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A Visible Light-Catalytic Oxidative Cleavage Method for Carbon-Carbon Bonds

A technology of catalytic oxidation and visible light, which is applied in chemical instruments and methods, catalyst activation/preparation, preparation of organic compounds, etc., can solve the problems of harsh reaction conditions and high cost, and achieve mild reaction conditions, easy separation, and simple preparation methods Effect

Active Publication Date: 2021-08-31
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The solid photocatalyst used in the present invention is cheap and easy to separate from the reaction system, which overcomes the shortcomings of traditional catalysts such as high cost and harsh reaction conditions

Method used

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  • A Visible Light-Catalytic Oxidative Cleavage Method for Carbon-Carbon Bonds
  • A Visible Light-Catalytic Oxidative Cleavage Method for Carbon-Carbon Bonds
  • A Visible Light-Catalytic Oxidative Cleavage Method for Carbon-Carbon Bonds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] In a 5mL quartz photoreaction tube, add 0.05mmol 1,2-diphenylethanol, 5mg V-P25-G-VTO (V load is 4wt%), magneton, and add 1mL solvent acetonitrile (substrate concentration is 0.05mol / L). Oxygen replaces the upper air in the reaction tube, seals it and places it in an integrated photoreaction device at a speed of 500r / min, the light source is a visible light LED lamp with a single wavelength of 455nm, the temperature is kept at 40 degrees, and the reaction is 6h. After the reaction, the product was detected by gas chromatography-mass spectrometry, and quantified by high performance liquid chromatography. The conversion rate of the substrate and the yield of the product are shown in Table 1.

Embodiment 2

[0024] In a 5mL quartz photoreaction tube, add 0.05mmol 1,2-diphenylethanol, 5mg V-P25-G-VTO (V loading is 4wt%), magneton, and add 1mL solvent acetone (substrate concentration is 0.05mol / L). Oxygen replaces the upper air in the reaction tube, seals it and places it in an integrated photoreaction device at a speed of 500r / min, the light source is a visible light LED lamp with a single wavelength of 455nm, the temperature is kept at 40 degrees, and the reaction is 6h. After the reaction, the product was detected by gas chromatography-mass spectrometry, and quantified by high performance liquid chromatography. The conversion rate of the substrate and the yield of the product are shown in Table 1.

Embodiment 3

[0026] In a 5 mL quartz photoreaction tube, add 0.05 mmol 1,2-diphenylethanol, 5 mg V-P25-G-VTO (V load is 4 wt%), magneton, and add 1 mL solvent 1,2-diphenyl Ethyl chloride (substrate concentration is 0.05mol / L). Oxygen replaces the upper air in the reaction tube, seals it and places it in an integrated photoreaction device at a speed of 500r / min, the light source is a visible light LED lamp with a single wavelength of 455nm, the temperature is kept at 40 degrees, and the reaction is 6h. After the reaction, the product was detected by gas chromatography-mass spectrometry, and quantified by high performance liquid chromatography. The conversion rate of the substrate and the yield of the product are shown in Table 1.

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Abstract

The invention relates to a method for catalyzing and oxidizing and breaking carbon-carbon bonds with visible light. The method uses transition metal vanadium-modified titanium dioxide solids as photocatalysts, and lignin β-1 model compounds as reaction substrates, under the excitation of visible light irradiation, directly catalyzes the oxidative cleavage of carbon-carbon bonds to prepare aromatic aldehydes and aromatic carboxylic compounds. . The reaction process is as follows: Add a certain amount of reaction substrate and catalyst into the quartz photoreactor, add an appropriate amount of organic solvent and magnetons, replace the air above the reaction tube with oxygen, seal it, and place it in an integrated photoreaction device for light reaction. The reaction temperature is 5-70 DEG C, the reaction time is 0.5-10 hours, and aromatic aldehydes and aromatic carboxylic acid compounds are obtained after the reaction. The method has mild conditions, simple operation, and easy separation and recovery of the catalyst. It is a new efficient and economical method to realize the direct oxidative cleavage of carbon-carbon bonds.

Description

technical field [0001] The invention relates to a method for catalyzing and oxidizing and breaking carbon-carbon bonds with visible light, specifically, a method using vanadium-modified solid titanium dioxide as a catalyst, with O 2 As an oxygen source, the lignin β-1 aromatic dimer model compound is directly oxidized to break carbon-carbon bonds under visible light irradiation at low temperature to synthesize aromatic aldehyde compounds. Background technique [0002] The selective oxidative cleavage of C–C bonds is one of the very important and challenging research directions in the field of organic synthesis and transformation. Due to the high bond energy of the C–C bond, it is difficult to activate. Traditional methods often require the catalysis of complex metal complexes and harsh reaction conditions (Chem.Rev.2015, 115, 9410-9464), to achieve C–C under mild conditions. Bond selective cleavage is a topic of great significance. Lignin is the only natural aromatic polym...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C47/54C07C47/575C07C45/51C07C63/06C07C65/21C07C51/00B01J23/22B01J37/02B01J37/08
CPCC07C45/512C07C51/00B01J23/002B01J23/22B01J37/0201B01J37/088B01J35/39C07C47/54C07C47/575C07C63/06C07C65/21
Inventor 王峰刘慧芳王敏李宏基罗能超黄志鹏
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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