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Method for preparing aldehyde ketone by catalyzing carbon-carbon double-bond oxidative cleavage

A technology of oxidative cleavage and carbon double bonds, applied in the field of chemical engineering, can solve problems such as low selectivity of by-products, waste discharge, and environmental pollution of metal ions

Active Publication Date: 2017-06-13
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the above-mentioned method has some disadvantages, such as excessive oxidant causing a large amount of waste discharge, the use of toxic metal ions causing environmental pollution, and the generation of by-products resulting in low selectivity, etc.

Method used

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  • Method for preparing aldehyde ketone by catalyzing carbon-carbon double-bond oxidative cleavage
  • Method for preparing aldehyde ketone by catalyzing carbon-carbon double-bond oxidative cleavage
  • Method for preparing aldehyde ketone by catalyzing carbon-carbon double-bond oxidative cleavage

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Add 0.05mmol of ABNO, 0.05mmol of FeCl3, 0.5mmol of α-methylstyrene, and 1mL of acetonitrile into a Schlenk bottle as a solvent, oxygen bulbs as an oxygen source, and stir and react at 60°C for 12h to obtain the target The product, the chromatographic yield is 90%.

Embodiment 2

[0016] Add 0.05mmol of ABNO, 0.05mmol of FeCl3, 0.5mmol of 4-methyl-α-methylstyrene, and 1mL of acetonitrile into a Schlenk bottle as a solvent, oxygen bulbs as an oxygen source, and stir the reaction at 60°C for 12h , the target product can be obtained with a chromatographic yield of 89%.

Embodiment 3

[0018] Add 0.05mmol of ABNO, 0.05mmol of FeCl3, 0.5mmol of 4-methoxy-α-methylstyrene, and 1mL of acetonitrile into a Schlenk bottle as a solvent, oxygen bulbs as an oxygen source, and stir the reaction at 60°C After 12 hours, the target product can be obtained with a chromatographic yield of 93%.

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Abstract

The invention relates to a method for preparing aldehyde ketone by catalyzing carbon-carbon double-bond oxidative cleavage and belongs to the technical field of chemistry and chemical engineering. Particularly, reaction is conducted at a temperature of 30 to 120 DEG C for 1 to 48 hours by taking nitroxide free radical and iron salt as catalysts and air or oxygen as an oxygen source, so that carbon-carbon double bonds (as shown in the description) can be oxidized and broken into corresponding aldehyde or ketone. The system provided by the invention has various advantages of high catalytic activity, high selectivity, mild condition and the like.

Description

technical field [0001] The invention belongs to the technical field of chemistry and chemical engineering, and specifically relates to a method for preparing aldehydes and ketones by catalyzing the oxidative cleavage of carbon-carbon double bonds. Background technique [0002] Oxidative cleavage of carbon-carbon double bonds in alkenes to aldehydes and ketones is a very important class of organic transformations. The main methods currently reported are: 1) traditional ozone, sodium periodate and osmium tetroxide mixed oxidant; 2) transition metals (Mn, Ru, Pd, Fe, Au, Ce, etc.) with peroxides; 3) chemical Metered oxidants (eg, m-chloroperoxybenzoic acid, etc.); 4) Photocatalytic pathways. However, the above-mentioned methods have some disadvantages, such as excessive oxidant causing a large amount of waste discharge, the use of toxic metal ions causing environmental pollution, and the generation of by-products resulting in low selectivity and other issues. [0003] The sel...

Claims

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Application Information

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IPC IPC(8): C07B41/06C07C49/78C07C49/76C07C49/84C07C49/807C07C49/786C07C47/048C07C47/54C07C45/36
CPCC07B41/06C07C45/36C07C49/78C07C49/76C07C49/84C07C49/807C07C49/786C07C47/04C07C47/54
Inventor 高爽陈波王连月吕迎
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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