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Method for synthesizing benzoquinone compound through catalytic oxidation of phenol compound

A phenolic compound, catalytic oxidation technology, applied in the preparation of quinone oxide, organic chemistry, etc., to achieve the effects of environmental friendliness, mild reaction conditions and good selectivity

Inactive Publication Date: 2016-11-23
INST OF METAL RESEARCH - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there is no public report on the selective catalytic oxidation of phenolic compounds to prepare corresponding benzoquinones using carbon materials such as onion carbon as heterogeneous catalysts.

Method used

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  • Method for synthesizing benzoquinone compound through catalytic oxidation of phenol compound
  • Method for synthesizing benzoquinone compound through catalytic oxidation of phenol compound
  • Method for synthesizing benzoquinone compound through catalytic oxidation of phenol compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add 0.1 mmol of 2,3,6-trimethylphenol, benzotrifluoride, solid catalyst onion carbon, and oxidant tert-butyl hydroperoxide into a closed glass container for mixing, and then ultrasonicate to form a suspension (5 min). Among them, benzotrifluoride is 5ml, and the molar ratio of onion carbon to 2,3,6-trimethyl-p-phenol is 6.66:1. The molar ratio of oxidizing agent to 2,3,6-trimethyl-p-phenol is 3.6:1. The mixed suspension was placed in an oil bath and heated to 80 °C under stirring. After reacting for 12 hours, take out reaction vessel from oil bath, cool to room temperature, pour out liquid-solid mixture, it is filtered, obtain solid catalyst and remaining liquid phase mixture, add a certain amount of internal standard (ethylbenzene), to This liquid phase mixture is analyzed, and the retention time ( figure 1 ) are: tert-butanol 6.9min, trifluorotoluene 7.4min, 2,3,6-trimethyl-p-benzoquinone 9.91min, 2,3,6-trimethylphenol 9.98min, ethylbenzene 8.4min. The selectivity ...

Embodiment 2

[0027] Add 0.1 mmol of 2,3,6-trimethylphenol, benzotrifluoride, solid catalyst onion carbon, and oxidant tert-butyl hydroperoxide into a closed glass container for mixing, and then ultrasonicate to form a suspension (5 min). Among them, benzotrifluoride is 5ml, and the molar ratio of onion carbon to 2,3,6-trimethylphenol is 6.66:1. The molar ratio of oxidizing agent to 2,3,6-trimethylphenol is 3.6:1. The mixed suspension was placed in an oil bath and heated to the temperature shown in Table 1 under stirring conditions. After reacting for 12 hours, take out reaction vessel from oil bath, cool to room temperature, pour out liquid-solid mixture, it is filtered, obtain solid catalyst and remaining liquid phase mixture, add a certain amount of internal standard (ethylbenzene), to The liquid phase mixture is analyzed, and the conversion rate of 2,3,6-trimethylphenol and the selectivity results of 2,3,6-trimethyl-p-benzoquinone are shown in Table 1. It can be seen that the temperatu...

Embodiment 3

[0032]Add 0.1 mmol of 2,3,6-trimethylphenol, trifluorotoluene, solid catalyst onion carbon, and oxidant tert-butyl hydroperoxide into a closed glass container and mix them, and form a suspension under ultrasonic treatment (5 minutes). Among them, benzotrifluoride is 5ml, and the molar ratio of onion carbon to 2,3,6-trimethylphenol is 6.66:1. The molar ratio of oxidizing agent to 2,3,6-trimethylphenol is 3.6:1. The mixed suspension was placed in an oil bath and heated to 80 °C under stirring. Reaction time to Table 2, take out reaction vessel from oil bath, cool to room temperature, pour out liquid-solid mixture, it is filtered, obtain solid catalyst and remaining liquid phase mixture, add a certain amount of internal standard (ethylbenzene), The liquid phase mixture is analyzed, and the conversion rate of 2,3,6-trimethylphenol and the selectivity of 2,3,6-trimethyl-p-benzoquinone are measured. The results are shown in Table 2. It can be seen that prolonging the time is benefi...

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Abstract

The present invention discloses a method for synthesizing a benzoquinone compound through catalytic oxidation of a phenol compound, and belongs to the technical field of synthesis of benzoquinone compounds. The method comprises: adding a reactant phenol compound, a solvent, a solid catalyst (onion carbon and the like) and an oxidant t-butyl hydroperoxide into a reactor, carrying out ultrasonic treatment to form a suspension, heating the suspension to a temperature of 70-100 DEG C, carrying out a reaction for 2-16 h, separating the reaction mixture to obtain a solid catalyst and a liquid mixture containing the benzoquinone compound, and carrying out separation purification on the liquid mixture to obtain the product benzoquinone compound. According to the present invention, the operation process is simple, and the used non-metal catalyst has characteristics of no corrosion, low price, green environmental protection and recycling; and the methyl phenol conversion rate is high, and the selectivity of the target product methyl-p-benzoquinone is good.

Description

technical field [0001] The invention relates to the technical field of synthesis of benzoquinone compounds, in particular to a method for synthesizing benzoquinone compounds by catalytic oxidation of phenol compounds. Background technique [0002] Benzoquinone compounds are not only widely used in medical treatment, chemical industry, biological medicine, etc., but also an important organic intermediate. For example, the common 2,3,6-trimethyl-p-benzoquinone is the main intermediate of vitamin E. This type of p-benzoquinone has been produced abroad, while the 2,3,6-trimethyl-p-benzoquinone needed in China mainly relies on imports. 2,6-Dimethyl-1,4-p-benzoquinone is a highly active antioxidant with anti-aging and other medical effects. The current reports on the catalytic reaction of benzoquinones generally involve two methods: one is the direct oxidation of phenols. The U.S. patent application with the publication number US4360469 provides a method for preparing p-benzoqu...

Claims

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Application Information

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IPC IPC(8): C07C46/06C07C50/02C07C50/10
CPCC07C46/06C07C50/02C07C50/10
Inventor 苏党生林扬明
Owner INST OF METAL RESEARCH - CHINESE ACAD OF SCI
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