Use of ruthenium complexes in olefin metathesis reaction
AssigneeApeiron Synthesis S.A.
InventorsKrzysztof SKOWERSKI, Rafal GAWIN, Michal Pawel CHWALBA
Life of this patent
Estimating the term…
Abstract
The invention relates to the use of ruthenium complexes, which are homogeneous catalysts and/or precatalysts of the olefin metathesis reaction, which lead to the production of alkenes containing an internal (non-terminal) double C═C bond.
Claims20
Use of a compound of formula 2,
- wherein:
- X1 and X2 are each an anionic ligand;
- X1 and X2 may be interconnected to form a cyclic system;
- G is a halogen atom or a substituent selected from OR′, SR′, S(O)R′, S(O)2R′ N(R′)(R″), P(R′)(R″)(R′″), where R′, R″ and R′″ are the same or different C1-C25 alkyl group, C3-C12 cycloalkyl group, C1-C25 alkoxy group, C2-C25 alkenyl group, C1-C12 perfluoroalkyl, C5-C20 aryl, C5-C24 aryloxy, C2-C20 heterocyclyl, C4-C20, heteroaryl, C5-C20, or which may involve the formation of a substituted or non-substituted cyclic C4-C10 or policyclic C4-C12 systems, which are optionally substituted with at least one C1-C12 alkyl, C1-C12 perfluoroalkyl, C1-C12 alkoxy, C5-C24 aryloxy, C2-C20 heterocyclyl, C4-C20 heteroaryl, C5-C20 heteroaryloxy, may also be substituted with an ester (—COOR′), amide (—CONR′2), formyl (—CHO), ketone (—COR′), hydroxamic (—CON(OR′)(R′)) groups, wherein R′ is C1-C12 alkyl, C3-C12 cycloalkyl, C2-C12 alkenyl, C5-C20 aryl, which are optionally substituted with at least one C1-C12 alkyl, C1-C12 perfluoroalkyl, C1-C12 alkoxy, C5-C20 aryl, C5-C24 aryloxy, C7-C24 aralkyl, C2-C20 heterocycle, C4-C20, heteroaryl, C5-C20 heteroaryloxy, or a halogen atom;
- Ar is an aryl group that is substituted by hydrogen atoms, or optionally is substituted by at least one C1-C12 alkyl, C1-C12 perfluoroalkyl, C1-C12 alkoxy, C5-C24 aryloxy, C2-C20 heterocyclic, C4-C20 heteroaryl, C5-C20 heteroaryloxy, C7-C24 aralkyl, C5-C24 perfluoroaryl groups, or a halogen atom;
- R1, R2, R3, R4 are each a hydrogen atom, a (—S(O)R′) sulphoxide group, a (—SO2NR′2) sulphonamide group, a (—P(O)(OR′)2) phosphonium group, a (—P(O)R′(OR′)) phosphinium group, a (—P(OR′)2) phosphonous group, a (—PR′2) phosphine group, a (—NO2) nitro group, a (—NO) nitroso group, a (—COOH) carboxy group, a (—COOR′) ester group, a (—CHO) formyl group, a (—COR′) ketone group, a —NC(O)R′ group, an amino group, an ammonium group, a (—OMe) alkoxy group, in which groups R′ is C1-C5 alkyl, C1-C5 perfluoroalkyl, C5-C24 aryl, C7-C24 aralkyl, C5-C24 perfluoroaryl, C4-C20 heteroaryl, C5-C20 heteroaryloxy, and wherein R1, R2, R3 and R4 may be interconnected to form a cyclic system;
- R5, R6, R7 and R8 are each a hydrogen atom or a C1-C25, alkyl, C3-C12 cycloalkyl, C1-C5 perfluoroalkyl, C2-C12 alkenyl, C5-C20, aryl C5-C24 aryloxy, C2-C20 heterocycle, C4-C20 heteroaryl, C5-C20 heteroaryloxy, C7-C24 aralkyl C5-C24, which are optionally substituted by at least one C1-C12 alkyl, C1-C12, perfluoroalkyl, C1-C12 alkoxy, C5-C24 aryloxy, C4-C20 heteroaryl, C5-C20 heteroaryloxy or a halogen atom;
- and wherein R5 and R6 and/or R7 and R8 may be interconnected to form a cyclic system;
- in olefin metathesis reactions where at least one compound is formed as the main product containing at least one non-terminal double C═C bond, involving the process of contacting at least one type of olefin in the presence of a compound of formula 2, and wherein the compound of formula 2 is used in an amount of less than 0.1 mol %.
The use according to any of the preceding claims, wherein the reaction is conducted in an organic solvent such as toluene, benzene, mesitylene, dichloromethane, ethyl acetate, methyl acetate, tertbutyl methyl ether, cyclopentylmethyl ether, or with no solvent.
The use according to any of the preceding claims, wherein the reaction is conducted at a temperature of from 20 to 150° C.
The use according to any of the preceding claims, wherein the reaction is conducted at a temperature of from 40 to 120° C.
The use according to any of the preceding claims, wherein the reaction is conducted at a temperature of from 40 to 90° C.
The use according to any of the preceding claims, wherein the reaction is conducted over from 5 minutes to 24 hours.
The use according to any of the preceding claims, wherein compound 2 is added to the reaction mixture in portions and/or continuously using a pump.
The use according to any of the preceding claims, wherein compound 2 is added to the reaction mixture as a solid and/or as a solution in an organic solvent.
The use according to any of the preceding claims, wherein the gaseous by-product of the reaction (ethylene, propylene, butylene) is actively removed from the reaction mixture using an inert gas or vacuum.
Dependencies are inferred from the claim text.