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Method for preparing p-benzoquinone compound by using dual-catalytic system

A technology of phenol compound and p-benzoquinone, which is applied in the preparation field of oxidative synthesis of p-benzoquinone compound under a dual catalyst system, can solve the problems of large amount of transition metal catalyst, non-recyclable catalyst, and affecting the economic benefits of mass production of products, etc. Achieve the effect of green production process, good catalytic activity and stability, and save production cost

Active Publication Date: 2020-03-24
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] There are researches disclosing the method of oxidizing phenolic compound to p-benzoquinone under the condition of oxygen or oxygen-containing gas, such as CN104844439A, CN104557487A, CN104292096A and CN104292095A, and propose a method in which a transition metal compound is used as the main catalyst and an N-substituted alkoxy compound , amphiphilic molecules or star-shaped molecules as co-catalysts in the catalytic system, but the amount of transition metal catalysts in this system is still relatively large (the molar ratio of the main catalyst to phenol = 1:10), and the catalyst cannot be recycled, directly Affected the economic benefits of mass production of products

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Add 94g of phenol, 0.94g of copper nitrate, 4.7g of 1-sulfopropyl-2-hydroxymethyl 3-methylimidazolium tetrafluoroborate ionic liquid, and 100ml of methanol into a 1L reactor equipped with an oil bath heating device in sequence, After closing the reactor, feed 50atm oxygen and keep constant pressure, heat to 90°C, stir for 2.5 hours, then cool down to room temperature naturally, after exhausting, the catalyst is separated from the reaction system, and the reaction mixture is analyzed to obtain p-benzoquinone: 15.7g .

Embodiment 2

[0026] Add 94g of phenol, 0.94g of copper nitrate, 4.7g of 1-sulfopropyl-2-hydroxymethyl 3-methylimidazolium tetrafluoroborate ionic liquid, and 100ml of methanol into a 1L reactor equipped with an oil bath heating device in sequence, After closing the reactor, feed 40 atm of oxygen and keep constant pressure, heat to 80°C, stir for 1.5 hours, then cool down to room temperature naturally, after exhausting, the catalyst is separated from the reaction system, and the reaction mixture is analyzed to obtain p-benzoquinone: 35.9g .

Embodiment 3

[0028] Add 60g of phenol, 1.2g of manganese nitrate, 3.6g of 1-sulfopropyl-2-hydroxymethyl 3-methylimidazolium tetrafluoroborate ionic liquid, and 100ml of methanol into a 1L reactor equipped with an oil bath heating device in sequence, After closing the reactor, feed 30 atm oxygen and keep constant pressure, heat to 70°C, stir and react for 2 hours, then cool down to room temperature naturally, remove the catalyst from the reaction system after degassing, analyze the reaction mixture, and obtain p-benzoquinone: 40.6g.

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PUM

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Abstract

The invention belongs to the technical field of organic synthesis, and relates to a p-benzoquinone compound preparation method, which comprises: 1) sequentially adding a phenol compound, a transitionmetal salt catalyst, an acidic ionic liquid and a solvent to a high pressure reaction kettle, introducing oxygen to achieve a specified pressure, heating to a specified temperature, continuously stirring, and carrying out a reaction for 0.5-5 h; and 2) after the reaction is finished, separating the catalyst from the reaction system, evaporating the solvent, washing the residual solid with a solvent, and carrying out steam stripping to obtain the p-benzoquinone compound. According to the method disclosed by the invention, high conversion rate and high selectivity are ensured, the dosage of thetransition metal catalyst is effectively reduced, the ionic liquid catalyst can be recycled multiple times, a low-emission and environment-friendly production process is realized, the economy is alsogreatly improved, and the method is suitable for industrial production.

Description

technical field [0001] The invention relates to a synthesis and preparation technology of benzoquinone compounds, in particular to a preparation method for oxidatively synthesizing p-benzoquinone compounds under a dual catalyst system. Background technique [0002] P-benzoquinone compounds are widely used in fine chemical industry and other fields. They are important raw materials for dyes and pharmaceutical intermediates. They are also used for the preparation of hydroquinone, developer for negative films, polymerization inhibitors for polymerization reactions, and rubber antioxidants. It is used as a raw material for acrylonitrile and vinyl acetate polymerization initiators and oxidants. Its synthesis method has always been the concern of researchers. At present, the production of p-benzoquinone compounds can be divided into two categories: electrochemical method and catalytic oxidation method. Among them, the conversion rate of benzene in the electrochemical method is l...

Claims

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Application Information

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IPC IPC(8): C07C46/08C07C50/04B01J31/28B01J31/32B01J31/04
CPCC07C46/08B01J31/28B01J31/32B01J31/04B01J31/0285B01J27/25B01J27/13B01J27/122B01J2231/70B01J35/19C07C50/04Y02P20/584Y02P20/54
Inventor 吴钊陈琛江洋洋孔京黄伟张楚璠
Owner CHINA PETROLEUM & CHEM CORP
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