Method for preparing p-hydroxyacetophenone by catalytically oxidizing paraethyl phenol with metalloporphyrin-metal salt composite catalyst

A technology of p-hydroxyacetophenone and composite catalysts, which is applied in the direction of organic compound/hydride/coordination complex catalysts, carbon-based compound preparation, chemical instruments and methods, etc., and can solve the problems of large catalyst consumption, environmental pollution, and three waste discharges To reduce resource consumption and operating costs, shorten response time, and save operating costs

Inactive Publication Date: 2015-05-06
BEIJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] (1) The amount of catalyst used is very large (up to 5000ppm), and it needs to be separated and recovered after the reaction, and the separation and recovery of the catalyst will cause high cost, high energy consumption, and a lot of three wastes, and serious environmental pollution;
[0008] (2) The reaction time is long (more than 10h), and the reaction efficiency is low, the energy consumption is larg...

Method used

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  • Method for preparing p-hydroxyacetophenone by catalytically oxidizing paraethyl phenol with metalloporphyrin-metal salt composite catalyst
  • Method for preparing p-hydroxyacetophenone by catalytically oxidizing paraethyl phenol with metalloporphyrin-metal salt composite catalyst
  • Method for preparing p-hydroxyacetophenone by catalytically oxidizing paraethyl phenol with metalloporphyrin-metal salt composite catalyst

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Experimental program
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Effect test

Embodiment 1

[0030] In a 100mL autoclave, add 12.2g p-ethylphenol successively, 4×10 -3 g tetraphenyl cobalt porphyrin chloride (i.e. R in the general formula (II) 21 for H, R 22 for H, R 23 for H, M 2 is Co, X is Cl), 8g of sodium hydroxide, 30mL of methanol, and oxygen at a pressure of 0.3MPa, reacted at 85°C for 4h. The reacted mixture was analyzed by high-performance liquid chromatography, and the selectivity of 4-hydroxyacetophenone was 31.42%, and the yield was 10.52%.

Embodiment 2

[0032] In a 100mL autoclave, add 12.2g p-ethylphenol successively, 4×10 -3 g tetraphenyliron porphyrin chloride (i.e. R in the general formula (II) 21 for H, R 22 for H, R 23 for H, M 2 Fe, X is Cl), 8g of sodium hydroxide, 30mL of methanol, the pressure of 0.3MPa of oxygen was introduced, and the reaction was carried out at 85°C for 4h. The reaction mixture was analyzed by high-performance liquid chromatography, and the selectivity of 4-hydroxyacetophenone was 16.84%, and the yield was 6.9%.

Embodiment 3

[0034] In a 100mL autoclave, add 12.2g p-ethylphenol successively, 4×10 -3 g tetrakis chloride - (p-methoxyphenyl) manganese porphyrin (i.e. R in the general formula (II) 21 for H, R 22 for H, R 23 for OCH 3 ,M 2 is Mn, X is Cl), 8g of sodium hydroxide, 30mL of methanol, and the oxygen at a pressure of 0.3MPa was introduced to react at 60°C for 4h. The reacted mixture was analyzed by high-performance liquid chromatography, and the selectivity of 4-hydroxyacetophenone was 15.67%, and the yield was 2.99%.

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Abstract

The invention relates to a method for preparing p-hydroxyacetophenone by catalytically and selectively oxidizing paraethyl phenol with a metalloporphyrin-metal salt composite catalyst. The method is characterized in that paraethyl phenol is taken as a raw material, methanol is taken as a solvent, metalloporphyrin expressed by a formula (I) or a formula (II) and a metal salt is taken as a composite catalyst or metalloporphyrin expressed by a formula (I), a formula (II) or a formula (III) is taken as the catalyst, the concentration of metalloporphyrin is 5-100ppm, the concentration of the metal salt is 500-2000ppm, the molar ratio of sodiumhydroxide to ethyl phenol is (1-2.5): 1, the oxygen pressure is 0.2-0.5MPa, the reaction temperature ranges from 60 to 90 DEG C, the reaction time is 3-7h, and p-hydroxyacetophenone is obtained under all the conditions. According to the invention, the dosage of the catalyst is extremely low and the reaction time is short; after reaction, the catalyst does not need to be separated and recovered; the consumption of resources and the operating cost are reduced in the reaction process, and the purposes of saving energy and reducing emission are achieved while the environmental pollution is reduced.

Description

technical field [0001] The invention relates to a method for preparing aromatic ketones, in particular to a method for preparing p-hydroxyacetophenone by catalyzing and selectively oxidizing p-ethylphenol with a metalloporphyrin-metal salt composite catalyst. Background technique [0002] p-Hydroxyacetophenone (its structural formula is as follows) is an important fine organic chemical, which is widely used in various fields such as medicine, pesticides, dyes, liquid crystal materials, etc., and it is also a synthetic choleretic, antipyretic and analgesic, and anti-premature drug , raw materials and important intermediates of asthma inhibitors, with important application value. [0003] [0004] At present, the preparation methods of p-hydroxyacetophenone mainly include the Fries rearrangement method using phenol and acetic anhydride as raw materials, the Friedel-Crafts acylation method using anisole and acetyl chloride as raw materials, and the direct method using p-ethy...

Claims

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Application Information

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IPC IPC(8): C07C49/825C07C45/36B01J31/22B01J31/28B01J31/26
Inventor 佘远斌杜晓雅宋旭锋于艳敏
Owner BEIJING UNIV OF TECH
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