Acesulfame potassium compositions and processes for producing same

Patent metadata

Field	Value
Publication number	US-10029998-B2
Application number	US-201715704356-A
Country	US
Kind code	B2
Filing date	Sep 14, 2017
Priority date	Sep 21, 2016
Publication date	Jul 24, 2018
Grant date	Jul 24, 2018

Abstract

Compositions and processes for producing high purity acesulfame potassium are described. One process comprises the steps of forming a cyclic sulfur trioxide adduct; hydrolyzing the cyclic sulfur trioxide adduct to form an acesulfame-H composition comprising acesulfame-H; neutralizing the acesulfame-H in the acesulfame-H composition to form a crude acesulfame potassium composition comprising acesulfame potassium and less than 2800 wppm acetoacetamide-N-sulfonic acid, wherein the neutralizing step is conducted or maintained at a pH at or below 11.0; and treating the crude acesulfame potassium composition to form the finished acesulfame potassium composition comprising acesulfame potassium and less than 37 wppm acetoacetamide-N-sulfonic acid.

First claim

We claim:

1. A process for producing a finished acesulfame potassium composition, the process comprising the steps of:
(a) forming a cyclic sulfur trioxide adduct;
(b) hydrolyzing the cyclic sulfur trioxide adduct to form an acesulfame-H composition comprising acesulfame-H;
(c) neutralizing the acesulfame-H in the acesulfame-H composition to form a crude acesulfame potassium composition comprising acesulfame potassium and less than 2800 wppm acetoacetamide-N-sulfonic acid, wherein the neutralizing step is conducted at a pH at or below 11.0; and
(d) treating the crude acesulfame potassium composition to form the finished acesulfame potassium composition comprising acesulfame potassium and less than 37 wppm acetoacetamide-N-sulfonic acid.

2. The process of claim 1 , wherein the neutralizing step (c) comprises:
reacting acesulfame-H with a neutralizing agent in an acesulfame-H/neutralizing agent reaction mixture to form the acesulfame potassium composition.

3. The process of claim 2 , wherein the neutralizing agent comprises potassium hydroxide.

4. The process of claim 3 , wherein the potassium hydroxide is produced via a membrane process and the finished acesulfame potassium composition comprises less than 10 wppm mercury.

5. The process of claim 2 , wherein the acesulfame-H/neutralizing agent reaction mixture comprises from 1 wt % to 95 wt % neutralizing agent and from 1 wt % to 95 wt % acesulfame-H, based on the total weight of the acesulfame-H/neutralizing agent reaction mixture.

6. The process of claim 1 , wherein the neutralizing step (c) comprises neutralizing the acesulfame-H in the acesulfame-H composition to form the crude acesulfame potassium composition further comprising acetoacetamide.

7. The process of claim 6 , wherein the crude acesulfame potassium composition comprises from 500 wppm to 2375 wppm acetoacetamide-N-sulfonic acid and the finished acesulfame potassium composition comprises less than 25 wppm acetoacetamide-N-sulfonic acid and further comprises less than 25 wppm acetoacetamide.

8. The process of claim 6 , wherein the neutralizing step (c) is conducted at a pH ranging from 9.0 to 11.0 and the crude acesulfame potassium composition comprises from 20 wppm to 2500 wppm acetoacetamide-N-sulfonic acid and the finished acesulfame potassium composition comprises less than 25 wppm acetoacetamide-N-sulfonic acid and less than 15 wppm acetoacetamide.

9. The process of claim 6 , wherein the neutralizing step (c) is conducted at a pH ranging from 8 to 10.3 and the crude acesulfame potassium composition comprises from 600 wppm to 1200 wppm acetoacetamide-N-sulfonic acid, and the finished acesulfame potassium composition comprises less than 10 wppm acetoacetamide-N-sulfonic acid and less than 10 wppm acetoacetamide.

10. The process of claim 6 , wherein the neutralizing step (c) is conducted at a pH ranging from 8 to 10.3 and the crude acesulfame potassium composition comprises less than 2400 wppm acetoacetamide-N-sulfonic acid, and the finished acesulfame potassium composition comprises less than 10 wppm acetoacetamide-N-sulfonic acid and less than 10 wppm acetoacetamide.

11. The process of claim 6 , wherein the finished acesulfame potassium composition comprises less than 37 wppm acetoacetamide.

12. The process of claim 1 , wherein the neutralizing step (c) is conducted at a pH ranging from 9.0 to 11.0.

13. The process of claim 1 , wherein the neutralizing step (c) is conducted at a pH ranging from 9.0 to 10.5.

14. The process of claim 1 , wherein the neutralizing step (c) is conducted at a pH ranging from 8.0 to 10.3.

15. The process of claim 1 , wherein the treating step (d) is conducted at a temperature below 90° C.

16. The process of claim 1 , wherein the treating step (d) comprises an evaporating step with a residence time less than 180 minutes.

17. The process of claim 1 , wherein the neutralizing step is maintained at a pH at or below 11.0.

18. The process of claim 1 , wherein the treating step (d) comprises concentrating the crude acesulfame potassium to yield an intermediate acesulfame potassium composition.

19. The process of claim 18 , wherein the treating step (d) further comprises separating the intermediate acesulfame potassium composition to yield the finished acesulfame potassium composition.

20. The process of claim 19 , wherein the intermediate acesulfame composition further comprises acetoacetamide-N-sulfonic acid.

21. The process of claim 19 , wherein the separating is conducted at a temperature below 35° C.

22. The process of claim 21 , wherein the concentrating is conducted at a temperature below 70° C. and the finished acesulfame potassium composition comprises less than 25 wppm acetoacetamide-N-sulfonic acid and less than 15 wppm acetoacetamide.

23. The process of claim 21 , wherein the concentrating is conducted at a temperature below 46° C. and at a residence time less than 30 minutes and the finished acesulfame potassium composition comprises less than 10 wppm acetoacetamide-N-sulfonic acid and less than 10 wppm acetoacetamide.

24. The process of claim 1 , wherein the forming step (a) comprises:
reacting sulfamic acid, acetic acid, and triethylamine to form an amidosulfamic acid salt;
reacting the amidosulfamic acid salt and diketene to form acetoacetamide salt;
contacting dichloromethane and a sulfur trioxide to form a cyclizing agent composition; and
reacting the acetoacetamide salt with sulfur trioxide in the cyclizing agent composition to form the cyclic sulfur trioxide adduct.

25. The process of claim 24 , wherein the process yields at least 100 grams of finished acesulfame potassium composition per hour.

26. The process of claim 1 , wherein the hydrolyzing step (b) comprises adding water to the cyclic sulfur trioxide adduct.

27. The process of claim 26 , wherein the weight ratio of water to acetoacetamide salt in the hydrolyzing step (b) is greater than 1.3:1.

28. The process of claim 27 , wherein the finished acesulfame potassium composition comprises less than 25 wppm acetoacetamide-N-sulfonic acid.

29. The process of claim 27 , wherein the weight ratio of water to acetoacetamide salt in the hydrolyzing step (b) is greater than 1.7:1, and wherein the finished acesulfame potassium composition comprises less than 10 wppm acetoacetamide-N-sulfonic acid and less than 10 wppm acetoacetamide.

30. The process of claim 27 , wherein the treating step (d) comprises concentrating the crude acesulfame potassium to yield an intermediate acesulfame potassium composition and separating the intermediate acesulfame potassium composition to yield the finished acesulfame potassium composition, and wherein the weight ratio of water to acetoacetamide salt in the hydrolyzing step (b) is greater than 1.7:1, and wherein the separating is conducted at a temperature below 35° C., and wherein the finished acesulfame potassium composition comprises less than 10 wppm acetoacetamide-N-sulfonic acid and less than 10 wppm acetoacetamide.

Assignees

• Celanese Int Corp

Inventors

• Mollenkopf Christoph
• Groer Peter
• Yadav Arvind

Classifications

• A23V2002/00

  Food compositions, function of food ingredients or processes for food or foodstuffs · CPC title

• A23L27/31

  containing amino acids, nucleotides, peptides or derivatives · CPC title

• C07D291/06 Primary

  Six-membered rings · CPC title

• A23L27/30

  Artificial sweetening agents · CPC title