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

A technology of diaminodicyclohexylmethane and diaminodiphenylmethane, which is applied in the fields of MACM products and synthesis, 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: 2014-04-02
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
  • Method for synthesizing 3,3'-dimethyl-4,4'-diamino dicyclohexyl methane
  • 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] 200 grams of MDT, 280 grams of solvent as described in Table 2, 10 grams of catalyst were put into a 1L hydrogenation kettle, and 1.60 grams of BaO was added. Start stirring, raise the temperature to 90°C after the leak test, and control the temperature at 88-93°C and the pressure at 11.5MPa. The reaction is stirred for 10 hours to complete the hydrogen absorption, and the temperature is continued for 1.5 hours to obtain the MACM product. Wherein MACM-a refers to MACM with a first isomer ratio of 20.1%; MACM-b refers to MACM with a first isomer ratio of 32.6%.

Embodiment 2 and 4

[0030] 200 grams of MDT, 280 grams of solvent as described in Table 2, 10 grams of catalyst were put into a 1L hydrogenation kettle, and 1.60 grams of BaO was added. Start stirring, raise the temperature to 55°C after leak testing, and control the temperature at 53-58°C and the pressure at 14.5MPa. The reaction is stirred for 10 hours to complete the hydrogen absorption, and the temperature is continued for 1.5 hours to obtain the MACM product. Wherein MACM-a refers to MACM with a first isomer ratio of 20.1%.

[0031] Table 2

[0032]

[0033] It can be seen from the data of the corresponding Examples 1 to 5 and Comparative Examples 1 to 2 in Table 2 that the first isomer ratios of the products obtained by catalyzing MDT hydrogenation by different catalysts are different, and the ruthenium-rhodium bimetallic catalyst Ru-Rh / SiO is used. 2 The resulting product has a low ratio of the first isomer. Different solvents are used in the catalytic MDT hydrogenation process so tha...

Embodiment 6～8 and comparative example 3

[0035] Put 200 grams of MDT, 160 grams of MACM with a peak of 20.1% as solvent, and 2.4 grams of Ru-Rh / SiO into a 1L hydrogenation kettle. 2 The catalyst was added with 1.0 g of alkali metal auxiliary as shown in Table 3 or no auxiliary was added, and after the feeding was completed, it was replaced with nitrogen three times, and then replaced with hydrogen three times. Start stirring, raise the temperature to 85°C after leak testing, and control the temperature to be between 83-88°C and the pressure of 11.5MPa. The reaction is stirred for 10 hours to complete the hydrogen absorption, and the temperature is 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, and in particular relates to a method for synthesizing 3,3'-dimethyl-4,4'-diaminodicyclohexylmethane (referred to as MACM for short); A MACM product that is composed of various 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-duty anti-corrosion paint and other industrial architectural paint), epoxy composite curing agent (such as wind blade curing agent, wind 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.; 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 ...

Claims

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Application Information

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Patent Type & Authority Patents(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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