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

Patent metadata

Field	Value
Publication number	US-9862673-B2
Application number	US-201715604873-A
Country	US
Kind code	B2
Filing date	May 25, 2017
Priority date	Jun 10, 2016
Publication date	Jan 9, 2018
Grant date	Jan 9, 2018

Abstract

A diamine 2-(3,3,5-trimethylcyclohexyl)propane-1,3-diamine of formula 1

and a process for producing 2-(3,3,5-trimethylcyclohexyl)propane-1,3-diamine by A) reacting isophorone (IP) and malononitrile to afford the intermediate 2-(3,5,5-trimethylcyclohex-2-en-1-ylidene)malononitrile, and B) hydrogenating 2-(3,5,5-trimethylcyclohex-2-en-1-ylidene)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 diamine 2-(3,3,5-trimethylcyclohexyl)propane-1,3-diamine of formula 1

2. A process for producing 2-(3,3,5-trimethylcyclohexyl)propane-1,3-diamine of formula 1

the process comprising the steps of
A) reacting isophorone (IP) and malononitrile to produce an intermediate 2-(3,5,5-trimethylcyclohex-2-en-1-ylidene)malononitrile, and
B) hydrogenating the intermediate 2-(3,5,5 -trimethylcyclohex-2-en-1-ylidene)malononitrile in the presence of at least one catalyst.

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

4. The process according to claim 2 , wherein the hydrogenation in step B) is performed in two stages at from at 40-100° C. and at from 25-150 bar.

5. The process according to claim 4 , wherein the hydrogenation in step B) is performed in two stages at from 20-120° C. and at from 20-300 bar.

6. The process according to claim 4 , wherein the hydrogenation is performed at from 40-100° C. and from 25-150 bar in the first stage and at from 50-115° C. and from 50-200 bar in the second stage.

7. The process according to claim 4 , wherein the hydrogenation is performed at from 60-90° C. and from 40-80 bar in the first stage and at from 80-110° C. and from 80-140 bar in the second stage.

8. The process according to claim 2 , wherein the at least one catalyst is selected from nickel, copper, iron, palladium, rhodium, ruthenium or cobalt catalysts.

9. The process according to claim 2 , wherein the at least one catalyst are palladium and/or cobalt catalysts.

10. The process according to claim 2 , wherein the at least one catalyst are Raney-type catalysts or supported catalysts.

11. The process according to claim 2 , wherein the at least one 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 per cent (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, or the pellet particles, having a statistical distribution between 3 to 7 millimetres (mm), wherein up to 10 per cent 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 per cent may be outside the stated range of the stated lower limit and upper limit.

12. The process according to claim 2 , wherein the hydrogenation is performed in fixed-bed reactors.

13. The process according to claim 3 , wherein the at least one catalyst is selected from the group consisting of nickel, copper, iron, palladium, rhodium, ruthenium or cobalt catalysts.

14. The process according to claim 3 , wherein the at least one catalyst is palladium and/or cobalt catalysts.

15. The process according to claim 3 , wherein the at least one catalyst are Raney-type catalysts or supported catalysts.

16. The process according to claim 3 , wherein the at least one 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 per cent (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, or the pellet particles, having a statistical distribution between 3 to 7 millimetres (mm), wherein up to 10 per cent 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 per cent may be outside the stated range of the stated lower limit and upper limit.

17. The process according to claim 2 , wherein the hydrogenation in step B) is performed in fixed-bed reactors selected from the group consisting of shaft furnaces, tray reactors or shell and tube reactors.

18. The process according to claim 5 , wherein at least one catalyst selected from the group consisting of nickel, copper, iron, palladium, rhodium, ruthenium or cobalt catalysts.

19. The process according to claim 5 , wherein the at least one catalyst is 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

• C07C211/18 Primary

  containing at least two amino groups bound to the carbon skeleton · CPC title

• C07C2601/14

  The ring being saturated · CPC title

• C07C209/48 Primary

  by reduction of nitriles · CPC title

• C07C253/30

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

• B01J23/44

  Palladium · CPC title