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Preparation method of cyclohexene oxide

A technology of epoxycyclohexane and cyclohexene, which is applied in the direction of organic chemistry, can solve the problems of high cost and difficulty in recycling catalysts, and achieve the effects of easy recycling, reduced reaction energy consumption, and good application prospects

Active Publication Date: 2016-05-18
HUIZHOU RES INST OF SUN YAT SEN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Chinese patent CN1915983A reported that metalloporphyrin homogeneously catalyzes cyclohexene to prepare epoxycyclohexane, but there are disadvantages such as difficult recovery of the catalyst and high cost

Method used

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  • Preparation method of cyclohexene oxide
  • Preparation method of cyclohexene oxide

Examples

Experimental program
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Effect test

Embodiment 1

[0018] In 25mL reactor, add 10mL1,2-dichloroethane solvent, 2.5mmol cyclohexene, 0.75mg catalyst (M=Mn in general formula (I), R 1 = R 2 = R 3 = R 4 = R 5 =H, X=Cl), feed 0.1MPa of oxygen, react at a temperature of 20°C for 2 hours, and detect by gas chromatography, the conversion rate of cyclohexene is 94%, and the selectivity of epoxycyclohexane is 99%.

Embodiment 2

[0020] In 25mL reactor, add 10mL acetonitrile solvent, 2.5mmol cyclohexene, 0.075mg catalyst (M=Fe in general formula (I), R 1 = NO 2 , R 2 = R 3 = R 4 = R 5 =H, X=Cl), feed 1.0MPa of oxygen, react at a temperature of 60°C for 2 hours, and detect by gas chromatography, the conversion rate of cyclohexene is 92%, and the selectivity of epoxycyclohexane is 91%.

Embodiment 3

[0022] In 25mL reactor, add 10mL THF solvent, 2.5mmol cyclohexene, 0.15mg catalyst (M=Cu in general formula (I), R 1 = R 5 =Cl,R 2 = R 3 = R 4 =H, X=imidazole), feed 0.1MPa of oxygen, react at a temperature of 25°C for 2 hours, and detect by gas chromatography, the conversion rate of cyclohexene is 98%, and the selectivity of epoxy cyclohexane is 99%.

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Abstract

The invention discloses a preparation method of cyclohexene oxide. According to the preparation method, with cyclohexene as a raw material, carbon nanotube-supported unidirectional metal porphyrin as a catalyst and oxygen as an oxygen source, a catalytic reaction is carried out under the conditions that the reaction temperature is controlled to be 20-60 DEG C and the reaction pressure is controlled to be 0.1-1 MPa, and then cyclohexene oxide is obtained. The preparation method has the advantages that the reaction conditions are mild, operation is convenient, catalytic efficiency is high, and the catalyst can be reused.

Description

technical field [0001] The invention relates to a method for preparing epoxycyclohexane, in particular to a method for preparing epoxycyclohexane by biomimetic catalysis of cyclohexene oxidation. Background technique [0002] Cyclohexane oxide is an important chemical product with important uses. For example: epoxycyclohexane is the raw material for the synthesis of acaricide propargite, and the product has a good insecticidal effect on mites; epoxycyclohexane can be used to synthesize trans-1,2-cyclohexanediol for surface activity Agents, rubber additives, polymer modifiers, etc. Cyclohexane oxide can react with CO 2 Baeyer-Villiger reaction occurs to generate caprolactone, which plays an important role in the synthesis of fine chemicals, fragrances, and pharmaceutical intermediates. At the same time, due to its active chemical properties, epoxycyclohexane also has a good application prospect in the field of optoelectronics. It can be predicted that with the continuous ...

Claims

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Application Information

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IPC IPC(8): C07D301/06C07D303/04
CPCC07D301/06C07D303/04
Inventor 纪红兵周贤太何千
Owner HUIZHOU RES INST OF SUN YAT SEN UNIV
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