Method for preparing isophorone diamine

A technology of isophorone diamine and isophorone, applied in the field of preparing isophorone diamine, can solve the problems of low yield, long reflux time and the like

Active Publication Date: 2015-07-08
ZHEJIANG XINHUA CHEM +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Although 3-nitromethyl-3,5,5-trimethylcyclohexanone is considered as a possible alternative to isophoronenitrile for the synthesis of isophoronenitrile However, so far, there are few reports on the synthesis of 3-nitromethyl-3,5,5-trimethylcyclohexanone from nitromethane and isophorone
Dorothy et al. (Nitroparaffins and Al...

Method used

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  • Method for preparing isophorone diamine
  • Method for preparing isophorone diamine
  • Method for preparing isophorone diamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1 Tetrabutylammonium fluoride as catalyst

[0037] In a 100ml glass bottle, add 10mmol of isophorone, 15mmol of nitromethane, and 1ml of tetrabutylammonium fluoride, react at 60°C for 1 hour, the conversion rate is 19%, and the conversion is 32% in 5 hours.

Embodiment 2

[0038] Embodiment 2 Tetrabutylammonium hydroxide as catalyst

[0039] In a 100ml glass bottle, add 10mmol of isophorone, 15mmol of nitromethane, and 5mmol of tetramethylammonium hydroxide, react at 70°C for 5 hours, and the conversion rate is 40%.

Embodiment 3

[0040] The catalytic effect of several secondary amines of embodiment 3

[0041]

[0042] Isophorone 10mmol, nitromethane 15mmol, catalyst 10mmol, reaction temperature 50°C.

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Abstract

The invention discloses a method for preparing isophorone diamine, and is characterized in that the method comprises the following steps: 1) under the condition of an organic amine catalyst, with isophorone and nitromethane as raw materials, synthesizing 3-nitromethyl-3,5,5-trimethylcyclohexanone, wherein the reaction temperature is 0 DEG C-150 DEG C, and the amount of the organic amine catalyst is 1-300% of the mass of the substance amount of isophorone; and 2) under conditions of liquid ammonia, hydrogen and a metal cobalt catalyst, allowing 3-nitromethyl-3,5,5-trimethylcyclohexanone to undergo a reaction to generate isophorone diamine, wherein the reaction temperature is 30-300 DEG C, the liquid ammonia amount is 1-50 times of the substance amount of 3-nitromethyl-3,5,5-trimethylcyclohexanone, and the hydrogen pressure is 0.1-10 MPa. The nitromethane with lower toxicity is used for replacing highly-toxic hydrogen cyanide or thiocyanate, and thus the method is a technical route which is safer in process and friendlier to the environment.

Description

technical field [0001] The invention relates to a method for preparing isophorone diamine, which uses nitromethane to improve the safety and greenness of isophorone diamine synthesis. Background technique [0002] Isophorone diamine (IPDA) is a high-end fine chemical with excellent performance. It is used as epoxy resin curing agent, coating crosslinking agent and polyester monomer. Its high-performance composite materials are widely used in High-tech industries such as wind turbines and auto parts. The molecular structure of IPDA endows it with excellent application performance, higher mechanical strength, high amino activity, good premixability, convenient use, excellent compatibility, and better light transmission, weather resistance, oil resistance, aging resistance, and water resistance. It is an ideal new chemical material. [0003] At present, the manufacturers of IPDA in the world mainly include German BASF, DEGUSSA, and American DuPont. The cyanidation route is a...

Claims

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Application Information

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IPC IPC(8): C07C209/34C07C211/36
Inventor 盛学斌王卫明应思斌杨维慎陈宏
Owner ZHEJIANG XINHUA CHEM
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