Method for preparing trioxane

Patent metadata

Field	Value
Publication number	US-9994544-B2
Application number	US-201515502098-A
Country	US
Kind code	B2
Filing date	Jul 17, 2015
Priority date	Aug 7, 2014
Publication date	Jun 12, 2018
Grant date	Jun 12, 2018

Abstract

The present invention concerns a method for preparing 1,3,5-trioxane by trimerization of formaldehyde in the presence of methanesulfonic acid. The invention also concerns the use of at least one catalyst comprising methanesulfonic acid for the trimerization of formaldehyde into 1,3,5-trioxane.

First claim

The invention claimed is:

1. A process for the trimerization of formaldehyde to produce trioxane, comprising:
(a) reacting formaldehyde in a reaction mixture comprising water, at least one protic organic solvent, or both, and no aprotic solvent, in the presence of a catalyst comprising at least methanesulfonic acid, to produce trioxane; and
(b) separating the trioxane from the reaction mixture.

2. The process as claimed in claim 1 , wherein the formaldehyde content ranges from 30% to 90% by weight, relative to the total weight of the reaction mixture, limits included.

3. The process as claimed in claim 1 , wherein the content of methanesulfonic acid in anhydrous form or in an aqueous solution in the reaction mixture ranges from 0.1% to 25% by weight, limits included, of methanesulfonic acid expressed in anhydrous form, relative to the total weight of the reaction mixture.

4. The process as claimed in claim 1 , wherein (a) is carried out at a temperature ranging from 0° C. to 200° C.

5. The process as claimed in claim 1 , wherein (a) is carried out at a pressure set between 0.1·10 5 Pa and 10·10 5 Pa.

6. The process as claimed in claim 1 , wherein the process is carried out continuously, with continuous withdrawal of the trioxane formed.

7. The process as claimed in claim 1 , wherein the catalyst is methanesulfonic acid in an aqueous solution.

8. The process as claimed in claim 1 , wherein the formaldehyde content ranges from 30% to 70% by weight relative to the total weight of the reaction mixture, limits included.

9. The process as claimed in claim 1 , wherein the formaldehyde content ranges from 30% to 60% by weight relative to the total weight of the reaction mixture, limits included.

10. The process as claimed in claim 1 , wherein the content of methanesulfonic acid in anhydrous form or in an aqueous solution in the reaction mixture ranges from 0.1% to 15% by weight, limits included, of methanesulfonic acid expressed in anhydrous form, relative to the total weight of the reaction mixture.

11. The process as claimed in claim 1 , wherein the content of methanesulfonic acid in anhydrous form or in an aqueous solution in the reaction mixture ranges from 2% to 10% by weight, limits included, of methanesulfonic acid expressed in anhydrous form, relative to the total weight of the reaction mixture.

12. The process as claimed in claim 1 , wherein (a) is carried out at a temperature ranging from 50° C. to 150° C.

13. The process as claimed in claim 1 , wherein (a) is carried out at a temperature ranging from 70° C. to 140° C.

14. The process as claimed in claim 1 , wherein (a) is carried out at a temperature ranging from 90° C. to 130° C.

15. The process as claimed in claim 1 , wherein (a) is carried out at a pressure set between 0.1·10 5 Pa and 5·10 5 Pa.

16. The process as claimed in claim 1 , wherein (a) is carried out at atmospheric pressure.

17. The process as claimed in claim 1 , wherein the reaction mixture comprises water.

18. The process as claimed in claim 1 , wherein the reaction mixture comprises at least one protic organic solvent.

19. The process as claimed in claim 1 , wherein the reaction mixture comprises; water in the absence of organic solvent.

20. The process as claimed in claim 1 , wherein the reaction mixture comprises water and wherein the water content of the reaction mixture is 10% to 70% by weight, limits included, relative to the total weight of the reaction mixture.

21. The process as claimed in claim 1 , wherein the reaction mixture comprises water and wherein the water content of the reaction mixture is 30% to 70% by weight, limits included, relative to the total weight of the reaction mixture.

22. The process as claimed in claim 1 , wherein the reaction mixture comprises water and wherein the water content of the reaction mixture is 50% to 70% by weight, limits included, relative to the total weight of the reaction mixture.

Assignees

• Arkema France

Inventors

• Monguillon Bernard
• Laffitte Jean-Alex

Classifications

• C07D323/06 Primary

  Trioxane · CPC title

• C07D323/04

  Six-membered rings · CPC title