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Method for synthesizing biphenol

A technology of biphenol and halophenol is applied in the field of organic chemical synthesis and achieves the effects of easy realization of reaction conditions, simple and efficient synthesis route, and cost reduction.

Active Publication Date: 2018-10-30
QINGDAO UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The invention discloses a method for preparing 4,4'-diphenol by one-step coupling reaction of p-chlorophenol promoted by metal samarium as catalyzed by cupric chloride in a small amount of ionic liquid solvent. This method has not been reported in domestic and foreign literatures yet.

Method used

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  • Method for synthesizing biphenol

Examples

Experimental program
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Effect test

example 1

[0016] Add 3g of newly prepared metal samarium powder and 0.26g of anhydrous copper chloride successively to the dry reaction vessel, and stir with magnetic force. Then, 3.4 g of p-chlorophenol and 10 mL of chlorobutylmethylimidazole that had been dehydrated and dried were added successively. The reaction was carried out at room temperature, the color of the reaction mixture became dark within 3 hours, and the reaction was continued for 8 hours. The reaction solution was extracted with ethyl acetate and post-processed to obtain a crude product of 4,4'-biphenol. Then it was further separated by column chromatography and purified by recrystallization to obtain 4,4'-biphenol with a yield of 87%.

[0017] White solid, melting point 280-284°C. 1 HNMR (500MHz, CDCl 3 )δppm 8.32(s, 2H), 7.41(d, J=8.8Hz, 4H), 6.89(d, J=8.4Hz, 4H).

[0018] Dichloromethane was added to the raffinate extracted with ethyl acetate, and the recovered ionic liquid was obtained after the solvent was reco...

example 2

[0020] According to the method in Example 1, copper bromide was used instead of copper chloride, and bromobutylmethylimidazole was used instead of chlorobutylmethylimidazole to obtain 4,4'-biphenyldiol with a yield of 85%.

example 3

[0022] According to the method of Example 1, after repeated use of [bmim]Cl for 5 times, the transformation of the substrate can still be achieved well, and 4,4′-biphenol was obtained with a yield of 78%.

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Abstract

The invention discloses a method for preparing 4,4'-biphenol by promoting parachlorophenol coupling reaction by virtue of metal samarium under the catalysis of cupric salt. The method comprises the following steps: mixing parachlorophenol in ionic liquid [bmim]Cl chlorobutyl methylimidazole while stirring for dissolving, and sequentially adding metal samarium powder, anhydrous copper chloride powder; carrying out a reaction system under an anhydrous condition; stirring at the room temperature until the reaction is complete; recycling ionic liquid from obtained reaction mixed liquid; and carrying out column chromatography separation on a crude product, so as to obtain 4,4'-biphenol, and carrying out recrystallization, so as to obtain a pure product, wherein the yield of the pure product is70%-95%.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, and in particular relates to a method for preparing 4,4'-diphenol in ionic liquid by using p-chlorophenol. Background technique [0002] 4,4′-Biphenol is widely used in the chemical industry to prepare engineering composite materials, polyester, polyurethane, poly Modified monomers of phenylsulfone, epoxy resin, etc., as well as rubber and latex, especially light-colored vulcanized rubber products, food packaging glue and medical latex products; in addition, 4,4'-biphenol can also be used as a dye Intermediates, can be used to synthesize photosensitive materials, etc. Among them, high-purity 4,4′-biphenyldiphenol is mainly used in thermotropic liquid crystal polymer engineering plastics. At present, my country’s high-purity 4,4′-biphenyldiphenol mainly relies on imports [Document 1. Geng Long. From LCP Recovery of high-purity 4,4′-biphenol and synthesis of 4,4′-biphenol from waste. East...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C37/18C07C39/15
CPCC07C37/18C07C39/15
Inventor 刘树峰齐燕刘永军
Owner QINGDAO UNIV OF SCI & TECH
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