Process for preparing 3-aminomethyl-3,5,5-trimethylcyclohexylamine

Patent metadata

Field	Value
Publication number	US-9937483-B2
Application number	US-201615082752-A
Country	US
Kind code	B2
Filing date	Mar 28, 2016
Priority date	Mar 30, 2015
Publication date	Apr 10, 2018
Grant date	Apr 10, 2018

Abstract

Isophoronediamine, is prepared by A) subjecting isophoronenitrile directly in one stage to aminating hydrogenation to give isophoronediamine in the presence of ammonia, hydrogen, a hydrogenation catalyst and an optional additive, and in the presence or absence of an organic solvent; or B) first converting isophoronenitrile fully or partly in at least two or more than two stages to isophoronenitrile imine, and subjecting the isophoronenitrile imine to aminating hydrogenation to give isophoronediamine as a pure substance or in a mixture with another component and/or isophoronenitrile, in the presence of at least ammonia, hydrogen and a catalyst.

First claim

The invention claimed is:

1. A process for preparing isophoronediamine, comprising:
A) subjecting isophoronenitrile directly in one stage to aminating hydrogenation to give isophoronediamine in the presence of ammonia, hydrogen, a catalyst and an optional additive, and in the presence or absence of an organic solvent;
or
B) converting isophoronenitrile to isophoronediamine in at least two or more than two stages,
wherein isophoronenitrile is first converted fully or partly to isophoronenitrile imine, and the isophoronenitrile imine is subjected to aminating hydrogenation to give isophoronediamine as a pure substance or in a mixture with another component and/or isophoronenitrile,
wherein the aminating hydrogenation proceeds in the presence of at least ammonia, hydrogen and a catalyst;
wherein the catalyst has, after catalyst activation, in its entirety, the following composition in percent by weight (% by weight), wherein the proportions add up to 100% by weight, based on the metals present:
cobalt: 55% to 85% by weight,
aluminium: 5% to 43.5% by weight,
chromium: 0.5% to 3% by weight, and
nickel: 1% to 7% by weight; and
wherein the catalyst is in the form of hollow spheres having a diameter of 1 to 8 mm.

2. The process for preparing isophoronediamine according to claim 1 , wherein the catalyst has, after catalyst activation, in its entirety, the following composition in percent by weight (% by weight), wherein the proportions add up to 100% by weight, based on the metals present:
cobalt: 57% to 84% by weight,
aluminium: 10% to 40% by weight,
chromium: 1% to 2% by weight, and
nickel: 2% to 4% by weight.

3. The process for preparing isophoronediamine according to claim 1 , wherein the diameter of the catalyst hollow spheres ranges from 2.5 to 5.5 millimeters (mm),
and/or
the diameter of the catalyst hollow spheres ranges from 3 to 8 millimeters (mm),
and/or
the diameter of the catalyst hollow spheres ranges from 1 to 3 millimeters (mm).

4. The process for preparing isophoronediamine according to claim 1 , wherein the catalyst has, after catalyst activation, in its entirety, the following composition in percent by weight (% by weight), wherein the proportions add up to 100% by weight, based on the metals present:
cobalt: 57% to 84% by weight,
aluminium: 10% to 40% by weight,
chromium: 1% to 2% by weight, and
nickel: 2% to 4% by weight; and
wherein the diameters of the catalyst hollow spheres have a statistical distribution between 2.5 and 5.5 millimeters (mm),
and/or
wherein the diameters of the catalyst hollow spheres have a statistical distribution between 3.5 and 6.5 millimeters (mm),
and/or
wherein the diameters of the catalyst hollow spheres have a statistical distribution between 1 and 3 millimeters (mm),
and/or
wherein the diameters of the catalyst hollow spheres have a statistical distribution between 3 and 8 millimeters (mm), and
wherein up to 10 percent of the catalyst hollow spheres are optionally outside said range of said lower limit or upper limit of said statistical distribution, but up to 10 percent in each case are optionally outside said range of said lower limit and upper limit of said statistical distribution.

5. The process for preparing isophoronediamine according to claim 1 , wherein the catalyst further comprises at least one doping metal selected from the group consisting of manganese, iron, vanadium, tantalum, titanium, tungsten, molybdenum, rhenium, metals of the platinum group and mixtures thereof.

6. The process for preparing isophoronediamine according to claim 5 , wherein the proportion of dopant metal in the catalyst is 0% to 5% by weight.

7. The process for preparing isophoronediamine according to claim 1 , wherein the proportion of oxygen in the catalyst is 0% to 25% by weight.

8. The process for preparing isophoronediamine according to claim 1 , wherein the catalyst comprises one or more layers and/or the layers comprise the same and/or a different catalyst material, and/or
wherein the hollow sphere catalyst has a bimodal or multimodal distribution in relation to the diameters of the hollow spheres.

9. The process for preparing isophoronediamine according to claim 1 , wherein at least some of the isophoronenitrile (IPN) used is converted, in the first stage by reaction with ammonia in the presence or absence of an imination catalyst and/or of a solvent, to isophoronenitrile imine (IPNI), and the conversion of IPN to IPNI after the imination being greater than 80%.

10. The process for preparing isophoronediamine according to claim 1 , wherein the first stage reaction product, as obtained or after a further treatment and/or addition of further ammonia, is subjected in the second stage to aminating hydrogenation over hydrogenation catalysts in the presence of at least ammonia and hydrogen and in the presence or absence of an organic solvent at a temperature of 20 to 150° C. and a pressure of 0.3 to 50 MPa.

11. The process for preparing isophoronediamine according to claim 1 , wherein the conversion of isophoronenitrile to isophoronediamine is effected in three separate reaction spaces, IPN being converted to isophoronenitrile imine with excess ammonia over imination catalysts in the first reaction space at temperatures between 20 and 150° C. and pressures between 5 and 30 MPa, the reaction products formed being hydrogenated with hydrogen in the presence of excess ammonia over hydrogenation catalysts in the second reaction space at temperatures between 20 and 130° C. and pressures of 5 to 30 MPa, and the reaction products formed being hydrogenated over catalysts in the third reaction space at temperatures between 100 and 160° C. and pressures of 5 to 30 MPa.

12. The process for preparing isophoronediamine according to claim 1 , wherein the imination reaction is effected in the presence of at least one imination catalyst.

13. The process for preparing isophoronediamine according to claim 1 , wherein the imination of isophoronenitrile with liquid ammonia is conducted without addition of further solvent.

14. The process for preparing isophoronediamine according to claim 1 , wherein between 1 and 500 mol of ammonia is used per mole of isophoronenitrile used in the imination stage.

15. The process for preparing isophoronediamine according to claim 1 , wherein the imination is conducted in the presence of a suspension catalyst or fixed bed catalyst.

16. The process for preparing isophoronediamine according to claim 1 , wherein isophoronenitrile and ammonia in the imination are conducted continuously from the bottom upward through a reaction tube filled with imination catalyst.

17. The process for preparing isophoronediamine according to claim 1 , wherein the hydrogen required for the hydrogenation is supplied to the reactor either in excess or in such an amount that the hydrogen consumed by reaction and the portion of the hydrogen which leaves the reactor dissolved in the product stream is replenished.

18. The process for preparing isophoronediamine according to claim 1 , wherein the hydrogenation is conducted in liquid ammonia as solvent, using between 1 and 500 mol of isophoronenitrile.

19. The process for preparing isophoronediamine according to claim 1 , wherein the catalyst is first conditioned with ammonia before it is used in the hydrogenation.

20. The process for preparing isophoronediamine according to claim 1 , wherein the hydrogenation is effected continuously in a fixed bed reactor.

21. The process for preparing isophoron

Assignees

• Evonik Degussa Gmbh

Inventors

• Kohlstruk Stephan
• Rittsteiger Anne
• Ruefer Alexander Martin
• Schlueter Norbert
• Schneider Sven
• Sowka Sabrina
• Streukens Guido
• Roeder Stefan
• Berweiler Monika

Classifications

• C07C211/36

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

• B01J35/023

  Operations & Transport · mapped topic

• B01J2523/845

  Cobalt · CPC title

• C07C255/46

  to carbon atoms of non-condensed rings · CPC title

• B01J35/026

  Operations & Transport · mapped topic