Metathesis of olefins using ruthenium based catalytic complexes
AssigneeCroda International PLC
InventorsBastiaan Wels, Hans Ridderikhoff, Tanja Van Bergen-Brenkman, Dessy Liminto
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Abstract
A self-metathesis process for the production of unsaturated dicarboxylic fatty diacids and/or unsaturated dicarboxylic fatty diesters, wherein unsaturated carboxylic fatty acids and/or esters of unsaturated carboxylic fatty acids are reacted in the presence of at least one defined ruthenium based catalyst compound. A catalyst enhancer compound selected from a sacrificial catalyst or a non-catalyst enhancer may also be used. The process exhibits improved reaction times and/or the catalyst can be used at very low concentrations.
Claims15
A self-metathesis process for the production of unsaturated dicarboxylic acids and/or unsaturated dicarboxylic acid diesters, wherein unsaturated fatty acids and/or esters of unsaturated fatty acids are reacted in the presence of at least one catalyst compound of Formula (I):
- wherein
- L represents a neutral ligand;
- R1 represents hydrogen, C1 to C6 alkyl, C2 to C6 alkenyl, C2 to C6 alkynyl, C5 or C6 aryl, aralkyl, hydroxyl, C1 to C6 alkoxy, aryloxy, or arylalkoxy;
- a, b, c, and d each independently represent hydrogen, C1 to C6 alkyl, C1 to C6 alkoxy, C5 or C6 aryl, or an electron withdrawing group;
- X1 and X2 each independently represent anionic ligands;
- R2 represents a C1 to C6 alkyl, C5 or C6 cycloalkyl, C5 or C6 aryl, C1 to C6 alkoxy, aryloxy, arylalkoxy, or alkanone;
- wherein the reaction is performed in the absence of solvents or in the presence of a solvent consisting of hydrocarbons and/or alcohols, and wherein a catalyst enhancer compound is also present during the reaction, said catalyst enhancer compound being a non-catalyst enhancer that is a titanium based compound.
A process for improving the efficiency of the catalyst compound of Formula (I) in a self-metathesis process for the production of unsaturated dicarboxylic acids and/or unsaturated dicarboxylic acid diesters, wherein unsaturated fatty acids and/or esters of unsaturated fatty acids are reacted in the presence of at least one catalyst compound of Formula (I):
- wherein
- L represents a neutral ligand that is a carbene ligand;
- R1 represents hydrogen, C1 to C6 alkyl, C2 to C6 alkenyl, C2 to C6 alkynyl, C5 or C6 aryl, aralkyl, hydroxyl, C1 to C6 alkoxy, aryloxy, or arylalkoxy;
- a, b, c, and d each independently represent hydrogen, C1 to C6 alkyl, C1 to C6 alkoxy, C5 or C6 aryl, or an electron withdrawing group;
- X1 and X2 each independently represent anionic ligands;
- R2 represents a C1 to C6 alkyl, C5 or C6 cycloalkyl, C5 or C6 aryl, C1 to C6 alkoxy, aryloxy, arylalkoxy, or alkanone;
- wherein the process comprises adding a catalyst enhancer to the reaction and wherein the reaction is performed in the absence of solvents or in a solvent consisting of hydrocarbons and/or alcohols.
Dependencies are inferred from the claim text.