IP Library Granted Patent US 10,781,164
Granted Patent B2
US 10,781,164 · App. 16/074,306 · Granted Sep 22, 2020

Reductive alkylation of amines with orthocarboxylic acid esters

Inventor: Renat Kadyrov (Frankfurt, DE)
Assignee: Evonik Operations GmbH
C07C227/18C07C209/26C07D207/06C07D211/16C07D265/30C07C211/48C07C229/24C07C229/36
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Quick Facts
Patent No.
US 10,781,164
App. No.
16/074,306
Granted
Sep 22, 2020
Kind
B2
Abstract

The present invention relates to a process for the N-alkylation of amines by reacting an amine with an orthocarboxylic acid ester and with hydrogen in the presence of a hydrogenation catalyst.

Claims (20)

1. A process for the N-alkylation of amines or of ammonia, comprising reacting an orthocarboxylic acid ester with an amine or with ammonia and with hydrogen in the presence of a hydrogenation catalyst.

2. The process of claim 1 , wherein the reaction takes place in the presence of an acid.

3. The process of claim 2 , wherein the reaction takes place at a molar ratio of acid to amine in a range from 0.01:100 to 10:100.

4. The process of claim 1 , wherein the reaction takes place at a molar ratio of hydrogenation catalyst to the amine used in a range from 1:10 to 1:100 000.

5. The process of claim 1 , wherein the reaction takes place at a hydrogen partial pressure in a range from 0.1 bar to 200 bar.

6. The process of claim 1 , wherein the reaction is carried out in a temperature range from 20° C. to 200° C.

7. The process of claim 1 , wherein the hydrogenation catalyst is a heterogeneous hydrogenation catalyst.

8. The process of claim 7 , wherein the heterogeneous hydrogenation catalyst comprises at least one active metal.

9. The process of claim 8 , wherein the active metal is a metal of group VII B and/or VIII B of the Periodic Table of the Elements.

10. The process of claim 1 , wherein the reaction takes place in a solvent.

11. The process of claim 10 , wherein the solvent is selected from the group consisting of hydrocarbons, chlorohydrocarbons, ethers, esters and alcohols.

12. The process of claim 1 , wherein the reaction is carried out without solvents.

13. The process of claim 4 , wherein the reaction takes place at a hydrogen partial pressure in a range from 0.1 bar to 200 bar.

14. The process of claim 13 , wherein the reaction is carried out in a temperature range from 20° C. to 200° C.

15. The process of claim 4 , wherein the hydrogenation catalyst is a heterogeneous hydrogenation catalyst.

16. The process of claim 15 , wherein the heterogeneous hydrogenation catalyst comprises at least one active metal.

17. The process of claim 16 , wherein the active metal is a metal of group VII B and/or VIII B of the Periodic Table of the Elements.

18. The process of claim 17 , wherein the reaction takes place in a solvent.

19. The process of claim 18 , wherein the solvent is selected from the group consisting of hydrocarbons, chlorohydrocarbons, ethers, esters and alcohols.

20. The process of claim 17 , wherein the reaction is carried out without solvents.

Assignments (2)
CHANGE OF NAME Recorded Dec 12, 2019
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 051271/0156 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 28, 2018
From: KADYROV, RENAT
To: EVONIK DEGUSSA GMBH
Reel/Frame 047333/0818 →
Priority Claims (1)
EP 16154092 · Feb 3, 2016 · regional
Continuity (1)
Related Publication 20200231537A1 · Jul 23, 2020