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Process for improving the catalytic activity of catalyst systems for reductive amination of aliphatic cyanoaldehydes to aliphatic diamines

A technology for the reduction of aldehydes to amines and catalytic activity, which can be used in chemical instruments and methods, preparation of reductive alkylation, preparation of amino compounds, etc., and can solve the problems of short catalyst life and low yield

Active Publication Date: 2012-11-14
DOW GLOBAL TECH LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, catalysts and conditions effective for complete reduction of the nitrile group may also tend to reduce the aldehyde to the corresponding alcohol, resulting in lower yields
On the other hand, the catalysts and conditions typically selected for the reductive amination of aldehydes are often ineffective for complete reduction of the nitrile group, leading to intermediate aminonitriles in lower yields
Moreover, the relatively short lifetime of existing catalysts introduces other challenges

Method used

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  • Process for improving the catalytic activity of catalyst systems for reductive amination of aliphatic cyanoaldehydes to aliphatic diamines
  • Process for improving the catalytic activity of catalyst systems for reductive amination of aliphatic cyanoaldehydes to aliphatic diamines
  • Process for improving the catalytic activity of catalyst systems for reductive amination of aliphatic cyanoaldehydes to aliphatic diamines

Examples

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Embodiment 1

[0053] A reactor mixture was prepared by combining crude cyanaldehyde (where the cyanaldehyde contained 85-90 wt% cyanaldehyde) and t-butanol (t-butanol) to obtain a crude cyanaldehyde concentrate of approximately 70 wt%. The mixture was passed through a bed of sodium carbonate. The reactor tube was charged with 7.0 g of BASF Co-0179T catalyst and diluted with 100 grit (150 μm) SiC (silicon carbide) fines. The temperature of the reactor was raised to 250°C. Under continuous hydrogen flow, the temperature of the reactor was maintained at 250°C for 14 hours, then the temperature was lowered to about less than 80°C. Once the temperature of the reactor was lowered to less than 80°C, an excess flow of ammonia (approximately 3-5 times the desired set point as described below) was introduced into the reactor. The temperature and pressure are then changed to the desired set points, ie about 100°C and about 1400 psig. After at least one hour, reduce the ammonia rate to the desired s...

Embodiment 2

[0055] A reactor mixture was prepared by combining crude cyanaldehyde (where the cyanaldehyde contained 85-90 wt% cyanaldehyde) and t-butanol (t-butanol) to obtain a crude cyanaldehyde concentrate of approximately 70 wt%. The mixture was passed through a bed of sodium carbonate. The reactor tube was charged with 7.0 g of BASF Co-0179T catalyst and diluted with 100 grit (150 μm) SiC (silicon carbide) fines. The temperature of the reactor was raised to 233°C. Under continuous hydrogen flow, the temperature of the reactor was maintained at 233°C for 14 hours, then the temperature was lowered to about less than 80°C. Once the temperature of the reactor is lowered to less than 80 °C. An excess flow of ammonia (approximately 3-5 times the desired set point as described below) is then introduced into the reactor. The temperature and pressure are then changed to the desired set points, ie about 100°C and about 2000 psig. After at least one hour, reduce the ammonia rate to the desi...

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Abstract

The instant invention provides a process for improving catalytic activity of catalyst systems for reductive amination of aliphatic cyanoaldehydes to aliphatic diamines. The process for improving catalytic activity of catalyst systems for reductive amination of aliphatic cyanoaldehydes to aliphatic diamines comprises the steps of: (1) feeding ammonia, optionally hydrogen, and optionally one or more solvents over one or more heterogeneous metal based catalyst systems having a reduced catalytic activity for a period of greater than 1 hour at a temperature in the range of from 50 DEG C to 500 DEG C; wherein said one or more heterogeneous metal based catalyst systems have a yield of less than 90 percent based on the molar conversion of cyanoaldehydes to diamines; and (2) thereby improving the catalytic activity of said one or more heterogeneous metal based catalyst systems.

Description

[0001] Cross References to Related Applications [0002] This application is a non-provisional patent application claiming U.S. Provisional Patent Application No. 61 / 230,362, filed July 31, 2009, entitled "PROCESS FOR IMPROVING THE CATALYTIC ACTIVITY OF CATALYST SYSTEMS FOR REDUCTIVE AMINATION OF ALIPHATIC CYANOALDEHYDES TO ALIPHATIC DIAMINES" Priority, the teachings of which are incorporated by reference into this application, as if reproduced in its entirety below. technical field [0003] The present invention relates to a process for improving the catalytic activity of catalyst systems for the reductive amination of aliphatic cyanoaldehydes to aliphatic diamines. Background technique [0004] Bis(aminomethyl)cyclohexane is a diamine that can be used as a precursor of an aliphatic diisocyanate (bis(isocyanatomethyl)cyclohexane). It can be used as a chain extender in certain polyurethane systems and as a curing agent for epoxy resins. Bis(aminomethyl)cyclohexane exists ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/26C07C209/48C07C211/09C07C211/18B01J35/00
CPCC07C209/48C07C2101/14C07C211/18C07C2601/14
Inventor D.希克曼S.费斯特E.莫利托D.莫尔赞S.桑萨尼A.舒伊特曼
Owner DOW GLOBAL TECH LLC