IP Library Granted Patent US 9,574,061
Granted Patent B2
US 9,574,061 · App. 14/359,223 · Granted Feb 21, 2017

Process for producing a cyclic acetal

Inventors: Michael Haubs (Bad Kreuznach, DE); Klaus Kurz (Kelsterbach, DE); Jurgen Lingnau (Mainz Laubenhelm, DE)
Assignee: Celanese Sales Germany GmbH
C08J11/28C07C47/04C07D323/04C07D323/06C08G2/10C08G2/36C08G65/06C08G65/16C08G65/30C08J11/16C08G2650/62C08J2359/02Y02P20/125
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Quick Facts
Patent No.
US 9,574,061
App. No.
14/359,223
Granted
Feb 21, 2017
Kind
B2
Abstract

The present invention relates to a process for producing cyclic acetal comprising i) preparing a reaction mixture comprising a) a formaldehyde source in a liquid medium and b) a catalyst; ii) converting the formaldehyde source into cyclic acetals, wherein the final conversion of said formaldehyde source to said cyclic acetal is greater than 10% on basis of the initial formaldehyde source.

Claims (37)

1. A process for producing a cyclic acetal comprising:

contacting gaseous formaldehyde with a liquid medium comprising a liquid aprotic compound, wherein the liquid aprotic compound is selected from the group consisting of organic sulfoxides, organic sulfones, organic sulfonate esters, and mixtures thereof, in the presence of a catalyst; and

at least partially converting the gaseous formaldehyde into a cyclic acetal comprising trioxane.

2. The process according to claim 1 , wherein the aprotic compound is a polar aprotic compound.

3. The process according to claim 1 , wherein the catalyst is heterogeneous with the liquid medium.

4. The process according to claim 1 , wherein the weight ratio of gaseous formaldehyde to the aprotic compound is from about 1:50 to about 1:3.

5. The process according to claim 1 , wherein the aprotic compound has a boiling point of 140° C. or higher, determined at 1 bar.

6. The process according to claim 1 wherein higher than 30%, of the gaseous formaldehyde is converted into one or more cyclic acetals during the reaction.

7. The process according to claim 1 wherein the liquid medium comprises at least 60 wt.-%, of the aprotic compound.

8. The process according to claim 1 wherein the aprotic compound is selected from the group consisting of cyclic or alicyclic organic sulfoxides, alicyclic or cyclic sulfones, and mixtures thereof.

9. The process according to claim 1 wherein the aprotic compound is represented by formula (I):

wherein

n is an integer ranging from 1 to 6, and

wherein the ring carbon atoms may optionally be substituted by one or more substituents, selected from C 1 -C 8 -alkyl which can be branched or unbranched.

10. The process according to claim 1 wherein the aprotic compound is sulfolane.

11. The process according to claim 1 wherein the aprotic compound is represented by formula (II):

wherein R 1 and R 2 are independently selected from C 1 -C 8 -alkyl which can be branched or unbranched.

12. The process according to claim 1 wherein the aprotic compound is represented by formula (III):

wherein

n is an integer ranging from 1 to 6, and

wherein the ring carbon atoms may optionally be substituted by one or more substituents, selected from C 1 -C 8 -alkyl which can be branched or unbranched; or

the aprotic compound is represented by formula (IV):

wherein R 3 and R 4 are independently selected from C 1 -C 8 -alkyl which can be branched or unbranched.

13. The process according to claim 1 wherein the reaction is carried out at a temperature ranging from 10° C. to 120° C.

14. The process according to claim 1 , wherein the catalyst comprises trifluoromethanesulfonic acid, perchloric acid, methanesulfonic acid, toluenesulfonic acid, sulfuric acid, or mixtures thereof.

15. The process according to claim 1 , wherein the catalyst is present in the liquid medium in an amount from about 0.001 wt % to about 15 wt %.

16. The process according to claim 1 , wherein the gaseous formaldehyde has a water content of less than about 5 wt.

17. The process according to claim 1 , further comprising the step of separating the cyclic acetal from the liquid medium by distillation.

18. The process according to claim 1 , further comprising the step of manufacturing polyoxymethylene from the cyclic acetal.

19. The process according to claim 1 , wherein the gaseous formaldehyde is absorbed in an absorption column containing the aprotic compound and the catalyst.

20. A process for producing cyclic acetal comprising

i) preparing a reaction mixture comprising

a) formaldehyde in a liquid medium and

b) a catalyst; that is heterogeneous with the liquid medium

ii) converting the formaldehyde into trioxane wherein the final conversion of the formaldehyde to the trioxane is greater than 10% on the basis of the formaldehyde.

21. The process according to claim 20 , wherein the catalyst comprises an acid ion-exchange material.

22. The process according to claim 1 , wherein the catalyst comprises an acid ion-exchange material.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 16, 2016
From: TICONA GMBH
To: NUTRINOVA NUTRITION SPECIALTIES & FOOD INGREDIENTS GMBH
Reel/Frame 038687/0784 →
CHANGE OF NAME Recorded May 16, 2016
From: NUTRINOVA NUTRITION SPECIALTIES & FOOD INGREDIENTS GMBH
To: CELANESE SALES GERMANY GMBH
Reel/Frame 038689/0595 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 23, 2014
From: HAUBS, MICHAEL; KURZ, KLAUS; LINGNAU, JURGEN
To: TICONA GMBH
Reel/Frame 033155/0252 →
Priority Claims (3)
EP 11190567 · Nov 24, 2011 · regional
EP 11190574 · Nov 24, 2011 · regional
EP 11190586 · Nov 24, 2011 · regional
Continuity (1)
Related Publication 20140343301A1 · Nov 20, 2014