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Method for preparing halogenated phenol compounds

A technology of halogenated phenols and compounds, which is applied in the field of preparation of halogenated phenols, can solve the problems of low yield and non-reaction, and achieve the effects of easy separation and treatment, reduced side reactions, and increased yield

Active Publication Date: 2015-04-08
中国中化股份有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The author directly uses solid acid instead of inorganic acid to catalyze the hydrolysis of halogenated aniline to prepare halogenated phenol, with lower yield or even no reaction

Method used

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  • Method for preparing halogenated phenol compounds
  • Method for preparing halogenated phenol compounds
  • Method for preparing halogenated phenol compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 12

[0035] Embodiment 12, the preparation of 5-dichlorophenol

[0036] 32.6g of 2,5-dichloroaniline and 100 mL of 15% hydrochloric acid aqueous solution were added to the reaction flask, heated to 90°C, cooled to 0°C after reaction for 1 hour, and filtered to obtain 2,5-dichloroaniline hydrochloride. The 2,5-dichloroaniline hydrochloride filter cake obtained by filtration was added to the autoclave, and then 100 mL of water, 100 mL of toluene, 0.163 g of phase transfer catalyst, 3.26 g of solid superacid SO were added. 4 2- / ZrO 2 , 150 ℃ closed reaction for 4 hours, cooled to 20 ℃, opened the kettle and discharged, filtered, the filtrate was left to stand for phase separation, the organic phase was distilled to remove toluene, the organic phase was analyzed by gas chromatography, the selectivity was 98%, the conversion rate was 100%, and the pressure was continued. Rectification, the pressure is 266.6Pa (2mm Hg column), the fraction of 68-73 ° C is collected to obtain 31.5g of ...

Embodiment 22

[0037] Example 22, Preparation of 5-dichlorophenol

[0038] Collect the filtrate of 2,5-dichloroaniline hydrochloride prepared in Example 1, add 32.6g of 2,5-dichloroaniline, and add 25g of 30% aqueous hydrochloric acid solution, heat to 90 ° C, and cool to 1 h after the reaction. 0 °C, filtration to obtain 2,5-dichloroaniline hydrochloride. The 2,5-dichloroaniline hydrochloride filter cake obtained by filtration is added in the autoclave, then 100mL of water, 100mL of toluene, 0.163g phase transfer catalyst are added, and the solid superacid SO that is collected by filtration in above-described embodiment 1 is recovered. 4 2- / ZrO 2, 150 ℃ closed reaction for 4 hours, cooled to 20 ℃, opened the kettle and discharged, filtered, the filtrate was left to stand for phase separation, the organic phase was distilled to remove toluene, the organic phase was analyzed by gas chromatography, the selectivity was 97%, the conversion rate was 100%, and the pressure was continued. Recti...

Embodiment 3

[0039] Example 3 Catalytic preparation of 2,5-dichlorophenol using different phase transfer catalysts

[0040] 32.6g of 2,5-dichloroaniline and 100 mL of 15% hydrochloric acid aqueous solution were added to the reaction flask, heated to 90°C, cooled to 0°C after reaction for 1 hour, and filtered to obtain 2,5-dichloroaniline hydrochloride. Add 2,5-dichloroaniline hydrochloride, 100mL water, 100mL toluene, phase transfer catalyst, 3.26g solid super acid SO to the autoclave 4 2- / ZrO 2 , 150 ℃ closed reaction for 4 hours, cooled to 20 ℃, opened the kettle and discharged, filtered, the filtrate was left to stand for phase separation, the organic phase was distilled to remove toluene, the organic phase was analyzed by gas chromatography, and the vacuum distillation was continued, the pressure was 266.6Pa (2mm Hg column), the 68-73 °C fractions were collected to give 2,5-dichlorophenol (see Table 1).

[0041] Table 1

[0042]

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Abstract

The invention belongs to the field of organic synthesis and particularly relates to a method for preparing halogenated phenol compounds. Halogenated phenylamine is used as raw materials, the halogenated phenylamine and mineral acid solutions are heated for dissolution, cooling precipitation is carried out, halogenated phenylamine inorganic acid salt is obtained, and solid halogenated phenylamine inorganic acid salt is obtained by filtering. Halogenated phenylamine inorganic acid salt, methylbenzene, water, phase transfer catalysts and solid acid catalysts are added into a high-pressure reactor, heating is carried out until temperature reaches 100-150 DEG C, hydrolysis reaction is carried out, after hydrolysis reaction, cooling and depressurization are carried out, the solid acid catalysts are removed by filtering, phase separation is carried out, organic phase distillation is carried out, the methylbenzene is removed, rectification is carried out, and halogenated phenol is obtained. The preparing method has the advantages of being simple in technology, low in raw material cost, mild in technology condition and the like.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and particularly relates to a method for preparing halogenated phenolic compounds. Background technique [0002] The structure of halogenated phenol compounds is shown in formula (I): [0003] [0004] In formula (I), X represents Cl, Br, F or I; R 1 Represents H or R, R is a C1-C8 alkane group; s, r represent numbers 1, 2 or 3, wherein s+r is less than or equal to 5. [0005] The halogenated phenol compounds of the formula (I) are important fine chemical intermediates, mainly used for the preparation of fine chemicals such as pesticides, medicines and dyes. Representative intermediates such as p-chlorophenol, o-chlorophenol, 2,4-dichlorophenol, 2,6-dichlorophenol and 2,5-dichlorophenol, etc. [0006] There are mainly two traditional industrial production methods for halogenated phenol compounds represented by formula (I): [0007] 1. The halogenation reaction is carried out with phenol as...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C37/05C07C39/30C07C39/27C07C39/28
CPCC07C37/05C07C209/00C07C39/30C07C39/27C07C39/28C07C211/52
Inventor 李付刚鄢冬茂闫士杰
Owner 中国中化股份有限公司
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