Method for photocatalytic oxidation of hydrocarbons

A technology for catalyzing hydrocarbons and photocatalysis, which is applied in chemical instruments and methods, oxidation preparation of carbonyl compounds, physical/chemical process catalysts, etc., can solve the problem of difficult and easy control of product selectivity, and achieve mild conditions, high selectivity, high The effect of conversion efficiency

Inactive Publication Date: 2018-12-28
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Due to these harsh conditions, the selectivity of the product is difficult to control, which often leads to the formation of some over-oxidized products.

Method used

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  • Method for photocatalytic oxidation of hydrocarbons

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Experimental program
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Effect test

Embodiment 1

[0012] In a 10mL pressure-resistant reaction tube, add 20mg N-doped TiO 2 (N content: 1wt%), 1mmol toluene, 5mL acetonitrile as solvent, 1atm oxygen, under stirring conditions at room temperature, irradiated by LED lamp for 12 hours, the light intensity is 20mW / cm –2 After the reaction, the GC-MS detection conversion rate was 48%, and the benzaldehyde selectivity was >99%. The catalyst was filtered off, the solvent was removed by rotary evaporation, petroleum ether and ethyl acetate (volume ratio 10:1) column separation, and the separation yield of benzaldehyde could reach 40%.

Embodiment 2

[0014] In a 10mL pressure-resistant reaction tube, add 20mg N-doped TiO 2 (N content: 2wt%), 1mmol ethylbenzene, 5mL acetonitrile as a solvent, 1atm oxygen, under room temperature stirring conditions, LED light irradiation for 12 hours, the light intensity is 20mW / cm –2 , after the reaction finished, the GC-MS detection conversion rate was 80%, and the acetophenone selectivity was >99%, and the catalyst was filtered off, and by rotary evaporation, the solvent was removed, sherwood oil and ethyl acetate (volume ratio 10:1) column Separation, the separation yield of acetophenone can reach 70%.

Embodiment 3

[0016] In a 10mL pressure-resistant reaction tube, add 20mg N-doped TiO 2 (N content: 5wt%), 1mmol cyclohexane, 5mL acetonitrile as a solvent, 1atm oxygen, under room temperature stirring conditions, LED light irradiation for 12 hours, the light intensity is 20mW / cm –2 , after the reaction finished, the GC-MS detection conversion rate was 28%, and the cyclohexanone selectivity was >99%, and the catalyst was filtered off, and by rotary evaporation, the solvent was removed, sherwood oil and ethyl acetate (volume ratio 10:1) column Separation, the separation yield of cyclohexanone can reach 15%.

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Abstract

The invention provides a method for preparing an aldehyde compound through photocatalytic oxidation of hydrocarbon C-H bonds. The method comprises the step that with nitrogen-doped titanium dioxide (N-doped TiO2) as a catalyst and air or oxygen as an oxygen source, the corresponding aldehyde, ketone or acid compound can be generated through the oxidation of the C-H bonds after illumination. The method has the advantages that the conditions are mild, the oxidation efficiency is high, and the product yield is high; under the illumination condition, with the air or oxygen as the oxygen source, the method is economical and environmentally friendly, accords with sustainable energy strategies and has broad application prospects.

Description

technical field [0001] The invention relates to the field of photocatalytic conversion of organic compounds, in particular to a method for preparing aldehydes, ketones or acid compounds by photocatalytic oxidation and cracking of C-H bonds of hydrocarbon compounds. Background technique [0002] Oxidative cleavage of C–H bonds plays an important role in organic synthesis. However, the inherent non-polarity, thermodynamic stability, and kinetic inertness of the C-H bond make the cleavage of the C-H bond difficult and challenging. In non-catalytic processes, some metered oxidants are mostly used under high temperature and high pressure conditions. In the catalytic process, some transition metal complexes or oxides are mainly used as catalysts, and hydrogen peroxide or oxygen is used as the oxygen source. However, in these processes, it is generally necessary to add complex ligands or alkali and other additives. Only then can it be realized. Because these conditions are relat...

Claims

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Application Information

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IPC IPC(8): B01J21/06B01J27/24C07C45/27C07C47/54C07C47/228C07C49/403C07C47/02C07C47/542C07C47/55C07C223/00C07C223/06C07C47/575C07C47/24
CPCC07C45/27C07C223/00B01J21/063B01J27/24B01J35/39C07C47/54C07C47/228C07C49/403C07C47/02C07C47/542C07C47/55C07C223/06C07C47/575C07C47/24
Inventor 王峰侯婷婷罗能超黄志鹏王业红
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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