Claims
- 1. The present invention is a process for producing
(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, comprising:contacting a substrate selected from the group consisting of (A) (B) and (C) wherein substrate (A) is 3-pentenenitrile, wherein substrate (B) is 3-pentenoic acid, and wherein substrate (C) is methyl 3-pentenoate, with a nucleophile (a), (b), or (c), respectively, wherein nucleophile (a)is alcohol or water, wherein nucleophile (b) is water and wherein nucleophile (c) is methanol, and carbon monoxide, in the presence of a Group VIII metal; a ligand having the formula 4wherein 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 a promoter, said promoter comprising a strong acid having a pKa in water of less than 1 and, when the nucleophile is water, at least one carboxylic acid.
- 2. The process of claim 1 wherein 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 at least one of R1, R4, R7, and R10 is H, C1, C2, or C6 to C12 alkyl.
- 6. The process of claim 1 wherein the substrate is (a) or (c).
- 7. The process of claim 6 wherein the nucleophile is water and the substrate is 3-pentenenitrile, said process further comprising adding a carboxylic acid.
- 8. The process of claim 7 wherein the carboxylic acid is acetic acid.
CROSS-REFERENCE TO RELATED APPLICATIONS
[0001] This application is a continuation of U.S. application Ser. No. 09/997,506 filed Nov. 19, 2001.
Continuations (1)
|
Number |
Date |
Country |
Parent |
09997506 |
Nov 2001 |
US |
Child |
10677519 |
Oct 2003 |
US |