Process for producing aromatic primary diamines

Patent metadata

Field	Value
Publication number	US-11066377-B2
Application number	US-202016781356-A
Country	US
Kind code	B2
Filing date	Feb 4, 2020
Priority date	Jul 10, 2014
Publication date	Jul 20, 2021
Grant date	Jul 20, 2021

Abstract

The present disclosure relates to a process for the production of aromatic primary amines, by reacting an aromatic dialdehyde with hydrogen and ammonia or an ammonia-liberating compound, in the presence of a hydrogenation catalyst and an amine, wherein the molar ratio of the amine to the aromatic dialdehyde is no less than 1:4 at the start of the reaction.

First claim

The invention claimed is:

1. A process for the production of an aromatic primary diamine, the process comprising reacting an aromatic dialdehyde, wherein the aromatic ring is a hydrocarbon ring, with hydrogen and ammonia or an ammonia-liberating compound selected from the group consisting of urea, uric acid, ammonium salts, symmetrical and unsymmetrical carbamates, carbaminates, semicarbazides, semicarbazoles, and aminium salts and organic/inorganic esters thereof, in the presence of a hydrogenation catalyst and an amine, wherein the molar ratio of the amine to the aromatic dialdehyde is no less than 1:4 at the start of the reaction.

2. The process of claim 1 , wherein the amine is selected from a group consisting of methylamine, ethylamine, propylamine, butylamine, pentylamine, hexylamine, benzylamine, cyclohexylamine, ethylene diamine, dimethylamine, diethylamine, diethanolamine, dicyclohexylamine, diallylamine, piperidine, pyrolidine, morpholine, N-methylbenzylamine, dibenzylamine, trimethylamine, triethylamine, triethanolamine, diisopropylethylamine, tricyclohexylamine, triallylamine, benzyldimethylamine, N-methylmorpholine, and N-methyldibenzylamine.

3. The process of claim 1 , wherein the aromatic ring is benzene.

4. The process of claim 1 , wherein the aromatic diamine is m-xylylenediamine and the aromatic dialdehyde is isophthalaldehyde.

5. The process of claim 4 , wherein the amine is a primary amine or a secondary amine.

6. The process of claim 5 , wherein the amine is a primary amine.

7. The process of claim 6 , wherein the primary amine is selected from a group consisting of methylamine, ethylamine, propylamine, butylamine, pentylamine, hexylamine, benzylamine, cyclohexylamine, and ethylene diamine.

8. The process of claim 4 , wherein the amine is a secondary amine selected from the group consisting of dimethylamine, diethylamine, diethanolamine, dicyclohexylamine, diallylamine, piperidine, pyrolidine, morpholine, N-methylbenzylamine, and dibenzylamine.

9. The process of claim 4 , wherein the amine is a tertiary amine selected from a group consisting of trimethylamine, triethylamine, triethanolamine, diisopropylethylamine, tricyclohexylamine, triallylamine, benzyldimethylamine, N-methylmorpholine, and N-methyldibenzylamine.

10. The process of claim 4 , wherein the molar ratio of the amine to isophthalaldehyde is no less than 1:1, at the start of the reaction.

11. The process of claim 4 , wherein the molar ratio of the amine to isophthalaldehyde is no more than 3:1 at the start of the reaction.

12. The process of claim 4 , wherein the molar ratio of isophthalaldehyde to the equivalents of ammonia is in the range of 1:5-1:20.

13. The process of claim 4 , wherein isophthalaldehyde is fed in a manner to ensure that the molar ratio of amine to isophthalaldehyde is in a range of 1:4 to 2:1.

14. The process of claim 4 , wherein the hydrogenation catalyst is Raney copper, Ni/PrO 2 -CeO 2 , or CuNiOx, optionally comprising another metal Zn or Pd.

15. The process of claim 4 , wherein ammonia is used.

16. The process of claim 1 , wherein the aromatic diamine is p-xylylenediamine and the aromatic dialdehyde is terephthalaldehyde.

17. The process of claim 16 , wherein the amine is a primary amine selected from a group consisting of methylamine, ethylamine, propylamine, butylamine, pentylamine, hexylamine, benzylamine, cyclohexylamine, and ethylene diamine.

18. The process of claim 16 , wherein the amine is a secondary amine selected from the group consisting of dimethylamine, diethylamine, diethanolamine, dicyclohexylamine, diallylamine, piperidine, pyrolidine, morpholine, N-methylbenzylamine, and dibenzylamine.

19. The process of claim 16 , wherein the amine is a tertiary amine selected from a group consisting of trimethylamine, triethylamine, triethanolamine, diisopropylethylamine, tricyclohexylamine, triallylamine, benzyldimethylamine, N-methylmorpholine, and N-methyldibenzylamine.

20. The process of claim 16 , wherein the molar ratio of the amine to terephthalaldehyde is no less than 1:1, at the start of the reaction.

Assignees

• Rhodia Operations

Inventors

• Li Peng
• Decampo Floryan

Classifications

• B01J25/02

  Raney nickel · CPC title

• C07D307/52 Primary

  Radicals substituted by nitrogen atoms not forming part of a nitro radical · CPC title

• C07C209/26 Primary

  by reduction with hydrogen · CPC title

• C07C211/26

  of an unsaturated carbon skeleton containing at least one six-membered aromatic ring · CPC title