# US 4,393,224 A · Telomerization of butadiene and carbon dioxide

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- Number: US 4,393,224 A
- Document ID: US4393224A
- Status: Granted
- Kind: A
- Application number: 06/312,914
- Filed: 1981-10-19
- Granted: 1983-07-12
- Earliest claimed: 1980-10-20
- Assignees: Imperial Chemical Industries PLC
- Inventors: James A. Daniels
- Web page: https://patentgrep.com/patent/US4393224A

## CPC

- C07D 315/00: Heterocyclic compounds containing rings having one oxygen atom as the only ring hetero atom according to more than one of groups C07D303/00 - C07D313/00
- C07C 2/406: {with hydrides or organic compounds}
- C07C 2531/24: Phosphines
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

A process for the manufacture of 2-ethylidenehept-6-en-5-olide which comprises reacting in a liquid medium 1,3-butadiene with carbon dioxide in the presence of a palladium complex catalyst and a tertiary amine.

## Claims

### Claim 1

A process for the manufacture of 2-ethylidenehept-6-en-5-olide which comprises reacting in a liquid medium 1,3-butadiene with carbon dioxide in the presence of
(a) a palladium complex catalyst which is a complex of palladium with a phosphorus (III) compound or pyridine or a substituted pyridine, and
(b) a tertiary amine having a pKa value in the range 10 to 14.

### Claim 2 (depends on 1)

A process according to claim 1 wherein the palladium complex has the structure:
[Pd(PR.sub.3.sup.1).sub.2 L]
wherein R.sup.1 is an alkyl, cycloalkyl or aryl group and L is a ligand containing one or more unsaturated double bonds which are capable of co-ordinating with the palladium atom.

### Claim 3 (depends on 2)

A process according to claim 2 wherein L is a quinone.

### Claim 4 (depends on 1)

A process according to claim 1 wherein the tertiary amine is triethylamine or N-ethylpiperidine.

### Claim 5 (depends on 1)

A process according to claim 1 wherein the tertiary amine is used in an amount of 10 to 100 mmol per mole of butadiene.

### Claim 6 (depends on 1)

A process according to claim 1 wherein the reaction mixture contains a quinone or a hydroquinone.

### Claim 7 (depends on 6)

A process according to claim 6 wherein the quinone or hydroquinone is used in an amount of 1 to 25 mmol per mole of butadiene.

### Claim 8 (depends on 1)

A process according to claim 1 wherein the reaction mixture contains a phosphorus (III) compound, pyridine or a substituted pyridine.

### Claim 9 (depends on 1)

A process according to claim 1 wherein the reaction mixture contains not more than 12.5 mmole of water per mole of butadiene.

### Claim 10 (depends on 9)

A process according to claim 9 wherein the reaction mixture is substantially anhydrous.

### Claim 11 (depends on 1)

A process according to claim 1 wherein the reaction is carried out at a pressure in the range 10 to 100 bar.

### Claim 12 (depends on 11)

A process according to claim 11 wherein the reaction is carried out at a pressure in the range 10 to 50 bar.