Process for preparing a carboxylic acid from a diol or from an epoxide by oxidative cleavage

Patent metadata

Field	Value
Publication number	US-9359280-B2
Application number	US-201314418562-A
Country	US
Kind code	B2
Filing date	Jul 30, 2013
Priority date	Jul 31, 2012
Publication date	Jun 7, 2016
Grant date	Jun 7, 2016

Abstract

A process for preparing a carboxylic acid, by oxidative cleavage of at least one vicinal diol, or an epoxide, wherein the reaction is carried out in the presence of a catalyst and of an oxidizing agent and in the absence of solvent.

First claim

The invention claimed is:

1. Method for preparing a carboxylic acid, by oxidative cleavage of at least one vicinal diol, or an epoxide, the reaction being conducted in the presence of a catalyst based on ruthenium or molybdenum, an oxidizing agent and in the absence of solvent, wherein the oxidizing agent is oxygen contained in air.

2. Method according to claim 1 , wherein the catalyst used has the formula M(OH)x/support, M being a metal selected from the group consisting of ruthenium, molybdenum, and a mixture thereof, and x is an integer from 0 to 8.

3. Method according to claim 2 , wherein the support is selected from the group consisting of alumina, zirconia, carbon, silica, a zeolite and a mixture thereof.

4. Method according to claim 2 , wherein M is ruthenium.

5. Method according to claim 4 , wherein the proportion of metal used is from 0.001 mol % to 50 mol % relative to the substrate and from 0.001% to 50% relative to the support.

6. Method according to claim 1 , wherein the reaction is conducted at a pressure from 10 −3 mbar to 15 bar.

7. Method according to claim 1 , wherein the reaction is conducted at a temperature from 0° C. to 200° C.

8. Method according to claim 1 , wherein the vicinal diol or the epoxide is also a fatty acid or a fatty acid ester with a carbon chain of 10 to 30 carbon atoms.

9. Method according to claim 8 , wherein the fatty acid or fatty acid ester is selected from the group consisting of myristoleic acid, palmitoleic acid, oleic acid, ricinoleic acid, gadoleic acid, erucic acid, nervonic acid, linoleic acid, alpha-linolenic acid, gamma-linolenic acid, di-homo-gamma-linolenic acid, arachidonic acid, timnodonic acid, and cervonic acid.

10. Method according to claim 1 , wherein the vicinal diol is 9,10-dihydroxystearic acid or cyclohexane diol.

11. Method according to claim 1 , for preparing a saturated or unsaturated dicarboxylic acid.

12. Method according to claim 1 , for preparing an unsaturated carboxylic acid.

13. Method according to claim 1 , wherein the products obtained are pelargonic acid and azelaic acid.

14. Method according to claim 1 , wherein the reaction is conducted at a pressure from 4 bar to 10 bar.

15. Method according to claim 1 , wherein the reaction is conducted at a temperature from 90° C. to 160° C.

Assignees

• Interoleagineuse D Assistance Et De Dev S I A Soc
• Univ Claude Bernard Lyon
• Centre Nat Rech Scient
• Oleon
• Interoleagineuse D Assistance Et De Dev Soc
• Univ Claude Bernard Lyon
• Centre Nat Rech Scient

Inventors

• Lemaire Marc
• Metay Estelle
• Sutter Marc
• Debray Julien
• Raoul Yann
• Duguet Nicolas

Classifications

• C07C53/126

  Acids containing more than four carbon atoms · CPC title

• C07C55/02

  Dicarboxylic acids · CPC title

• C07C59/105

  having five or more carbon atoms, e.g. aldonic acids · CPC title

• C07C51/367 Primary

  by introduction of functional groups containing oxygen only in singly bound form · CPC title

• C07C51/23 Primary

  of oxygen-containing groups to carboxyl groups · CPC title