Production of amines utilizing zeolite catalysts

Patent metadata

Field	Value
Publication number	US-10919837-B2
Application number	US-201716083594-A
Country	US
Kind code	B2
Filing date	Mar 10, 2017
Priority date	Mar 11, 2016
Publication date	Feb 16, 2021
Grant date	Feb 16, 2021

Abstract

The present invention concerns a process for forming a primary or a secondary amine via amination reaction comprising: reacting an alcohol with an amine in the presence of a zeolite comprising a transition metal chosen in the group consisting of Group 8 to 12 elements of the Periodic Table and any combination thereof.

First claim

The invention claimed is:

1. A process for forming a primary or a secondary amine, comprising reacting:
A first reactant having 5-30 carbon atoms and one or two primary hydroxyl functionalities, with
A second reactant being NH 3 or a reactant having primary amine functionality,
in the presence of at least one zeolite comprising a transition metal selected from the group consisting of Ru, Rh, Pd, and any combination thereof, and
wherein the reaction is conducted on a gas-liquid-solid tri-phase reactor connected with a condense column and a collection tank, and wherein the gas pressure is from 0 barg to 10 barg.

2. The process according to claim 1 , wherein the first reactant is a compound of formula (I):
R 1 (—OH) x   (I)

Wherein:
x is 1 or 2
R 1 is a straight, branched or cyclic C 5 -C 30 hydrocarbon group.

3. The process according to claim 2 , wherein R 1 is selected from the group consisting of: C 5 -C 12 straight aliphatic hydrocarbon group, benzyl, furfuryl and tetrahydrofurfuryl.

4. The process according to claim 3 , wherein the first reactant is selected from the group consisting of: 1-pentanol, 1-hexanol, 1-heptanol, 1-octanol, 1-nonanol, 1-decanol, furfuryl alcohol, 2,5 furandimethanol, 2,5-tetrahydrofuranedimethanol, benzyl alcohol, 1,6-hexandiol and 1,7-heptandiol.

5. The process according to claim 1 , wherein the second reactant is a compound of formula (II):
R 2 —NH 2   (II)

Wherein:
R 2 is H or a straight, branched or cyclic hydrocarbon group.

6. The process according to claim 5 , wherein R 2 is H or C 1 -C 5 alkyl.

7. The process according to claim 1 , wherein the primary or secondary amine produced is a compound of formula (III):
R′(—NHR 2 ) x   (III)

Wherein:
x is 1 or 2
le is a straight, branched or cyclic C 5 -C 30 hydrocarbon group
R 2 is H or a straight, branched or cyclic hydrocarbon group.

8. The process according to claim 1 , wherein a secondary amine is produced and is a compound of formula (IV):
R 1 2 NH  (IV)

Wherein:
R 1 is a straight, branched or cyclic C 5 -C 30 hydrocarbon group.

9. The process according to claim 1 , wherein the primary amine or secondary amine produced is selected from the group consisting of: 1-pentylamine, 1-hexylamine, 1-heptylamine, 1-octylamine, 1-nonylamine and 1-decylamine, benzylamine, furan-2-ylmethanamine, (tetrahydrofuran-2,5-diyl) dimethanamine, (furan-2,5-diyl) dimethanamine, 1,6-hexamethylenediamine, and 1,7-heptamethylenediamine.

10. The process according to claim 1 , wherein the process comprises a third reactant being hydrogen.

11. The process according to claim 1 , wherein the molecular ratio of silica/alumina in zeolite is comprised between 5 and 300.

12. The process according to claim 1 , wherein the zeolite is selected from the group consisting of: ZSM-5, Beta, zeolite Y and mordenite.

13. The process according to claim 1 , wherein the loading amount of transition metal on zeolite is between 5% and 10% by weight.

14. The process according to claim 1 , wherein the weight ratio of zeolite comprising a transition metal selected from the group consisting of Ru, Rh, Pd, and any combination thereof to first reactant is between 5% and 20% by weight.

15. The process according to claim 1 , wherein the reaction temperature is between 120 and 280° C.

Assignees

• Rhodia Operations

Inventors

• Fang Lin
• Yan Zhen
• Diaz-Maroto Carpintero Javier

Classifications

• B01J23/755

  Nickel · CPC title

• B01J23/462

  Ruthenium · CPC title

• B01J37/0201

  Impregnation · CPC title

• B01J29/7415

  Zeolite Beta · CPC title

• B01J29/7007

  Zeolite Beta · CPC title