Acesulfame potassium compositions and processes for producing same

Patent metadata

Field	Value
Publication number	US-10030000-B2
Application number	US-201715704419-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

A process for producing acesulfame potassium, the process comprising the steps of providing a cyclizing agent composition comprising a cyclizing agent and a solvent and having an initial temperature, cooling the cyclizing agent composition to form a cooled cyclizing agent composition having a cooled temperature less than 35° C., reacting an acetoacetamide salt with the cyclizing agent in the cooled cyclizing agent composition to form a cyclic sulfur trioxide adduct composition comprising cyclic sulfur trioxide adduct; and, forming from the cyclic sulfur trioxide adduct in the cyclic sulfur trioxide adduct composition the finished acesulfame potassium composition comprising non-chlorinated acesulfame potassium and less than 39 wppm 5-chloro-acesulfame potassium. The cooled temperature is at least 2° C. less than the initial temperature.

First claim

We claim:

1. A process for producing a finished acesulfame potassium composition, the process comprising the steps of:
(a) providing a cyclizing agent composition comprising a cyclizing agent and a solvent and having an initial temperature;
(b) cooling the cyclizing agent composition to form a cooled cyclizing agent composition having a cooled temperature less than 35° C., wherein the cooled temperature is at least 2° C. less than the initial temperature;
(c) reacting an acetoacetamide salt with the cyclizing agent in the cooled cyclizing agent composition to form a cyclic sulfur trioxide adduct composition comprising cyclic sulfur trioxide adduct; and
(d) forming the finished acesulfame potassium composition from the cyclic sulfur trioxide adduct, wherein the finished acesulfame composition comprises non-chlorinated acesulfame potassium and less than 39 wppm 5-chloro-acesulfame potassium.

2. The process of claim 1 , wherein the forming comprises:
hydrolyzing the cyclic sulfur trioxide adduct in the cyclic sulfur trioxide adduct composition to form an acesulfame-H composition; and
neutralizing the acesulfame-H in the acesulfame-H composition to form a crude acesulfame potassium composition comprising non-chlorinated acesulfame potassium and less than 39 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 providing step (a) comprises the step of contacting the solvent and the cyclizing agent to form the cyclizing agent composition; and wherein a contact time from the beginning of the contacting step to the beginning of reacting step (c) is less than 60 minutes.

4. The process of claim 2 , wherein the finished acesulfame potassium composition comprises from 1 wppb to 5 wppm 5-chloro-acesulfame potassium.

5. The process of claim 2 , wherein the cooled cyclizing agent composition has a cooled temperature less than 25° C. and the crude acesulfame potassium composition comprises from 1 wppb to 39 wppm 5-chloro-acesulfame potassium and the finished acesulfame potassium composition comprises from 1 wppb to 5 wppm 5-chloro-acesulfame potassium.

6. The process of claim 2 , wherein the cooled cyclizing agent composition has a cooled temperature ranging from −35° C. to 15° C. and 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 2.7 wppm 5-chloro-acesulfame potassium.

7. The process of claim 3 , wherein the cooled cyclizing agent composition has a cooled temperature less than 25° C. and the contact time is less than 15 minutes and the crude acesulfame potassium composition comprises from 1 wppb to 39 wppm 5-chloro-acesulfame potassium and the finished acesulfame potassium composition comprises from 1 wppb to 5 wppm 5-chloro-acesulfame potassium.

8. The process of claim 3 , wherein the cooled cyclizing agent composition has a cooled temperature ranging from −35° C. to 15° C. and the contact time is less than 5 minutes and the crude acesulfame potassium composition comprises from 1 wppb to 39 wppm 5-chloro-acesulfame potassium and the finished acesulfame potassium composition comprises from 1 wppb to 5 wppm 5-chloro-acesulfame potassium.

9. 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.

10. The process of claim 7 , 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.

11. 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.

12. The process of claim 1 , wherein the cooled cyclizing agent composition comprises less than 1 wt % cyclizing agent/solvent reaction product selected from the group consisting of chloromethyl chlorosulfate and meth-bis-chlorosulfate.

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

14. The process of claim 1 , wherein the cooled cyclizing agent composition comprises less than 1 wt % chlorosulfates.

15. The process of claim 1 , wherein the cyclic sulfur trioxide adduct composition comprises from 10 wppm to 0.75 wt % chlorosulfates.

16. The process of claim 15 , wherein the chlorosulfates comprise chloromethyl chlorosulfates, methyl-bis-chlorosulfates, and combinations thereof.

17. The process of claim 3 , wherein the cooled cyclizing agent composition has a cooled temperature less than 25° C., the contact time is less than 5 minutes, the cooled cyclizing agent composition comprises from 10 wppm to 1 wt % chlorosulfates, and the crude acesulfame potassium composition comprises from 1 wppb to 39 wppm 5-chloro-acesulfame potassium.

18. The process of claim 3 , wherein the cooled cyclizing agent composition has a cooled temperature less than 25° C., the contact time is less than 5 minutes, the cooled cyclizing agent composition comprises from 10 wppm to 1 wt % chlorosulfates, the cyclic sulfur trioxide adduct composition comprises from 10 wppm to 0.75 wt % chlorosulfates, and the crude acesulfame potassium composition comprises from 1 wppb to 33 wppm 5-chloro-acesulfame potassium.

19. The process of claim 3 , wherein the cooling step reduces the temperature of the cyclizing agent composition by at least 3° C., the contact time is less than 5 minutes, and the crude acesulfame potassium composition comprises from 1 wppb to 33 wppm 5-chloro-acesulfame potassium.

20. The process of claim 19 , wherein the cooling step reduces the temperature of the cyclizing agent composition by at least 10° C.

21. The process of claim 11 , 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.

22. The process of claim 2 , wherein the neutralizing step is conducted at a pH ranging from 6.0 to 10.0 and the crude acesulfame potassium composition further comprises from 20 wppm to 2500 wppm acetoacetamide-N-sulfonic acid.

23. The process of claim 2 , further comprising
reacting sulfamic acid and trimethylamine in the presence of acetic acid to form an amidosulfamic acid salt;
reacting the amidosulfamic acid salt and diketene to form acetoacetamide salt;
wherein reacting step (c) comprises reacting the acetoacetamide salt with the cyclizing agent in the cooled cyclizing agent composition to form the cyclic sulfur trioxide adduct composition comprising cyclic sulfur trioxide adduct; and
wherein the process yields at least 100 grams of finished acesulfame potassium composition per hour.

24. The process of claim 11 , wherein the intermediate acesulfame potassium composition comprises acetoacetamide-N-sulfonic acid and acetoacetamide in an amount ranging from 10 wppb to 25 wppm.

Assignees

• Celanese Int Corp

Inventors

• Mollenkopf Christoph
• Groer Peter
• Yadav Arvind

Classifications

• A23L27/30

  Artificial sweetening agents · CPC title

• A23L27/31

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

• C07D291/06 Primary

  Six-membered rings · CPC title

• A23V2002/00

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