ACESULFAME POTASSIUM COMPOSITIONS AND PROCESSES FOR PRODUCING SAME

• US 20180079736A1
• Filed: 09/14/2017
• Published: 03/22/2018
• Est. Priority Date: 09/21/2016
• Status: Active Grant

• Current Assignee: Celanese International Corporation (Celanese Corporation)
• Original Assignee: Celanese International Corporation (Celanese Corporation)
• Inventors: MOLLENKOPF, Christoph, Groer, Peter, Yadav, Arvind
• Granted Patent: US 10,023,546 B2
• Time in Patent Office: Days
• CPC Class Codes: A23L 27/30 Artificial sweetening agents
• CPC Class Codes: A23V 2002/00 Food compositions, function of food ingredients or processes for food or foodstuffs
• CPC Class Codes: C07C 235/74 of a saturated carbon skeleton
• CPC Class Codes: C07D 291/06 Six-membered rings

Abstract

Improved processes for producing high purity acesulfame potassium. In one embodiment, the process comprises the steps of contacting a solvent, e.g., dichloromethane, and a cyclizing agent, e.g., sulfur trioxide, to form a cyclizing agent composition and reacting an acetoacetamide salt with the cyclizing agent in the composition to form a cyclic sulfur trioxide adduct. The contact time is less than 60 minutes. The process also comprises forming from the cyclic sulfur trioxide adduct composition a finished acesulfame potassium composition comprising non-chlorinated, e.g., non-chlorinated, acesulfame potassium and less than 35 wppm 5-halo acesulfame potassium, preferably less than 5 wppm.

Claims

1. A process for producing a finished acesulfame potassium composition, the process comprising the steps of:

(a) contacting a cyclizing agent and a solvent selected from the group consisting of halogenated aliphatic hydrocarbons, esters of carbonic acid with lower aliphatic alcohols, nitroalkanes, alkyl-substituted pyridines, aliphatic sulfones, acetone, acetic acid, and dimethylformamide to form a cyclizing agent composition;

(b) reacting an acetoacetamide salt with the cyclizing agent in the cyclizing agent composition to form a cyclic sulfur trioxide adduct; and

(c) forming from the cyclic sulfur trioxide adduct the finished acesulfame potassium composition comprising non-chlorinated acesulfame potassium and less than 35 wppm 5-chloro-acesulfame potassium;

wherein contact time from the beginning of step (a) to the beginning of step (b) is less than 60 minutes.

2. The process of claim 1, wherein the forming comprises:

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 non-chlorinated acesulfame potassium and less than 35 wppm 5-chloro-acesulfame potassium; and

forming the finished acesulfame potassium composition from the crude acesulfame potassium composition.

3. The process of claim 2, wherein the finished acesulfame potassium composition comprises from 0.001 wppm to 5 wppm 5-chloro-acesulfame potassium.

4. The process of claim 2, wherein the contact time is less than 15 minutes and the crude acesulfame potassium composition comprises from 0.001 wppm to 5 wppm 5-chloro-acesulfame potassium and the finished acesulfame potassium composition comprises from 0.001 wppm to 5 wppm 5-chloro-acesulfame potassium.

5. The process of claim 2, wherein the contact time is less than 5 minutes and the crude acesulfame potassium composition comprises from 0.001 wppm to 5 wppm 5-chloro-acesulfame potassium and the finished acesulfame potassium composition comprises from 0.001 wppm to 2.7 wppm 5-chloro-acesulfame potassium.

6. The process of claim 2, wherein the crude acesulfame potassium composition comprises less than 35 wppm 5-chloro-acesulfame potassium.

7. The process of claim 5, wherein the finished acesulfame potassium composition comprises at least 90% by weight of the 5-chloro-acesulfame potassium present in the crude acesulfame potassium composition.

8. The process of claim 2, wherein the hydrolyzing comprises adding water to the cyclic sulfur trioxide adduct to form a hydrolysis reaction mixture, and wherein the temperature of the hydrolysis reaction mixture is maintained at a temperature ranging from −

35°

C. to 0°

C.

9. The process of claim 8, wherein the finished acesulfame potassium composition comprises from 0.001 wppm to 5 wppm organic impurities.

10. The process of claim 1, further comprising:

reacting sulfamic acid and an amine to form an amidosulfamic acid salt; and

reacting the amidosulfamic acid salt and acetoacetylating agent to form the acetoacetamide salt.

11. The process of claim 1, wherein the finished acesulfame potassium composition comprises from 0.001 wppm to 2.7 wppm 5-chloro-acesulfame potassium.

12. The process of claim 1, wherein the finished acesulfame potassium composition comprises from 0.001 wppm to 5 wppm organic impurities.

13. The process of claim 1, wherein the finished acesulfame potassium composition comprises from 0.001 wppm to 5 wppm heavy metals.

14. The process of claim 1, wherein the cyclizing agent composition comprises less than 1 wt % of compounds selected from chloromethyl chlorosulfate, methyl-bis-chlorosulfate, and mixtures thereof.

15. The process of claim 1, wherein the reacting is conducted for a cyclization reaction time, from the start of the reactant feed to the end of the reactant feed, less than 35 minutes.

16. The process of claim 1, wherein the weight ratio of solvent to cyclizing agent in the cyclizing agent composition is at least 1:

1.

17. The process of claim 1, further comprising cooling the cyclizing agent composition to a temperature less than 15°

C.

18. The process of claim 1, wherein the cyclizing agent comprises sulfur trioxide and the solvent comprises dichloromethane.

29. The process of claim 2, wherein the contact time ranges from 1 second to 10 minutes, the crude acesulfame potassium composition comprises from 1 wppb to 35 wppm 5-chloro-acesulfame potassium, and the finished acesulfame potassium composition comprises from 1 wppb to 35 wppm 5-chloro-acesulfame potassium.

30. The process of claim 2, wherein the contact time ranges from 1 second to 10 minutes, the crude acesulfame potassium composition comprises from 1 wppb to 5 wppm 5-chloro-acesulfame potassium, and the finished acesulfame potassium composition comprises from 1 wppb to 5 wppm 5-chloro-acesulfame potassium.

31. The process of claim 2, wherein the contact time ranges from 1 second to 30 minutes, the crude acesulfame potassium composition comprises from 10 wppb to 10 wppm 5-chloro-acesulfame potassium, and the finished acesulfame potassium composition comprises from 10 wppb to 10 wppm 5-chloro-acesulfame potassium.

32. The process of claim 1, further comprising cooling the cyclizing agent composition to a temperature ranging from −

20°

C. to 15°

C., and wherein the cooling step reduces the temperature of the cyclizing agent composition by at least 10°

C.

33. The process of claim 2, wherein the finished acesulfame potassium composition comprises at least 90% by weight of the 5-chloro-acesulfame potassium present in the crude acesulfame potassium composition.

34. The process of claim 2, wherein the hydrolyzing step comprises adding water to the cyclic sulfur trioxide adduct, and wherein the weight ratio of water to acetoacetamide salt in the hydrolyzing step is greater than 1.3:

1.

35. The process of claim 34, 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.

36. The process of claim 33, wherein the finished acesulfame potassium composition comprises from 1 wppb to 5 wppm 5-chloro-acesulfame potassium.

37. The process of claim 1, wherein the process yields at least 100 grams of finished acesulfame potassium composition per hour.

38. The process of claim 36, wherein the reacting is conducted for a cyclization reaction time, from the start of the reactant feed to the end of the reactant feed, less than 35 minutes.

39. The process of claim 2, wherein the forming of the finished acesulfame potassium composition from the crude acesulfame potassium composition comprises the steps of:

concentrating the crude acesulfame composition to form an intermediate acesulfame potassium composition comprising at least 10 wt % acesulfame potassium; and

separating the intermediate acesulfame potassium composition to form the finished acesulfame potassium composition comprising at least 15 wt % acesulfame potassium.

40. The process of claim 39, wherein the intermediate acesulfame potassium composition comprises acetoacetamide-N-sulfonic acid and acetoacetamide in an amount ranging from 10 wppb to 25 wppm.

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