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Polymerized metalloporphyrin and N-hydroxyl phthalimide synergistically catalytically oxidizing cyclohexylbenzene

A technology of hydroxyphthalimide and polymerized metal is applied in the field of preparing 1-cyclohexylbenzene hydroperoxide and can solve the problems of high reaction cost, large amount of catalysis and the like

Inactive Publication Date: 2018-07-27
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

NHPI is a homogeneous catalyst. When used alone, an initiator is required to initiate the reaction. It is decomposed and invalidated during the reaction, and the amount of catalyst is large, which makes the reaction cost very high.

Method used

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  • Polymerized metalloporphyrin and N-hydroxyl phthalimide synergistically catalytically oxidizing cyclohexylbenzene
  • Polymerized metalloporphyrin and N-hydroxyl phthalimide synergistically catalytically oxidizing cyclohexylbenzene
  • Polymerized metalloporphyrin and N-hydroxyl phthalimide synergistically catalytically oxidizing cyclohexylbenzene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] 5 mg of the metalloporphyrin polymer with structural formula (I), R 1 =R 2 =H, m=0, n=216, M=Cu, the specific surface area is 260m 2 / g, the average pore diameter is 1.91 nm. It was added to 50 ml (47.5 g) of cyclohexylbenzene, heated to 120° C. and air was passed through at a flow rate of 150 ml / min, and the reaction was continuously stirred for 8 hours. The conversion rate of cyclohexylbenzene was 29.84%, and the selectivity of 1-cyclohexylbenzene hydroperoxide was 90.70%.

Embodiment 2

[0015] 5 mg of the metalloporphyrin polymer with structural formula (I), R 1 =Cl,R 2 =CH 3 , m=1, n=520, M=Cu, the specific surface area is 340m 2 / g, the average pore diameter is 2.7 nm. NHPI (241.8 mg) was added to 50 ml (47.5 g) of cyclohexylbenzene, heated to 110° C., and oxygen was introduced at a flow rate of 200 ml / min, and the reaction was continued for 6 hours with stirring. The conversion rate of cyclohexylbenzene was 35.72%, and the selectivity of 1-cyclohexylbenzene hydroperoxide was 91.40%.

Embodiment 3

[0017] 5 mg of the metalloporphyrin polymer with structural formula (I), R 1 =R 2 =Cl, m=2, n=830, M=Ni, the specific surface area is 676m 2 / g, the average pore diameter is 2.4 nm. NHPI (193.4 mg) was added to 50 ml (47.5 g) of cyclohexylbenzene, heated to 110° C. and air was passed through at a flow rate of 200 ml / min, and the reaction was continued for 6 hours with stirring. The conversion rate of cyclohexylbenzene was 39.98%, and the selectivity of 1-cyclohexylbenzene hydroperoxide was 92.15%.

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Abstract

The invention discloses a method of preparing 1-cyclohexylphenyl hydrogen peroxide by means that a metalloporphyrin polymer and N-hydroxyl phthalimide synergistically catalyze air or oxygen to oxidizecyclohexylbenzene. The method includes the steps of: with polymerized metalloporphyrin and N-hydroxyl phthalimide, which are linked by means of azo bonds and phenylene bonds, as the catalyst, performing catalytic oxidization to the cyclohexylbenzene, wherein 1-40 atm air or oxygen is added, reaction temperature is 70-130 DEG C, addition amount of the metalloporphyrin is 1*10<-4> - 3*10<-3> wt% ofthe cyclohexylbenzene, addition amount of the N-hydroxyl phthalimide is 0 - 1.1*10<-2> wt% of the cyclohexylbenzene, and a solvent is one or a mixture of chlorobenzene, nitrobenzene, or cyanobenzene;the method is high in conversion rate and is high in selectivity of the 1-cyclohexylphenyl hydrogen peroxide. In the method, the cyclohexylbenzene is subjected to catalytic oxidization by means of the metalloporphyrin polymer and N-hydroxyl phthalimide to prepare the 1-cyclohexylphenyl hydrogen peroxide. The method has gentle reaction conditions and is low in usage amount of catalyst, wherein thecatalyst can be repeatedly used.

Description

technical field [0001] The invention relates to the use of polymeric metalloporphyrins linked by azo bonds and phenylene bonds and N-hydroxyphthalimide to jointly catalyze the oxidation of cyclohexylbenzene with air or oxygen under mild conditions, and to prepare efficiently and selectively 1-Cyclohexylbenzene hydroperoxide approach. Background technique [0002] Phenol is an important chemical raw material with great market demand and is widely used in the production of important chemical products such as synthetic resins, drugs and preservatives. The traditional industrial production method of phenol is based on the oxidation of cumene to obtain cumene hydroperoxide, and then the cumene hydrogen peroxide is decomposed with an acid catalyst to obtain phenol and acetone. However, this method also produces a large amount of acetone with little industrial demand as a by-product, so that the production capacity of phenol is severely limited by the market sales of acetone. The...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C407/00C07C409/14
CPCC07C407/00C07C409/14
Inventor 阳卫军谭志伟朱军辉
Owner HUNAN UNIV