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Synthetic method of chlorobenzene glyceryl ether

A technology of chlorphenesin and synthesis method, which is applied in the direction of ether preparation, ester reaction preparation of ether, ether separation/purification, etc., can solve the problems of strong corrosiveness of organic acids, reduced reaction yield, complex reaction raw materials, etc., and achieves Reduce the discharge of waste liquid, reduce the cost of raw materials, and improve the effect of purification yield

Active Publication Date: 2015-11-04
BEIJING SUNPU BIOCHEM TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Chinese patent CN101445436A discloses a method for preparing chlorphenesin with epichlorohydrin and p-chlorophenol as raw materials and sulfuric acid as a catalyst. The reaction raw materials of this method are complicated, and 3-chloro-1,2 -Propylene glycol, and then synthesize chlorphenesin, the two-step reaction will inevitably reduce the reaction yield, and the yield of the product obtained by repeated experiments according to this method is low, and the first step reaction cannot be monitored, so the reaction process cannot be effectively controlled. In addition, this method The introduction of highly corrosive chemical solvents such as organic acids and difficult post-processing is not suitable for scale-up production
No researchers have applied this type of catalyst in this type of reaction

Method used

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  • Synthetic method of chlorobenzene glyceryl ether
  • Synthetic method of chlorobenzene glyceryl ether
  • Synthetic method of chlorobenzene glyceryl ether

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0075] Take a 500ml three-necked flask, add 36.6g (content 99.5%) (0.33mol) of 3-chloro-1,2-propanediol, 16.6g (0.13mol) of p-chlorophenol, 34.0g of NaOH solution with a concentration of 18%, and heat the reaction system to 105°C, react for 1h. Add p-chlorophenol 9.0g (0.07mol), 18% NaOH solution 48.4g, 3-chloro-1,2-propanediol 4.5g (content 99.5%) (0.04mol), at this moment, in the system, p-chlorophenol and The molar ratio of the total amount of 3-chloro-1,2-propanediol added is 1:1.85, the molar ratio of the total added amount of p-chlorophenol and sodium hydroxide is 1:1.85, continue to react for 2 hours, cool down to 20°C, add dilute Hydrochloric acid to adjust the pH to 6.0. After standing for a period of time, the two phases were separated, and the lower organic phase was monitored by gas chromatography. The conversion rate was 89.3%, and then 150ml chloroform and 100ml water were added. The volume ratio of chloroform and water was 3:2, and the Stir in ice water, a whi...

Embodiment 2

[0077] Take a 500ml three-necked flask, add 36.6g (content 99.5%) (0.33mol) of 3-chloro-1,2-propanediol, 16.6g (0.13mol) of p-chlorophenol, 34.0g of NaOH solution with a concentration of 18%, tetrabutyl bromide Ammonium chloride 0.32g, the reaction system was heated to 105°C, and reacted for 1h. Add p-chlorophenol 9.0g (0.07mol), 18% NaOH solution 48.4g, 3-chloro-1,2-propanediol 4.5g (content 99.5%) (0.04mol), at this moment, in the system, p-chlorophenol and The mol ratio of 3-chloro-1,2-propanediol total addition is 1:1.85, and the mol ratio of p-chlorophenol and sodium hydroxide total addition is 1:1.85, and the mol ratio of p-chlorophenol and tetrabutylammonium bromide The molar ratio was 1:0.005, and the reaction was continued for 2 hours, the temperature was lowered to 20°C, and the pH value was adjusted to 6.0 by adding dilute hydrochloric acid. After standing for a period of time, two phases were separated, and the lower organic phase was monitored by gas chromatograp...

Embodiment 3

[0079] Take a 500ml three-necked flask, add 35.6g (content 99.5%) (0.32mol) of 3-chloro-1,2-propanediol, 16.6g (0.13mol) of p-chlorophenol, 73.2g of KOH solution with a concentration of 12%, tetrabutylsulfuric acid Ammonium hydrogen 0.5g, the reaction system was heated to 105°C, and reacted for 1h. Add p-chlorophenol 9.0g (0.07mol), 12% KOH solution 104.1g, 3-chloro-1,2-propanediol 4.3g (content 99.5%) (0.04mol), at this moment, p-chlorophenol and The molar ratio of the total amount of 3-chloro-1,2-propanediol added is 1:1.80, the molar ratio of the total added amount of p-chlorophenol and potassium hydroxide is 1:1.90, and the molar ratio of p-chlorophenol and tetrabutylammonium bisulfate The molar ratio was 1:0.007, and the reaction was continued for 2 hours, the temperature was lowered to 20°C, and the pH value was adjusted to 6.0 by adding dilute hydrochloric acid. After standing for a period of time, two phases were separated, and the lower organic phase was monitored by...

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Abstract

The invention relates to a synthetic method of chlorobenzene glyceryl ether. 3-chloro-1,2-propanediol and parachlorophenol are directly used as raw materials, high-corrosion chemical solvents are not introduced, a reaction is simple, the yield is high, and the yield can reach 95 percent or more under the optimal reaction condition. By adding a few phase transfer catalysts, the reaction can be promoted to be conducted quickly and effectively, and the reaction time can be shortened by at least two hours.

Description

technical field [0001] The invention relates to a method for synthesizing chlorphenesin. Background technique [0002] Chlorphenesin, also known as chlorophenesin, chlorphenesin, English trade name Chlorphenesin, chemical name 3-(4-chlorophenoxy)-1,2-propanediol, the structural formula is as follows: [0003] [0004] Molecular formula is C 9 h 11 ClO 3 , is white powder, bitter taste, almost odorless, molecular weight 202.63, slightly soluble in water, easily soluble in ethanol, melting point 78℃~81℃. [0005] Main uses of chlorphenesin: [0006] ①In terms of medicine, it is mainly used as a muscle relaxant, and can also be used as an antifungal drug for antifungal, bacterial, vaginal mold, trichomonas and other diseases, and there are many drug dosage forms; [0007] ② In terms of cosmetics, chlorphenesin can effectively resist Gram-positive and negative bacteria, especially against Aspergillus niger IMI149007 and Penicillium pinophilum IMI87160 (fungi), and agains...

Claims

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Application Information

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IPC IPC(8): C07C43/23C07C41/16C07C41/40
CPCC07C41/16C07C41/40C07C43/23
Inventor 温杰胡文静潘咏梅蒙雪艳张慧明
Owner BEIJING SUNPU BIOCHEM TECH
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