Method for preparing diphenyl ketone employing biomimetic catalysis of diphenylmethane and oxygen oxidation

A technology for biomimetic catalysis of diphenylmethane and oxygen oxidation. It is applied in the preparation of carbon-based compounds, chemical instruments and methods, and the preparation of organic compounds. It can solve problems such as the difficulty of benzophenone and the large steric hindrance of diphenylmethane. , to achieve the effect of high product selectivity, reduced energy consumption, and less dosage

Active Publication Date: 2015-04-01
SUN YAT SEN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although there is a series of patents to disclose metalloporphyrin catalysis or metalloporphyrin / transition metal salt composite catalysis for the oxidation of cyclohexane, o-chlorotoluene, p-nitrotoluene, 2-methylbutane or methylcyclohexane (CN 1269343A, CN 1944395, CN 1405131, etc.), but due to the large steric hindrance of diphenylmethane, it is more difficult to be directly oxidized to generate benzophenone. At present, there is no method based on metalloporphyrin as a catalyst to directly catalyze the oxygen oxidation of diphenylmethane to prepare Benzophenone reports

Method used

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  • Method for preparing diphenyl ketone employing biomimetic catalysis of diphenylmethane and oxygen oxidation
  • Method for preparing diphenyl ketone employing biomimetic catalysis of diphenylmethane and oxygen oxidation

Examples

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Effect test

Embodiment 1

[0021] Containing 5ppm metalloporphyrin (M) with general formula (I) structure in 5mL 1 =Mn,X=H,R 1 = R 2 = R 3 = R 4 = R 5 =H) in the n-hexane solution, add 2mmol of diphenylmethane and 0.1mmol of cyclohexene, and fill with 2.0MPa of oxygen, and stir the reaction at a temperature of 50°C. After detection and analysis, the conversion rate of diphenylmethane is 22%, the selectivity of benzophenone is greater than 99%.

Embodiment 2

[0023] Containing 50ppm metalloporphyrin (M) with general formula (I) structure in 5mL 1 =Zn,X=H,R 1 = NO 2 , R 2 = R 3 = R 4 = R 5 =H) in the acetonitrile solution, add 2mmol of diphenylmethane and 1mmol of 2-methylcyclohexene, and fill with 0.2MPa of oxygen, and stir the reaction at a temperature of 100°C. After detection and analysis, the conversion of diphenylmethane The rate is 26%, and the selectivity of benzophenone is greater than 99%.

Embodiment 3

[0025] Containing 100ppm metalloporphyrin (M) with general formula (I) structure in 5mL 1 =Mg,X=H,R 3 =Cl,R 1 = R 3 = R 4 = R 5 =H) in the ethyl acetate solution, add 2mmol of diphenylmethane and 2mmol of 3-methylcyclohexene, and fill with 1MPa of oxygen, and stir the reaction at a temperature of 120°C. After detection and analysis, the content of diphenylmethane The conversion rate was 32%, and the selectivity to benzophenone was greater than 99%.

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Abstract

The invention discloses a method for preparing diphenyl ketone employing biomimetic catalysis of diphenylmethane and oxygen oxidation. The method comprises the following steps: with diphenylmethane as a raw material and oxygen as a catalyst, adding a hydrogen carrier; with a metal porphyrin compound as a catalyst, carrying out catalytic reaction under the conditions that the reaction temperature is controlled to 50-150 DEG C and the reaction pressure is controlled to 0.2-2.0MPa, so as to obtain diphenyl ketone. The method has the advantages of mild reaction condition, and good catalysis effect; and the product is high in selectivity and simple in process.

Description

technical field [0001] The invention relates to a method for preparing benzophenone, in particular to a method for preparing benzophenone by biomimetic catalyzing the oxygen oxidation of diphenylmethane. Background technique [0002] Benzophenone is an important intermediate in organic synthesis and an important additive in fine chemicals. It is widely used in organic coatings, chemically synthesized drugs, plastics, flavors and fragrances, ultraviolet absorbers for polymer materials, photosensitizers for film coatings, and pharmaceutical intermediates. Body, etc., and its derivatives are also important dye intermediates. [0003] At present, the main method of industrial production of benzophenone is nitric acid oxidation. In industry, benzyl chloride is generally used as raw material to prepare diphenylmethane, which is then oxidized with nitric acid to obtain benzophenone. This process has rich raw materials, simple equipment, and a yield of up to 84%. However, due to t...

Claims

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Application Information

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IPC IPC(8): C07C45/36C07C49/786
CPCC07C45/36C07C49/786
Inventor 纪红兵蒋军周贤太
Owner SUN YAT SEN UNIV
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