IP Library Granted Patent US 11,084,776
Granted Patent B2
US 11,084,776 · App. 16/074,556 · Granted Aug 10, 2021

Macroporous catalyst for the preparation of aliphatic amines

Inventors: Shengyin Ye (Shanghai, CN); Javier Diaz-Maroto Carpintero (Shanghai, CN); Fabien Ocampo (La Courneuve, FR); Philippe Leconte (Saint Genis-Laval, FR)
Assignee: RHODIA OPERATIONS
C07C209/16B01J21/04B01J23/72B01J23/78B01J23/889B01J35/1014B01J35/1019B01J35/1038B01J35/1042B01J35/1066B01J2208/00017B01J2523/22B01J2523/25B01J2523/27B01J2523/31B01J2523/37B01J2523/67B01J2523/72B01J2523/842B01J2523/845B01J2523/847C07C211/08
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Quick Facts
Patent No.
US 11,084,776
App. No.
16/074,556
Granted
Aug 10, 2021
Kind
B2
Abstract

A process for the preparation of aliphatic amines, comprises reacting an aliphatic alcohol with an aminating agent in the presence of a catalyst. The catalyst contains copper oxide on a support made of porous alumina, wherein the porous alumina has a volume, corresponding to pores greater than 500 Å in diameter, of from 10 ml/100 g to 95 ml/100 g.

Claims (16)

1. A process, comprising reacting an aliphatic alcohol of formula (I)

R 1 CH 2 OH  (I),

wherein R 1 is a linear or branched, saturated or unsaturated aliphatic group having from 3 to 21 carbon atoms, with an aminating agent of formula (II)

wherein R 2 and R 3 , the same or different, are hydrogen or a linear or branched, saturated or unsaturated aliphatic group having from 1 to 24 carbon atoms, for obtaining an aliphatic amine of formula (III), (IV) or (V)

wherein the reaction is carried out in the presence of a catalyst, wherein the catalyst comprises from 5 wt % to 50 wt % of copper oxide; optionally from 0.1 wt % to 20 wt % of a compound of at least one element selected from Fe, Co, Zn, Ni, Cr, Mn, Mg, Ba and rare earth metals; the balance being a support made of porous alumina, weight percentage based on the total weight of the catalyst; wherein the porous alumina has a volume, corresponding to pores greater than 500 Å in diameter, of from greater than 30 ml/100 g to 95 ml/g, as determined by mercury porosimetry.

2. The process according to claim 1 , wherein the porous alumina has a specific surface area of from 10 m 2 /g to 280 m 2 /g.

3. The process according to claim 1 , wherein the porous alumina has a specific surface area of from 50 m 2 /g to 280 m 2 /g.

4. The process according to claim 1 , wherein the aminating agent has the formula (VI)

wherein R 4 and R 5 , the same or different, are a linear or branched, saturated or unsaturated aliphatic group having from 1 to 24 carbon atoms, the aliphatic amine has the formula (VII):

wherein R 1 is a linear or branched, saturated or unsaturated aliphatic group having from 3 to 21 carbon atoms, R 4 and R 5 are as defined in formula (VI).

5. The process according to claim 1 , wherein the aliphatic alcohol and the aminating agent are mixed together with a flow of hydrogen and the mixture is continuously introduced into a reaction zone, wherein the molar ratio of the aliphatic alcohol/the aminating agent/the hydrogen is in the range of from 1:1:5 to 1:2:20.

6. The process according to claim 5 , wherein the molar ratio of the aliphatic alcohol/the aminating agent/the hydrogen is in the range of from 1:1:5 to 1:1.2:15.

7. The process according to claim 1 , wherein the reaction is carried out at a temperature of from 150° C. to 350° C.

8. The process according to claim 1 , wherein the reaction is carried out at a temperature of from 2° C. to 250° C.

9. The process according to claim 1 , wherein the reaction is carried out under a pressure of from 0 to 5 barg.

10. The process according to claim 1 , wherein the reaction is carried out under a pressure of from 0 to 0.5 barg.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 26, 2024
From: RHODIA OPERATIONS
To: SPECIALTY OPERATIONS FRANCE
Reel/Frame 066374/0642 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 7, 2023
From: RHODIA OPERATIONS
To: SPECIALTY OPERATIONS FRANCE
Reel/Frame 065488/0365 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 18, 2021
From: YE, SHENGYIN; DIAZ-MAROTO CARPINTERO, JAVIER; OCAMPO, FABIEN; LECONTE, PHILIPPE
To: RHODIA OPERATIONS
Reel/Frame 056277/0664 →
Continuity (1)
Related Publication 20190031596A1 · Jan 31, 2019