Process for making 5-cyanovaleric acid, adipic acid or dimethyl adipate

1. A process for producing a compond of the formula NC—CH 2 —CH 2 —CH 2 —CH 2 —CO 2 R′, wherein R′ is H or C 1 to C 12 alkyl, comprising: contacting 3-pentenenitrile with a nucleophile wherein the nucleophile is R′OH or water, wherein R′is a C 1 to C 12 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 R 1 , R 4 , R 7 , and R 10 , independently are H, or C 1 to C 12 alkyl;

provided that R 2 , R 3 , R 5 , R 6 , R 8 , R 9 , R 11 , and R 12 , independently are C 1 to C 12 alkyl or cycloalkyl,

wherein R 2 and R 3 ; R 5 and R 6 ; R 8 and R 9 ; and R 11 and R 12 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.

2. The process of claim 1 wherein water is the nucleophile and the ligand is selected from the group consisting of the

3. The process of claim 1 wherein said Group VIII metal is palladium.

4. The process of claim 1 wherein said promoter is methanesulphonic acid.

5. The process of claim 1 wherein water is the nucleophile and at least one of R 1 , R 4 , R 7 , and R 10 is H, C 1 , C 2 , or C 6 to C 12 alkyl.

6. The process of claim 1 wherein water is the nucleophile and the carboxylic acid promoter is acetic acid.