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Method for preparing aromatic ketone or aromatic aldehyde by selectively oxidizing alkyl arene

A technology of aromatic ketones and selectivity, applied in chemical instruments and methods, preparation of carbonyl compounds by oxidation, organic chemistry, etc., can solve the problems of poor atom economy, poor product selectivity, high reaction temperature, etc., and achieve high selectivity and low production cost , The effect of simple reaction system

Inactive Publication Date: 2009-07-29
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] The benzylic selective oxidation of aromatic hydrocarbons is an important transformation process in organic chemistry. The products obtained from aromatic ketones and aromatic aldehydes are widely used fine chemical products and intermediates in the synthesis of natural products; the traditional oxidation method mainly uses metering Oxidation of aromatic hydrocarbons by manganese dioxide, dichromic acid and other oxidants is serious pollution and poor atom economy; in recent years, green catalytic processes using hydrogen peroxide and molecular oxygen as oxidants have begun to attract attention is the most competitive route
In this research field, most of the catalysts currently used are transition metal compounds (J.Mol.Catal.A: Chemical, 2003,201,9-22; Adv.Synth.Catal.2005,347,703-705), such Many systems have disadvantages such as high reaction temperature and poor product selectivity

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Example 1: Catalytic oxidation of indane

[0020] Dissolve 1ml (8.1mmol) of indane in 10ml of acetonitrile, add 0.20mmol of acriflavine, 0.24mmol of molecular bromine and 0.67mmol of N-hydroxyphthalimide, at 75°C, 0.3MPa of O 2 Under pressure, after reacting for 5 hours, analyze the reaction result with a gas chromatograph; the conversion rate of indane can reach 92%, and the selectivity of indan-1-one can reach 79%; at this time, it can be cooled, distilled, and the product can be collected.

Embodiment 2

[0021] Example 2: Catalytic oxidation of indane

[0022] Dissolve 1ml (8.1mmol) of indane in 10ml of methanol, add 0.01mmol of acriflavine, 0.08mmol of molecular bromine and 0.67mmol of N-hydroxyphthalimide, at 50°C, 0.3MPa of O 2 Under pressure, after reacting for 25 hours, analyze the reaction result with a gas chromatograph; the conversion rate of indan can reach 73%, and the selectivity of indan-1-one can reach 54%; at this time, it can be cooled and distilled to collect the product.

Embodiment 3

[0023] Example 3: Catalytic oxidation of indane

[0024] Dissolve 1ml (8.1mmol) indane in 10ml ethyl acetate, add 0.20mmol acridine, 0.24mmol molecular bromine and 0.08mmol N-hydroxyphthalimide, at 200°C, 0.001MPa O 2 Under pressure, after reacting for 5 hours, analyze the reaction result with a gas chromatograph; the conversion rate of indane can reach 19%, and the selectivity of indan-1-one can reach 13%; at this time, it can be cooled, distilled, and the product can be collected.

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Abstract

A non-metallic catalytic system with pyramine compound, molecule bromine and N-hydroxy-o-dimethyl-acylimine is prepared by catalyzing aryl radical oxide with molecular oxygen as oxygen source to generate aryl ketone or aryl aldehyde under gentle condition and oxidation reacting selectively. It costs low, is non-toxic and has less environmental pollution.

Description

technical field [0001] The invention relates to a catalyst system for catalyzing the benzylic selective oxidation reaction of various aromatic hydrocarbons, in particular, it provides a catalyst system composed of small organic molecules that can be used to directly and efficiently oxidize aromatic hydrocarbons into aromatic ketones or aromatic aldehydes Non-metallic catalytic system, which can generate organic free radicals with high activation function to activate the C-H bond and oxygen molecules of aromatic hydrocarbons, so as to realize the efficient oxidation process of aromatic hydrocarbons. Background technique [0002] The benzylic selective oxidation of aromatic hydrocarbons is an important transformation process in organic chemistry. The products obtained from aromatic ketones and aromatic aldehydes are widely used fine chemical products and intermediates in the synthesis of natural products; the traditional oxidation method mainly uses metering Oxidation of aroma...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/28C07C47/52C07C49/76C07C49/385B01J31/02
Inventor 徐杰仝新利
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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