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Preparation method of 2,5-dichlorophenol

A technology of dichlorophenol and dichlorobenzene is applied in the field of manufacture of 2, pesticides and pharmaceutical intermediates, and achieves the effects of few operation steps, mild conditions and few by-products

Active Publication Date: 2017-09-05
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the method of preparing 2,5-dichlorophenol by metalloporphyrin catalytic oxidation of 1,4-dichlorobenzene has not been reported in the literature

Method used

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  • Preparation method of 2,5-dichlorophenol
  • Preparation method of 2,5-dichlorophenol
  • Preparation method of 2,5-dichlorophenol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment example 1

[0027] In a 1000mL four-necked reaction flask, sequentially add 14.7g 1,4-dichlorobenzene, 100mL acetonitrile, vanadium porphyrin compound (M=vanadium, Ar=phenyl, R=H), 0.5g cocatalyst phosphoric acid, slowly drop The oxidizing agent was 5 mL of 30% hydrogen peroxide, the reaction temperature was controlled at 20° C., and the reaction was carried out for 6 hours. After the reaction was completed, the reaction solution was filtered to remove insoluble matter, and the conversion rate of 1,4-dichlorobenzene was 98.0% and the selectivity of 2,5-dichlorophenol was 95.3% through quantitative analysis by high performance liquid chromatography.

Embodiment example 2

[0029] In a 1000mL four-necked reaction flask, add 14.7g1,4-dichlorobenzene, 100mL acetic acid, 0.02g vanadium porphyrin compound (M=vanadium, Ar=phenyl, R=H), 0.5g cocatalyst phosphoric acid, slowly 5 mL of 30% hydrogen peroxide was added dropwise, the reaction temperature was controlled at 20° C., and the reaction was carried out for 6 h. After the reaction, the reaction liquid was filtered to remove insoluble matter, and the conversion rate of 1,4-dichlorobenzene was 85.0% and the selectivity of 2,5-dichlorophenol was 92.3% through quantitative analysis by high performance liquid chromatography.

Embodiment example 3

[0031] In a 1000mL four-necked reaction flask, add 14.7g1,4-dichlorobenzene, 100mL methanol, 0.02g vanadium porphyrin compound (M=vanadium, Ar=phenyl, R=H), 0.5g cocatalyst phosphoric acid, slowly 5 mL of 30% hydrogen peroxide was added dropwise, the reaction temperature was controlled at 20° C., and the reaction was carried out for 6 h. After the reaction, the reaction solution was filtered to remove insoluble matter, and quantitative analysis by high performance liquid chromatography showed that the conversion rate of 1,4-dichlorobenzene was 75.0%, and the selectivity of 2,5-dichlorophenol was 96.3%.

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Abstract

The invention provides a preparation method of 2,5-dichlorophenol, and belongs to the field of preparation of compounds. The preparation method comprises the following steps: taking 1,4-dichlorobenzene as a raw material and taking a combination of one or more of water, methanol, acetonitrile and acetic acid as a solvent under the effects of an oxidizing agent, a metal porphyrin catalyst and a cocatalyst, and reacting at the temperature of 5-80 DEG C for 0.5-20 hours to obtain 2,5-dichlorophenol. By a catalyst system, efficiency and yield of oxidation reaction can be improved remarkably, reaction conditions are gentle relatively, side effects are less, products are separated favorably, the reaction time is greatly shortened, and the 2,5-dichlorophenol can be industrially produced on a large scale.

Description

technical field [0001] The invention provides a method for preparing 2,5-dichlorophenol, which belongs to the field of compound manufacture, in particular to the manufacture technology of pesticides and pharmaceutical intermediates. [0002] technical background [0003] 2,5-dichlorophenol is a relatively important organic synthesis intermediate and pesticide intermediate, which can be used to synthesize 3,6-dichlorosalicylic acid, condense with acetic acid to form ester, and is mainly used for nitrogen fertilizer synergist and herbicide manufacture Dicamba, leather antifungal agent and DP antifungal agent, etc. [0004] WO2015049160A1, WO2015049360A1 and RO114785 etc. disclose methods for preparing 2,5-dichlorophenol by hydrolysis of trihalogenated benzene. This method has the advantages of simple technology and low investment, but the process needs to use a large amount of acid and alkali, high temperature and high pressure, and the reaction conditions are relatively harsh...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/30C07C37/60C07C37/58B01J31/22
CPCC07C37/58C07C37/60B01J31/183B01J2531/16B01J2531/847B01J2531/845B01J2531/842B01J2531/66B01J2531/56B01J2531/72B01J2531/26B01J2231/70C07C39/30
Inventor 朱红军宋广亮楚庆岩徐杰高尚何广科刘睿
Owner NANJING UNIV OF TECH
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