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 PDFInfo
- 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
- Authority
- FR
- France
- Prior art keywords
- activator
- catalyst
- delaying agent
- metathesis process
- olefins
- 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.)
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Links
- 150000001336 alkenes Chemical class 0.000 title abstract 3
- 238000005649 metathesis reaction Methods 0.000 title abstract 3
- 239000012190 activator Substances 0.000 title abstract 2
- 239000003054 catalyst Substances 0.000 title abstract 2
- 239000003795 chemical substances by application Substances 0.000 title 1
- 239000003446 ligand Substances 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 239000002841 Lewis acid Substances 0.000 abstract 1
- 150000007517 lewis acids Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract 1
- 150000002978 peroxides Chemical class 0.000 abstract 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 abstract 1
- 239000003340 retarding agent Substances 0.000 abstract 1
- 229910052707 ruthenium Inorganic materials 0.000 abstract 1
Classifications
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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
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- 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
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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
- 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]
Landscapes
- 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.
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 |
Family
ID=65685776
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
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 |
Country Status (4)
Country | Link |
---|---|
FR (1) | FR3088641B1 (fr) |
IL (1) | IL283146A (fr) |
MX (1) | MX2021005690A (fr) |
WO (1) | WO2020099750A1 (fr) |
Families Citing this family (3)
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)
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 |
-
2018
- 2018-11-16 FR FR1860602A patent/FR3088641B1/fr active Active
-
2019
- 2019-10-23 MX MX2021005690A patent/MX2021005690A/es unknown
- 2019-10-23 WO PCT/FR2019/052531 patent/WO2020099750A1/fr active Application Filing
-
2021
- 2021-05-12 IL IL283146A patent/IL283146A/en unknown
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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Owner name: VIPO FRANCE SAS, FR Effective date: 20240503 Owner name: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE, FR Effective date: 20240503 |