Metathesis process
AssigneeCroda International PLC
InventorsBastiaan Wels, Hans Ridderikhoff, Tanja Van Bergen-Brenkman, Dessy Liminto
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Abstract
A process of metathesizing a feedstock in the presence of a metathesis catalyst and at least one catalyst enhancer. The catalyst enhancer can be selected from a sacrificial catalyst or a non-catalyst enhancer. The process exhibits improved reaction times and/or the metathesis catalyst can be used at very low concentrations.
Claims23
A process of metathesising a feedstock, wherein the feedstock comprises unsaturated fatty acids and/or esters of unsaturated fatty acids, in the presence of a metathesis catalyst and at least one catalyst enhancer compound in a reaction mixture,
- wherein the at least one catalyst enhancer is selected from the group consisting of a sacrificial catalyst and a non-catalyst enhancer,
- wherein the sacrificial catalyst is selected from the group consisting of dichloro-(3-phenyl-1H-inden-1-ylidene)bis(tricyclohexylphosphine)ruthenium(II), dichloro-(3-phenyl-1H-inden-1-ylidene)bis(isobutylphobane)ruthenium(II), [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro-(3-phenyl-1H-inden-1-ylidene)(tricyclohexylphosphine)ruthenium(II), [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro-(3-phenyl-1H-inden-1-ylidene)(pyridyl)ruthenium(II), [1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]-[2-[[(4-methylphenyl)imino]methyl]-4-nitro-phenolyl]chloro-[3-phenyl-indenylidene]ruthenium(II), and [1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]-[2-[[(2-methylphenyl)imino]methyl]-phenolyl]chloro-(3-phenyl-indenylidene)ruthenium(II),
- wherein the non-catalyst enhancer is selected from the group consisting of a Lewis acid and a titanium based compound,
- wherein the process is carried out without a solvent or in a solvent consisting of hydrocarbons and/or alcohols, wherein the metathesis catalyst efficiency is less than 100.
A process of metathesising a feedstock, wherein the feedstock comprises unsaturated fatty acids and/or esters of unsaturated fatty acids, in the presence of a metathesis catalyst and at least one catalyst enhancer compound in a reaction mixture,
- wherein the at least one catalyst enhancer is selected from the group consisting of a sacrificial catalyst and a non-catalyst enhancer,
- wherein the sacrificial catalyst is selected from the group consisting of dichloro-(3-phenyl-1H-inden-1-ylidene)bis(tricyclohexylphosphine)ruthenium(II), dichloro-(3-phenyl-1H-inden-1-ylidene)bis(isobutylphobane)ruthenium(II), [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro-(3-phenyl-1H-inden-1-ylidene)(tricyclohexylphosphine)ruthenium(II), [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro-(3-phenyl-1H-inden-1-ylidene)(pyridyl)ruthenium(II), [1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]-[2-[[(4-methylphenyl)imino]methyl]-4-nitro-phenolyl]chloro-[3-phenyl-indenylidene]ruthenium(II), and [1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]-[2-[[(2-methylphenyl)imino]methyl]-phenolyl]chloro-(3-phenyl-indenylidene)ruthenium(II),
- wherein the non-catalyst enhancer is selected from the group consisting of copper iodide, sodium iodide, tetrabutylgermanium, tetraethylsilicon, tin oxide, tin octoate, tin oxalate, dibutyltin dilaurate, tin(IV) chloridetetrabutyl orthotitanate, palladium acetate, tris(dibenzylideneacetone)palladium, tetrakis(triphenylphosphine)palladium, bis(diphenylferrocenyl)palladium dichloride, nickel chloride, bis(cyclooctadiene)nickel, nickelocene iron chloride, iron bromide, ferrocene, silver chloride, silver iodide, silver oxide, iodine, silver trifluoromethanesulfonate, sodium borohydride, boric acid, zinc ethylhexanoate, zircon (IV) oxide chloride octahydrate, acetic acid, butylated hydroxytoluene (BHT), quinones, activated charcoal, alumina, bleaching earth, titanium compounds having the general formula Ti.[Q]4 wherein each Q independently represents hydrogen, a C1 to C10 alkoxy group, a C4 to C8 aryl group, a C12 to C18 fatty alcohol, or a C6 to C18 fatty acid,
- wherein the non-catalyst enhancer is present in an amount ranging from 10 ppm to 1,000 ppm with respect to the reaction mixture.
A process of metathesising a feedstock, wherein the feedstock comprises unsaturated fatty acids and/or esters of unsaturated fatty acids, in the presence of a metathesis catalyst and at least one catalyst enhancer compound in a reaction mixture,
- wherein the at least one catalyst enhancer is selected from the group consisting of a sacrificial catalyst and a non-catalyst enhancer,
- wherein the sacrificial catalyst is selected from the group consisting of dichloro-(3-phenyl-1H-inden-1-ylidene)bis(tricyclohexylphosphine)ruthenium(II), dichloro-(3-phenyl-1H-inden-1-ylidene)bis(isobutylphobane)ruthenium(II), [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro-(3-phenyl-1H-inden-1-ylidene)(tricyclohexylphosphine)ruthenium(II), [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro-(3-phenyl-1H-inden-1-ylidene)(pyridyl)ruthenium(II), [1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]-[2-[[(4-methylphenyl)imino]methyl]-4-nitro-phenolyl]chloro-[3-phenyl-indenylidene]ruthenium(II), and [1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]-[2-[[(2-methylphenyl)imino]methyl]-phenolyl]chloro-(3-phenyl-indenylidene)ruthenium(II),
- wherein the non-catalyst enhancer is selected from the group consisting of a Lewis acid and a titanium based compound,
- wherein the process is carried out without a solvent or in a solvent consisting of hydrocarbons and/or alcohols,
- wherein the metathesis catalyst retains over 75% of its activity after 30 minutes.
A process of metathesising a feedstock, wherein the feedstock comprises unsaturated fatty acids and/or esters of unsaturated fatty acids, in the presence of a metathesis catalyst and at least one catalyst enhancer compound in a reaction mixture,
- wherein the at least one catalyst enhancer is selected from the group consisting of a sacrificial catalyst and a non-catalyst enhancer,
- wherein the sacrificial catalyst is selected from the group consisting of dichloro-(3-phenyl-1H-inden-1-ylidene)bis(tricyclohexylphosphine)ruthenium(II), dichloro-(3-phenyl-1H-inden-1-ylidene)bis(isobutylphobane)ruthenium(II), [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro-(3-phenyl-1H-inden-1-ylidene)(tricyclohexylphosphine)ruthenium(II), [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro-(3-phenyl-1H-inden-1-ylidene)(pyridyl)ruthenium(II), [1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]-[2-[[(4-methylphenyl)imino]methyl]-4-nitro-phenolyl]chloro-[3-phenyl-indenylidene]ruthenium(II), and [1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]-[2-[[(2-methylphenyl)imino]methyl]-phenolyl]chloro-(3-phenyl-indenylidene)ruthenium(II),
- wherein the non-catalyst enhancer is selected from the group consisting of titanium compounds having the general formula Ti.[Q]4 wherein each Q independently represents hydrogen, a C1 to C10 alkoxy group, a C4 to C8 aryl group, a C12 to C18 fatty alcohol, or a C6 to C18 fatty acid.
Dependencies are inferred from the claim text.