Acesulfame potassium compositions and processes for producing same

Patent metadata

Field	Value
Publication number	US-10233164-B2
Application number	US-201816014471-A
Country	US
Kind code	B2
Filing date	Jun 21, 2018
Priority date	Sep 21, 2016
Publication date	Mar 19, 2019
Grant date	Mar 19, 2019

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, wherein the neutralizing step is conducted at a pH at or below 11.0; and
(d) treating the crude acesulfame potassium composition to form a 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) is conducted at a pH ranging from 9.0 to 11.0.

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

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

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

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

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

12. The process of claim 1 , wherein the cyclic sulfur trioxide adduct is formed by a process that comprises (a) reacting sulfamic acid and triethylamine to form an amidosulfamic acid salt; (b) reacting the amidosulfamic acid salt and diketene to form acetoacetamide salt; (c) contacting dichloromethane and a sulfur trioxide to form a cyclizing agent composition; and (d) reacting the acetoacetamide salt with sulfur trioxide in the cyclizing agent composition to form the cyclic sulfur trioxide adduct.

13. The process of claim 1 , wherein the finished acesulfame potassium composition comprises less than 37 wppm acetoacetamide.

14. The process of claim 1 , wherein the finished acesulfame potassium composition comprises less than 25 wppm acetoacetamide.

15. The process of claim 1 , wherein the finished acesulfame potassium composition comprises less than 20 wppm acetoacetamide.

16. The process of claim 1 , wherein the finished acesulfame potassium composition comprises less than 25 wppm acetoacetamide-N-sulfonic acid.

17. The process of claim 1 , wherein the finished acesulfame potassium composition comprises less than 10 wppm acetoacetamide-N-sulfonic acid.

18. The process of claim 1 , wherein the finished acesulfame potassium composition comprises less than 25 wppm acetoacetamide-N-sulfonic acid and comprises less than 25 wppm acetoacetamide.

19. The process of claim 1 , wherein the finished acesulfame potassium composition comprises less than 25 wppm acetoacetamide-N-sulfonic acid and less than 15 wppm acetoacetamide.

20. The process of claim 1 , wherein the finished acesulfame potassium composition comprises less than 10 wppm acetoacetamide-N-sulfonic acid and less than 10 wppm acetoacetamide.

21. The process of claim 1 , wherein the crude acesulfame potassium composition comprises acetoacetamide, acetoacetamide-N-sulfonic acid, or a combination thereof.

22. The process of claim 1 , wherein the crude acesulfame potassium composition comprises less than 2800 wppm acetoacetamide-N-sulfonic acid.

23. The process of claim 1 , wherein the crude acesulfame potassium composition comprises from 500 wppm to 2375 wppm acetoacetamide-N-sulfonic acid.

24. The process of claim 1 , wherein the neutralizing step (c) is conducted at a pH ranging from 9.0 to 11.0 and the finished acesulfame potassium composition comprises less than 25 wppm acetoacetamide-N-sulfonic acid and less than 15 wppm acetoacetamide.

25. The process of claim 1 , wherein the neutralizing step (c) is conducted at a pH ranging from 8 to 10.3 and the finished acesulfame potassium composition comprises less than 10 wppm acetoacetamide-N-sulfonic acid and less than 10 wppm acetoacetamide.

26. The process of claim 1 , wherein the neutralizing step (c) is conducted at a pH ranging from 8 to 10.3 and 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

• C07D291/06 Primary

  Six-membered rings · CPC title

• A23L27/31

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

• A23V2002/00

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

• A23L27/30

  Artificial sweetening agents · CPC title