Method of synthesizing 3,3'-dichloro-4,4'-diaminodiphenylmethane by using heteropoly acid

A technology of diaminodiphenylmethane and heteropolyacids, which is applied in the preparation of amino compounds, chemical instruments and methods, and the preparation of organic compounds, etc. It can solve problems that do not conform to the development concept of green chemistry, long reaction time, low product yield, etc. problems, to achieve the effect of easy control, less by-products and intermediate products, and high yield

Inactive Publication Date: 2017-12-01
NINGBO INST OF TECH ZHEJIANG UNIV ZHEJIANG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But the product yield is low, 32.5%; the reaction time is 7h too long, the energy consumption is too high, and it does not conform to the concept of green chemical development

Method used

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  • Method of synthesizing 3,3'-dichloro-4,4'-diaminodiphenylmethane by using heteropoly acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] In a high-temperature and high-pressure reactor equipped with a magnetic stirrer, weigh 204g (1.6mol) of o-chloroaniline solution, 16.2g (0.2mol) of formaldehyde solution (37.0-40.0% by mass), and 16.2g of phosphotungstic acid . After mixing, react at a constant temperature for 0.5 h at a temperature of 160° C. After the reaction, a small amount of the mixed solution (before the crystals were precipitated) was analyzed by a high-performance liquid chromatograph, and the selectivity of MOCA was 84.2%. The remaining mixed solution was cooled to room temperature, filtered with suction, and the obtained filter cake was recrystallized with a mixed solvent of DMF and ethanol with a volume ratio of 4:1, filtered, and dried to obtain a solid MOCA mass of 42.8 g, and the yield of MOCA was 80.1%. . The yield of MOCA measured by high-performance liquid chromatography is almost consistent with the yield obtained by the above-mentioned method, so the MOCA yields in the following e...

Embodiment 2

[0029] The reaction time was controlled for 1 h, and the others were as in Example 1. As a result, the MOCA selectivity was measured to be 88.8%, and the yield was 83.6%.

Embodiment 3

[0031] The reaction time was controlled for 8 hours, and the others were as in Example 1. As a result, the MOCA selectivity was measured to be 83.2%, and the yield was 78.9%.

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Abstract

The invention discloses a method of synthesizing 3,3'-dichloro-4,4'-diaminodiphenylmethane by using heteropoly acid. The method comprises the following steps: (1) adding o-chloroaniline and a formaldehyde solution into a reaction vessel in a room temperature; (2) adding a heteropoly acid catalyst into the reaction vessel; (3) under a magnetic stirring condition, performing heating to ensure the temperature in a range of 50-160 DEG C and performing a reaction for 0.5-8 hours; (4) after the reaction is completed, performing cooling to the room temperature, performing pumping filtration, removing the filtrate, and collecting the filter cake; and (5) performing recrystallization on the obtained filter cake by using an organic mixed solvent, and performing filtering and drying to obtain the solid heteropoly acid synthesized 3,3'-dichloro-4,4'-diaminodiphenylmethane. The method provided by the invention is mild in condition, simple in operation, high in yield and good in product quality.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a method for synthesizing 3,3'-dichloro-4,4'-diaminodiphenylmethane with a heteropolyacid. Background technique [0002] 3,3'-dichloro-4,4'-diaminodiphenylmethane (MOCA) is an important organic intermediate with a wide range of uses. The main use of MOCA is as a chain extension curing agent for TDI-based prepolymers, as a vulcanizing agent for cast polyurethane rubber, as a crosslinking agent for polyurethane coatings and adhesives, and as a curing agent for epoxy resins; liquid MOCA can be used for Prepare polyurethane curing agent and spray polyurea curing agent. Although people have always hoped to develop new products that can replace MOCA to play the role of cross-linking and curing, the development results are not ideal. None of the developed products meet the relevant requirements, and it is difficult to replace MOCA. Therefore, it is of great significance to explore t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/78C07C211/52
CPCC07C209/78C07C211/52
Inventor 葛飞龙赵迎宪
Owner NINGBO INST OF TECH ZHEJIANG UNIV ZHEJIANG
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