Betaine esters and process for making and using

Patent metadata

Field	Value
Publication number	US-9487805-B2
Application number	US-201514844072-A
Country	US
Kind code	B2
Filing date	Sep 3, 2015
Priority date	Apr 28, 2011
Publication date	Nov 8, 2016
Grant date	Nov 8, 2016

Abstract

A variety of betaine esters, including dialkylaminoalkyl cocoate betaines and dialkylaminoalkyl hydrogenated cocoate betaines are disclosed. These betaines can be advantageously prepared in high yield and purity by a three-step transiterification chemoenzymatic process or a two-step direct esterficiation chemoenzymatic process. These betaine esters have excellent surfactant properties.

First claim

We claim:

1. A method for the preparation of a betaine represented by general formula 1,

comprising:
a) producing an ester of formula 2:

wherein R is selected from the group consisting of C 5 -C 17 alkyl, C 5 -C 17 alkenyl, C 5 -C 17 dienyl, C 5 -C 17 trienyl, and mixtures thereof; and R 6 is a C 1 -C 6 alkyl;
b) reacting a dialkylamino alcohol 3:

with ester 2 in the presence of an enzyme and an azeotroping solvent to form an intermediate 4:

wherein R 1 is methyl, R 2 is C 1 -C 5 alkyl, and A is C 3 -C 10 alkylene; and

c) reacting intermediate 4 with sodium chloroacetate to produce a betaine.

2. The method according to claim 1 , wherein R is selected from the group consisting of C 5 -C 17 alkyl and mixtures thereof, R 1 is methyl, R 2 is C 1 -C 5 alkyl, and A is C 3 -C 8 alkylene.

3. The method according to claim 1 , wherein the ester is produced by solvolysis of non-hydrogenated or hydrogenated triglycerides in the presence of a lower alcohol and a base, acid or enzyme catalyst.

4. The method according to claim 3 , wherein the lower alcohol is a C 1 -C 4 alcohol, R 2 is methyl, and A is C 3 -C 8 alkylene.

5. The method according to claim 4 , wherein the lower alcohol is selected from the group consisting of methanol, ethanol, 1-propanol and 2-propanol, and A is 1,3-propylene.

6. The method according to claim 1 , wherein the enzyme is a protease, a lipase, or an esterase.

7. A method for the preparation of a betaine represented by general formula 1,

comprising:
a) reacting a carboxylic acid

with a dialkylamino alcohol 3:

in the presence of an enzyme and an azeotroping solvent to form an intermediate 4:

wherein R selected from the group consisting of C 5 -C 17 alkyl, C 5 -C 17 alkenyl, C 5 -C 17 dienyl, C 5 -C 17 trienyl, and mixtures thereof; R 1 is methyl; R 2 is C 1 -C 5 alkyl; and A is C 3 -C 10 alkylene; and
b) reacting intermediate 4 with sodium chloroacetate to produce a betaine.

8. The method according to claim 7 , wherein R is C 5 -C 17 alkyl, R 1 is methyl, R 2 is C 1 -C 5 alkyl, and A is C 3 -C 8 alkylene.

9. The method according to claim 7 , wherein R 2 is methyl, and A is C 3 -C 8 alkylene.

10. The method according to claim 9 , wherein A is 1,3-propylene.

11. The method according to claim 7 , wherein the enzyme is a protease, a lipase, or an esterase.

12. The method according to claim 1 , wherein the azeotroping solvent comprises heptane.

13. The method according to claim 7 , wherein the azeotroping solvent comprises heptane.

Assignees

• Eastman Chem Co

Inventors

• Burk Christopher Harlan
• Clendennen Stephanie Kay
• Boaz Neil Warren

Classifications

• C12P13/04 Primary

  Alpha- or beta- amino acids {(other amino acids C12P13/005)} · CPC title

• C07C229/12 Primary

  to carbon atoms of acyclic carbon skeletons · CPC title

• C07C219/08

  having at least one of the hydroxy groups esterified by a carboxylic acid having the esterifying carboxyl group bound to an acyclic carbon atom of an acyclic unsaturated carbon skeleton · CPC title

• C07C219/06

  having the hydroxy groups esterified by carboxylic acids having the esterifying carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms of an acyclic saturated carbon skeleton · CPC title

• C11D1/90

  Betaines · CPC title