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Preparation method of p-benzoquinone compound

A technology of phenol compounds and compounds, which is applied in the field of preparation of p-benzoquinone compounds, and can solve the problems of excessive catalyst consumption and the like

Inactive Publication Date: 2015-04-29
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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  • Preparation method of p-benzoquinone compound
  • Preparation method of p-benzoquinone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] In a 250mL reactor, add cobalt nitrate hexahydrate (2.91g, 10.0mmol), N,N-diethylethoxyamine (1.18g, 10mmol), phenol (9.4g, 100mmol) and acetonitrile (78.5g, 100mL ), after mixing evenly, close the reactor and fill it with 30atm oxygen, stir and heat 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: 5.4g, p-benzoquinone: 3.8g.

Embodiment 2-9

[0030] project Main catalyst (g, mmol) Phenol (g) p-Benzoquinone (g) 1. -- 9.2 0 2. Vanadium pentoxide (1.82, 10) 5.7 2.6 3. Manganese sulfate monohydrate (1.69, 10) 4.4 4.8 4. Iron Phthalocyanine (5.68, 10) 5.8 3.4 5. Copper iodide (1.9, 10) 6.9 2.3 6. Ruthenium trichloride (2.1, 10) 3.5 5.7 7. Rhodium trichloride hydrate (2.1, 10) 5.7 2.4 8. Potassium chloroplatinate (4.86, 10) 5.0 4.0

Embodiment 10-18

[0032] project Cocatalyst (g, mmol) Phenol (g) p-Benzoquinone (g) 1. -- 8.4 0.9 2. N,N-Dimethylmethoxylamine (0.75, 10) 6.0 3.1 3. N,N-Dipropylpropoxylamine (1.59, 10) 7.3 2.0 4. N,N-Diisopropylisopropoxyamine (1.59, 10) 3.1 6.0 5. N,N-dioctyloctyloxyamine (3.7, 10) 6.5 2.7 6. Hydroxylamine (0.33, 10) 6.9 2.1 7. 2,2,6,6-Tetramethylpiperidine-N-hydroxyl (1.6, 10) 8.4 0.9 8. 4-Hydroxy-2,2,6,6-tetramethylpiperidine-N-hydroxyl (1.73, 10) 8.9 0.3 9. N,N-Diphenylmethoxylamine (2.0, 10) 5.1 4.1

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Abstract

The invention provides a preparation method of a p-benzoquinone compound. The preparation method is characterized in that the p-benzoquinone compound is prepared from a phenol compound with high selectivity under a mild condition by taking oxygen or oxygen-containing gas in a liquid solvent as an oxidizing agent in the presence of a transitional metal compound serving as a main catalyst and N-substituted hydrocarbon oxy-compound serving as an assistant catalyst.

Description

technical field [0001] The invention relates to a preparation method of a p-benzoquinone compound, in particular to a catalyst capable of highly selectively catalyzing a phenol compound to prepare a p-benzoquinone compound under an oxygen-containing atmosphere. Background technique [0002] P-benzoquinone, namely benzoquinone and 1,4-benzoquinone, is an important chemical raw material widely used in analysis, dyes, polymer materials, organic synthesis, fine chemicals and other fields. At present, p-benzoquinone is mainly used in the manufacture of hydroquinone and dye intermediates, rubber antioxidants, acrylonitrile and vinyl acetate polymerization initiators, and chlorinating agents. It is also used as styrene, vinyl acetate, methyl methacrylate It is a polymerization inhibitor for monomers such as esters and unsaturated polyester resins, as well as an initiator for the polymerization of acrylonitrile and vinyl acetate. It is also used as an antioxidant for natural ru...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C46/08C07C50/04C07C50/02
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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