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A kind of photochemical oxidation method of alcohol dehydrogenation to aldehydes and ketones

A technology of aldehydes and ketones and photocatalysts, which is applied in the field of photochemical organic synthesis, can solve the problem of less application of selective oxidation of organic substances, and achieve the effect of high yield

Active Publication Date: 2018-06-29
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the strong oxidation of hydroxyl radicals and the combined action of oxygen, the TiO in the water phase 2 The semiconductor photocatalytic system will directly lead to the deep oxidation of organic matter, so TiO 2 Photocatalytic selective oxidation of organic compounds has few applications

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Add platinum-loaded titanium dioxide and 1-hexanol in a molar ratio of 1:1 (0.02mmol:0.02mmol) into a temperature-controlled transparent reaction bottle filled with acetonitrile and control the temperature at 25°C, so that platinum-loaded titanium dioxide is in the reaction system The concentration of 1-hexanol in the reaction system is 10g / L, the concentration of 1-hexanol in the reaction system is 0.5mmol / L, airtightly seal, feed inert gas, and make the inert gas pressure in the temperature-controlled transparent reaction bottle be 0.01MPa, control Stir at 25°C for half an hour to make the adsorption of 1-hexanol reach equilibrium, then irradiate the temperature-controlled transparent reaction bottle with a 300-watt xenon lamp and keep the temperature at 25°C, stop the reaction after 1 hour of irradiation, and the reaction product is mainly 1-hexanal , with a selectivity of 73% and a yield of 74%.

Embodiment 2

[0039] Add palladium-supported titanium dioxide and 2-methyl-1-pentanol in a molar ratio of 1:2 (0.01mmol:0.02mmol) into a temperature-controlled transparent reaction bottle filled with benzotrifluoride and control the temperature at 25°C, so that the loaded The concentration of palladium-titanium dioxide in the reaction system is 1g / L, and the concentration of 2-methyl-1-pentanol in the reaction system is 2mmol / L, and the airtight seal is passed into an inert gas, and the temperature-controlled transparent reaction flask is The inert gas pressure is 0.01MPa, the temperature is controlled at 25°C and stirred for half an hour to allow the adsorption of 2-methyl-1-propanol to reach equilibrium, and then a 300-watt xenon lamp is used to irradiate the temperature-controlled transparent reaction bottle and keep the temperature at 25°C. The reaction was stopped after one hour, and the reaction product was mainly 2-methyl-1-pentanal with a selectivity of 85% and a yield of 90%.

Embodiment 3

[0041] Add gold-loaded titanium dioxide and 3-phenyl-1-butanol into a temperature-controlled transparent reaction bottle filled with DMF at a molar ratio of 1:10 (0.002mmol:0.02mmol), so that the gold-loaded titanium dioxide is in the reaction system. The concentration of 3-phenyl-1-butanol in the reaction system is 2g / L, and the concentration of 3-phenyl-1-butanol in the reaction system is 5mmol / L, and the seal is sealed, and an inert gas is introduced, and the pressure of the inert gas in the temperature-controlled transparent reaction bottle is 0.01MPa , control the temperature at 25°C and stir for half an hour to allow the adsorption of 3-phenyl-1-butanol to reach equilibrium, then irradiate the temperature-controlled transparent reaction bottle with sunlight and keep the temperature at 25°C, stop the reaction after 3 hours of irradiation, and the reaction product Mainly 3-phenyl-1-butyraldehyde with a selectivity of 99% and a yield of 92%.

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Abstract

The invention belongs to the field of photochemical organic synthesis and particularly relates to a photochemical oxidation method for producing aldehyde or ketone by dehydrogenizing alcohol. The method comprises the step that with the existence of light and a photocatalyst, the alcohol is subjected to a dehydrogenation reaction in solvent, so that the aldehyde or ketone is obtained. According to the method to synthesize the aldehyde or ketone selectively by dehydrogenizing the alcohol by means of the photocatalyst, under the induction of ultraviolet light or visible light and under the action of the photocatalyst, two hydrogen groups are removed from the alcohol dissolved in the organic solvent, so that the aldehyde or ketone is obtained, and by controlling reaction time, the dehydrogenation product aldehyde or ketone with higher yield can be obtained. After the reaction, aldoketones compounds high in selectivity and hydrogen are obtained, and selectivity can reach 99% and above to the maximum.

Description

technical field [0001] The invention belongs to the technical field of photochemical organic synthesis, and in particular relates to a photochemical oxidation method for producing aldehydes and ketones through dehydrogenation of alcohol compounds. Background technique [0002] In industry, aldehydes and ketones are widely used as important chemical intermediates in food, pharmaceuticals, spices, pesticides and herbicides. Its conventional preparation method is obtained by equivalent oxidation and oxidation of alcohol. However, these equivalent oxidants usually cause environmental pollution because they contain high-valent chromium, organic sulfur, and organic iodine reagents, and the production cost is also relatively expensive. Therefore, there is an urgent need to develop a green catalytic method for preparing aldehydes and ketones from alcohols. [0003] In recent years, TiO 2 The research on semiconductor photocatalysis has made great progress. Using ultraviolet light...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B41/06C07C47/02C07C47/228C07C45/29C07C271/18C07C269/06C01B3/22
CPCC01B3/22C01B2203/0277C07B41/06C07C45/29C07C269/06C07C47/02C07C47/228C07C271/18
Inventor 赵进才马东阁刘阿楠陈春城籍宏伟
Owner INST OF CHEM CHINESE ACAD OF SCI