Preparation of lactylates directly from oil

Patent metadata

Field	Value
Publication number	US-9714399-B2
Application number	US-201414783283-A
Country	US
Kind code	B2
Filing date	Apr 10, 2014
Priority date	Apr 11, 2013
Publication date	Jul 25, 2017
Grant date	Jul 25, 2017

Abstract

A process includes the transesterification of a fatty acid triglyceride ester with a salt of hydroxycarboxylic acid without making use of organic solvents. The process can carried out with natural oils as starting material and produces a mixture of medium chain mono and diglycerides and medium chain esters of hydroxycarboxylic acid.

First claim

The invention claimed is:

1. A process for the preparation of a salt of a fatty acid ester of hydroxycarboxylic acid which comprises heating an oil, comprising a mixture consisting essentially of a triglyceride fatty acid ester, a salt of hydroxycarboxylic acid and a catalyst at a temperature at or above the melting temperature of the salt of hydroxycarboxylic acid and subjecting the mixture to ester interchange to form an end product, wherein the removal of an organic solvent is not required during or after completion of the ester interchange, wherein said hydroxycarboxylic acid is a mono- or dicarboxylic acid having 2-6 carbon atoms and 1-3 hydroxyl groups, and wherein the end product does not require removal of an organic solvent.

2. The process according to claim 1 wherein the temperature is kept between 150 and 220° C.

3. The process of claim 2 wherein the temperature is kept between 180 and 200° C.

4. The process of claim 1 wherein said hydroxycarboxylic acid is lactic acid.

5. The process of claim 4 wherein the salt of hydroxycarboxylic acid is sodium lactate.

6. The process of claim 1 wherein said catalyst is alkaline-OR wherein R is H.

7. The process of claim 1 wherein said catalyst is alkaline-OR wherein R is Me.

8. A process according to claim 1 wherein the natural oil is coconut oil.

9. A process according to claim 1 wherein the natural oil is palm kernel oil.

10. The process of claim 1 wherein the molar ratio of salt of hydroxycarboxylic acid to the triglyceride fatty acid ester is from 10:1 to −0.5:1.

11. The process according to claim 1 and further comprising adding a surfactant to the mixture during the ester interchange.

12. The process according to claim 11 wherein the surfactant is added in an amount ranging from 0-20% on a mass basis as compared to the starting materials.

13. A process according to claim 1 wherein in addition to the salt of a fatty acid ester of hydroxycarboxylic acid, mono- and di-fatty acid esters of glycerol are produced.

14. The process according to claim 1 , wherein the process is carried out under inert atmosphere.

15. The process according to claim 1 , wherein the molar ratio of the salt of the hydroxycarboxylic acid to the triglyceride fatty acid ester is from 25:1 to 0.5:1.

16. The process according to claim 1 were in the triglyceride fatty acid ester comprises C12 to C16 fatty acid chains.

17. The process according to claim 1 wherein the natural oil is a mixture of coconut oil and palm kernel oil.

18. The process according to claim 1 wherein the ester interchange is completed without using an organic solvent.

19. The process according to claim 1 , and further comprising adding a surfactant to the mixture.

Assignees

• Purac Biochem Bv

Inventors

• Verkuijl Bastiaan Jeroen Victor
• Kok Symone

Classifications

• A61K8/375

  the alcohol moiety containing more than one hydroxy group · CPC title

• C07C59/235

  Saturated compounds containing more than one carboxyl group · CPC title

• C11C3/003 Primary

  by esterification of fatty acids with alcohols (C11C3/02 takes precedence) · CPC title

• C07C67/02

  by interreacting ester groups, i.e. transesterification · CPC title

• A61K2800/10

  General cosmetic use · CPC title