Method for synthesizing 3,3'-dimethyl-4,4'-diamino dicyclohexyl methane

A technology of diaminodicyclohexylmethane and diaminodiphenylmethane, applied in the field of synthesis of 3,MACM products, can solve problems such as turbidity or even crystallization, inconvenient production, storage, transportation and use, and affect the quality of downstream products, and achieve Low freezing point, quality improvement effect

Active Publication Date: 2012-08-08
JIANGSU QINGQUAN CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The most important thing is that the freezing point temperature of the MACM product obtained by using the existing technology is relatively high, such as solidification (liquid turbidity or even crystallization) phenomenon occurs at about 5°C, which brings great inconvenience to production, storage, transportation and use, and even Will affect the quality of its downstream products; this problem is especially serious in winter or in cold regions of high latitudes

Method used

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  • Method for synthesizing 3,3'-dimethyl-4,4'-diamino dicyclohexyl methane
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  • Method for synthesizing 3,3'-dimethyl-4,4'-diamino dicyclohexyl methane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1、3、5 and comparative example 1～2

[0028] Put 200 grams of MDT, 280 grams of solvents as described in Table 2, 10 grams of catalyst, and add 1.60 grams of BaO into a 1L hydrogenation kettle. After feeding, replace with nitrogen three times, and then replace with hydrogen three times. Stirring was started, and after leak testing, the temperature was raised to 90°C and controlled at a temperature of 88-93°C and a pressure of 11.5MPa. The reaction was stirred for 10 hours to end hydrogen absorption, and the temperature was continued for 1.5 hours to obtain the MACM product. Wherein MACM-a refers to the MACM whose first isomer ratio is 20.1%; MACM-b refers to the MACM whose first isomer ratio is 32.6%.

Embodiment 2 and 4

[0030] Put 200 grams of MDT, 280 grams of solvents as described in Table 2, 10 grams of catalyst, and add 1.60 grams of BaO into a 1L hydrogenation kettle. After feeding, replace with nitrogen three times, and then replace with hydrogen three times. Stirring was started, and after the leak test, the temperature was raised to 55°C and controlled at a temperature of 53-58°C and a pressure of 14.5MPa. The reaction was stirred for 10 hours to end the hydrogen absorption, and the temperature was continued for 1.5 hours to obtain the MACM product. Wherein MACM-a refers to MACM with the ratio of the first isomer being 20.1%.

[0031] Table 2

[0032]

[0033] It can be seen from the corresponding examples 1 to 5 and comparative examples 1 to 2 data in table 2 that the first isomer ratio of the product obtained by catalytic MDT hydrogenation of different catalysts is different, wherein the ruthenium-rhodium bimetallic catalyst Ru-Rh / SiO 2 The resulting product had a low proportion...

Embodiment 6～8 and comparative example 3

[0035] Put 200 grams of MDT, 160 grams of MACM with a peak of 20.1% as a solvent, and 2.4 grams of Ru-Rh / SiO in a 1L hydrogenation kettle 2 Catalyst, and add 1.0 grams of alkali metal additives as shown in Table 3 or no additives, after feeding, replace with nitrogen three times, and then replace with hydrogen three times. Stirring was started, and after leak testing, the temperature was raised to 85°C, and the temperature was controlled between 83-88°C, and the pressure was 11.5MPa. The reaction was stirred for 10 hours to end the hydrogen absorption, and the temperature was continued for 1.5 hours to obtain the MACM product.

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Abstract

The invention relates to a method for synthesizing 3,3'-dimethyl-4,4'-diamino dicyclohexyl methane (MACM), comprising the following steps of: using 3,3'-dimethyl-4,4'-diamino dibenzyl methane (MDT) as a raw material, and performing catalytic hydrogenation to obtain the product MACM. In addition, the content of a first isomer as shown in the formula I in the MACM product is less than or equal to 26 wt%. Correspondingly, the invention also provides an MACM product composed of a plurality of isomers with the first isomer in the composition accounts for a specific proportion. During the preferred reaction, a noble metal catalyst is used and an alkaline earth metal auxiliary agent is added; the preferred reaction temperature is 50-150 DEG C, the reaction pressure is 8-30MPa, and the reaction time is 3-50 hours. The MACM is prepared at low temperature and at low pressure. The method provided by the invention has advantages of short reaction time, mild condition and simple technology. The MACM product has low freezing point, which is beneficial to production, storage and usage of the product. In addition, the quality of downstream products can be raised.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, in particular to a method for synthesizing 3,3'-dimethyl-4,4'-diaminodicyclohexylmethane (abbreviated as MACM); A MACM product composed of two isomers and the first isomer in the composition accounts for a specific proportion. Background technique [0002] MACM is widely used in epoxy resin curing agent, epoxy coating curing agent (such as marine paint, heavy anti-corrosion paint and other industrial architectural paint), epoxy composite material curing agent (such as wind blade curing agent, wind power mold material curing agent, rubber roller Curing agent, etc.) and as a chain extender and auxiliary agent for the synthesis of polyurethane (PU), polyurea spray elastomer (SPUA), etc.; it is also used in the synthesis of polyaspartate, polyamide (PA), etc. The polyurethane synthesized by MACM not only has the elasticity of rubber, but also has the strength of plastic and excellent proc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/36C07C209/72
Inventor 邵建华杨荣强张永明王凌云潘智伟王天发郑志荣冯珍会刘航洋
Owner JIANGSU QINGQUAN CHEM CO LTD
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