Cycloaliphatic diamines and method of making the same

Patent metadata

Field	Value
Publication number	US-9233908-B2
Application number	US-201013383361-A
Country	US
Kind code	B2
Filing date	Jul 30, 2010
Priority date	Jul 31, 2009
Publication date	Jan 12, 2016
Grant date	Jan 12, 2016

Abstract

The instant invention provides cycloaliphatic diamines and a method of making the same. The cycloaliphatic diamines according to the instant invention comprise the reaction product of one or more cycloaliphatic cyanoaldehydes selected from the group consisting of 1,3-cyanocyclohexane carboxaldehyde, 1,4-cyanocyclohexane carboxaldehyde, mixtures thereof, and combinations thereof, hydrogen, and ammonia fed into a continuous reductive amination reactor system; wherein the one or more cycloaliphatic cyanoaldehydes, hydrogen, and ammonia are contacted with each other in the presence of one or more heterogeneous metal based catalyst systems at a temperature in the range of from 80° C. to about 160° C. and a pressure in the range of from 700 to 3500 psig; and wherein one or more cycloaliphatic diamines are formed; and wherein said one or more cycloaliphatic diamines are selected from the group consisting of 1,3-bis(aminomethyl)cyclohexane, 1,4-bis(aminomethyl)cyclohexane, combinations thereof, and mixtures thereof.

First claim

We claim:

1. A process for producing cycloaliphatic diamines comprising the steps of:
feeding one or more cycloaliphatic cyanoaldehydes selected from the group consisting of 3-cyanocyclohexane-1-carboxaldehyde, 4-cyanocyclohexane-1-carboxaldehyde, mixtures thereof, and combinations thereof, hydrogen, and ammonia into a reductive amination reactor system;
contacting said one or more cycloaliphatic cyanoaldehydes, hydrogen, and ammonia with each other in the presence of one or more heterogeneous metal based catalyst systems at a temperature in the range of from 80° C. to about 160° C. and a pressure in the range of from 700 to 3500 psig, wherein said catalyst system has a space velocity in the range of from 0.1 to 5.0 per hour, wherein space velocity is defined as the ratio of the mass of the mixture of one or more cycloaliphatic cyanoaldehydes to the mass of catalyst per hour;
thereby forming one or more cycloaliphatic diamines, wherein said one or more cycloaliphatic diamines are diamines selected from the group consisting of 1,3-bis(aminomethyl)cyclohexane, 1,4-bis(aminomethyl)cyclohexane, combinations thereof, and mixtures thereof.

2. The process according to claim 1 , wherein said reductive amination reactor system comprises one or more continuous reactors in series, in parallel, or combinations thereof.

3. The process according to claim 1 , wherein said one or more heterogeneous metal based catalyst systems comprises a metal selected from the group consisting of Co, Ni, Ru, Fe, Cu, Re, Pd, oxides thereof, mixtures thereof, and combinations thereof.

4. The process according to claim 1 , wherein said one or more heterogeneous metal based catalyst systems is a bulk metal catalyst system, sponge-metal catalyst system, supported metal catalyst system, mixtures thereof, or combinations thereof.

5. The process according to claim 1 , wherein said one or more heterogeneous metal based catalyst systems comprises a bulk Co based catalyst system.

6. The process according to claim 1 , wherein said one or more heterogeneous metal based catalyst systems further comprises one or more promoters or one or more binding agents.

7. The process according to claim 6 , wherein said one or more promoters are selected from the group consisting of alkali metals and alkaline earth metals.

8. The process according to claim 6 , wherein said one or more binding agents comprise silicon oxide, aluminum oxide, titanium oxide, zirconium oxide, mixtures thereof, or combinations thereof.

9. The process according to claim 1 , wherein the catalyst lifetime facilitates a weight ratio of said one or more cycloaliphatic diamines to said one or more heterogeneous metal based catalyst systems that is greater than 300.

10. A method of improving the production yield of cycloaliphatic diamines comprising the steps of: contacting one or more cycloaliphatic cyanoaldehydes selected from the group consisting of 1,3-cyanocyclohexane carboxaldehyde, 1,4-cyanocyclohexane carboxaldehyde, mixtures thereof, and combinations thereof, hydrogen, and ammonia with each other in the presence of one or more heterogeneous metal based catalyst systems at a temperature in the range of from 80° C. to about 160° C. and a pressure in the range of from 1400 to 2500 psig, wherein said catalyst system has a space velocity in the range of from 0.1 to 5.0 per hour, wherein space velocity is defined as the ratio of the mass of the mixture of one or more cycloaliphatic cyanoaldehydes to the mass of catalyst per hour; thereby improving the product yield of one or more cycloaliphatic diamines, wherein said one or more cycloaliphatic diamines are diamines selected from the group consisting of 1,3-bis(aminomethyl)cyclohexane, 1,4-bis(aminomethyl)cyclohexane, combinations thereof, and mixtures thereof.

Assignees

• Schuitman Abraham D
• Feist Shawn D
• Fish Barry B
• Hickman Daniel A
• Molitor Erich J
• Tulchinsky Michael L
• Dow Global Technologies Llc

Inventors

• Schuitman Abraham D
• Feist Shawn D
• Fish Barry B
• Hickman Daniel A
• Molitor Erich J
• Tulchinsky Michael L

Classifications

• C07C2101/14

  Chemistry & Metallurgy · mapped topic

• C07C211/18

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

• C07C209/26

  by reduction with hydrogen · CPC title

• C07C209/48 Primary

  by reduction of nitriles · CPC title

• C07C2601/14

  The ring being saturated · CPC title