Process for the preparation of light-colored oleic acid sulfonates

• US 5,294,726 A
• Filed: 02/10/1992
• Issued: 03/15/1994
• Est. Priority Date: 08/09/1989
• Status: Expired due to Fees

• Current Assignee: Henkel KGaA (Henkel AG & Co KGaA)
• Original Assignee: Henkel KGaA (Henkel AG & Co KGaA)
• Inventors: Vogt, Michael, Behler, Ansgar, Anzinger, Hermann
• Primary Examiner(s): Dees, Jose G.
• Assistant Examiner(s): Carr, Deborah D.
• Application Number:
  US07/834,252
• Time in Patent Office: 764 Days
• Field of Search: 554/98
• US Class Current: 554/98
• CPC Class Codes: C07C 303/02 of sulfonic acids or halides thereof
• CPC Class Codes: C07C 303/06 by reaction with sulfuric acid or sulfur trioxide
• CPC Class Codes: C07C 303/32 of salts of sulfonic acids
• CPC Class Codes: C07C 309/17 containing carboxyl groups bound to the carbon skeleton
• CPC Class Codes: C07C 309/22 containing carboxyl groups bound to the carbon skeleton

Abstract

A process for the preparation of light-colored oleic acid sulfonates by continuous sulfonation of an industrial oleic acid having an oleic acid content of 65 to 85% by weight and a linoleic acid content of up to 13% by weight with gaseous sulfur trioxide in a molar ratio of industrial oleic acid to sulfur trioxide of 1 : 0.8 to 1 : 1.0, neutralization and hydrolysis of the acid sulfonation product with aqueous bases and bleaching of the neutralized and hydrolyzed sulfonation product give oleic acid sulfonates having Klett color numbers of not more than 100.

Claims

1. A process for the preparation of oleic acid sulfonate having a Klett color number of not more than 100 from oleic acid containing relatively large quantities of linoleic acid comprising the steps of

A. continuously sulfonating crude oleic acid having an oleic acid content in the range of from about 65 to about 85% by weight, a linoleic acid content of from about 4 to about 13% by weight, and wherein the remainder of the crude oleic acid is comprised predominantly of other saturated and/or unsaturated fatty acids having from 10 to 22 carbon atoms, and wherein the crude oleic acid is distilled industrial oleic acid which has not been stored in air following distillation for more than one month, with gaseous sulfur trioxide in a molar ratio of olefinic double bonds present in the crude oleic acid to sulfur trioxide of about 1:

0.8 to 1.0 to form an acid sulfonation product;

B. neutralizing and hydrolyzing the acid sulfonation product from step A with at least one aqueous base; and

C. bleaching the resulting aqeuous solution of oleic acid sulfonate with a bleaching agent to produce oleic acid sulfonate having a Klett color number of not more than 100.

2. The process of claim 1 wherein in step A said molar ratio is about 1:

0.90 to 0.98.

3. The process of claim 1 wherein step A is carried out in a falling film reactor.

4. The process of claim 1 wherein step A is carried out using an inert gas containing from about 1 to about 10% by volume of sulfur trioxide.

5. The process of claim 1 wherein step A is carried out at a temperature in the range of from about 40 to about 80°

C.

6. The process of claim 5 wherein said temperature is in the range of from about 40 to about 60°

C.

7. The process of claim 1 wherein step B is carried out at a temperature in the range of from about 60 to about 95°

C.

8. The process of claim 7 wherein step B is carried out a temperature in the range of from about 80 to about 90°

C.

9. The process of claim 1 wherein the bleached aqueous solution of oleic acid sulfonate from step C is concentrated by removal of water therefrom.

10. The process of claim 1 wherein step B is carried out over a period of from about 1 to about 8 hours.

11. The process of claim 1 wherein step B is carried out at a pH in the range of from about 5 to about 9.

12. The process of claim 1 wherein step B is carried out with an aqueous solution of an alkali metal hydroxide.

13. The process of claim 1 wherein step C is carried out with aqueous hydrogen peroxide solution.

14. The process of claim 1 wherein step C is carried out at a pH in the range of from about 5 to about 9.

15. The process of claim 1 wherein in step A the crude oleic acid has a linoleic acid content of from about 4 to about 12% by weight, in step A said molar ratio is about 1:

0.90 to 0.98 and the reaction temperature is in the range of from about 40 to about 80°

C., step B is carried out at a temperature in the range of from about 60 to about 95°

C. and at a pH in the range of from about 5 to about 9 and with an aqeuous solution of an alkali metal hydroxide, and step C is carried out with an aqueous hydrogen peroxide solution.

16. The process of claim 15 wherein the temperature in step A is from about 40 to about 60°

C., and the temperature in step B is from about 80 to about 90°

C. and step B is carried out for a period of from about 1 to about 8 hours.

17. A process for the preparation of oleic acid sulfonate having Klett color number of not more than 100 from oleic acid containing relatively large quantities of linoleic acid comprising the steps of:

A. continuously sulfonating crude oleic acid having an oleic acid content in the range of from about 65 to about 85% by weight, a linoleic acid content of from about 4 to about 13% by weight, and wherein the remainder of the crude oleic acid is comprised predominantly of other saturated and/or unsaturated fatty acids having from 10 to 22 carbon atoms, and wherein the crude oleic acid is distilled industrial oleic acid which has not been stored in air following distillation for more than one month, with gaseous sulfur trioxide in a molar ratio of olefinic double bonds present in the crude oleic acid to sulfur trioxide to about 1;

0.8 to 1.0 to form an acid sulfonation production;

B. simultaneously neutralizing, hydrolyzing, and bleaching the acid sulfonation product from step A with at least one aqueous base and a bleaching agent to produce oleic acid sulfonate having a Klett color number of not more than 100.

18. The process of claim 17 wherein step B is carried out with an aqueous alkali metal hydroxide and aqueous hydrogen peroxide.

19. The process of claim 17 wherein step B is carried out at a temperature in the range of from about 60 to about 95°

C., at a pH in the range of from about 5 to about 9, and for a period of from about 1 to about 8 hours.