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Method of catalyzed oxidation of olefin to produce enol, ketenes and epoxy compound

A technology for catalytic oxidation of epoxy compounds, applied in the direction of hydrocarbon oxidation to prepare oxygenated compounds, oxidation to prepare carbonyl compounds, chemical instruments and methods, etc., can solve the problems of losing catalytic effect and not yet put into industrial production

Inactive Publication Date: 2004-11-10
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method can improve the selectivity of olefin oxidation reaction, but NaClO oxidizes single metal porphyrin at the same time and makes it lose its catalytic effect, so it has not been put into industrial production

Method used

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  • Method of catalyzed oxidation of olefin to produce enol, ketenes and epoxy compound
  • Method of catalyzed oxidation of olefin to produce enol, ketenes and epoxy compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] 5 mg of metalloporphyrins with structural formula (I), R 1 = R 2 = R 3 =CH 3 , M=Mn, and 20mgCu 2 Cl 2 Add 300ml of cyclohexene, and introduce 4atm air. The reactant was stirred at 55° C. for 3 hours, the conversion rate of cyclohexene was 4.2%, and the yield of α, β-cyclohexenol, α, β-cyclohexenone and epoxycyclohexane in the reaction product was 90%.

Embodiment 2

[0017] 3 mg of a metalloporphyrin of formula (II), R 1 = R 2 =OH, R 3 =Cl,M 1 = M 2 =Fe, and 20 mg of sodium phosphate were added in 400 ml of styrene, 5 atm air was introduced, and the reactant was stirred at 80° C. for 4 hours, the conversion of styrene was 10.8%, and the yield of styrene oxide in the reaction product was 60%.

Embodiment 3

[0019] 7 mg of metalloporphyrins of formula (I), R 1 =OCH 3 , R 2 = R 3 = H, M 1 =Co, and 24mg of triethylamine are added in 400ml of 2-butene, feed 8atm air, stir reactant 2 hours at 80 ℃, butene conversion rate is 30.8%, butene oxide and crotonaldehyde are collected in reaction product Rate 80%.

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Abstract

According to the present invention, the oxidation agent uses air or oxygen, or mixture gas of oxygen and inert gas, or other chemical oxidation agent, the reaction pressure is controlled to be 1-10 atm, the temperature being 20-150 deg. C, mu-oxygen single metalloporphyrin or double metalloporphyrin, or their carrier is separately selected as catalyst, or they form composite catalyst along with filtering metallic salts or oxidants, the catalyst concentration being 1-50PPM, reaction time being 0.5-5 hours, thus alpha, beta-enol, alpha, beta-ketene and epoxy compounds are obtained through catalytic oxidation of olefin or cyclomonoolefin.

Description

technical field [0001] The invention relates to a method for preparing α, β-enol, α, β-enone and epoxy compound through the selective oxidation of olefin or cycloolefin by air or chemical oxidant under metalloporphyrin catalysis. Background technique [0002] The air oxidation of olefins generally needs to be catalyzed by gold, silver and other noble metals under high temperature conditions. Due to the poor selectivity of the reaction to the carbon-carbon double bond and allyl hydrogen, there are many side reactions, the product is difficult to separate, and the reaction yield is not high. The chemical oxidation of olefins cannot be controlled and utilized due to the formation of more deeply oxidized products. The way to reduce the side reactions of olefin air oxidation and to utilize the chemical oxidation of olefin is to use a suitable catalyst to improve the selectivity of the reaction. There have been some reports using monometalloporphyrins...

Claims

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Application Information

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IPC IPC(8): C07C29/50C07C45/34C07C45/35C07C45/36C07D301/06C07D301/12
CPCC07C29/50C07C45/34C07D301/06C07C45/35C07D301/12C07C2601/10C07C2601/16C07C2601/18C07C2602/08C07C2602/42
Inventor 郭灿城刘文马金勇毛彦利
Owner HUNAN UNIV
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