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

A technology of trimethylcyclohexylamine and trimethylcyclohexanone, which is applied in the field of preparation of aliphatic amines, can solve the problems of unspecified product IPDA cis/trans isomer ratio and low yield of IPDA, etc. Achieve the effect of simplifying the reaction process, simple method and reducing equipment construction cost

Active Publication Date: 2009-03-18
WANHUA CHEM GRP CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But the yield of this method gained IPDA only has 80%, and contains a large amount of IPAA by-products in the product; Patent JP4300852 discloses a kind of method similar to patent US3,352,913, but the yield of IPDA is lower; In addition, these two None of the patents stated the cis / trans isomer ratio of the product IPDA

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Add 40g of IPN, 120g of methanol, 80g of ammonia, 0.16g of 25% KOH aqueous solution into a tank reactor, add 10g of commercial Raney cobalt catalyst, the hydrogen pressure is 10MPa, the reaction temperature is 80°C, and the stirring speed is 400 rpm for addition. hydrogen reaction. After the reaction, the product was analyzed by gas chromatography, and the IPDA content in the product was 94.6%, and the cis / trans isomer ratio was 73 / 27.

Embodiment 2

[0017] Add 40g of IPN, 120g of methanol, 80g of ammonia, 0.32g of 25% KOH aqueous solution into a tank reactor, add 10g of commercial Raney cobalt catalyst, the hydrogen pressure is 10MPa, the reaction temperature is 80°C, and the stirring speed is 400 rev / min. hydrogen reaction. After the reaction, the product was analyzed by gas chromatography. The IPDA content in the product was 95.1%, and the cis / trans isomer ratio was 75 / 25.

Embodiment 3

[0019] Add 40g of IPN, 120g of methanol, 80g of ammonia, 0.48g of 2% KOH aqueous solution into a tank reactor, add 10g of commercial Raney cobalt catalyst, the hydrogen pressure is 10MPa, the reaction temperature is 80°C, and the stirring speed is 400 rev / min. hydrogen reaction. After the reaction, the product was analyzed by gas chromatography. The IPDA content in the product was 96.1%, and the cis / trans isomer ratio was 81 / 19.

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Abstract

The present invention discloses a method for preparing 3-aminomethyl-3,5,5-trimethyl cyclohexylamine(isophorone diamine, IPDA) from 3-cyan-3,5,5-trimethyl cyclohexanone(IPN). The method comprises the following steps 3-cyan-3,5,5-trimethyl cyclohexanone, ammonia, an alcohol and / or ether solvent, a hydrogenation catalyst and a promoter are reacted at a temperature of between 50 and 120 DEG C and a hydrogen pressure of between 5 and 15 MPa so as to obtain 3-aminomethyl-3,3,3-trimethyl cyclohexylamine. The method simplifies the prior process for preparing IPDA from IPN, is low in equipment cost, mild in reaction conditions and high in offspring yield.

Description

technical field [0001] The present invention relates to a preparation method of aliphatic amine, in particular to the preparation of 3-aminomethyl-3,5,5- from 3-cyano-3,5,5-trimethylcyclohexanone in a reaction vessel Trimethylcyclohexylamine (IPDA) method. Background technique [0002] 3-Aminomethyl-3,5,5-trimethylcyclohexylamine (isophoronediamine, referred to as IPDA) is a raw material for preparing isophorone diisocyanate (IPDI), polyamide, etc., and can also be used as a hardener for epoxy resins. IPDA is usually prepared from 3-cyano-3,5,5-trimethylcyclohexanone (isophorone nitrile, referred to as IPN), ammonia, and hydrogen through amination hydrogenation under the action of a hydrogenation catalyst; The obtained IPDA was a mixture of cis-isomers and trans-isomers, and IPDA with different ratios of cis- / trans-isomers had different reactivity. According to DE-A 4,211,454, IPDA with a cis-isomer content of less than 60% can be used as a reactive component of epoxy res...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/35C07C209/26
Inventor 陈长生黎源崔洪寅华卫琦
Owner WANHUA CHEM GRP CO LTD
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