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Process for the preparation of a pentenoate ester
| Details |
Inventors: Sielcken, Otto E.; Agterberg, Frank P. W.; Haasen, Nicolaas F.;
Assignee: DSM N.W. (Heerlen, NL); E. I. Du Pont de Nemours and Company (Wilmington, DE)
Primary Examiner: Killos; Paul J.
Assistant Examiner:
Attorney, Agent or Firm: Cushman Darby & Cushman
A process is described for the preparation of a pentenoate ester by carbonylation of butadiene or butadiene derivate in the presence of carbon monoxide, a alcohol and a catalyst system comprising palladium, an carboxylic acid and a phosphine ligand, wherein the carboxylic acid is pentenoic acid. |
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DETAILED DESCRIPTION What we claim is: 1.
A process for the preparation of a pentenoate ester by carbonylation of butadiene or a butadiene derivative in the presence of carbon monoxide, alcohol and a catalyst system comprising palladium, a carboxylic acid and a phosphine ligand, wherein the carboxylic acid is pentenoic acid.
2.
A process according to claim 1, wherein the molar ratio of pentenoic acid to palladium is greater than 10:1.
3.
A process according to claims 1 wherein the molar ratio of alcohol to butadiene or butadiene derivative is between 1:1 and 3:1.
4.
A process according to claim 1 wherein the alcohol is methanol or ethanol.
5.
A process according to claim 1 wherein a part of the pentenoic ester is hydrolyzed to pentenoic acid, and the thus obtained pentenoic acid is recycled to the carbonylation reaction.
6.
A process according to claim 1 wherein an amount of water is present during the carbonylation in an amount sufficient to maintain a catalytically active level of pentenoic acid.
7.
A process according to claim 2, wherein the phosphine ligand is a monodentate phosphine ligand, the carbonylation is performed continuously or semi-continuously, and the amounts of the reactants are substantially maintained during the carbonylation such that the molar ratio of butadiene or butadiene derivative to palladium is less than 20:1, and the molar ratio of alcohol to butadiene or butadiene derivate is less than 2:1.
8.
A process according to claims 1, 2 or 7, wherein the carboxylic acid present is the pentenoic acid.
9.
A process for preparing a pentenoate ester comprising conducting the carbonylation of at least one member selected from the group consisting of butadiene and a butadiene derivative in a reaction mixture in the presence of carbon monoxide, an alcohol selected from the group consisting of methanol and ethanol, and a catalyst system, wherein said catalyst system is the combination palladium, a phosphine ligand, and pentenoic acid, wherein in said carbonylation the molar ratio of pentenoic acid to palladium is greater than 10:1, the molar ratio of said alcohol to butadiene or butadiene derivative is between 1:1 and 3:1
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