IP Library Granted Patent US 9,994,544
Granted Patent B2
US 9,994,544 · App. 15/502,098 · Granted Jun 12, 2018

Method for preparing trioxane

Inventors: Bernard Monguillon (Bayonne, FR); Jean-Alex Laffitte (Pau, FR)
Assignee: Arkema France
C07D323/06
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Quick Facts
Patent No.
US 9,994,544
App. No.
15/502,098
Granted
Jun 12, 2018
Kind
B2
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.

Claims (24)

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.

Assignments (2)
CHANGE OF ADDRESS Recorded Jul 4, 2025
From: ARKEMA FRANCE
To: ARKEMA FRANCE
Reel/Frame 071814/0739 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 10, 2017
From: MONGUILLON, BERNARD; LAFFITTE, JEAN-ALEX
To: ARKEMA FRANCE
Reel/Frame 041224/0697 →
Priority Claims (1)
FR 14 57676 · Aug 7, 2014 · national
Continuity (1)
Related Publication 20170233366A1 · Aug 17, 2017