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Preparation method of cyclohexene oxide

A technology for epoxy cyclohexane and cyclohexene, which is applied to the preparation field of epoxy cyclohexane, can solve the problems of difficult recovery of catalyst, high catalyst cost, complicated process and the like, and achieves easy recovery, abundant sources and simple operation process. Effect

Active Publication Date: 2020-04-21
HUIZHOU RES INST OF SUN YAT SEN UNIV
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  • Summary
  • 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
Chinese patent CN105585541A reports the preparation process of epoxycyclohexane with carbon nanotube-supported unidirectional metal porphyrin compound as catalyst. This process solves the problem of catalyst recovery, but there are problems such as high catalyst cost and complicated process.

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

[0022] In 25mL containing the acetonitrile solution that adds 10mmol of cyclohexene and 1mmol oleic acid, add the metalloporphyrin hypercrosslinked polymer (M=Fe, R=H) catalyst with general formula (I), its consumption is 2.0% of raw material % by weight, feed air, stir and react at a temperature of 100°C for 4 hours, quantitatively detect and analyze through gas chromatography internal standard method, the conversion rate of cyclohexene is 82%, and the selectivity of product epoxycyclohexane is greater than 99% .

Embodiment 2

[0024] In 25mL containing the butyl acetate solution that adds 10mmol cyclohexene and 20mmol oleic acid, add the metalloporphyrin hypercrosslinked polymer (M=Mn, R=Cl) catalyst with general formula (I), its consumption is raw material 1.0wt% of 1.0wt%, feeding into air, stirring and reacting for 4 hours at a temperature of 30° C., through gas chromatography internal standard method quantitative detection and analysis, the transformation rate of cyclohexene is 84%, and the selectivity of product epoxy cyclohexane is greater than 99%.

Embodiment 3

[0026] In 25mL containing the sec-butyl acetate solution that added 10mmol of cyclohexene and 10mmol oleic acid, add metalloporphyrin hypercrosslinked polymer (M=Co, R=NO) with general formula (I) 2 ) catalyzer, its consumption is 0.1wt% of raw material, feeds into air, is that 40 ℃ of temperature are stirred and reacted 4 hours, through gas chromatography internal standard method quantitative detection and analysis, the conversion rate of cyclohexene is 90%, product epoxy The selectivity of cyclohexane is greater than 99%.

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Abstract

A preparation method of cyclohexene oxide is disclosed. According to the method, cyclohexene is used as a raw material, air is used as an oxidizing agent, porous aromatic framework metalloporphyrin isused as a catalyst, and a catalytic reaction is carried out at the reaction temperature of 30-90 DEG C to obtain the cyclohexene oxide with high selectivity. The method has the advantages of simple process, high yield, catalyst recyclability, mild conditions and the like.

Description

technical field [0001] The invention relates to a method for preparing epoxycyclohexane, in particular to a method for preparing epoxycyclohexane by air oxidation of cyclohexene catalyzed by porous aromatic frame metal porphyrin. Background technique [0002] Epoxycyclohexane is an important intermediate in organic synthesis, and it is the raw material for the synthesis of acaricide propargite. The product has a good insecticidal effect on mites; epoxycyclohexane can be used to synthesize trans-1,2-cyclohexane Alcohol, used in surfactants, rubber additives, polymer regulators, 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. [0003] The main synthesis methods are: cyclohexene and hypochlorous acid addition, peroxide oxidation, molecular oxygen oxidation, etc., especially molecular oxygen oxidation is the most g...

Claims

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Application Information

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IPC IPC(8): C07D303/04C07D301/06
CPCC07D303/04C07D301/06Y02P20/584
Inventor 纪红兵周贤太王结祥韩琦
Owner HUIZHOU RES INST OF SUN YAT SEN UNIV