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Method for green, efficient and selective synthesis of chlorphenesin

A chlorphenesin, selective technology, applied in the fields of pharmaceutical synthesis and cosmetic production, can solve the problems of coma, increased reaction steps, high toxicity and the like

Inactive Publication Date: 2018-08-24
GUANGXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, the hydrolysis of the main raw material epichlorohydrin and the preparation of sodium p-chlorophenol not only use highly corrosive substances such as strong acid and strong alkali, but also increase the cost correspondingly with the increase of reaction steps
Especially in the step of converting epichlorohydrin into 3-chloro-1,2-propanediol, this intermediate is flammable, highly toxic, and a suspected carcinogen, which can be poisoned by inhalation, ingestion or absorption through the skin
It has effects on the lungs, liver, kidneys and brain. Even inhaling a small amount of steam may cause nausea, headache, dizziness, coma and other symptoms, which can cause pulmonary edema, and severe cases can be fatal, which is not conducive to production expansion.

Method used

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  • Method for green, efficient and selective synthesis of chlorphenesin
  • Method for green, efficient and selective synthesis of chlorphenesin
  • Method for green, efficient and selective synthesis of chlorphenesin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] A kind of method of green efficient selective synthesis of chlorphenesin, concrete operation is as follows:

[0031] In a 500ml three-necked flask, 55.25g (0.60mol) of glycerol, 25.3g (0.28mol) of dimethyl carbonate, 25.8g (0.20mol) of p-chlorophenol, and 0.8g (0.02mol) of sodium hydroxide were added successively. Wherein, the molar ratio of glycerin: diethyl carbonate: p-chlorophenol in the system is 3:1.4:1, and the molar ratio of p-chlorophenol and sodium hydroxide is 1:0.1. When feeding, keep stirring at a low speed of 30 rpm, heat to 110°C, and react for 11 hours. After the reaction, cool down to 22°C, add 552.5g of the supernatant of saturated sodium chloride solution to the above-mentioned reaction solution for washing, then add 552.5g of dichloromethane, mix well and let stand, separate layers, take the organic phase, Concentrate to obtain a yellow-white solid, which is recrystallized with dichloromethane and filtered with suction to obtain a pure white powder ...

Embodiment 2

[0033] A kind of method of green efficient selective synthesis of chlorphenesin, concrete operation is as follows:

[0034]In a 1000ml three-necked flask, 110.5g (1.20mol) of glycerin, 66g (0.56mol) of diethyl carbonate, 51.6g (0.40mol) of p-chlorophenol, and 4.04g (0.04mol) of triethylamine were added in sequence. The molar ratio of glycerin: diethyl carbonate: p-chlorophenol in the system is 3:1.4:1, and the molar ratio of p-chlorophenol and triethylamine is 1:0.1. When feeding, keep stirring at a low speed of 40 rpm, heat to 120°C, and react for 12 hours. After the reaction, lower the temperature to 24°C, add 1105g of saturated sodium chloride solution to the above-mentioned reaction solution for washing, then add 1105g of dichloromethane, mix well, let stand, separate layers, take the organic phase, concentrate to obtain a yellow-white solid , recrystallized with chloroform, and suction filtered to obtain a pure white powder product. The solid powder was vacuum-dried at 5...

Embodiment 3

[0036] A method for the selective synthesis of chlorphenesin in a green high position, the specific operations are as follows:

[0037] In a 3000ml three-necked flask, 331.5g (3.60mol) of glycerol, 245.6g (1.68mol) of dipropyl carbonate, 154.8g (1.20mol) of p-chlorophenol, and 6.72g (0.12mol) of potassium hydroxide were added successively. The molar ratio of glycerin: dipropyl carbonate: p-chlorophenol in the system is 3:1.4:1, and the molar ratio of p-chlorophenol and potassium hydroxide is 1:0.1. When feeding, keep stirring at a low speed of 50 rpm, heat to 130°C, and react for 13 hours. After the reaction, lower the temperature to 26°C, add 3315g of saturated sodium chloride solution to the above-mentioned obtained reaction solution for washing, then add 3315g of ethyl acetate, mix well, let stand, separate layers, take the organic phase, concentrate to obtain a yellow-white solid , recrystallized with ethyl acetate, and suction filtered to obtain a pure white powder produ...

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Abstract

The invention discloses a method for green, efficient and selective synthesis of chlorphenesin. Glycerol and 4-chlorophenol directly serve as raw materials, diethyl carbonate serves as a selective synthesis agent, separate synthesis can be performed in situ, orientation reaction is ensured, other by-products are omitted, separation and purification are simple, yield is 95% under proper conditions,and purity is 99.5% or more. The yield of the chlorphenesin is greatly improved, high-toxic and expensive 3-chlorine-1, 2-propanediol is abandoned by the aid of low-cost and non-toxic glycerin, reaction conditions are mild, and industrial production is facilitated.

Description

technical field [0001] The invention belongs to the fields of medicine synthesis and cosmetics production. Specifically, it is a green and efficient method for selectively synthesizing chlorphenesin. Background technique [0002] Chlorphenesin, Chinese aliases: chlorphenesin, chlorophenol ether, 3-p-chlorophenoxy-1,2-propanediol. English name Chlorphenesin, English aliases: Chlorophenesin; Gecophen; Adermykon; Chlorphenesinum, 3-(4-chlorophenoxy)propane-1,2-dio. Chemical name: 3-(4-chlorophenoxy)-1,2-propanediol, the structural formula is as follows: [0003] [0004] Molecular formula C 9 h 11 ClO 3 , molecular weight 202.635, melting point 77-79°C. It is a white crystalline powder, odorless, bitter in taste, slightly soluble in water, soluble in ethanol, dichloromethane, ethyl acetate and most other organic solvents. [0005] Chlorphenesin is mainly used in the following two aspects: [0006] In medicine, chlorphenesin-related preparations are antigen-related im...

Claims

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Application Information

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IPC IPC(8): C07C41/16C07C43/23
CPCC07C41/16C07C68/06C07C43/23C07C69/96
Inventor 刘旭梁跃辉凌碗梦刘仰厚王立升
Owner GUANGXI UNIV
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