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Reduction method of diphenyl methyl ketone kind compound

A technology for benzophenones and compounds, which is applied in the field of reduction reaction of benzophenones, can solve the problems of no industrial use value, harsh reaction conditions, high operational danger and the like, and achieves easy control and simple reaction conditions. , the effect of wide application prospects

Inactive Publication Date: 2006-11-29
FUDAN UNIV
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  • Abstract
  • Description
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  • Application Information

AI Technical Summary

Problems solved by technology

[0009] However, these reactions have their limitations, the reaction conditions are harsh, the reagents are highly toxic, the cost is too high, the operation is dangerous, and there is no industrial use value.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Embodiment 1: in the three-necked bottle of 500 milliliters, install thermometer, stirrer, add benzophenone (10 millimoles, 1.82 milligrams), Ni-Al alloy (2g), water (50 milliliters), then start stirring and heating to 90°C. A 1% aqueous potassium hydroxide solution (50 ml) was added dropwise over half an hour. Control the reaction temperature to be 90°C-100°C. After the dropwise addition of 1% potassium hydroxide aqueous solution was completed, stirring was continued at this temperature for 8 hours. Then it was cooled to room temperature, filtered, and the insoluble matter was removed by filtration, the aqueous solution was extracted with ethyl acetate, the organic layer was dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure. The concentrated product was then analyzed by gas chromatography, and the conversion rate of benzophenone was 100%. The product composition is dicyclohexylmethane / benzylcyclohexane / diphenylmethane=7.4 / 29.5 / 61.3...

Embodiment 2

[0018] Embodiment 2: in the three-necked bottle of 500 milliliters, install thermometer, stirrer, add benzophenone (10 millimoles, 1.82 milligrams), Ni-Al alloy (4g), water (55 milliliters), then start stirring and heating to 60°C. A 1% aqueous potassium hydroxide solution (50 ml) was added dropwise over 1 hour. Control reaction temperature is 60 ℃-70 ℃. After the dropwise addition of 1% potassium hydroxide aqueous solution was completed, stirring was continued at this temperature for 9 hours. Then it was cooled to room temperature, filtered, and the insoluble matter was removed by filtration, the aqueous solution was extracted with ethyl acetate, the organic layer was dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure. The concentrated product was then analyzed by gas chromatography, and the conversion rate of benzophenone was 100%. The product composition is dicyclohexylmethane / benzylcyclohexane / diphenylmethane=9.4 / 46.3 / 38.8 (gas chromato...

Embodiment 3

[0019] Embodiment 3: in the three-necked flask of 500 milliliters, install thermometer, stirrer, add benzophenone (10 millimoles, 1.82 milligrams), Ni-Al alloy (6g), water (60 milliliters), then start stirring and heating to 50°C. A 1% aqueous potassium hydroxide solution (50 ml) was added dropwise over 1 hour. Control reaction temperature is 50 ℃-60 ℃. After the dropwise addition of 1% aqueous potassium hydroxide solution was completed, stirring was continued at this temperature for 7 hours. Then it was cooled to room temperature, filtered, and the insoluble matter was removed by filtration, the aqueous solution was extracted with ethyl acetate, the organic layer was dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure. The concentrated product was then analyzed by gas chromatography, and the conversion rate of benzophenone was 100%. The product composition is dicyclohexylmethane / benzylcyclohexane / diphenylmethane=15.0 / 55.9 / 26.3 (gas chromato...

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Abstract

A reducing process for diphenyl methanone compounds is a great improvement to famous Clemmensen reduction reaction and Wolf-Kishner-Huang reduction reaction. It includes such steps as dripping the aqueous solution of alkali into the mixture of diphenyl methanone compound, Ni-Al alloy and water under stirring and heating, reaction between the aqueous solution of alkali and Ni-Al alloy to generate H2, and hydroreducing the diphenyl methanone to generate diphenyl methane whose carbonyl has been reduced.

Description

technical field [0001] The invention belongs to the technical field of organic compounds, in particular to the reduction reaction of benzophenone compounds. Background of the invention [0002] The well-known Clemmensen reduction reaction in organic reactions, the Wolf-Kishner-Huang reduction reaction is the reaction of carbonyl to methylene. Generally harsh reaction conditions are required. It is an important topic in the research of organic chemistry to seek an improved method for the Wolf-Kishner-Huang reduction reaction of the Clemmensen reduction reaction and to explore the reaction conditions for reducing carbonyl to methylene. [0003] As a representative of carbonyl compounds, benzophenone compounds are important chemical products, which are of great significance for their deep processing and manufacturing of high value-added chemical intermediates. [0004] So far, the main processing methods are: [0005] (1) Clemmensen Reduction [Clemmensen Reduction, (a) E. Cl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C5/02C07C5/10C07C5/11C07C13/18C07C13/19C07C15/02C07C15/16
Inventor 刘国斌朱佳达戴鹭何鸿洁杨虹洁高翔李妙葵
Owner FUDAN UNIV
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