2-(3-(aminomethyl)-3,5,5-trimethylcyclohexyl)propane-1,3-diamine, a process for its production and use

Patent metadata

Field	Value
Publication number	US-10160717-B2
Application number	US-201715604988-A
Country	US
Kind code	B2
Filing date	May 25, 2017
Priority date	Jun 10, 2016
Publication date	Dec 25, 2018
Grant date	Dec 25, 2018

Abstract

A process for producing 2-(3-(aminomethyl)-3,5,5-trimethylcyclohexyl)propane-1,3-diamine by A) reacting isophorone nitrile and malononitrile to afford the intermediate 2-(3-cyano-3,5,5-trimethylcyclohexylidene)malononitrile, and B) hydrogenating 2-(3-cyano-3,5,5-trimethylcyclohexylidene)malononitrile in the presence of at least one catalyst. In another embodiment, the hydrogenation in step B) of the process is performed at 20-120° C. and at 20-300 bar.

First claim

The invention claimed is:

1. A process for producing 2-(3-(aminomethyl)-3,5,5-trimethylcyclohexyl)propane-1,3-diamine by
A) reacting isophoronenitrile and malononitrile to afford intermediate 2-(3-cyano-3,5,5-trimethylcyclohexylidene)malononitrile, and
B) hydrogenating the 2-(3-cyano-3,5,5-trimethylcyclohexylidene)malononitrile in the presence of a catalyst.

2. The process according to claim 1 , wherein the hydrogenation in step B) is performed at 20-120° C. and at 20-300 bar.

3. The process according to claim 1 , wherein the hydrogenation in step B) is performed in two stages at 20-120° C. and at 20-300 bar.

4. The process according to claim 3 , wherein the hydrogenation in step B) is performed in two stages at 80-110° C. and at 80-140 bar.

5. The process according to claim 3 , wherein the hydrogenation is performed at 40-100° C. and 25-150 bar in the first stage and at 50-115° C. and 50-200 bar in the second stage.

6. The process according to claim 3 , wherein the hydrogenation is performed at 60-90° C. and 40-80 bar in the first stage and at 80-110° C. and 80-140 bar in the second stage.

7. The process according to claim 1 , wherein the catalyst is selected from the group consisting of nickel, copper, iron, palladium, rhodium, ruthenium and cobalt.

8. The process according to claim 1 , wherein the catalysts employed are palladium and/or cobalt catalysts.

9. The process according to claim 1 , wherein the catalysts are Raney-type catalysts or supported catalysts.

10. The process according to claim 1 , wherein the catalyst employed is a catalyst composed of activated Raney cobalt alloy pellets, wherein after activation the catalyst in its entirety has the following composition in weight percent (wt %), the proportions summing to 100 wt % based on the metals present:
cobalt: 57 to 84 wt %
and
with particle sizes of the catalyst, i.e. the pellet particles, having a statistical distribution between 3 to 7 millimeters (mm), wherein up to 10 percent of the particles may also be outside the stated range of the stated lower limit or upper limit but also in each case up to 10 percent may be outside the stated range of the stated lower limit and upper limit.

11. The process according to claim 1 , wherein the hydrogenation is performed in fixed-bed reactors, preferably in shaft furnaces, tray reactors or shell and tube reactors.

12. The process according to claim 2 , wherein the catalyst is selected from the group consisting of nickel, copper, iron, palladium, rhodium, ruthenium and cobalt.

13. The process according to claim 2 , wherein the catalysts are palladium and/or cobalt catalysts.

14. The process according to claim 2 , wherein the catalysts are Raney-type catalysts or supported catalysts.

15. The process according to claim 2 , wherein the catalyst is a catalyst composed of activated Raney cobalt alloy pellets, wherein after activation the catalyst in its entirety has the following composition in weight percent (wt %), the proportions summing to 100 wt % based on the metals present:
cobalt: 57 to 84 wt %
aluminium: 10 to 40 wt %
chromium: 1 to 2 wt %
nickel: 2 to 4 wt %
and
with particle sizes of the catalyst, i.e. the pellet particles, having a statistical distribution between 3 to 7 millimeters (mm), wherein up to 10 percent of the particles may also be outside the stated range of the stated lower limit or upper limit but also in each case up to 10 percent may be outside the stated range of the stated lower limit and upper limit.

16. The process according to claim 2 , wherein the hydrogenation is performed in fixed-bed reactors, preferably in shaft furnaces, tray reactors or shell and tube reactors.

17. The process according to claim 2 , wherein the catalyst is selected from the group consisting of nickel, copper, iron, palladium, rhodium, ruthenium and cobalt.

18. The process according to claim 2 , wherein the catalysts are palladium and/or cobalt catalysts.

Assignees

• Evonik Degussa Gmbh

Inventors

• Rüfer Alexander Martin
• Rittsteiger Anne
• Nitz Jörg-Joachim
• Kohlstruk Stephan
• Ortelt Martina
• Fuchsmann Dirk
• Demming Michael
• Stemmer Christine
• Ott Denise
• Stasch Anja

Classifications

• C07C209/48 Primary

  by reduction of nitriles · CPC title

• C07C255/46

  to carbon atoms of non-condensed rings · CPC title

• B01J23/44

  Palladium · CPC title

• B01J21/04

  Alumina · CPC title

• C07C253/30

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