Method for preparing p-benzoquinone compound by 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: 2022-05-27
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] 94g of phenol, 0.94g of copper nitrate, 4.7g of 1-sulfopropyl-2-hydroxymethyl 3-methylimidazolium tetrafluoroborate ionic liquid, and 100ml of methanol were successively added to the 1L reactor equipped with an oil bath heating device, After the reactor was closed, 50 atm of oxygen was introduced and kept at constant pressure, heated to 90°C, stirred and reacted for 2.5 hours and then cooled to room temperature naturally. After exhausting, the catalyst was separated from the reaction system, and the reaction mixture was analyzed to obtain p-benzoquinone: 15.7g .

Embodiment 2

[0026] 94g of phenol, 0.94g of copper nitrate, 4.7g of 1-sulfopropyl-2-hydroxymethyl 3-methylimidazolium tetrafluoroborate ionic liquid, and 100ml of methanol were successively added to the 1L reactor equipped with an oil bath heating device, After the reactor was closed, 40 atm of oxygen was introduced and kept at constant pressure, heated to 80°C, stirred and reacted for 1.5 hours and then cooled to room temperature naturally. After exhausting the catalyst, the catalyst was separated from the reaction system, and the reaction mixture was analyzed to obtain p-benzoquinone: 35.9g .

Embodiment 3

[0028] 60g of phenol, 1.2g of manganese nitrate, 3.6g of 1-sulfopropyl-2-hydroxymethyl 3-methylimidazolium tetrafluoroborate ionic liquid and 100ml of methanol were successively added to the 1L reactor equipped with an oil bath heating device, After the reactor was closed, 30 atm of oxygen was introduced and kept at constant pressure, heated to 70°C, stirred and reacted for 2 hours and then cooled to room temperature naturally.

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Abstract

The invention belongs to the technical field of organic synthesis, and relates to a preparation method of p-benzoquinone compound, comprising the following steps: 1) Adding phenol compound, transition metal salt catalyst, acidic ionic liquid and solvent into a high-pressure reactor in sequence, and filling oxygen to a specified pressure, heated to a specified temperature and continuously stirred, and reacted for 0.5-5 hours; 2) After the reaction, the catalyst was separated from the reaction system and the solvent was evaporated, and the remaining solid was washed by the solvent and then stripped to obtain the p-benzoquinone compound; the method of the present invention While ensuring high conversion rate and high selectivity, it effectively reduces the amount of transition metal catalyst, and the ionic liquid catalyst can be recycled for many times, realizing a low-emission, green and environmentally friendly production process, and the economy is also greatly improved, suitable for industrialization Production.

Description

technical field [0001] The invention relates to a synthesis and preparation technology for benzoquinone compounds, in particular to a preparation method for oxidatively synthesizing p-benzoquinone compounds under a dual catalytic system. Background technique [0002] The p-benzoquinone compound has a wide range of uses in fine chemicals and other fields. It is an important raw material for dyes and pharmaceutical intermediates. It is used as the raw material of acrylonitrile and vinyl acetate polymerization initiator and oxidant. Its synthesis method has always attracted the attention of researchers. At present, the production of p-benzoquinone compounds can be divided into two categories: electrochemical methods and catalytic oxidation methods. Among them, the conversion rate of benzene by electrochemical method is low and the reaction time is long; while catalytic oxidation method mainly includes aniline oxidation method and phenol oxidation method. The aniline oxidation...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C46/08C07C50/04B01J31/28B01J31/32B01J31/04
CPCC07C46/08B01J31/28B01J31/32B01J31/04B01J31/0285B01J35/0006B01J27/25B01J27/13B01J27/122B01J2231/70C07C50/04Y02P20/584Y02P20/54
Inventor 吴钊陈琛江洋洋孔京黄伟张楚璠
Owner CHINA PETROLEUM & CHEM CORP
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