# US 5,350,876 A · Carbonylation of conjugated dienes

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- Number: US 5,350,876 A
- Document ID: US5350876A
- Status: Granted
- Kind: A
- Application number: 08/082,213
- Filed: 1993-06-24
- Granted: 1994-09-27
- Earliest claimed: 1992-06-29
- Assignees: Shell Oil Company
- Inventors: Eit Drent; Willem W. Jager
- Web page: https://patentgrep.com/patent/US5350876A

## CPC

- C07C 67/38: by addition to an unsaturated carbon-to-carbon bond
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

The invention relates to a process for the preparation of alkenoic acid derivatives by reaction of an aliphatic conjugated diene with carbon monoxide and a hydroxyl group-containing compound. The reaction is carried out in a liquid reaction medium of controlled polarity in the presence of a catalyst system containing a palladium compound, a multidentate phosphine ligand, and optionally a protonic acid. By controlling the polarity of the reaction medium to a calculated dielectric constant .epsilon..sub.calc of below a value of 8, higher reaction rates are achieved.

## Claims

### Claim 1

A process for the preparation of alkenoic acid derivatives comprising reacting an aliphatic conjugated diene with carbon monoxide and a hydroxyl group-containing compound in a reaction medium having a calculated dielectric constant at 25.degree. C. .epsilon..sub.calc of below a value of 8 in the presence of a catalyst system comprising a palladium compound, a multidentate phosphine ligand, and optionally a protonic acid.

### Claim 2 (depends on 1)

The process of claim 1 wherein the calculated dielectric constant of the reaction medium is maintained at a value of .epsilon..sub.calc within the range of from about 4.5 to about 7.5.

### Claim 3 (depends on 2)

The process of claim 2 wherein the hydroxyl group-containing compound is an alkanol having an dielectric constant .epsilon. at 25.degree. C. of below 20.

### Claim 4 (depends on 3)

The process of claim 3 wherein the alkanol is tert-butanol.

### Claim 5 (depends on 2)

The process of claim 2 wherein the hydroxyl group-containing compound is an alkanol having an dielectric constant at 25.degree. C. of above 20 and the concentration of said alkanol is maintained below 20% vol of the reaction medium during the course of the reaction.

### Claim 6 (depends on 5)

The process of claim 5 wherein the hydroxyl group-containing compound is an alkanol having an dielectric constant at 25.degree. C. of above 30 and the concentration of said alkanol is maintained below 12% vol of the reaction medium during the course of the reaction.

### Claim 7 (depends on 6)

The process of claim 6 wherein further amounts of the alkanol are continuously or intermittently added during the course of the reaction at an rate substantially corresponding with the consumption of the alkanol.

### Claim 8 (depends on 1)

The process of claim 1 wherein the reaction medium further comprise a solvent having an dielectric constant .epsilon. at 25.degree. C. of equal or below about 6.

### Claim 9 (depends on 8)

The process of claim 8 wherein the solvent is an ether.

### Claim 10 (depends on 1)

The process of claim 1 wherein the reaction medium further comprise an organic nitrogen-containing base present at a concentration of below 5% vol.