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Preparation method of 4, 4'-bis(chloromethyl)-1, 1'-biphenyl

A biphenyl dichlorobenzyl and biphenyl technology, which is applied in the field of preparation of biphenyl dichlorobenzyl, can solve problems such as hidden dangers of human health and safety, and achieve the effects of low volatility, mild reaction conditions and less dosage

Inactive Publication Date: 2015-11-25
SHAANXI RES DESIGN INST OF PETROLEUM CHEM IND
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] An object of the present invention is to mainly overcome the problem of producing low-boiling volatile chloromethyl methyl ether or chloromethyl ether and other carcinogenic compounds in the process of directly synthesizing biphenyl dichlorobenzyl from formaldehyde, thus causing potential safety hazards to human health.

Method used

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  • Preparation method of 4, 4'-bis(chloromethyl)-1, 1'-biphenyl
  • Preparation method of 4, 4'-bis(chloromethyl)-1, 1'-biphenyl
  • Preparation method of 4, 4'-bis(chloromethyl)-1, 1'-biphenyl

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Embodiment 1

[0023] The preparation process of 4,4'-bischloromethoxy-1,1'-biphenyl of the present invention is carried out in 2 steps:

[0024] I. Add 78.701g 1,6-hexanediol (0.666mol), 40.000g paraformaldehyde (1.332mol), and 250ml n-hexane into a 500ml four-neck round bottom flask. The flask is placed in a constant temperature water bath, and the thermometer is inserted into the side port of the operator. The mercury bulb of the thermometer is located below the liquid surface; the right port is equipped with a reflux condenser, and the top of the pipe is connected to a tube. The escaping hydrogen chloride gas is absorbed by the sodium hydroxide solution. Hydrogen chloride gas is produced by the reaction of concentrated sulfuric acid and ammonium chloride and is introduced from the left port. Ammonium chloride produces more uniform bubbles than sodium chloride.

[0025] Turn on mechanical stirring. Adjust the dropping rate of concentrated sulfuric acid in the constant pressure funnel, so tha...

Embodiment 2

[0028] ⅠAdd 591.56g 1,6-hexanediol (5.006mol), 300.90g paraformaldehyde (10.02mol), 1.8L petroleum ether (re-distilled, take 60-90℃ fraction) into a 5L 4-neck flask equipped with mechanical stirring . The flask is placed in a constant temperature water bath, and the thermometer is inserted into the side port of the operator. The mercury bulb of the thermometer is located below the liquid surface; the right port is equipped with a reflux condenser, and the top of the pipe is connected to a tube. The excess hydrogen chloride gas is absorbed by the sodium hydroxide solution. Hydrogen chloride gas is produced by the reaction of concentrated sulfuric acid and ammonium chloride, and is introduced from the side port.

[0029] Turn on mechanical stirring. Adjust the dropping rate of concentrated sulfuric acid in the constant pressure funnel, so that the hydrogen chloride flow rate is controlled at 14-20L / h. Adjust the temperature of the water bath, and control the system temperature be...

Embodiment 3

[0032] I. Add 69.36g 1,5-pentanediol (0.666mol), 40.000g paraformaldehyde (1.332mol), and 300ml n-hexane into a 500ml four-necked round bottom flask. The flask is placed in a constant temperature water bath, and the thermometer is inserted into the side of the operator. The mercury bulb of the thermometer is below the liquid surface; a reflux condenser is added to the mouth, and a tube is connected to the top of the tube. The excess hydrogen chloride gas is absorbed by the sodium hydroxide solution. Hydrogen chloride gas is produced by the reaction of concentrated sulfuric acid and ammonium chloride and is introduced from the left port.

[0033] Turn on mechanical stirring. Adjust the dropping rate of the concentrated sulfuric acid in the constant pressure funnel so that the bubble generation speed in the gas scrubber is roughly 2-3 bubbles in 1 second. The temperature of the system is controlled between 15-17°C, and the hydrogen chloride gas is stopped after 2 hours of reaction....

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Abstract

The invention relates to a preparation method of 4, 4'-bis(chloromethyl)-1, 1'-biphenyl. The preparation method includes the steps of 1, at 15-18 DEG C, reacting 1, 6-hexanediol or 1, 5-pentanediol with paraformaldehyde in a solvent, normal hexane or petroleum ether, continuously introducing hydrogen chloride gas until paraformaldehyde suspension disappears, and preparing 1, 6-bis(chloromethyl)hexane or 1, 5-dichloromethoxypentane; 2, at 50-60 DEG C, reacting biphenyl with the 1, 6-bis(chloromethyl)hexane or 1, 5-dichloromethoxypentane using a catalyst, zinc chloride, and a solvent, normal hexane or petroleum ether, to prepare 4, 4'-bis(chloromethyl)-1, 1'-biphenyl. Diol is nearly quantitatively converted into corresponding bis(chloromethyl) alkane. The generated bis(chloromethyl) alkane has a high boiling point, low volatility and stability; conditions of reaction with the biphenyl are mild, consumption of the zinc chloride is low, and post-treatment is convenient. The reaction is carried out under the mild conditions, environmental pollution is low, and the yield is up to 65%.

Description

Technical field [0001] The invention relates to a method for preparing biphenyldichlorobenzyl. Background technique [0002] The 4,4'-dichloromethylated product of biphenyl, biphenyl dichlorobenzyl, is the precursor for the synthesis of stilbene biphenyl fluorescent whitening agents and a pharmaceutical intermediate 4,4'-dimethylol Raw material for biphenyl. In addition, biphenyldichlorobenzyl is also used in the synthesis of many materials. The synthesis method and process research of 4,4’-dichloromethyl biphenyl has attracted much attention. [0003] The most direct way to synthesize biphenyl dichlorobenzyl is to use biphenyl as raw materials, formaldehyde and hydrogen chloride as sources of chloromethyl to catalyze para-chloromethylation. This method is widely used in chemical production, and its advantages are direct, simple and effective. But at the same time there are many disadvantages: the amount of zinc chloride used in the catalyst is large, and the post-treatment wil...

Claims

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Application Information

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IPC IPC(8): C07C17/32C07C22/04C07C43/12C07C41/01
Inventor 李华杰沈寒晰张存社习娟周魁
Owner SHAANXI RES DESIGN INST OF PETROLEUM CHEM IND
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