Method for producing methylmethacrylate

Patent metadata

Field	Value
Publication number	US-9890105-B2
Application number	US-201414784320-A
Country	US
Kind code	B2
Filing date	Apr 11, 2014
Priority date	Apr 19, 2013
Publication date	Feb 13, 2018
Grant date	Feb 13, 2018

Abstract

The present invention relates to a process for producing methyl methacrylate, comprising the following steps:
A) producing methacrolein and B) reacting the methacrolein obtained in step A) in an oxidative esterification reaction to give methyl methacrylate,

characterized in that the two steps A) and B) take place in a liquid phase at a pressure of from 2 to 100 bar, and step B) is carried out in the presence of a heterogeneous noble-metal-containing catalyst comprising metals and/or comprising metal oxides.

First claim

The invention claimed is:

1. A process for producing methyl methacrylate, the process comprising:
A) producing methacrolein from propanal and formaldehyde and
B) reacting the methacrolein in an oxidative esterification reaction to obtain methyl methacrylate,
wherein no dewatering occurs after the producing A) and before the reacting B), and wherein the producing A) and the reacting B) take place in a liquid phase at a pressure of from 2 to 100 bar, and
wherein the reacting B) is carried out in the presence of a heterogeneous noble-metal-comprising catalyst comprising one or more ultra-finely dispersed metals with an average particle size of <20 nm selected from the group consisting of gold, palladium, ruthenium, rhodium, and silver.

2. The process according to claim 1 , wherein the producing A) is carried out in the presence of from 0.1 to 20 mol% of organic base and from 0.1 to 20 mol% of acid, based in each case on propanal.

3. The process according to claim 1 , wherein the producing A) is carried out at a temperature of from 100 to 300 ° C.

4. The process according to claim 1 , wherein the producing A) is carried out at a pressure of from 5 to 100 bar.

5. The process according to claim 2 , wherein the organic base comprises a secondary amine.

6. The process according to claim 2 , wherein the acid comprises at least one organic acid.

7. The process according to claim 2 , wherein a molar ratio of the acid to the organic base ranges from 20:1 to 1:20.

8. The process according to claim 1 , wherein the producing A) is carried out with a residence time ranging from 0.1 to 300 seconds.

9. The process according to claim 1 , wherein the reacting B) is carried out with a pressure ranging from 2 to 50 bar.

10. The process according to claim 1 , wherein the oxidative esterification reaction is carried out at a temperature ranging from 10 to 200 ° C.

11. The process according to claim 1 , wherein the oxidative esterification reaction takes place with a molar ratio of methanol to methacrolein ranging from 1:1 to 50:1.

12. The process according to claim 1 , wherein the producing A) and the reacting B) are carried out in a continuous process.

13. The process according to claim 1 , wherein a volume ratio of a reactor in the producing A) to a reactor in the reacting B) ranges from 1:1000 to 1:100.

14. A process for producing methyl methacrylate, the process comprising:
A) producing methacrolein from propanal and formaldehyde and
B) reacting methacrolein in an oxidative esterification reaction to obtain methyl methacrylate,
wherein
the producing A) and the reacting B) take place in a liquid phase at a pressure of from 2 to 100 bar, and
the reacting B) is carried out in the presence of a heterogeneous noble-metal-comprising catalyst comprising one or more ultra-finely dispersed metals with an average particle size of <20 nm selected from the group consisting of gold, palladium, ruthenium, rhodium, and silver, and
wherein no water is separately added in the producing A) and the reacting B) during the process.

15. The process according to claim 1 , wherein a content of water in reaction mixture during the reacting B) is at most 10% by weight based on a total weight of the reaction mixture.

Assignees

• Krill Steffen
• Balduf Torsten
• Koestner Martin
• Groemping Matthias
• Lygin Alexander
• Burghardt Rudolf
• Evonik Roehm Gmbh

Inventors

• Krill Steffen
• Balduf Torsten
• Koestner Martin
• Groemping Matthias
• Lygin Alexander
• Burghardt Rudolf

Classifications

• C07C45/75

  Reactions with formaldehyde · CPC title

• C07C67/39 Primary

  by oxidation of groups which are precursors for the acid moiety of the ester · CPC title

• C07C47/22

  Acryaldehyde; Methacryaldehyde · CPC title

• C07C69/54

  Acrylic acid esters; Methacrylic acid esters · CPC title

• C07C67/44 Primary

  by oxidation-reduction of aldehydes, e.g. Tishchenko reaction · CPC title