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Catalytic oxidation synthesis method of diaryl ketone compound

A technology of diaryl ketone and synthesis method, which is applied in the field of catalytic oxidation synthesis of diaryl ketone compounds, can solve the problems of complicated operation, difficult separation, equipment corrosion, etc., and achieves simplified operation steps, convenient and safe operation, The effect of mild reaction conditions

Inactive Publication Date: 2015-10-21
ZHEJIANG UNIV OF TECH +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The acylation method mostly uses aluminum trichloride as a catalyst, and reacts with substituted benzene and substituted benzoyl chloride as raw materials. Because there are many isomers in the target product, it is difficult to separate, and a large amount of waste acid is generated during the reaction process, which corrodes production Equipment; the carbonylation method generally reacts under high temperature and high pressure, and the operation is complicated, and one of the raw materials used is carbon monoxide, which is more dangerous; the nitric acid oxidation method uses nitric acid to oxidize diphenylmethane compounds, and the reaction time of this method is long. Equipment Severe corrosion, difficult product post-processing

Method used

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  • Catalytic oxidation synthesis method of diaryl ketone compound
  • Catalytic oxidation synthesis method of diaryl ketone compound
  • Catalytic oxidation synthesis method of diaryl ketone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment 1: the preparation of benzophenone (formula (2-1))

[0030] In a 200mL Teflon-lined autoclave, add benzhydryl acetate (formula (1-1), 0.45g, 2mmol), 1,1,2,2-tetrachloroethane (8ml), DDQ (0.14g, 0.6mmol), TBN (41.2mg, 0.4mmol), seal the autoclave, fill it with oxygen until the pressure gauge is 0.3MPa, put the autoclave into an oil bath preheated to 130°C, and react for 3h. After lowering the temperature and carefully releasing the pressure, the reaction solution was sampled and analyzed by gas chromatography (GC), the conversion rate was 100%, and the product selectivity was 99%. The reaction liquid was evaporated to remove the solvent under reduced pressure, passed through a silica gel column, and a mixture of ethyl acetate and petroleum ether with a volume ratio of 1:200 was used as the eluent to collect the eluate containing the target compound, evaporated to remove the solvent, and then dried to obtain two Benzophenone 0.35g, the isolated yield of benzop...

Embodiment 2

[0031] Embodiment 2: the preparation of phenyl o-tolyl ketone (formula (2-2))

[0032] In a 200mL polytetrafluoroethylene-lined autoclave, add phenyl-o-tolylmethanol acetate (formula (1-2), 0.48g, 2mmol), 1,1,2,2-tetrachloroethane (8ml ), DDQ (0.14g, 0.6mmol), TBN (41.2mg, 0.4mmol), a closed autoclave, filled with oxygen until the pressure gauge is 0.3MPa, put the autoclave into an oil bath heated to 130°C in advance, and react 6h. After the temperature was lowered and the pressure was carefully released, the reaction solution was sampled and analyzed by gas chromatography (GC), the conversion rate was 97%, and the product selectivity was 99%. The reaction solution was evaporated to remove the solvent under reduced pressure, passed through a silica gel column, and the mixture of ethyl acetate and petroleum ether with a volume ratio of 1:200 was used as the eluent to collect the eluate containing the target compound, evaporated to remove the solvent, and then dried to obtain b...

Embodiment 3

[0033] Embodiment 3: the preparation of phenyl m-tolyl ketone (formula (2-3))

[0034] In a 200mL polytetrafluoroethylene-lined autoclave, add phenyl-m-tolylmethanol acetate (formula (1-3), 0.48g, 2mmol), 1,1,2,2-tetrachloroethane (8ml ), DDQ (0.14g, 0.6mmol), TBN (41.2mg, 0.4mmol), a closed autoclave, filled with oxygen until the pressure gauge is 0.3MPa, put the autoclave into an oil bath heated to 130°C in advance, and react 3h. After lowering the temperature and carefully releasing the pressure, the reaction solution was sampled and analyzed by gas chromatography (GC), the conversion rate was 100%, and the product selectivity was 99%. The reaction solution was evaporated to remove the solvent under reduced pressure, passed through a silica gel column, and the mixture of ethyl acetate and petroleum ether with a volume ratio of 1:200 was used as the eluent to collect the eluate containing the target compound, evaporated to remove the solvent, and then dried to obtain benzen...

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Abstract

The invention provides a catalytic oxidation synthesis method of a diaryl ketone compound. In an organic solvent, ester derivatives of diaryl methanol are used as reaction substrates, DDQ and TBN are used as catalysts, oxygen is used as an oxidant, so as to react for 1 to 12 h under the conditions of oxygen pressure of 0.1 to 0.4 MPa and temperature of 110 to 140 DEG C, and post processing is performed on reaction liquid, so as to obtain a product of the diaryl ketone compound; structural formulas of the ester derivatives of the diaryl methanol as the reaction substrates are shown in the formulas (V), (VI), (VII) or (VIII), and structural formulas of products which are correspondingly obtained one by one are shown in the formulas (I), (II), (III) or (IV). The catalytic oxidation synthesis method has the advantages of simplicity, convenience and safety in operation, mild reaction condition, high product selectivity and environmental friendliness.

Description

(1) Technical field [0001] The invention relates to a catalytic oxidation synthesis method of diaryl ketone compounds. (2) Background technology [0002] Diaryl ketones have special physical, chemical and biological properties. These compounds can be used as intermediates for drug synthesis, monomers for the synthesis of high-performance engineering plastics, and ultraviolet absorbers. They have been widely used in plastics, cosmetics, Coatings, agrochemicals and electronics industries and other fields. Among the diaryl ketone compounds, benzophenone is the simplest in structure. This compound is a transparent crystal at normal temperature and pressure. It is an important intermediate in organic synthesis and an important additive in fine chemicals. It is widely used in organic coatings and medicines. Synthesis, plastics, flavors and fragrances, UV absorbers for polymer materials, photosensitizers for film coatings, etc. In addition, diaryl ketone compounds are the most wi...

Claims

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Application Information

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IPC IPC(8): C07B41/06C07C45/51C07C49/786C07C49/784C07C49/813C07C49/84C07D213/50C07D333/22
Inventor 沈振陆马佳颀胡志明李美超胡信全莫卫民
Owner ZHEJIANG UNIV OF TECH
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