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A kind of method that catalyst catalyzes the hydroxylation of benzene to prepare phenol

A catalyst technology for catalyzing phenylhydroxyl groups, catalysts, applied in chemical instruments and methods, preparation of organic compounds, catalysts for physical/chemical processes, etc., can solve the problems of graphene oxide nanosheet grafted ferrocene materials without literature reports, etc., Achieve stable performance, mild reaction conditions, and improve activity.

Active Publication Date: 2018-01-23
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The use of graphene oxide nanosheets to graft ferrocene materials has not been reported in the field of benzene hydroxylation

Method used

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  • A kind of method that catalyst catalyzes the hydroxylation of benzene to prepare phenol
  • A kind of method that catalyst catalyzes the hydroxylation of benzene to prepare phenol
  • A kind of method that catalyst catalyzes the hydroxylation of benzene to prepare phenol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Get 1000mg graphene oxide and join in 400ml toluene, after ultrasonic (ultrasonic electric power 400W) 12h, in N 2 Under protection, add 4.0ml APTMS to reflux for 24h, wash off the physically adsorbed APTMS with a large amount of ethanol, and dry at 80°C for 12h. Disperse the above-mentioned APTMS grafted graphene oxide in 250ml ethanol, add 33mmol ferrocene formaldehyde and stir at 100°C for 24h, then add 44mmol NaBH 3 CN continued to stir for 3 days, and then the obtained solid was washed with ether in a Soxhlet extractor for 3 days to finally obtain 620 mg of a black solid.

[0023] Use the obtained catalytic material for benzene hydroxylation reaction, put 80mg catalyst, 0.78g benzene (10mmol), 6.8mL acetonitrile, 3.4g 30% H2O2 into a 25mL flask for reaction, magnetically stir, the reaction temperature is 60°C, keep for 2h , the yield of phenol was 14.3%.

Embodiment 2

[0025] Get 1000mg graphene oxide and join in 400ml toluene, after ultrasonic (ultrasonic electric power 400W) 14h, in N 2 Under protection, add 6.0ml APTMS to reflux for 24h, wash off the physically adsorbed APTMS with a large amount of ethanol, and dry at 80°C for 12h. Disperse the above-mentioned APTMS grafted graphene oxide in 250ml ethanol, and add 22mmol ferrocene formaldehyde and stir at 80 degrees for 24h, then add 33mmol NaBH 3 CN continued to stir for 3 days, and then the obtained solid was washed with diethyl ether in a Soxhlet extractor for 3 days to finally obtain 560 mg of a black solid.

[0026] Using the obtained catalytic material for benzene hydroxylation reaction, 80mg catalyst, 0.78g benzene (10mmol), 6.8mL acetonitrile, 3.4g 30%H 2 o 2 , added to a 25mL flask for reaction, stirred by magnetic force, the reaction temperature was 80°C, kept for 2h, and the yield of phenol was 13.1%.

Embodiment 3

[0028] Take 1000mg of graphene oxide and add it to 400ml of toluene. After ultrasonic (ultrasonic electric power 400W) for 16h, add 7.0ml of APTMS under the protection of N2 and reflux for 24h. Wash off the physically adsorbed APTMS with a large amount of ethanol and dry at 80°C for 12h. Disperse the above-mentioned APTMS grafted graphene oxide in 250ml ethanol, and add 44mmol ferrocene formaldehyde at 60 and stir for 24h, then add 22mmol NaBH 3 CN continued to stir for 3 days, and then the obtained solid was washed with ether in a Soxhlet extractor for 3 days to finally obtain 570 mg of a black solid.

[0029] Using the obtained catalytic material for benzene hydroxylation reaction, 80mg catalyst, 0.78g benzene (10mmol), 6.8mL acetonitrile, 3.4g 30%H 2 o 2 , added to a 25mL flask for reaction, stirred by magnetic force, the reaction temperature was 40°C, kept for 1h, and the yield of phenol was 11.2%.

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Abstract

The invention discloses a method for preparing phenol by catalyzing the hydroxylation of benzene with a catalyst, wherein the catalyst is ferrocene-grafted aminosilane-graphene oxide, graphene oxide is added to toluene, ultrasonically, and aminosilane is added under nitrogen atmosphere , at 25-100°C, react for 12h-24h, wash, dry, disperse the obtained substance in ethanol, add ferrocene formaldehyde and stir for 6h-24h at 25-80°C, then add cyanoboron Sodium hydride (NaBH3CN), stirred and reacted for 12h to 72h, and the obtained solid was washed with ether to obtain a catalyst; the obtained catalyst was mixed with benzene, acetonitrile and H2O2, and stirred for 4h at 25 to 80°C to obtain phenol. Grafting ferrocene on graphene oxide nanosheets, through the adsorption and activation of graphene oxide to benzene and the activation of ferrocene to H2O2, the activity of the catalytic system for benzene hydroxylation is greatly improved, the reaction conditions are mild, and the catalyst material Stable performance.

Description

technical field [0001] The invention belongs to the field of preparing phenol by hydroxylation of benzene, and specifically provides a method for preparing phenol by catalyzing the hydroxylation of benzene with a catalyst. Background technique [0002] Phenol is an important chemical intermediate, which can be used to produce bisphenol A, phenolic resin, dyes, antioxidants and medicines. At present, the global demand for phenol is close to 10 million tons, while my country's demand for phenol accounts for about 10% of the world's total demand. The traditional production method of phenol is the cumene method, and currently 95% of the world's phenol is produced by this method. In this method, the hydrolysis of cumene requires a large amount of inorganic acid, which brings certain environmental problems; at the same time, it will be restricted by the market of co-product acetone. Especially in the overall process, the total yield of phenol based on raw material benzene is onl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C39/04C07C37/60B01J31/22
CPCY02P20/52
Inventor 高爽尚森森王连月赵公大杨华
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI