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A kind of 2,5-dichlorophenol preparation method

A kind of technology of dichlorophenol and dichlorobenzene is applied in the field of compound manufacturing, and achieves the effects of few by-products, mild conditions and few operation steps

Active Publication Date: 2021-01-26
NANJING TECH UNIV
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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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  • A kind of 2,5-dichlorophenol preparation method
  • A kind of 2,5-dichlorophenol preparation method
  • A kind of 2,5-dichlorophenol preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment example 1

[0026] 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

[0028] 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

[0030] 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 method for preparing 2,5-dichlorophenol, which belongs to the field of compound production. Under the action of oxidant, metal porphyrin catalyst and cocatalyst, 1,4-dichlorobenzene is used as raw material, and one or more combinations of water, methanol, acetonitrile and acetic acid are used as solvent, and the reaction temperature is 5-80 °C, and the reaction time is 0.5-20h to obtain 2,5-dichlorophenol. The catalyst system used in the invention can remarkably improve the efficiency and yield of the oxidation reaction, the reaction conditions are relatively mild, the side reactions are few, the products are easy to separate, the reaction time is greatly shortened, and it can be extended to large-scale industrial production.

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 Patents(China)
IPC IPC(8): C07C39/30C07C37/60C07C37/58B01J31/22
CPCB01J31/183B01J2231/70B01J2531/16B01J2531/26B01J2531/56B01J2531/66B01J2531/72B01J2531/842B01J2531/845B01J2531/847C07C37/58C07C37/60C07C39/30
Inventor 朱红军宋广亮楚庆岩徐杰高尚何广科刘睿
Owner NANJING TECH UNIV
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