# US 2014/0155647 A1 · Method for the Synthesis of Diacids or Diesters from Natural Fatty Acids and/or Esters

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- Number: US 2014/0155647 A1
- Document ID: US20140155647A1
- Status: Published application
- Kind: A1
- Application number: 13/946,292
- Filed: 2013-07-19
- Published: 2014-06-05
- Earliest claimed: 2007-06-13
- Assignees: Arkema France
- Applicants: Arkema France
- Inventors: Jean-Luc Dubois
- Web page: https://patentgrep.com/patent/US20140155647A1

## CPC

- C07C 51/36: by hydrogenation of carbon-to-carbon unsaturated bonds
- C07C 51/09: from carboxylic acid esters or lactones
- C07C 51/353: by isomerisation; by change of size of the carbon skeleton
- C07C 67/303: by hydrogenation of unsaturated carbon-to-carbon bonds
- C07C 67/333: by isomerisation; by change of size of the carbon skeleton (introduction or elimination of carboxyl groups C07C67/313, C07C67/32)
- C07C 67/475: by splitting of carbon-to-carbon bonds and redistribution, e.g. disproportionation or migration of [IMAGE cpc-sch-C07C-0963.gif] groups between different molecules
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

Disclosed herein a process for the synthesis of diacids or diesters of general formula ROOC—(CH2)x-COOR, in which n represents an integer between 5 and 14 and R is either H or an alkyl radical of 1 to 4 carbon atoms, starting from long-chain natural monounsaturated fatty acids or esters comprising at least 10 adjacent carbon atoms per molecule, of formula CH3—(CH2)n-CHR1—CH2—CH═CH—(CH2)p-COOR, in which R represents H or an alkyl radical comprising from 1 to 4 carbon atoms, R1 is either H or OH, and n and p, which are identical or different, are indices between 2 and 11.

## Claims

### Claim at position 1

1-11. (canceled)

### Claim 12

A process for the synthesis of diacids or diesters of the general formula ROOC—(CH2)x—COOR, in which x represents an integer between 5 and 24 and R is either H or an alkyl radical of 1 to 4 carbon atoms, starting from long-chain natural monounsaturated fatty acids or esters comprising at least 10 adjacent carbon atoms per molecule, of the formula CH3—(CH2)nCHR1—CH2—CH═CH—(CH2)p—COOR, in which R represents H or an alkyl radical comprising from 1 to 4 carbon atoms, R1 is either H or OH, and n and p, which are identical or different, are indices between 3 and 11, which comprises:
converting said natural monounsaturated fatty acid or ester, into an ω-monounsaturated fatty acid or ester of the general formula CH2═CH—(CH2)m—COOR, in which m is equal to p or p+1, then,
subjecting the product thus obtained to cross-metathesis with a compound of the formula R2OOC—(CH2)r—CH═CH—R3, in which R2 is either H or an alkyl radical comprising from 1 to 4 carbon atoms, r is either 0 or 1 or 2 and R3 is H, CH3 or COOR2, in the last case forming a cyclic or noncyclic molecule, to obtain an unsaturated compound of the formula ROOC—(CH2)m—CH═CH—(CH2)r—COOR2, and then,
converting, by hydrogenation, the unsaturated compound to a saturated compound.

### Claim 13 (depends on 12)

The process as claimed in claim 12, wherein the converting said natural monounsaturated fatty acid or ester of general formula CH3—(CH2)n—CHOH—CH2—CH═CH—(CH2)p—COOR is via a pyrolysis reaction.

### Claim 14 (depends on 13)

The process as claimed in claim 13, wherein the co-monounsaturated acid or the ester of formula CH2═CH—(CH2)p+1—COOR is subjected to a cross-metathesis, the product of which is hydrogenated.

### Claim 15 (depends on 12)

The process as claimed in claim 12, wherein converting said natural monounsaturated fatty acid or ester of general formula CH3—(CH2)n—CHOH—CH2—CH═CH—(CH2)p—COOR is via an ethenolysis reaction.

### Claim 16 (depends on 15)

The process as claimed in claim 15, wherein the ω-monounsaturated acid or the ester of formula CH2═CH—(CH2)p—COOR is subjected to a cross-metathesis, the product of which is hydrogenated.

### Claim 17

A process for the synthesis of a diester of the formula CH3OOC—(CH2)8—COOCH3 starting from the methyl ester of ricinoleic acid comprising
pyrolysis, to form an ester of the formula CH2═CH—(CH2)8—COOCH3, and subsequently cross-metathesis with methyl acrylate to form a diester of the formula CH3OOC—CH═CH—(CH2)8—COOCH3, which is subsequently hydrogenated.

### Claim 18

A process for the synthesis of the diester of the formula CH3OOC(CH2)12—COOCH3 starting from the methyl ester of lesquerolic acid comprising
pyrolysis of the methyl ester of lesquerolic acid to form an ester of the formula CH2═CH—(CH2)10—COOCH3, followed by cross-metathesis with methyl acrylate and thereafter hydrogenation.

### Claim 19

A process for the synthesis of a diacid or diester of formula ROOC—(CH2)12—COOR starting from vaccenic acid or ester comprising ethenolysis of the acid or ester to give an unsaturated acid or ester of the formula CH2═CH—(CH2)9—COOR, followed by cross-metathesis with an acid or ester of the formula CH3—CH═CH—CH2—COOR and, thereafter hydrogenation.