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Synthesis method of 4,4'-dihydroxybiphenyl

A dihydroxybiphenyl and synthesis method technology, applied in 4 fields, can solve the problems of difficult to use high-grade manufacturing products, high equipment requirements, high energy consumption, etc., to reduce the risk factor, corrosion of equipment, and reaction selectivity High, high product purity effect

Pending Publication Date: 2020-09-01
安徽中羰碳一工业技术有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] Although this method has a simple process and less waste, the catalyst preparation process in the early stage is complicated, which affects the overall economic benefits.
[0017] It can be seen from the above that at present, high-purity 4,4'-dihydroxybiphenyl cannot be produced in large quantities in China, and its use mainly depends on imports from the United States. The existing domestic technologies have the following problems:
[0018] First, the use of strong acid, strong alkali and high temperature reaction conditions not only requires high energy consumption and high equipment requirements, but also produces a large amount of waste acid, waste water and high-temperature coking waste that is difficult to handle and seriously pollutes the environment;
[0019] Second, in the production process, whether it is due to high temperature or poor reaction selectivity, there are many by-products, which are difficult to separate and purify, which affects the purity and appearance of the final product, and are difficult to use in high-end manufacturing products.

Method used

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  • Synthesis method of 4,4'-dihydroxybiphenyl
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  • Synthesis method of 4,4'-dihydroxybiphenyl

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] A kind of synthetic method of 4,4'-dihydroxy biphenyl, specifically comprises the steps:

[0059] (1) Put anhydrous aluminum trichloride (0.4g, 0.003mol) into a dry 500mL three-necked flask, then add biphenyl (46.3g, 0.3mol), chloroform (250mL), and stir to dissolve the biphenyl Completely, slowly add cyclopentene (40.9g, 0.6mol) dropwise under stirring conditions, control the reaction temperature at 0°C, after the dropwise addition, stir at room temperature for 10 hours, take a small amount of organic phase for gas chromatography analysis, biphenyl conversion The yield was 98.5%, and then the reaction system was poured into a separatory funnel, washed 3 times with 100mL water, the organic phase was distilled under reduced pressure, and the solvent was recovered to obtain 4,4'-dicyclopentyl biphenyl solid crude product, gas phase The content of the product measured by the chromatographic internal standard method is 83.5%;

[0060] (2) In a 500mL three-necked flask, add...

Embodiment 2

[0063] The specific reaction process and detection method are the same as in Example 1, except that cyclopentene is changed to cyclohexene, and the resulting product 4,4'-dihydroxybiphenyl has a final yield of 71.5%.

Embodiment 3

[0065] The specific reaction process and detection method are the same as in Example 1, except that cyclopentene is changed into chlorocyclohexane to obtain 4,4'-dihydroxybiphenyl with a final yield of 71.3%.

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PUM

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Abstract

The invention provides a synthesis method of 4,4'-dihydroxybiphenyl. Biphenyl is used as an initial raw material undergoes a Friedel-Crafts alkylation reaction to obtain 4,4'-dicyclopentylbiphenyl or4,4'-dicyclohexylbiphenyl, an oxidation reaction is carried out to obtain hydroperoxide, and then the hydroperoxide is subjected to a cracking reaction to prepare the target product 4,4'-dihydroxybiphenyl. The whole synthesis method is high in selectivity, high in yield, convenient to operate and environmentally friendly, and is suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a synthesis method of 4,4'-dihydroxybiphenyl. Background technique [0002] 4,4'-Dihydroxybiphenyl is an important organic intermediate and has a wide range of uses in the chemical industry. It can be used as an antioxidant for plastics, a stabilizer for dyes and an anti-aging agent for rubber, etc. It can also be used to make excellent composite materials and liquid crystal polymers. In recent years, the world has gradually banned the use of bisphenol A in the production of baby-related plastic products, and 4,4'-dihydroxybiphenyl has become the best substitute for bisphenol A. [0003] At present, the methods for large-scale industrial production of 4,4'-dihydroxybiphenyl mainly include: [0004] 1. Preparation of 4,4'-dihydroxybiphenyl from biphenyl and its derivatives by sulfonated alkali fusion, refer to US Patent US6410238, [0005] [0006] Although this me...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/15C07C37/52
CPCC07C37/52C07C51/255C07C2/68C07C2/70C07C2/861C07C2/864C07C2601/08C07C2601/14C07C2527/1206C07C2527/126C07C39/15C07C61/39C07C13/28
Inventor 刘显伟马心旺马青松孙东艳魏力璟刘娇苏建
Owner 安徽中羰碳一工业技术有限责任公司
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