Process for the preparation of azeleic acid from 9-octadecenedioic acid

Patent metadata

Field	Value
Publication number	US-9302972-B2
Application number	US-201214366051-A
Country	US
Kind code	B2
Filing date	Dec 12, 2012
Priority date	Dec 20, 2011
Publication date	Apr 5, 2016
Grant date	Apr 5, 2016

Abstract

The invention relates to a process for the preparation of azelaic acid or alkyl azelate starting from mono-unsaturated 9-octadecenedioic acid or its corresponding alkylester characterized in that the process comprises at least the following step: •reacting the mono-unsaturated 9-octadecene dioic acid or its corresponding alkylester with hydrogen peroxide in the presence of an organic carboxylic acid other than 9-octadecene dioic acid and a suitable catalyst to effect cleavage of the double bond in the mono-unsaturated 9-octadecene dioic acid or its corresponding alkylester. The invention further relates to the azelaic acid or alkyl azelate obtainable by the process according to the invention and to the use of azelaic acid or alkyl azelate or monomers derived there from for the preparation of a polymer, especially a polyamide.

First claim

The invention claimed is:

1. A process for the preparation of azelaic acid or alkyl azelate starting from mono-unsaturated 9-octadecenedioic acid or its corresponding alkylester, wherein the process comprises reacting 9-octadecenedioic acid or its corresponding alkylester in a reaction medium with aqueous hydrogen peroxide in the presence of 10-300 wt. %, based weight % of the 9-octadecanedioic acid, of an organic carboxylic acid other than 9-octadecene dioic acid and a tungsten-based catalyst to effect cleavage of the double bond in 9-octadecenedioic acid or the corresponding alkylester.

2. The process according to claim 1 , wherein the alkyl groups in the alkyl azelate are independently chosen to contain 1 to 6 carbon atoms.

3. The process according to claim 1 , wherein the organic carboxylic acid other than 9-octadecene dioic acid is a mono- or dicarboxylic acid with 1-12 carbon atoms.

4. The process according to claim 1 , wherein the organic carboxylic acid other than 9-octadecene dioic acid is at least 80% soluble in the reaction medium.

5. The process according to claim 3 , wherein the organic carboxylic acid other than 9-octadecene dioic acid is acetic acid or azelaic acid.

6. Azelaic acid obtained by the process according to claim 1 .

7. Alkyl azelate obtained by the process according to claim 1 .

8. A monomer or polymer derived from the alkyl azelate of claim 7 .

9. A method for preparing a polyamide comprising reacting the alkyl azelate according to claim 7 , under polyamide formation conditions.

Assignees

• Alsters Paulus Lamburtus
• Dsm Ip Assets Bv

Inventors

• Alsters Paulus Lamburtus

Classifications

• C07C55/18

  Azelaic acid · CPC title

• C07C51/285 Primary

  with peroxy-compounds · CPC title

• C07C67/333 Primary

  by isomerisation; by change of size of the carbon skeleton (introduction or elimination of carboxyl groups C07C67/313, C07C67/32) · CPC title

• C07C69/48

  Azelaic acid esters · CPC title

• C08G69/00

  Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule (products obtained from isocyanates or isothiocyanates C08G18/00; polyamide-imides C08G73/14) · CPC title