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Method for preparing 3-aminomethyl-3,5,5-trimethyl cyclohexylamine

A technology of trimethylcyclohexylamine and trimethylcyclohexanone is applied in the field of preparation of aliphatic amines to achieve the effect of reducing usage

Active Publication Date: 2009-04-29
WANHUA CHEMICAL (NINGBO) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The technical defect of this method is that the highly toxic reactant hydrazine hydrate is introduced

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Add 200g of 95% ethanol and 80g of 3-cyano-3,5,5-trimethylcyclohexanone into a three-neck flask equipped with a stirrer and a thermometer, and install a dropping funnel. Take 120g of hydroxylammonium hydrochloride and 105g of sodium carbonate and add them into a container with 200ml of water, stir and dissolve them. After dissolving without bubbles, transfer them to the dropping funnel, slowly add them dropwise into the three-necked bottle while stirring, and drop After the addition, raise the reaction temperature to 60-65°C, keep the temperature constant for 1 hour, then pour the reactant into an ice-water bath, a white precipitate precipitates, wash with distilled water, and air-dry naturally to obtain 3-cyano-3,5, 5-trimethylcyclohexanone oxime (ie IPN-oxime), the obtained IPN-oxime has a mass of 86.4 g.

Embodiment 2

[0026] Add 80g of IPN-oxime, 200g of methanol, 15g of T-1 type Raney nickel catalyst, 22g of liquid ammonia into a 1L autoclave, feed hydrogen at 90-100°C to reach a total pressure of 10MPa, and react for 1 hour. According to gas chromatography analysis, the content of 3-aminomethyl-3,5,5-trimethylcyclohexylamine (IPDA) in the product was 96.1%, and no IPAA was formed.

Embodiment 3

[0028] Except changing the catalyst in embodiment 2 into T-1 type Raney cobalt catalyst, other experimental conditions are the same as embodiment 2. The test product was analyzed by gas chromatography, and the content of IPDA was 96.5%, and no IPAA was formed.

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PUM

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Abstract

The invention discloses a method for preparing 3-aminomethyl-3, 5, 5-trimethyl cyclohexylamine (isophorone diamine, IPDA) by 3-cyano-3, 5, 5-trimethyl cyclohexanone (IPN, isophorone nitrile), which comprises the following steps: a) 3-cyano-3, 5, 5-trimethyl cyclohexanone and oxyammonia are arranged in an organic solvent for reaction under a temperature ranging from 40 DEG C to 80 DEG C, and 3-cyano-3, 5, 5-trimethyl cyclohexanone oxime is generated; b) 3-cyano-3, 5, 5-trimethyl cyclohexanone oxime, hydrogen and liquid ammonia are arranged in an organic solvent for reaction under a temperature ranging from 50 DEG C to 120 DEG C, a total pressure ranging from 5 MPa to 15 MPa and the effect of a hydrogenation catalyst, and 3-aminomethyl-3, 5, 5-trimethyl cyclohexylamine is obtained. The method has the advantages that, the production of a by-product 3-aminomethyl-3, 5, 5-trimethyl cyclohexanol (IPAA) which is hard to be separated from IPDA is avoided; simultaneously, the amount of liquid ammonia is largely decreased.

Description

technical field [0001] The present invention relates to a preparation method of aliphatic amine, more specifically to a preparation method of 3-aminomethyl-3,5,5-trimethylcyclohexylamine (IPDA, namely isophorone diamine). 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 it can also be Used as a hardener for epoxy resins. IPDA is usually prepared by amination and hydrogenation of 3-cyano-3,5,5-trimethylcyclohexanone (isophorone nitrile, IPN for short), ammonia and hydrogen under the action of a hydrogenation catalyst. Various methods for the preparation of IPDA have been described in the prior art. [0003] US Patent No. 3,352,913 discloses a method for preparing IPDA by reacting IPN with ammonia and hydrogen under the action of a Group VIII metal-supported catalyst. In the method, the molar ratio of ammonia to IPN (hereina...

Claims

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Application Information

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IPC IPC(8): C07C211/36C07C209/44C07C209/40
Inventor 黎源陈长生崔洪寅赵文娟华卫琦
Owner WANHUA CHEMICAL (NINGBO) CO LTD
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