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Method for preparing 4,4'-bis(hydroxymethyl)biphenyl

A technology of hydroxymethylbiphenyl and dichloromethylbiphenyl, which is applied in the field of organic compound preparation, can solve problems such as long reaction time, low reaction efficiency, and influence on yield, and achieve short reaction time, simple process, and high yield. high effect

Active Publication Date: 2009-12-23
BAOWU CHARCOAL MATERIAL TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the process yield is above 98%, the reaction time is too long, the reaction efficiency is low, and the recrystallization solvent dichloromethane has a low boiling point. The solubility does not change much, which affects the yield, and it is inconvenient to operate with low boiling point solvents

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Get 4,4'-dichloromethylbiphenyl 5g, dimethyl sulfoxide 20ml, 10% sodium carbonate solution 20ml, respectively add it in the round-bottomed flask that has stirrer, thermometer, recovery condensing tube successively, in normal Pressure, 70 ℃ under reflux and stirring, continue to react for 6 hours, liquid chromatography tracking, after the reaction, add 20ml of water, filter to obtain 4,4'-dimethylol biphenyl crude product, the crude product is a white solid. Use methanol to heat and dissolve the crude 4,4'-dimethylolbiphenyl to methanol at a mass ratio of 1:2, and place it to crystallize. After the crystals are precipitated, filter to obtain a white solid, and dry the white solid in vacuum to obtain the refined product 4,4' -Dihydroxymethylbiphenyl. After determination, the purity was 99.4%, and the yield was 96.1%.

Embodiment 2

[0027] Take 5g of 4,4'-dichloromethylbiphenyl, 40ml of dimethyl sulfoxide, 50ml of 20% sodium carbonate solution, heat to reflux at 90°C, and continue the reaction for 4 hours. After the reaction, add 20ml of water. Heat to dissolve with methanol according to the mass ratio of 4,4'-dimethylol biphenyl crude product to methanol 1:2. The refined product 4,4'-dimethylol biphenyl obtained at last has a purity of 99.1% and a yield of 95.3%. Others are the same as embodiment 1.

Embodiment 3

[0029] Take 5g of 4,4'-dichloromethylbiphenyl, 40ml of N,N-dimethylformamide, 40ml of 10% sodium bicarbonate solution, heat to reflux at 90°C, and continue the reaction for 5 hours. After the reaction, add 40ml of water. Heat and dissolve with ethanol according to the mass ratio of 4,4'-dimethylol biphenyl crude product to ethanol 1:2. The refined product 4,4'-dimethylol biphenyl obtained at last has a purity of 99.1% and a yield of 95.3%. Others are the same as embodiment 1.

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Abstract

The invention provides a method for preparing 4,4'-bis(hydroxymethyl)biphenyl, which comprises the following steps: mixing 4,4'-bis(chloromethyl)biphenyl, a solvent and alkaline liquor according to the mass ratio of 1:4-10:4-10; heating, refluxing and stirring the mixture under the normal pressure and at the temperature of 60 to 100 DEG C; continuously reacting the mixture for at least 4 hours, adding water into the mixture, and filtrating the mixture to obtain a crude product of the 4,4'-bis(hydroxymethyl)biphenyl; and recrystallizing the crude product by an alcoholic solvent to obtain a fine product of the 4,4'-bis(hydroxymethyl)biphenyl. The method has simple operation and short reaction time and is suitable for industrialized production; and the solvent for reaction and the solvent for crystallization can be recycled.

Description

technical field [0001] The invention relates to the field of organic compound preparation, in particular to a method for preparing 4,4'-dimethylol biphenyl. Background technique [0002] 4,4'-dimethylolbiphenyl (4,4'-bis(hydroxymethyl)biphenyl, BHMBP) is mainly used as a monomer for synthesizing polymers with low hygroscopicity and flame retardancy, as a monomer for liquid crystal polymers, It can also be used to synthesize other biphenyl derivatives, for example, 4,4'-biphenyl dicarboxylic acid. [0003] At present, the synthesis of 4,4'-biphenyl dimethanol mainly adopts 4,4'-bis(chloromethyl)biphenyl as raw material for production. A method for preparing 4,4'-dimethylolbiphenyl is disclosed in Japanese Patent JP9208510. 4,4'-Dihydroxymethylbiphenyl is prepared by hydrolysis of 4,4'-dichloromethylbiphenyl (4,4'-bis(chloromethyl)biphenyl, BCMBP) in water. According to this patent, the reaction is carried out in an organic solvent / water medium in the presence of a strong b...

Claims

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Application Information

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IPC IPC(8): C07C33/28C07C29/58C07C29/09
Inventor 侯文杰朱春燕夏烨
Owner BAOWU CHARCOAL MATERIAL TECH CO LTD
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