Process for preparing sebacic acid

Patent metadata

Field	Value
Publication number	US-9834798-B2
Application number	US-201314423448-A
Country	US
Kind code	B2
Filing date	Sep 3, 2013
Priority date	Sep 7, 2012
Publication date	Dec 5, 2017
Grant date	Dec 5, 2017

Abstract

A process for preparing sebacic acid by reacting in a first step (i) linoleic acid with water catalyzed by an oleate hydratase to form 10-hydroxy-12-octadecenoic acid, in a second step (ii) pyrolysing the 10-hydroxy-12-octadecenoic acid to 1-octene and 10-oxo-decanoic acid and in a third step (iii) oxidizing the 10-oxo-decanoic acid to sebacic acid.

First claim

The invention claimed is:

1. A process for preparing sebacic acid comprising
in a first step reacting (i) linoleic acid with water catalyzed by an oleate hydratase to form 10-hydroxy-12-octadecenoic acid,
in a second step (ii) pyrolysing the 10-hydroxy-12-octadecenoic acid to 1-octene and 10-oxo-decanoic acid, and
in a third step(iii) oxidizing the 10-oxo-decanoic acid to sebacic acid, wherein the oleate hydratase is a polypeptide having the amino acid sequence depicted in SEQ ID NO:2 or an amino acid sequence which is at least 95% identical to the amino acid sequence depicted in SEQ ID NO:2.

2. The process according to claim 1 , wherein the oleate hydratase is a polypeptide having SEQ ID NO:2.

3. The process according to claim 1 , wherein after step (i) the 10-hydroxy-12-octadecenoic acid is esterified to a 10-hydroxy-12-octadecenoic acid ester and subsequently the 10-hydroxy-12-octadecenoic acid ester is pyrolysed in step (ii).

4. The process according to claim 3 , wherein the 10-hydroxy-12-octadecenoic acid ester is a methyl ester.

5. The process according to claim 1 , wherein the pyrolysis in step (ii) is performed at a temperature between 400 and 800° C.

6. The process according to claim 1 , wherein the pyrolysis is carried out in a microstructured apparatus.

7. The process according to claim 1 , wherein the pyrolysis in step (ii) is performed in tetrahydrofuran as a solvent.

8. The process according to claim 1 , wherein the oxidation in step (iii) is performed using air.

9. The process according to claim 1 , wherein the oxidation step (iii) is catalyzed by a redox active metal.

10. The process according to claim 1 , wherein the pyrolysis in step (ii) is performed at a temperature between 500 and 600° C.

11. The process according to claim 1 , wherein the oleate hydratase has the Enzyme Commission number EC 4.2.1.53.

12. The process according to claim 1 , wherein the oleate hydratase has at least 97% identity to SEQ ID NO:2.

Assignees

• Basf Se

Inventors

• Piatesi Andrea
• Baldenius Kai-Uwe
• Ditrich Klaus
• Kindler Alois
• Zajaczkowski-Fischer Marta
• Boehling Ralf
• Rehfinger Alwin

Classifications

• C12P7/6427 Primary

  Polyunsaturated fatty acids [PUFA], i.e. having two or more double bonds in their backbone · CPC title

• C07C51/235

  of —CHO groups or primary alcohol groups · CPC title

• C07C55/20 Primary

  Sebacic acid · CPC title

• C07C51/373

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

• C12Y402/01053 Primary

  Oleate hydratase (4.2.1.53) · CPC title