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Method for direct oxidation of phenol compound to prepare p-benzoquinone compound

A technology of phenol compounds and compounds, applied in the field of direct oxidation of phenol compounds to prepare p-benzoquinone compounds, which can solve the problem of excessive catalyst consumption

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 process requires an almost stoichiometric amount of catalyst, and the amount of catalyst used is too large

Method used

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  • Method for direct oxidation of phenol compound to prepare p-benzoquinone compound
  • Method for direct oxidation of phenol compound to prepare p-benzoquinone compound
  • Method for direct oxidation of phenol compound to prepare p-benzoquinone compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Add manganese nitrate (2.5g, 10.0mmol), p-aminobenzoic acid (1.37g, 10mmol), phenol (9.4g, 100mmol) and acetonitrile (78.5g, 100mL) into a 250mL reactor, mix well, and close the reactor and filled with 30atm oxygen, stirred and heated to 60 o C, after reacting for 3 hours, cool to room temperature, take out the mixture for analysis after degassing, and obtain remaining phenol: 6.4g, p-benzoquinone: 2.9g.

[0033]

Embodiment 2-9

[0035] Manganese nitrate in embodiment 1 is replaced with different transition metal compounds, and the impact on reaction result is shown in the following table:

[0036] project Main catalyst (g, mmol) Phenol (g) p-Benzoquinone (g) 1. -- 9.2 0 2. Vanadium pentoxide (1.82, 10) 8.8 0.5 3. Copper Chloride Dihydrate (1.7, 10) 7.4 1.8 4. Iron Phthalocyanine (5.68, 10) 4.8 4.4 5. Cobalt nitrate hexahydrate (2.91, 10) 6.4 2.7 6. Ruthenium trichloride (2.1, 10) 7.1 2.2 7. Nickel acetate (1.76, 10) 4.1 4.8 8. Palladium chloride (1.77, 10) 6.1 3.2

Embodiment 10-18

[0038] The p-aminobenzoic acid in Example 1 is replaced with different amphiphilic compounds, and the impact on the reaction result is shown in the following table:

[0039] project Cocatalyst (g, mmol) Phenol (g) p-Benzoquinone (g) 1. -- 8.9 0.4 2. Ethanolamine (0.61, 10) 8.2 1.1 3. 2-Aminoacetic acid (0.75, 10) 6.0 3.1 4. 2-Aminophenylacetic acid (1.51, 10) 8.3 0.9 5. p-toluenesulfonic acid (1.72, 10) 7.1 2.1 6. 4,4'-biphenol (3.7, 10) 7.6 1.7 7. Ethyl 2-aminoacetate (1.03, 10) 5.9 3.1 8. Ethyl N,N-dimethylaminoacetate (1.32, 10) 8.6 0.6 9. Sodium octyl sulfonate (2.34, 10) 8.6 0.7

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Abstract

The invention provides a method for direct oxidation of a phenol compound to prepare a p-benzoquinone compound. The method is characterized in that: the phenol compound is taken as the raw material, oxygen or an oxygen-containing gas is used as an oxidant in a liquid medium, under the action of a transition metal compound main catalyst and an amphipathic molecule cocatalyst, and under mild conditions, highly selective preparation of the p-benzoquinone compound is carried out.

Description

[0001] [0002] Cross References to Related Applications [0003] This application is the continuation and extension of the Chinese patent application No. 201410443854.7 (submitted on September 3, 2014) entitled "A Preparation Method of p-Benzoquinone Compound". technical field [0004] The invention relates to a method for preparing a p-benzoquinone compound by direct oxidation of a phenol compound, in particular to a catalyst capable of highly selectively catalyzing a phenol compound to prepare a p-benzoquinone compound in an oxygen-containing atmosphere. Background technique [0005] p-Benzoquinone is an important raw material widely used in dyestuffs, polymer materials, fine chemicals and other fields. At present, the use of p-benzoquinone is mainly concentrated in the following aspects: 1) As a raw material for hydroquinone, dye intermediates, pesticides and rubber antioxidants; 2) As an initiator for the polymerization of acrylonitrile and vinyl acetate; 3 ) Inhibito...

Claims

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Application Information

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