IP Library Granted Patent US 9,611,204
Granted Patent B2
US 9,611,204 · App. 14/904,777 · Granted Apr 4, 2017

Method of regulating the water content in a continuous method for producing methacrolein

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Quick Facts
Patent No.
US 9,611,204
App. No.
14/904,777
Granted
Apr 4, 2017
Kind
B2
Abstract

The present invention concerns regulating the water content in a process for production of methacrolein. Methacrolein is used in chemical synthesis particularly as an intermediate for production of methacrylic acid, methyl methacrylate or else of active, aroma or flavor chemicals. The present invention is particularly concerned with regulating the water content in a process for production of methacrolein from formaldehyde and propionaldehyde via a Mannich condensation.

Claims (20)

1. A process for continuous operation of a Mannich reaction, the process comprising:

separating an aqueous phase which contains at least one amine catalyst by at least one membrane separation stage into a stream consisting predominantly of water and a stream of reduced water content.

2. The process according to claim 1 , wherein the reaction product is at least partially separated off in a column and in that a water-containing effluent is withdrawn underneath the feedpoint for this column and is subsequently separated at least partially by at least one membrane separation stage.

3. The process according to claim 2 , wherein the water-containing effluent is divided and one portion is directed onto the membrane separation stage and the other portion is directed back into the reaction space.

4. The process according to claim 1 , wherein the stream which consists predominantly of water is the permeate of the membrane separation stage and the stream of reduced water content is the retentate of the membrane separation stage.

5. The process according to claim 1 , wherein propanal or another aldehyde comprising 2 to 6 carbon atoms is reacted with formaldehyde in a reaction space to form methacrolein or another unsaturated aldehyde.

6. The process according to claim 5 , wherein the reaction is carried out in the presence of 0.1 to 20 mol % of an organic base, optionally a secondary amine, and 0.1 to 20 mol % of an acid, each based on the aldehyde comprising 2 to 6 carbon atoms, at a temperature of 100 to 300° C. and a pressure of 5 to 100 bar.

7. The process according to claim 1 , wherein the stream which consists predominantly of water is separated by a second membrane separation stage into a second stream consisting predominantly of water and a second stream of reduced water content.

8. The process according to claim 1 , wherein the membranes comprise a separation-active layer of polyamide, cellulose acetate or polyether sulphone.

9. The process according to claim 1 , wherein the local temperature at the membrane is between 10 and 70° C. and the transmembrane pressure is between 20 and 100 bar.

10. The process according to claim 1 , wherein the first stream of reduced water content is wholly or partly returned into the reaction space.

11. The process according to claim 10 , wherein the water content and/or catalyst content in the production plant is determined and the additional water and/or catalyst is as necessary fed into the reaction space.

12. The process according to claim 11 , wherein the water content and/or catalyst content is determined using an on-line probe or by measuring the water removed by the membrane separation stages.

13. The process according to claim 1 , wherein the water content in the inlet to the reaction space is not greater than 75% of the overall mass.

14. The process according to claim 1 , wherein at least one stream removed by the membrane separation stages which consists predominantly of water is sent for a biological work-up.

15. The process according to claim 7 , wherein the stream which was removed by the second membrane separation stage and consists predominantly of water is sent for a biological work-up.

16. The process according to claim 1 , wherein a stream of reduced water content is sent for incineration.

17. The process according to claim 1 , wherein the second stream of reduced water content is sent either for incineration and/or to the first membrane separation stage and/or to the reaction space.

18. The process according to claim 1 , wherein the first stream of reduced water content is directed either back into the reaction space and/or into an incineration.

19. The process according to claim 1 , wherein the aqueous effluent from the bottom part of the distillation column is directed either to the first membrane separation stage and/or back into the reaction space.

Assignments (3)
CORPORATE ADDRESS CHANGE Recorded Jul 31, 2020
From: ROEHM GMBH
To: ROEHM GMBH
Reel/Frame 053837/0501 →
CHANGE OF NAME Recorded Sep 30, 2019
From: EVONIK RÖHM GMBH
To: RÖHM GMBH
Reel/Frame 050587/0022 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 13, 2016
From: BURGHARDT, RUDOLF; GLUTH, FREDERIK; KOELBL, GERHARD; KRILL, STEFFEN; BALDUF, TORSTEN
To: EVONIK ROEHM GMBH
Reel/Frame 037509/0066 →