# US 5,345,007 A · Process for the preparation of octadienols

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- Number: US 5,345,007 A
- Document ID: US5345007A
- Status: Granted
- Kind: A
- Application number: 08/148,257
- Filed: 1993-11-05
- Granted: 1994-09-06
- Earliest claimed: 1992-11-06
- Assignees: Elf Atochem S.A.
- Inventors: Eric Monflier; Paul Bourdauducq; Jean-Luc Couturier
- Web page: https://patentgrep.com/patent/US5345007A

## CPC

- C07C 29/36: increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

A process for the preparation of octadienols, comprising the hydrodimerization reaction of 1,3-butadiene with water in the presence of a transition metal in the metal form or in the form of a compound of the said metal, of a water-soluble tertiary or quaternary phosphorus-containing compound and of at least one nitrogen-containing compound selected from the group consisting of a tertiary amine and a quaternary ammonium salt of general formula (I) or (II): ##STR1## in which R.sub.p, R.sub.q and R.sub.s are identical or different and each is a methyl or ethyl group; R.sub.r is an alkyl group containing from 6 to 22 carbon atoms; X is a counter-anion selected from the group consisting of HCO.sub.3.sup.-, CO.sub.3.sup.2-, HSO.sub.3.sup.-, SO.sub.3.sup.2-, SiO.sub.3.sup.2-, PO.sub.4.sup.3-, HPO.sub.3.sup.2-, AsO.sub.4.sup.3-, SO.sub.4.sup.2-, HSO.sub.4.sup.-, RSO.sub.3.sup.-, RCO.sub.2.sup.-, and OH.sup.-, R being an alkyl group; the said reaction being carried out in the presence of carbon dioxide.

## Claims

### Claim 1

A process for the preparation of an octa-2,7-dien-1-ol comprising hydrodimerizing 1,3-butadiene with water in the presence of:
a transition metal in the metal form or in the form of a compound of the said metal;
a water-soluble tertiary or quarternary phosphorus-containing compound; and
at least one nitrogen-containing compound, selected from the group consisting of a tertiary amine and a quaternary ammonium salt of formula (I) or (II): ##STR6## in which R.sub.p, R.sub.q and R.sub.s are identical or different and each is a methyl or ethyl group; R.sub.r is an alkyl group containing from 6 to 22 carbon atoms; X is a counter-anion selected from the group consisting of:
HCO.sub.3.sup.-, CO.sub.3.sup.2-, HSO.sub.3.sup.-, SO.sub.3.sup.2-, SiO.sub.3.sup.2-,
PO.sub.4.sup.3-, HPO.sub.3.sup.2-, AsO.sub.4.sup.3-, SO.sub.4.sup.2-, HSO.sub.4.sup.-, RSO.sub.3.sup.-, RCO.sub.2.sup.-, and OH.sup.-,
wherein R is an alkyl group; said reaction being carried out in the presence of carbon dioxide.

### Claim 2 (depends on 1)

A process according to claim 1, wherein the 1,3-butadiene has a purity equal to or greater than 98% by weight.

### Claim 3 (depends on 1)

A process according to claim 1, wherein the 1,3-butadiene forms pan of a C.sub.4 or C.sub.4 H cut used as such in the said hydrodimerization reaction.

### Claim 4 (depends on 1)

A process according to claim 1, wherein the said reaction of butadiene and water is carried out in the absence of a water-miscible or partially water-miscible solvent.

### Claim 5 (depends on 2)

A process according to claim 2, wherein the said hydrodimerization reaction is carried out in the presence of a monoethylenic or saturated hydrocarbon having from 4 to 7 carbon atoms.

### Claim 6 (depends on 3)

A process according to claim 3, wherein the transition metal is palladium.

### Claim 7 (depends on 2)

A process according to claim 2, wherein the transition metal is palladium.

### Claim 8 (depends on 1)

A process according to claim 1, wherein the transition metal is palladium.

### Claim 9 (depends on 3)

A process according to claim 3, wherein the transition metal compound is a palladium compound.

### Claim 10 (depends on 2)

A process according to claim 2, wherein the transition metal compound is a palladium compound.

### Claim 11 (depends on 1)

A process according to claim 1, wherein the transition metal compound is a palladium compound.

### Claim 12 (depends on 1)

A process according to claim 1, wherein R.sub.p, R.sub.q and R.sub.s each is a methyl group.

### Claim 13 (depends on 1)

A process according to claim 1, wherein R.sub.r is the radical --(CH.sub.2).sub.n CH.sub.3 in which n is an integer between 5 and 21.

### Claim 14 (depends on 9)

A process according to claim 9, wherein n is between 9 and 17.

### Claim 15 (depends on 10)

A press according to claim 10, wherein n is 11.

### Claim 16 (depends on 1)

A process according to claim 1, wherein the said reaction is carried out at a temperature between 20.degree. and 100.degree. C.