Process for preparing fatty acid chlorides and N-acyl amino acid salts

Patent metadata

Field	Value
Publication number	US-11807598-B2
Application number	US-201917290502-A
Country	US
Kind code	B2
Filing date	Oct 30, 2019
Priority date	Oct 31, 2018
Publication date	Nov 7, 2023
Grant date	Nov 7, 2023

Abstract

The invention relates to a process for preparing fatty acid chlorides. In a subsequent step, the fatty acid chlorides can be used to prepare N-acyl amino acid salts. The process comprises the formation of a fatty acid chloride in an amine catalyzed reaction of a fatty acid with phosphorous trichloride, thionyl chloride or phosgene, preferably thionyl chloride. The process for preparing N-acyl amino acid salts further comprises the reaction of the fatty acid chloride with an amino acid or an amino ethane sulfonic acid.

First claim

The invention claimed is:

1. A process for preparing a fatty acid chloride of formula R—COCl, wherein R is a linear or branched, saturated alkyl group having from 6 to 30 carbon atoms, or a linear or branched, mono- or polyunsaturated alkenyl group having from 6 to 30 carbon atoms,
wherein the process comprises the steps of
i) providing a fatty acid of formula R—COOH, and
ii) reacting the fatty acid of step i) with phosphorous trichloride, thionyl chloride or phosgene, in the presence of a catalyst to form a fatty acid chloride of formula R—COCl, wherein the catalyst is an amine, and wherein the amine is selected from the group consisting of amino acids and amino ethane sulfonic acids.

2. The process of claim 1 , wherein the amine is glycine, taurine or N-methyl taurine.

3. The process of claim 1 , wherein step ii) is carried out with an excess of phosphorous trichloride, thionyl chloride or phosgene, of at least 5%, based on the stoichiometric amount of fatty acid.

4. The process of claim 1 , wherein step ii) is carried out with an excess of phosphorous trichloride, thionyl chloride or phosgene, of from 5 to 25%, based on the stoichiometric amount of fatty acid.

5. The process of claim 1 , wherein step ii) is carried out with an excess of phosphorous trichloride, thionyl chloride or phosgene, of from 7 to 10%, based on the stoichiometric amount of fatty acid.

6. The process of claim 1 , wherein step ii) is carried out in the presence of from 0.5 to 10 wt.-% of catalyst, based on the total weight of the fatty acid.

7. The process of claim 1 , wherein step ii) is carried out in the presence of from 2.5 to 3 wt.-% of catalyst, based on the total weight of the fatty acid.

8. The process of claim 1 , wherein step ii) is carried out at a temperature of from 25 to 65° C.

9. The process of claim 1 , wherein the process is carried out in the absence of formamides and acetamides.

10. The process of claim 1 , wherein R is an alkyl or alkenyl group derived from lauric acid, myristic acid, palmitic acid, stearic acid, palm oil, palm kernel oil or coconut oil.

11. A process for preparing an N-acyl amino acid salt of formula (I)

wherein
R is a linear or branched, saturated alkyl group having from 6 to 30 carbon atoms, or a linear or branched, mono- or polyunsaturated alkenyl group having from 6 to 30 carbon atoms,
R 1 is selected from the group consisting of the residues on the α-carbon of natural α-amino acids,
R 2 is H or an alkyl group with 1 to 4 carbon atoms,
R 3 is selected from the group consisting of COOQ and CH 2 —SO 3 Q, and
Q is a cation or a combination of more than one cation,
wherein the process comprises the steps of
i) providing a fatty acid of formula R—COOH, wherein R is a linear or branched, saturated alkyl group having from 6 to 30 carbon atoms, or a linear or branched, mono- or polyunsaturated alkenyl group having from 6 to 30 carbon atoms,
ii) reacting the fatty acid of step i) with phosphorous trichloride, thionyl chloride or phosgene, in the presence of a catalyst to form a fatty acid chloride of formula R—COCl, wherein the catalyst is an amine, and wherein the amine is selected from the group consisting of amino acids and amino ethane sulfonic acids, and
iii) reacting the fatty acid chloride of step ii) with a compound of formula (II)

to form the N-acyl amino acid salt of formula (I), wherein step iii) is carried out in water, and in the presence of a base providing cations Q.

12. The process of claim 11 , wherein the compound of formula (II) is selected from the group consisting of natural and non-natural amino acids, and amino ethane sulfonic acids.

13. The process of claim 11 , wherein the compound of formula (II) is glycine, taurine or N-methyl taurine.

14. The process of claim 11 , wherein the compound of formula (II) is the same as the catalyst used in step.

15. The process of claim 11 , wherein the process is carried out in the absence of formamides and acetamides.

16. The process of claim 11 , wherein R is an alkyl or alkenyl group derived from lauric acid, myristic acid, palmitic acid, stearic acid, palm oil, palm kernel oil or coconut oil.

17. The process of claim 11 , wherein Q is Na + , K + , or a combination thereof.

18. The process of claim 11 , wherein R 1 is H.

19. The process of claim 11 , wherein R 2 is H.

20. The process of claim 11 , wherein R 3 is COOQ.

21. The process of claim 11 , wherein R 1 is H, R 2 is H, and R 3 is COOQ.

22. The process of claim 11 , wherein the base used in step iii) is sodium hydroxide, potassium hydroxide, or a combination thereof.

23. The process of claim 11 , wherein the molar ratio of fatty acid chloride to compound of formula (II) is in the range of from 1:1 to 1:1.1.

24. The process of claim 11 , wherein step iii) is carried out at a pH of 9-13.

25. The process of claim 11 , wherein step iii) is carried out at temperature of 25 to 50° C.

26. A process for preparing a personal care composition comprising
A) preparing an N-acyl amino acid salt of formula (I) according to claim 11 ; and
B) formulating the N-acyl amino acid salt of formula (I) into a composition comprising a cosmetically acceptable carrier and at least one cosmetic benefit agent to form a personal care composition.

Assignees

• Clariant Int Ltd
• Transpek Industry Ltd

Inventors

• Contractor Prerak Rajendrakumar
• Patil Raju Dayaram
• Soni Jignalkumar Nurpeshkumar

Classifications

• C07C51/60 Primary

  by conversion of carboxylic acids or their anhydrides {or esters, lactones, salts} into halides with the same carboxylic acid part · CPC title

• A61K8/44

  Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof · CPC title

• A61K2800/10

  General cosmetic use · CPC title

• A61K2800/805

  Corresponding aspects not provided for by any of codes A61K2800/81 - A61K2800/95 · CPC title

• C07C53/42

  of acids containing three or more carbon atoms · CPC title