FR3088641B1 - Procede de metathese d'olefines utilisant un catalyseur en presence d'un activateur et d'un agent retardateur - Google Patents

Procede de metathese d'olefines utilisant un catalyseur en presence d'un activateur et d'un agent retardateur Download PDF

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Publication number
FR3088641B1
FR3088641B1 FR1860602A FR1860602A FR3088641B1 FR 3088641 B1 FR3088641 B1 FR 3088641B1 FR 1860602 A FR1860602 A FR 1860602A FR 1860602 A FR1860602 A FR 1860602A FR 3088641 B1 FR3088641 B1 FR 3088641B1
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France
Prior art keywords
activator
catalyst
delaying agent
metathesis process
olefins
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Active
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FR1860602A
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English (en)
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FR3088641A1 (fr
Inventor
Mathieu Rouen
Fadwa Kamal
Marc Mauduit
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VIPO FRANCE SAS, FR
Centre National de la Recherche Scientifique CNRS
Original Assignee
Centre National de la Recherche Scientifique CNRS
Demeta SAS
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Priority to FR1860602A priority Critical patent/FR3088641B1/fr
Priority to MX2021005690A priority patent/MX2021005690A/es
Priority to PCT/FR2019/052531 priority patent/WO2020099750A1/fr
Publication of FR3088641A1 publication Critical patent/FR3088641A1/fr
Priority to IL283146A priority patent/IL283146A/en
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    • 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
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0255—Phosphorus containing compounds
    • B01J31/0257—Phosphorus acids or phosphorus acid esters
    • B01J31/0259—Phosphorus acids or phosphorus acid esters comprising phosphorous acid (-ester) groups ((RO)P(OR')2) or the isomeric phosphonic acid (-ester) groups (R(R'O)2P=O), i.e. R= C, R'= C, H
    • 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
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/06—Halogens; Compounds thereof
    • B01J27/08—Halides
    • B01J27/10—Chlorides
    • 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
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/02—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/16—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a six-membered ring
    • C07C13/20—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a six-membered ring with a cyclohexene ring
    • 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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
    • C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
    • C08G61/06—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds
    • C08G61/08—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/11—Homopolymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/33—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain
    • C08G2261/332—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms
    • C08G2261/3324—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms derived from norbornene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/40—Polymerisation processes
    • C08G2261/41—Organometallic coupling reactions
    • C08G2261/418—Ring opening metathesis polymerisation [ROMP]

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

Abstract

La présente invention concerne un procédé de métathèse d'oléfines, comprenant la mise en contact de : - au moins une oléfine, - un catalyseur de métathèse constitué d'au moins un complexe de ruthénium alkylidène comprenant deux ligands diaminocarbènes N-hétérocycliques identiques ou différents, dont au moins un ligand 1-aryl-3-cycloalkyl-imidazoline-2-ylidène, - un agent retardateur constitué d'au moins un phosphite, - et un activateur choisi parmi les acides de Lewis, les peroxydes et leurs mélanges. Elle concerne également un kit pour la mise en œuvre de ce procédé.
FR1860602A 2018-11-16 2018-11-16 Procede de metathese d'olefines utilisant un catalyseur en presence d'un activateur et d'un agent retardateur Active FR3088641B1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
FR1860602A FR3088641B1 (fr) 2018-11-16 2018-11-16 Procede de metathese d'olefines utilisant un catalyseur en presence d'un activateur et d'un agent retardateur
MX2021005690A MX2021005690A (es) 2018-11-16 2019-10-23 Metodo para la metatesis de olefinas utilizando un catalizador en la presencia de un activador y un agente retardante.
PCT/FR2019/052531 WO2020099750A1 (fr) 2018-11-16 2019-10-23 Procede de metathese d'olefines utilisant un catalyseur en presence d'un activateur et d'un agent retardateur
IL283146A IL283146A (en) 2018-11-16 2021-05-12 A method for the metathesis of olefins using a catalyst in the presence of an activating and inhibiting agent

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR1860602A FR3088641B1 (fr) 2018-11-16 2018-11-16 Procede de metathese d'olefines utilisant un catalyseur en presence d'un activateur et d'un agent retardateur

Publications (2)

Publication Number Publication Date
FR3088641A1 FR3088641A1 (fr) 2020-05-22
FR3088641B1 true FR3088641B1 (fr) 2021-11-19

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FR1860602A Active FR3088641B1 (fr) 2018-11-16 2018-11-16 Procede de metathese d'olefines utilisant un catalyseur en presence d'un activateur et d'un agent retardateur

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FR (1) FR3088641B1 (fr)
IL (1) IL283146A (fr)
MX (1) MX2021005690A (fr)
WO (1) WO2020099750A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11718710B2 (en) * 2020-10-14 2023-08-08 The Board Of Trustees Of The University Of Illinois Method of light-promoted frontal ring-opening metathesis polymerization
US11753501B2 (en) 2021-01-12 2023-09-12 The Board Of Trustees Of The University Of Illinois Frontally polymerized polymeric body and method of producing a polymeric body having spatially varying properties
WO2022265865A1 (fr) * 2021-06-15 2022-12-22 Exxonmobil Chemical Patents Inc. Procédé d'activation de complexes carbène et carbyne et leur utilisation dans la polymérisation par métathèse

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4933402A (en) 1988-12-30 1990-06-12 Hercules Incorporated Phosphorus compounds that delay the metathesis polymerization of cycloolefins
US5939504A (en) 1995-12-07 1999-08-17 Advanced Polymer Technologies Method for extending the pot life of an olefin metathesis polymerization reaction
JP2004017500A (ja) * 2002-06-17 2004-01-22 Nippon Zeon Co Ltd 水硬性組成物積層体、その製造方法および未硬化の水硬性組成物成形体の表面保護方法
EP2460587B1 (fr) 2010-12-01 2017-10-18 Rimtec Corporation Système de catalyseur au ruthénium pour la métathèse des oléfines
FR2999180B1 (fr) 2012-12-12 2015-04-10 Ecole Nationale Superieure De Chimie De Rennes Procede de preparation de sels d'imidazolium dissymetriques
FR2999184B1 (fr) 2012-12-12 2015-01-09 Ecole Nationale Superieure De Chimie De Rennes Complexes de ruthenium comprenant un diaminocarbene n-heterocyclique insature dissymetrique
PL2982709T3 (pl) * 2014-08-07 2017-12-29 Telene Sas Kompozycja utwardzalna i wytwór formowany zawierający kompozycję
US10487446B2 (en) 2016-03-18 2019-11-26 The Board Of Trustees Of The University Of Illinois Frontal polymerization for fiber-reinforced composites

Also Published As

Publication number Publication date
IL283146A (en) 2021-06-30
FR3088641A1 (fr) 2020-05-22
MX2021005690A (es) 2021-07-07
WO2020099750A1 (fr) 2020-05-22

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