Method for preparing p-benzoquinone compound through selective catalytic oxidation of phenol compound

A technology for selective catalytic oxidation and phenolic compounds, applied in the preparation of oxidized quinones, organic chemistry, etc., can solve the problem of excessive catalyst usage

Inactive Publication Date: 2015-01-21
QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above method requires almost stoichiometric catalyst, and the amount of catalyst is too large

Method used

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  • Method for preparing p-benzoquinone compound through selective catalytic oxidation of phenol compound
  • Method for preparing p-benzoquinone compound through selective catalytic oxidation of phenol compound
  • Method for preparing p-benzoquinone compound through selective catalytic oxidation of phenol compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Add cobalt nitrate hexahydrate (2.91g, 10.0mmol), triphenylphosphine (2.62g, 10mmol), phenol (9.4g, 100mmol) and DMF (94.0g, 100mL) into a 250mL reactor, mix well, and close Reactor and filled with 20atm oxygen, stirred and heated to 60 o C, after reacting for 1 hour, cool to room temperature, take out the mixture for analysis after degassing, and obtain remaining phenol: 7.4g, p-benzoquinone: 1.9g.

[0035]

Embodiment 2-8

[0037] project Main catalyst (g, mmol) Phenol (g) p-Benzoquinone (g) 1. -- 9.3 0 2. Vanadium nitrate (1.82, 10) 8.3 0.6 3. Ferric chloride (1.62, 10) 8.6 0.6 4. Manganese acetate (1.73, 10) 5.7 3.4 5. Ruthenium trichloride (2.07, 10) 5.1 4.0 6. Cerium sulfate tetrahydrate (4.04, 10) 6.8 2.3 7. Palladium chloride (1.77, 10) 7.2 2.0

Embodiment 9-17

[0039] project Cocatalyst (g, mmol) Phenol (g) p-Benzoquinone (g) 1. -- 8.7 0.4 2. Triphenylamine (2.45, 10) 8.2 0.9 3. Triethylamine (1.01, 10) 8.5 0.6 4. Trioctylamine (3.53, 10) 8.6 0.5 5. Dibenzylamine (1.97, 10) 8.1 1.1 6. Chlorotrimethylsilane (1.08, 10) 8.3 0.6 7. Isopropylpyridine (1.21, 10) 6.2 2.5 8. Methylquinoline (1.4, 10) 6.5 2.5 9. Diphenyl-2-pyridylphosphine (2.63, 10) 7.6 1.6

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PUM

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Abstract

The invention provides a method for preparing a p-benzoquinone compound through selective catalytic oxidation of a phenol compound. The method is characterized in that the p-benzoquinone compound is highly selectively prepared through a reaction of a raw material the phenol compound in a liquid medium under mild conditions under the action of a transition metal compound primary catalyst and a stellate molecule cocatalyst with oxygen or an oxygen-containing gas as an oxidant.

Description

[0001] [0002] Cross References to Related Applications [0003] The applications are entitled "A Preparation Method for P-Benzoquinone Compounds" (Application No.: 201410443854.7, submitted on September 3, 2014) and "A Method for Preparing P-Benzoquinone Compounds by Direct Oxidation of Phenol Compounds" (Application No. No.: 201410449008.6, submitted on September 5, 2014), the extension and supplement of the Chinese patent, and the former has priority over the latter. [0004] technical field [0005] The invention relates to a method for selectively catalytically oxidizing phenol compounds to prepare p-benzoquinone compounds, in particular to a catalyst capable of highly selectively catalyzing phenol compounds to prepare p-benzoquinone compounds in an oxygen-containing atmosphere. [0006] Background technique [0007] P-benzoquinone compounds are important raw materials, intermediates and auxiliary agents for the synthesis of pesticides, dyes, rubber, plastics, and f...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C50/04C07C50/02C07C46/08
CPCC07C46/08C07C50/02C07C50/04
Inventor 安增建万晓波
Owner QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
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