Method of zyme catalyzing cyclo-olefin oxidation

A technology for epoxidation and epoxy compounds, which is applied in the field of bromoperoxidase to catalyze the epoxidation of olefins, can solve the problems of no olefins, etc., and achieve the effects of avoiding potential pollution, saving resources, and reducing waste water discharge

Inactive Publication Date: 2008-01-23
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
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  • Application Information

AI Technical Summary

Problems solved by technology

The application of bromoperoxidase to the oxidation of organic sulfur has been reported, but there has been no report on the epoxidation of olefins (Inorg Chem, 1998, 37:6780-6784)

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Add 10 mg of bromoperoxidase to 50 ml of PBS buffer solution with pH=4, add 2 mol of cyclohexene, and when the temperature is 25°C, add 1 mol of hydrogen peroxide to start the reaction, stir for 2 hours, let stand to take the organic phase, Perform chromatographic analysis. The yield of epoxycyclohexane to hydrogen peroxide is 100%, and the selectivity of epoxycyclohexane is 90%.

Embodiment 2

[0018] Add 100 mg of bromoperoxidase to 200 ml of citric acid buffer solution with pH=7, then add 5 mol of cyclohexene, at a temperature of 70° C., start the reaction by feeding 3 mol of oxygen at a rate of 20 ml / min, and stir for 9 hours. Stand still to take the organic phase for chromatographic analysis. The yield of epoxycyclohexane to hydrogen peroxide is greater than 50%, and the selectivity of epoxycyclohexane is 85%.

Embodiment 3

[0020] Reuse the enzyme and buffer system separated from the reaction product after the reaction in Example 2, add 2 mol cyclohexene at a temperature of 70°C, add 0.5 mol to start the reaction, stir for 9 hours, let stand to take the organic phase, and perform chromatography analyze. The yield of epoxycyclohexane to hydrogen peroxide is 50%, and the selectivity of epoxycyclohexane is 90%.

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PUM

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Abstract

The invention relates to a method of enzyme catalyzing olefin expoxidation. In the aqueous solution, the bromine peroxidase is applied for biological catalyst and hydrogen peroxide or oxygen is taken as oxygen source to oxidate the olefin into expoxidation. Take the cyclohexen as example. The hydrogen peroxide is applied as the source. They react under the 20 DEG C. to 70 DEG C. for two to ten hours. The yield of epoxy cyclohexane to the hydrogen peroxide is more than 50 per cent and the selectivity of the epoxy cyclohexane is more than 85 per cent. After the reaction, the water phase is separated from the organic phase automatically, and the enzymes left in the water phase can be recycled. Boasting easy technical process, recycled enzymes and easy yield separation, the method is an environment-friendly green chemical process.

Description

technical field [0001] The invention relates to an enzyme-catalyzed method for the epoxidation of olefins, in particular to a method for catalyzing the epoxidation of olefins with bromoperoxidase (such as cyclohexene to generate epoxycyclohexane). Background technique [0002] Epoxy compounds are a class of very useful synthetic intermediates, widely used in petrochemical, fine chemical and organic synthesis. But so far, the main methods of industrial production of epoxy compounds are chemical methods: including haloalcohol method and Halcon method. Domestically, the haloalcohol method is the main method. These methods have serious environmental pollution or problems of co-products. There are heavy metals in the catalysts for the synthesis of epoxy compounds by chemical catalysis, which is a potential source of environmental pollution. Most of the processes are protected by patents and require a large investment (Science, 2001, 292: 1139-1141). The use of enzymes to catalyz...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P17/02
Inventor 靳艳张卫于瑶
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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