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Process for preparing epoxy cyclohexane by catalytic cyclooxidation of cyclohexene

A cyclohexene catalytic ring, epoxy cyclohexane technology, applied in organic chemistry and other directions, can solve the problems of unknown catalyst cycle stability, long distance, etc., to achieve simple and easy reaction process, simple post-processing, convenient separation and purification. The effect of recycling

Inactive Publication Date: 2003-03-12
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the excess of cyclohexene in this system is more than 9 times, and the concentration of hydrogen peroxide is 65%. Although the catalyst can be recovered, the cycle stability of the catalyst is still unknown, and the distance from industrial production is still far away

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

[0020] Example 1 Epoxidation of cyclohexene

[0021] 40mmol cyclohexene was dissolved in 40mL mixed mesitylene, 20mmol of 15% hydrogen peroxide aqueous solution (w / w) was added, 0.2mmol of catalyst [(C 2 h 5 ) 3 NCH 2 Ph] 2 HAsMo 2 o 10. At 65°C, after reacting for 1 hour, the conversion rate of cyclohexene was 49.0%, and the selectivity of epoxycyclohexane was 95.2%. At this time, the catalyst was precipitated from the reaction system, and the catalyst was recovered after centrifugation and dried in vacuum. Unreacted raw material cyclohexene and product epoxycyclohexane in the organic layer were distilled off. Add the recovered epoxidation catalyst, cyclohexene and hydrogen peroxide to the obtained distillation bottom liquid, and perform the same circular reaction as above, and the reaction results are shown in the table below.

[0022] The recovered catalyst can be recycled for the above reaction five times, and the reaction results are shown in the table below. Ca...

example 2

[0028] Example 2 Epoxidation of cyclohexene

[0029] Dissolve 20 mmol of 2-menaphthoquinone in a mixed solvent of 15 mL dimethyl phthalate and 15 mL diisobutyl carbinol, add 2% of 5% Pd-C (W / W) catalyst, 6 atm hydrogen, 45 °C for 6 hours to hydrogenate 2-menaphthoquinone up to 50%. The hydrogenation was stopped, and the Pd-C catalyst was removed by filtration. Then in the filtrate, add cyclohexene 30mmol, catalyst (NH 4 ) 2 HAs 2 o 10 0.09mmol, under 1atm O2, react at 65°C for 2 hours, at this time the catalyst has been precipitated from the reaction system, the conversion rate of cyclohexene is 33.0%, and the selectivity of cyclohexene oxide is 98.3%. The catalyst was recovered by suction filtration, and the obtained catalyst was naturally dried in air at room temperature. Unreacted starting material cyclohexene and product cyclohexene oxide are distilled off. Add 2% Pd-C (W / W) catalyst to the resulting distillation bottom liquid, add the recovered epoxidation catalys...

example 3

[0035] Example 3 Epoxidation of cyclohexene

[0036] 30mmol cyclohexene was dissolved in 60mL toluene, and 40mmol of 1mol / L cumene hydroperoxide / cumene solution was added. Add 0.3mmol of [(CH 3 ) 4 N] 3 PMo 4 o 16 catalyst. After reacting at 60° C. for 2 hours, the conversion rate of cyclohexene reached 100%, and the selectivity of epoxycyclohexane was 95%. Let the reaction solution continue to react at 80°C for 2 hours, the unreacted H 2 o 2 After complete decomposition, the catalyst precipitates out from the reaction system. The catalyst is recovered by centrifugation, and the obtained catalyst can be recycled for the above reaction after vacuum drying at <50°C. Unreacted raw material cyclohexene and product epoxycyclohexane in the organic layer were distilled off. Add the recovered epoxidation catalyst and cyclohexene, cumene hydroperoxide / cumene solution to the toluene solvent obtained by distillation, and perform the same circular reaction as above.

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PUM

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Abstract

A process for preparing epoxy cyclohexane by catalytic epoxidation of cyclohexene is disclosed. It is characterized by use of a phase-transfer catalyst which is insoluble in reaction medium but can become the active substance soluble in reactino medium under action of hydrogen peroxide. Said catalyst can be cyclically used. Its advantages are high selectivity (97%), easy recovery of catalyst, no by-product and low cost.

Description

technical field [0001] The invention relates to a catalytic epoxidation reaction, and in particular provides a new reaction process for preparing epoxycyclohexane by catalytic epoxidation of cyclohexene with a reaction-controlled phase transfer catalyst. Background technique [0002] Cyclohexane oxide is an important fine chemical raw material and intermediate. It can be used as a reactive diluent for epoxy resins, and can also be made into dicyclohexyl-18-crown-6, dicyclohexyl triaza-18-crown-6 and other crown ether compounds, and can synthesize new types of high-efficiency and low toxicity Pesticides such as decantate and organic compounds such as cyclohexanediol, cyclohexadiene, and catechol. At the same time, due to the relatively active chemical properties of epoxy cyclohexane, it has a good application prospect in the field of high-efficiency photocuring. With the continuous development of the use of epoxy cyclohexane, the demand for it is also increasing. [0003] ...

Claims

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Application Information

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IPC IPC(8): C07D301/12C07D303/04
Inventor 李坤兰奚祖威孙渝周宁
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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