Process for preparing a carboxylic acid

Patent metadata

Field	Value
Publication number	US-9822056-B2
Application number	US-201415107855-A
Country	US
Kind code	B2
Filing date	Dec 24, 2014
Priority date	Dec 24, 2013
Publication date	Nov 21, 2017
Grant date	Nov 21, 2017

Abstract

A process for preparing a carboxylic acid, including a step of bringing at least one vicinal diol or at least one vicinal polyol into contact with an atmosphere including oxygen, and a catalyst, and in the absence of additional solvent.

First claim

The invention claimed is:

1. A process for preparing carboxylic acid comprising a step of placing at least one vicinal diol or at least one vicinal polyol in contact with an atmosphere comprising oxygen, a catalyst and in the absence of additional solvent, the catalyst having the formula I below:
[Al n Si m O p M q ][A] r   (I)

wherein:
n, m and q are natural integers ( ), which may be identical or different, chosen, independently of each other, such that n, m and q may simultaneously be equal to 0;
p is a nonzero natural integer ( *);
r is zero or 1;
M corresponds to at least one chemical element chosen from zirconium, tungsten, titanium and rare-earth metals, and
A corresponds to at least one chemical element chosen from alkaline-earth metals, alkali metals, rare-earth metals and titanium;

wherein the catalyst is one of the following catalysts: Al 2 O 3 , SiO 2 , TiO 2 , and ZrO 2 .

2. The process according to claim 1 , wherein the catalyst has a specific surface area of from 50 to 200 m 2 /g.

3. The process according to claim 1 , comprising a prior step of hydroxylation of an olefin or of hydrolysis of an epoxide.

4. The process according to claim 1 , wherein the at least vicinal diol or the at least vicinal polyol is derived from a plant oil.

5. The process according to claim 3 , wherein the olefin is a fatty acid or a fatty acid ester bearing a carbon-based chain of 10 to 30 carbon atoms.

6. The process according to claim 5 , wherein the fatty acid or the fatty acid ester is chosen from the group consisting of myristoleic acid, palmitoleic acid, oleic acid, ricinoleic acid, gadoleic acid, erucic acid, nervonic acid, linoleic acid, α-linolenic acid, γ-linolenic acid, di-homo-γ-linolenic acid, arachidonic acid, timnodonic acid, and cervonic acid.

7. The process according to claim 1 , wherein the at least vicinal diol is methyl 9,10-dihydroxystearate.

8. The process according to claim 1 , wherein the carboxylic acid is a monocarboxylic acid or a dicarboxylic acid, or a mixture thereof.

9. The process according to claim 1 , wherein the carboxylic acid obtained from the process is a mixture of pelargonic acid and azelaic acid.

10. The process according to claim 1 , wherein the reaction step is performed at a pressure from 1 to 40 bar.

11. The process according to claim 1 , wherein a mole ratio between dioxygen and said at least one vicinal diol or said at least one vicinal polyol is from 0.6 to 3.5 equivalents.

12. The process according to claim 2 , wherein the catalyst has a specific surface area of 150 m 2 /g.

13. The process according to claim 3 , wherein the olefin is derived from a plant oil.

Assignees

• Avril
• Oleon SA
• Univ Claude Bernard Lyon
• Centre National De La Recherche Scient (Cnrs)

Inventors

• Lemaire Marc
• Metay Estelle
• Sutter Marc
• Raoul Yann
• Da Silva Eric
• Sambou Sophie
• Blach Philippe

Classifications

• C07C51/23 Primary

  of oxygen-containing groups to carboxyl groups · CPC title

• C08K5/11

  of acyclic polycarboxylic acids · CPC title

• B01J37/08

  Heat treatment {(B01J37/0009, B01J37/0018 take precedence)} · CPC title

• C10M129/40

  monocarboxylic · CPC title

• A61K8/362

  Polycarboxylic acids · CPC title