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

A technology of trimethylcyclohexylamine and aminomethyl, which is applied in the field of preparation of aliphatic amines, can solve the problems of reduced production ratio, unstable cyano group, and intensified IPN decyanation reaction, so as to improve yield and operate simple effect

Active Publication Date: 2013-03-20
WANHUA CHEM GRP CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] 2) The cyano group in IPN is extremely unstable under alkaline conditions and is easily removed to form 3,5,5-trimethyl-2-cyclohexenone, while 3,5,5-trimethyl-2- 3,3,5-trimethylcyclohexanol, the product of hydrogenation of cyclohexenone, is not the desired product
[0013] Although the method disclosed in CN101568516A reduces the generation ratio of IPAA by increasing the alkalinity of the IPNI reaction solution, the decyanation reaction of IPN is intensified due to the addition of additional alkali

Method used

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

Examples

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Embodiment 1

[0058] use as figure 1 The reaction setup shown was used for this example.

[0059] The reactive distillation tower (2) has an internal diameter of 40mm and a length of 1000mm, and is equipped with a 2mm-sized θ ring packing inside, and the feed inlet is located in the middle of the reactive distillation tower. The reactor (6) is 200mm in length and 25mm in inner diameter, and gamma-alumina pellets with a diameter of 1mm are housed in the reactor. The reactor (9) is 400 mm in length and 25 mm in inner diameter, and is equipped with a G62RS hydrogenation catalyst of 1 mm in diameter from Germany Southern Company.

[0060] In the first step, IPN enters the reactive distillation column (2) at 165g / h and IPDA at 510g / h from the middle of the reactive distillation column (2). The pressure of the reactive distillation column is controlled at 50Kpa by a vacuum pump, and the temperature of the bottom of the column is about 200°C , the top temperature is about 81°C.

[0061] In the ...

Embodiment 2-4

[0072] Carry out embodiment 2-4 according to the method identical with embodiment 1, just change the IPDA as primary amine in the first step into ethylenediamine, hexamethylenediamine and aniline respectively of the same molar amount.

[0073] The composition of the hydrogenation reaction product was also analyzed, and the results are shown in Table 2 below.

[0074] Table 2

[0075]

[0076] The main by-products IPAA and 3,3,5-trimethylcyclohexanol in the traditional method were not detected.

Embodiment 5-7

[0078] Carry out embodiment 5-7 according to the same method as embodiment 1, just change the ammonolysis catalyst in the second step into commercially available 1mm titanium dioxide pellets, silica pellets and ion exchange resins by gamma-alumina (Nankai University D72).

[0079] The composition of each product in the hydrogenation reaction product was also analyzed, and the results are shown in Table 3 below.

[0080] table 3

[0081]

[0082] The main by-products IPAA and 3,3,5-trimethylcyclohexanol in the traditional method were not detected.

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Abstract

The invention provides a method for preparing 3-aminomethyl-3,5,5-trimethyl cyclohexylamine. The method includes: a) reacting 3-cyano-3,5,5-trimethyl cyclohexanone with excess primary amine, while removing water of the reaction, so that IPN is substantially completely converted to an imine compound; b) in the presence of an aminolysis catalyst, mixing the resulting product from step a) with liquid ammonia so as to carry out the aminolysis reaction on the imine compound to form 3-cyano-3,5,5-trimethyl cyclohexylimine and the primary amine; and c) performing the hydrogenation reaction to 3-cyano-3,5,5-trimethyl cyclohexylimine obtained in step b) to get 3-carbamoylyl-3,5,5-trimethyl cyclohexylamine in the presence of hydrogen and a hydrogenation catalyst. The method of the present invention prevents the generation of major byproducts of 3,5,5-trimethyl cyclohexanol, and 3-aminomethyl-3,5,5-trimethyl cyclohexanol in the prior art, thereby improving the yield of 3-aminomethyl-3,5,5-trimethyl cyclohexylamine.

Description

technical field [0001] The invention relates to a preparation method of aliphatic amines, in particular to the preparation of 3-aminomethyl-3,5,5-trimethylcyclohexyl from 3-cyano-3,5,5-trimethylcyclohexanone amine method. Background technique [0002] 3-Aminomethyl-3,5,5-trimethylcyclohexylamine (also known as isophorone diamine, referred to as IPDA) is the preparation of 3-isocyanate group methylene-3,5,5-trimethyl Cyclohexyl isocyanate (also known as isophorone diisocyanate, referred to as IPDI), polyamide and other raw materials can also be used as a curing agent for epoxy resin. [0003] On an industrial scale, IPDA is formed by reacting 3-cyano-3,5,5-trimethylcyclohexanone (also known as isophoronenitrile, or IPN for short) with ammonia to form 3-cyano-3,5, 5-Trimethylcyclohexyl imine (also known as isophorone nitrile imine, referred to as IPNI), IPNI is then prepared by catalytic reductive amination reaction with hydrogen in the presence of ammonia. Its reaction pro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/35C07C209/52C07C209/48
Inventor 陈长生姜进科陈忠英崔娇英王静李付国吕成戈赵文娟黎源华卫琦
Owner WANHUA CHEM GRP CO LTD
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