Process for preparing amino compounds from nitrile compounds

Patent metadata

Field	Value
Publication number	US-10519096-B2
Application number	US-201815982590-A
Country	US
Kind code	B2
Filing date	May 17, 2018
Priority date	May 23, 2017
Publication date	Dec 31, 2019
Grant date	Dec 31, 2019

Abstract

The present invention relates to a process for hydrogenating nitrile compounds to amino compounds, in which the cross-sectional loading of the reactor during the hydrogenation is less than or equal to 4.0 kg/m2*s, based on the liquid phase.

First claim

The invention claimed is:

1. A process for hydrogenating nitrile compounds to amino compounds, wherein the process is selected from the group consisting of
(a) hydrogenating a mixture in the ratio of from 50:50 to 70:30 of 2,4,4-trimethylhexamethylenedinitrile and 2,2,4-trimethylhexamethylenedinitrile to form a mixture consisting of 2,4,4-trimethylhexamethylenediamine and 2,2,4-trimethylhexamethylenediamine;
(b) hydrogenating an isophoronenitrile to an isophoronediamine; and
(c) hydrogenating an isophoronenitrile imine to an isophoronediamine,

wherein the cross-sectional loading of a tubular reactor during the hydrogenation is from 0.01 kg/m 2 *s to 4.0 kg/m 2 *s, based on the liquid phase.

2. The process according to claim 1 , wherein the nitrile compound is a mixture of 2,4,4-trimethylhexamethylenedinitrile and 2,2,4-trimethylhexamethylenedinitrile in the ratio of from 50:50 to 70:30 wherein the cross-sectional loading of the tubular reactor during the hydrogenation is from 0.05 kg/m 2 *s to 2.0 kg/m 2 *s, based on the liquid phase, wherein the tubular reactor is a fixed-bed reactor.

3. The process according to claim 1 , wherein isophoronenitrile is subjected to aminating hydrogenation to give isophoronediamine, wherein the tubular reactor is a trickle bed reactor.

4. The process according to claim 3 , wherein
A) isophoronenitrile is subjected directly in one stage to aminating hydrogenation to give isophoronediamine in the presence of ammonia, hydrogen, a catalyst and possibly further additions, and in the presence or absence of organic solvents;
or
B) isophoronenitrile is reacted in at least two stages, wherein said isophoronenitrile in initially converted in a first stage entirely or partly to isophoronenitrile imine which, as a pure substance or in a mixture with other components and possibly unreacted isophoronenitrile, is hydrogenated in at least one subsequent stage to give isophoronediamine in the presence of at least ammonia, hydrogen and a catalyst.

5. The process according to claim 4 , wherein the cross-sectional loading is from 0.05 to 3.0 kg/m 2 *s.

6. The process according to claim 3 , wherein the process for preparing isophoronediamine is carried out in two or more stages and in that isophoronenitrile is converted in a first stage to isophoronenitrile imine by reaction with ammonia in the presence or absence of an imination catalyst or solvent.

7. The process according to claim 6 , wherein the reaction product of the first stage is hydrogenated in the presence of at least one hydrogenation catalyst in the presence of ammonia and hydrogen and in the presence or absence of an organic solvent at a temperature of from 20 to 150° C. and a pressure of from 0.3 to 50 MPa.

8. The process according to claim 3 , wherein isophoronenitrile is subjected directly in one stage to aminating hydrogenation to give isophoronediamine in the presence of ammonia, hydrogen, a catalyst and possibly further additions.

9. The process according claim 8 , wherein the ratio of circulation stream to the feedstock stream supplied is in the range from 0:1 to 0.49:1.

10. The process according claim 8 , wherein the hydrogenation is carried out at temperatures between 20 and 150° C. and pressures of from 0.3 to 50 MPa.

11. The process according to claim 3 , wherein isophoronenitrile is reacted in at least two stages, wherein said isophoronenitrile is initially converted in a first stage entirely or partly to isophoronenitrile imine which, as a pure substance or in a mixture with other components and unreacted isophoronenitrile, is hydrogenated in at least one subsequent stage to give isophoronediamine in the presence of at least ammonia, hydrogen and a catalyst.

12. The process according to claim 1 , wherein the ratio of circulation stream to the feedstock stream supplied is in the range from 0:1 to 0.49:1, wherein the tubular reactor is a trickle bed reactor.

13. The process according to claim 1 , wherein the hydrogenation is carried out at temperatures between 20 and 150° C. and pressures of from 0.3 to 50 MPa, wherein the tubular reactor is a trickle bed reactor.

14. The process according to claim 1 , wherein a catalyst is used for the hydrogenation selected from the group consisting of nickel, copper, iron, palladium, rhodium, ruthenium and cobalt catalysts, wherein the tubular reactor is a trickle bed reactor.

15. The process according to claim 14 , wherein the hydrogenation catalyst is selected from the group consisting of Raney-type and supported catalysts.

16. The process according to claim 15 , wherein the catalyst after activation has a composition in its entirety, in percent by weight based on all proportions of metals present, of

cobalt:
from 55 to 95
wt %

aluminium:
from 5 to 45
wt %

chromium:
from 0 to 3
wt %

nickel:
from 0 to 7
wt %.

17. The process according to claim 1 , wherein the process for hydrogenating nitrile compounds to amino compounds comprises the step of hydrogenating isophoronenitrile or isophoronenitrile imine to isophoronediamine having a ratio of a circulation stream to a feedstock stream supplied is in the range from 0:1 to 0.49:1.

18. The process according to claim 17 , wherein the ratio of a circulation stream to a feedstock stream supplied is in the range from 0:1 to 0.25:1.

19. The process according to claim 17 , wherein the ratio of a circulation stream to a feedstock stream supplied is in the range from 0:1 to 0.1:1.

20. The process according to claim 1 , wherein the cross-sectional loading is from 0.05 kg/m 2 *s to 3.0 kg/m 2 *s.

Assignees

• Evonik Degussa Gmbh

Inventors

• Rittsteiger Anne
• Kohlstruk Stephan
• Hoppe Dirk
• Rüfer Alexander Martin
• Sowka Sabrina
• Schneider Sven
• Schlüter Norbert
• Hengstermann Axel
• Galle Markus
• Röder Stefan
• Berweiler Monika

Classifications

• C07C253/30

  by reactions not involving the formation of cyano groups · CPC title

• C07C209/52 Primary

  by reduction of imines or imino-ethers (C07C209/24 takes precedence) · CPC title

• C07C2523/86

  Chromium · CPC title

• C07C209/48

  by reduction of nitriles · CPC title

• C07C2521/02

  Boron or aluminium; Oxides or hydroxides thereof · CPC title