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A method for preparing aldehyde compounds by photocatalytic oxidative cleavage of β-hydroxy compound c-c bonds

A technology for hydroxyl compounds and aldehyde compounds is applied in the field of photocatalytic oxidation and cleavage of C-C bonds of β-hydroxy compounds to prepare aldehyde compounds. Highly selective effect

Active Publication Date: 2020-07-21
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

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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  • A method for preparing aldehyde compounds by photocatalytic oxidative cleavage of β-hydroxy compound c-c bonds
  • A method for preparing aldehyde compounds by photocatalytic oxidative cleavage of β-hydroxy compound c-c bonds
  • A method for preparing aldehyde compounds by photocatalytic oxidative cleavage of β-hydroxy compound c-c bonds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] In a 10mL pressure-resistant photoreaction tube, add 20mg CuO x · CeO 2 (Cu:Ce=1:4, the catalyst is prepared by co-precipitation method), 1mmol benzphenyl ethanol, 5mL acetonitrile as solvent, 1atm oxygen, under room temperature stirring conditions, LED light irradiation for 12 hours, the light intensity is 20mW / cm –2 , after the reaction, the conversion rate detected by GC-MS was 98%, and the selectivity of benzaldehyde was >99%. The catalyst was filtered off, the solvent was removed by rotary evaporation, petroleum ether and ethyl acetate (volume ratio 10:1) were separated on a column, and the separation yield of benzaldehyde could reach 90%.

Embodiment 2

[0043] In a 10mL pressure-resistant photoreaction tube, add 20mg CeO 2 ·TiO 2 (Ce:Ti=1:10, the catalyst is prepared by deposition and precipitation method), 1mmol benzphenyl ethanol, 5mL acetonitrile as solvent, 1atm oxygen, under room temperature stirring conditions, LED light irradiation for 12 hours, the light intensity is 20mW / cm –2, after the reaction, the GC-MS detection conversion rate was 98%, and the selectivity of benzaldehyde 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 86%.

Embodiment 3

[0045] In a 10mL pressure-resistant reaction tube, add 20mg CuO x · CeO 2 ·TiO 2 (Cu:Ce:Ti=1:4:40, the catalyst is prepared by deposition and precipitation), 1mmol benzphenyl ethanol, 5mL acetonitrile as solvent, 1atm oxygen, under room temperature stirring conditions, LED light irradiation for 12 hours, the light intensity is 20mW / cm –2 , after the reaction, the GC-MS detection conversion rate was 98%, and the selectivity of benzaldehyde was >99%. The catalyst was filtered off, the solvent was removed by rotary evaporation, petroleum ether and ethyl acetate (volume ratio 10:1) were separated on a column, and the separation yield of benzaldehyde could reach 90%.

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Abstract

The invention provides a method for preparing aldehyde compounds by photocatalytically cracking the C-C bond of a β-hydroxy compound. The method uses a β-hydroxy compound as a substrate and an oxygen-containing gas as an oxygen source. In the presence of a catalyst , illumination can generate C–C bond cleavage products, the corresponding aldehydes. This method has mild conditions, high oxidation efficiency and high product yield. Under light conditions, oxygen-containing gas is used as the oxygen source, which is economical, environmentally friendly, green, in line with the sustainable development energy strategy, and has broad application prospects.

Description

technical field [0001] The invention relates to the field of photocatalytic organic compounds and biomass conversion, in particular to a method for preparing aldehyde compounds by photocatalytic oxidation and cracking of C-C bonds of β-hydroxyl compounds. Background technique [0002] C–C bond cleavage plays an important role in organic synthesis and biomass conversion. However, the inherent nonpolarity, thermodynamic stability, and kinetic inertness of the C–C bond make the cracking of the C–C 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 relativ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/38C07C47/54C07C47/565C07C47/575C07C201/12C07C205/44B01J23/83B01J23/10B01J23/22B01J23/36
CPCC07C45/38C07C201/12B01J23/002B01J23/10B01J23/22B01J23/36B01J23/83B01J2523/00B01J35/39C07C47/54C07C47/565C07C47/575C07C205/44B01J2523/17B01J2523/3712B01J2523/47B01J2523/3718B01J2523/48B01J2523/67B01J2523/824
Inventor 王峰侯婷婷王业红罗能超张志鑫张健李宏基王敏安静华
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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