[go: up one dir, main page]

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

Info

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.)
Expired - Fee Related
Application number
FR1860602A
Other languages
English (en)
Other versions
FR3088641A1 (fr
Inventor
Mathieu Rouen
Fadwa Kamal
Marc Mauduit
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.)
Vipo France Sas Fr
Centre National de la Recherche Scientifique CNRS
Original Assignee
Centre National de la Recherche Scientifique CNRS
Demeta SAS
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
Application filed by Centre National de la Recherche Scientifique CNRS, Demeta SAS filed Critical Centre National de la Recherche Scientifique CNRS
Priority to FR1860602A priority Critical patent/FR3088641B1/fr
Priority to PCT/FR2019/052531 priority patent/WO2020099750A1/fr
Priority to MX2021005690A priority patent/MX2021005690A/es
Publication of FR3088641A1 publication Critical patent/FR3088641A1/fr
Priority to IL283146A priority patent/IL283146A/en
Application granted granted Critical
Publication of FR3088641B1 publication Critical patent/FR3088641B1/fr
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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]

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.
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 Expired - Fee Related 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
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
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.
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 Expired - Fee Related 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)

* 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
US20240278223A1 (en) * 2021-06-15 2024-08-22 Exxonmobil Chemical Patents Inc. Method to Activate Carbene and Carbyne Complexes and Their Use in Metathesis Polymerization

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
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
FR2999180B1 (fr) 2012-12-12 2015-04-10 Ecole Nationale Superieure De Chimie De Rennes Procede de preparation de sels d'imidazolium dissymetriques
ES2639302T3 (es) * 2014-08-07 2017-10-26 Telene Sas Composición curable y artículo moldeado que comprende la composición
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
WO2020099750A1 (fr) 2020-05-22
MX2021005690A (es) 2021-07-07

Similar Documents

Publication Publication Date Title
FR3088641B1 (fr) Procede de metathese d'olefines utilisant un catalyseur en presence d'un activateur et d'un agent retardateur
SA522431586B1 (ar) مركب ببتيد ثنائي الحلقة متغاير الترادف
EP4464721A3 (fr) Complexes peptidiques bicycliques hétérotandem
MX2020010444A (es) Complejos de péptidos bicíclicos en heterotándem.
PE20190201A1 (es) Receptores quimericos de flt3 y metodos de uso de los mismos
MX2023008168A (es) Complejos peptidicos biciclicos heterotandem.
WO2016149027A3 (fr) Procédé d'oligomérisation
EP4041778A4 (fr) Photopolymères de métathèse d'oléfines
MY139903A (en) Process for the telomerization of acyclic olefins
EA200701383A1 (ru) Способ получения катализатора полимеризации олефинов
EA202192130A1 (ru) Специфичные к ltbp-комплексу ингибиторы tgf и их применение
WO2018017864A3 (fr) Agents de liaison à pvrig et leurs utilisations
JP2019510733A5 (fr)
EP4279170A3 (fr) Systeme de distribution d'un produit cosmetique
MA29958B1 (fr) Procede pour olefines internes
DE59912097D1 (de) Alkylidenkomplexe des rutheniums mit n-heterozyklischen carbenliganden; verwendung als katalysatoren für die olefin-metathese
CR9393A (es) Anticuerpos anti-ccr5 y usos de los mismos
PL364370A1 (en) Method for telomerizing non-cyclic olefins
PL419421A1 (pl) Zastosowanie kompleksów rutenu w reakcji metatezy olefin
WO2004055513A3 (fr) Utilisation d'antagonistes de cd137 pour le traitement de tumeurs
EA201791753A1 (ru) Способы получения полинуклеотидов с использованием композиций солей поливалентных катионов
WO2020109217A3 (fr) Composés organométalliques
CY1110441T1 (el) Μεθοδος για τον καθορισμο μιας μη-ανοσοσφαιρινικης πρωτεϊνης η οποια περιλαμβανει μια ανοσοσφαιρινη-ομοια (ig-ομοια) περιοχη
FR2975607B1 (fr) Produit d'addition d'halogenure de magnesium,constituant catalytique et catalyseur le comprenant, et leur preparation
WO2019067274A8 (fr) Catalyseurs de type bis-phényl-phénoxy-polyoléfine ayant deux ligands de type méthylènetrialkylsilicium sur le métal pour une solubilité améliorée

Legal Events

Date Code Title Description
PLFP Fee payment

Year of fee payment: 2

PLSC Publication of the preliminary search report

Effective date: 20200522

PLFP Fee payment

Year of fee payment: 3

PLFP Fee payment

Year of fee payment: 4

PLFP Fee payment

Year of fee payment: 5

PLFP Fee payment

Year of fee payment: 6

TQ Partial transmission of property

Owner name: VIPO FRANCE SAS, FR

Effective date: 20240503

Owner name: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE, FR

Effective date: 20240503

ST Notification of lapse

Effective date: 20250705