Method of enhanced conversion of taurine salts to alkyl taurate amides

Patent metadata

Field	Value
Publication number	US-11059776-B2
Application number	US-201816649784-A
Country	US
Kind code	B2
Filing date	Sep 24, 2018
Priority date	Oct 3, 2017
Publication date	Jul 13, 2021
Grant date	Jul 13, 2021

Abstract

The invention relates to a method of enhancing conversion of alkali metal salt, preferably aqueous salt, preferably aqueous sodium salt of N-methyl taurine to alkyl taurate amides. In one aspect, the starting salt is pre-concentrated (at least 75% up to 99% taurine salt in the aqueous solutions after water is removed from a starting aqueous solution of the salt) and, in another aspect, the starting salt is not pre-concentrated.

First claim

The invention claimed is:

1. A process for making alkyl taurate amides which comprises the steps of (1) reacting C 8 to C 20 fatty acid with alkali metal salt of N-methyl taurine, (2) heating the C 8 to C 20 fatty acid with alkali metal salt of N-methyl taurine mixture to a reaction temperature of less than 200° C., (3) adding a catalyst; and (4) stirring the reaction mixture at the temperature of less than 200° C. for two hours or greater, thereby forming the alkyl taurate amides, wherein
a) the molar ratio of total fatty acid to alkali metal salt, both total fatty acid and salt measured as anhydrous basis, is greater or equal to 2:1; and
b) the catalyst is used in an amount ranging from 0.4 to 0.7% by wt. based on the total reaction mixture on an anhydrous basis, wherein the catalyst is selected from the group consisting of inorganic zinc compounds; magnesium oxide; phosphoric acid; and mixtures thereof.

2. A process according to claim 1 , wherein 50 to 100% of the C 8 to C 20 fatty acid is C 12 .

3. A process according to claim 2 , wherein the fatty acid reacted is C 10 to C 14 fatty acid.

4. A process according to claim 1 , wherein fatty acid is saturated, straight chain fatty acid.

5. A process according to claim 1 , wherein the starting the salt taurine salt is not pre-concentrated, by which is meant that salt is not heated to remove water such that the reactant is 75% or more salt.

6. A process according to claim 1 , wherein the salt is an aqueous salt solution.

7. A process for making alkyl taurate amide which comprises the steps of (1) pre-concentrating sodium salt of N-methyl taurine salt to at least 75% of taurine salt in water before reacting with fatty acid by heating the sodium salt of N-methyl taurine salt to a temperature of about 150° C. to remove water (2) reacting C 8 to C 20 fatty acid with said sodium salt of N-methyl taurine; (3) heating the C 8 to C 20 fatty acid with alkali metal salt mixture to a reaction temperature of less than 200° C., and (4) adding a catalyst; and (5) stirring the reaction mixture at the temperature of less than 200° C. for less than two hours, thereby forming the alkyl taurate amides, wherein
a) the molar ratio of fatty acid to salt of N-methyl taurine is greater than 1.5:1;
b) the catalyst level is 0.1 to 1.5 by wt. based on the total reaction mixture on an anhydrous basis, wherein the catalyst is selected from the group consisting of inorganic zinc compounds; magnesium oxide; phosphoric acid; and mixtures thereof.

8. A process according to claim 7 , wherein 50 to 100% of the C 8 to C 20 fatty acid is C 12 .

9. A process according to claim 8 , wherein the fatty acid is C 10 to C 14 fatty acid.

10. The process according to claim 1 , wherein the alkali metal salt is sodium salt of N-methyl taurine.

11. The process according to claim 1 , wherein the molar ratio of total fatty acid to alkali metal salt is 2:1 to 5:1.

12. The process according to claim 1 , wherein the reaction time temperature is 190 to 199° C.

13. The process according to claim 1 , wherein the time of reaction is 2 to 4 hours.

14. The process according to claim 7 , wherein the catalyst level is 0. 5 to 1.5% by wt.

15. The process according to claim 14 , wherein the catalyst level is 0.8 to 1.2% by wt.

16. The process according to claim 7 , wherein the temperature of reaction is 190 to 199° C.

Assignees

• Conopco Inc

Inventors

• Harichian Bijan
• Au Van
• Shiloach Anat
• Winters John Robert
• Dunn Erin Whitfield

Classifications

• C07C309/14

  containing amino groups bound to the carbon skeleton · CPC title

• C07C303/22 Primary

  from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; {from sulfonic halides by reactions not involving the formation of halosulfonyl groups} · CPC title

• C07C309/15

  the nitrogen atom of at least one of the amino groups being part of any of the groups [IMAGE cpc-sch-C07C-0975.gif], X being a hetero atom, Y being any atom · CPC title