
Renuka Ganesh
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.)
ExxonMobil Chemical Patents Inc
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 claimed from PCT/US2010/055302 external-priority patent/WO2011056874A2/fr
Publication of CA2777176A1 publication Critical patent/CA2777176A1/fr
Application granted granted Critical
Publication of CA2777176C publication Critical patent/CA2777176C/fr
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • 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
    • 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
    • C07F15/002—Osmium compounds
    • 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
    • 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
    • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0261—Complexes comprising ligands with non-tetrahedral chirality
    • 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
    • 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
    • B01J2531/825—Osmium
    • 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
    • C07C2531/22—Organic complexes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un composé catalyseur de métathèse qui comprend un catalyseur de métathèse à base d'un carbène N-hétérocyclique à substitution asymétrique (NHC) et un procédé de fabrication d'alpha-oléfines linéaires qui comprend la mise en contact d'un matériau d'alimentation et d'un alcène optionnel (tel que l'éthylène) avec ledit catalyseur, le matériau d'alimentation étant un triacylglycéride, un acide gras, un ester alkylique d'acide gras et/ou un ester d'acide gras, généralement dérivé de biodiesel.
CA2777176A 2009-11-09 2010-11-03 Catalyseurs de metathese et leurs procedes d'utilisation Expired - Fee Related CA2777176C (fr)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US25952109P 2009-11-09 2009-11-09
US61/259,521 2009-11-09
US12/705,136 2010-02-12
US12/705,136 US8237003B2 (en) 2009-11-09 2010-02-12 Metathesis catalyst and process for use thereof
US31438810P 2010-03-16 2010-03-16
US61/314,388 2010-03-16
PCT/US2010/055302 WO2011056874A2 (fr) 2009-11-09 2010-11-03 Catalyseurs de métathèse et leurs procédés d'utilisation

Publications (2)

Publication Number Publication Date
CA2777176A1 CA2777176A1 (fr) 2011-05-12
CA2777176C true CA2777176C (fr) 2014-05-20

Family

ID=46731240

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2777176A Expired - Fee Related CA2777176C (fr) 2009-11-09 2010-11-03 Catalyseurs de metathese et leurs procedes d'utilisation

Country Status (2)

Country Link
CN (1) CN102655935B (fr)
CA (1) CA2777176C (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MY172162A (en) * 2013-03-14 2019-11-15 Wilmar Trading Pte Ltd Methods for treating a metathesis feedstock with metal alkoxides
CN103464201B (zh) * 2013-09-25 2015-06-10 陕西合盛生物柴油技术开发有限公司 生物柴油酯化复合酸催化剂
GB2522640B (en) * 2014-01-30 2018-04-25 Univ Court Univ St Andrews Method of alkene metathesis
EP3219778A1 (fr) * 2016-03-15 2017-09-20 Umicore AG & Co. KG Biocarburant et procédé de préparation par isomérisation de métathèse

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100823365B1 (ko) * 1999-05-24 2008-04-17 캘리포니아 인스티튜트 오브 테크놀로지 이미다졸리딘계 금속 카르벤 복분해 촉매

Also Published As

Publication number Publication date
CA2777176A1 (fr) 2011-05-12
CN102655935A (zh) 2012-09-05
CN102655935B (zh) 2016-01-13

Similar Documents

Publication Publication Date Title
US8063232B2 (en) Metathesis catalyst and process for use thereof
US8809563B2 (en) Metathesis catalyst and process for use thereof
EP2498909B1 (fr) Catalyseur de métathèse et son procédé d'utilisation
US8227371B2 (en) Class of olefin metathesis catalysts, methods of preparation, and processes for the use thereof
CA2785897C (fr) Catalyseur de metathese et procede d'utilisation associe
Malacea et al. Renewable materials as precursors of linear nitrile-acid derivatives via cross-metathesis of fatty esters and acids with acrylonitrile and fumaronitrile
US8524930B2 (en) Class of olefin metathesis catalysts, methods of preparation, and processes for the use thereof
Miao et al. Polyamide precursors from renewable 10-undecenenitrile and methyl acrylate via olefin cross-metathesis
US8329921B2 (en) Metathesis catalyst and process for use thereof
US11414446B1 (en) Compounds and the use thereof in metathesis reactions
EP2498908A2 (fr) Catalyseurs de métathèse et leurs procédés d'utilisation
Bruneau et al. Cross‐metathesis with acrylonitrile and applications to fatty acid derivatives
CA2777176C (fr) Catalyseurs de metathese et leurs procedes d'utilisation
US9024034B2 (en) Metathesis catalysts and processes for use thereof
EP3129347A1 (fr) Réactions en présence de complexes de ruthénium
EP2925705A1 (fr) Procédés de fabrication d'oléfines internes fonctionnalisées et leurs utilisations
US9120736B2 (en) Method for producing unsaturated compounds
WO2014004089A1 (fr) Catalyseur de métathèse et son procédé d'utilisation
EP2618930A2 (fr) Nouvelle classe de catalyseurs de métathèse d'oléfines, méthodes de préparation, et procédés d'utilisation
Malacea et al. Alkene metathesis and renewable materials: selective transformations of plant oils
WO2012166259A2 (fr) Nouvelle classe de catalyseurs de métathèse d'oléfine, procédés de préparation et procédés pour l'utilisation de celle-ci
KR20150024396A (ko) 불포화 화합물의 제조 방법
John Dehydrative Decarbonylation

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20201103