Process for making 5-cyanovaleric acid, adipic acid or dimethyl adipate
AssigneeInvista North America S.A.R.L.
InventorsEmilio E. Bunel, David A. Clark
Life of this patent
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Abstract
Disclosed in a process for making (1) a compound of the formula NC—CH2—CH2—CH2—CH2—CO2R′, wherein R′ is H or C1 to C12 alkyl, or (2) adipic acid or (3) dimethyl adipate, using as the substrate, 3-pentenenitrile, (2) 3-pentenoic acid or methyl 3-pentenoate, respectively, by contacting the substrate with carbon monoxide and a nucleophile in the presence of a Group VIII metal, a selected ligand, and an acid promoter. The nucleophile, which (a) an alcohol or water, or (b) water or (c) methanol, respectively, in the presence of a Group VIII metal, preferably palladium, a selected phosphine ligand, and an acid promoter.
Claims6
A process for producing a compond of the formula NC—CH2—CH2—CH2—CH2—CO2R′, wherein R′ is H or C1 to C12 alkyl, comprising:
- contacting 3-pentenenitrile with a nucleophile wherein the nucleophile is R′OH or water, wherein R′is a C1 to C12 alkyl, and carbon monoxide, in the presence of
- a Group VIII metal;
- a diphosphine ligand;
- and
- a promoter, wherein, when the nucleophile is R′OH, the ligand is selected from Ligand 1 or Ligand 2 below
- and said promoter comprises a strong acid having a pKa in water of less than 1 or,
- when the nucleophile is water, the ligand is selected from the formula below,
- wherein
- X is a substituted or unsubstituted bridging group selected from the group consisting of a divalent aryl, a divalent alkylene group, and a divalent combination of alkylene and aromatic groups;
- and
- wherein R1, R4, R7, and R10, independently are H, or C1 to C12 alkyl;
- provided that R2, R3, R5, R6, R8, R9, R11, and R12, independently are C1 to C12 alkyl or cycloalkyl,
- wherein R2 and R3;
- R5 and R6;
- R8 and R9;
- and R11 and R12 may be taken together to form a cycloalkyl group;
- and said promoter comprises a strong acid having a pKa in water of less than 1 and at least one carboxylic acid.
Dependencies are inferred from the claim text.