IP Library Granted Patent US 8,791,296
Granted Patent B2
US 8,791,296 · App. 14/113,228 · Granted Jul 29, 2014

Process for preparing methacrylic acid

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Quick Facts
Patent No.
US 8,791,296
App. No.
14/113,228
Granted
Jul 29, 2014
Kind
B2
Abstract

The present invention relates to a process for preparing methacrylic acid based on the hydrolysis of methacrylic esters.

Claims (23)

1. A process for preparing methacrylic acid, the process comprising:

converting acetone cyanohydrin to methacrylamide;

esterifying the methacrylamide in the presence of at least one alcohol, thereby obtaining at least one methacrylic ester; and

hydrolyzing the at least one methacrylic ester in the presence of at least one heterogeneous catalyst, thereby obtaining methacrylic acid,

wherein:

a feed stream to the hydrolyzing comprises a water stream, and a methacrylic ester stream from the esterifying;

a recirculation stream to the hydrolyzing comprises a first circulation stream from the input of a vacuum rectifying column for low boiler removal, and a second circulation stream from the output of a rectifying column for alcohol removal; and

the mass ratio or the volume ratio of the recirculation stream to the feed stream ranges from 5-50.

2. The process according to claim 1 , wherein the at least one heterogeneous catalyst is selected from the group consisting of a zeolite, an ion exchange resin, and an amorphous acid catalyst.

3. The process according to claim 1 , wherein, during the hydrolyzing, the flow through a catalyst bed is from bottom or from top.

4. The process according to claim 1 , wherein the hydrolyzing occurs at a temperature of 50-200° C.

5. The process according to claim 1 , wherein the hydrolyzing occurs at an elevated pressure.

6. The process according to claim 1 , wherein the ratio of the at least one methacrylic ester to water in the hydrolyzing is between 0.5 and 5.

7. The process according to claim 1 , wherein the residence time during the hydrolyzing is 10-120 min.

8. The process according to claim 1 , wherein the mass ratio or the volume ratio of the recirculation stream to the feed stream ranges from 15 to 30.

9. The process according to claim 1 , wherein a methanol/methyl methacrylate mixture is supplied during said esterifying.

10. The process according to claim 1 , wherein the hydrolyzing occurs at a temperature of 70-150° C.

11. The process according to claim 1 , wherein the hydrolyzing occurs at a temperature of 90-120° C.

12. The process according to claim 1 , wherein the hydrolyzing occurs at a temperature of 100-110° C.

13. The process according to claim 1 , wherein the hydrolyzing occurs at an elevated pressure of from 0.1 to 9 bar gauge.

14. The process according to claim 1 , wherein the hydrolyzing occurs at an elevated pressure of from 2 to 4 bar gauge.

15. The process according to claim 1 , wherein the ratio of the at least one methacrylic ester to water in the hydrolyzing is between 1 and 4.

16. The process according to claim 1 , wherein the ratio of the at least one methacrylic ester to water in the hydrolyzing is between 1.5 and 3.

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 Oct 25, 2013
From: BROELL, DIRK; SIEGERT, HERMANN; HILTNER, HORST; KRAUSS, THOMAS
To: EVONIK ROEHM GMBH
Reel/Frame 031475/0345 →