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Preparation method of sodium phenoxyacetate

A technology of sodium phenoxyacetate and chloroacetic acid, which is applied in the direction of carboxylate preparation, organic compound preparation, chemical instruments and methods, etc., can solve the problems of low solubility of sodium chloroacetate, unfavorable large-scale production, unfavorable industrial production, etc. Achieve the effects of low price, shortened reaction path, and easy industrial production

Pending Publication Date: 2021-12-14
ANQING ROUNDCARE PHARM CO LTD
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  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Preparation of sodium phenoxyacetate mainly comprises at present: utilize phenol and sodium hydroxide to react sodium phenate, chloroacetic acid and sodium carbonate prepare sodium chloroacetate solution, then sodium phenoxide solution and sodium chloroacetate solution are mixed and reacted (as Chinese patent CN1044458A) , the method is complicated to operate, the solubility of sodium chloroacetate is low, and a large amount of solvent is required for complete dissolution, which is not conducive to industrial production; Chinese patent CN109180491A discloses the method for preparing sodium phenoxyacetate by using sodium phenate and sodium chloroacetate solution to remove water in toluene , but this method needs to use a large amount of toluene as an organic solvent, toluene is toxic, and its volume concentration can explode when its volume concentration is in a low range, and there are also hidden dangers in production safety
Chinese patent CN106397177A discloses the preparation of sodium phenoxyacetate in a full cycle of sodium phenate and sodium chloroacetate solution. This method uses excessive sodium phenoxide, and the sodium phenoxyacetate obtained by crystallization contains a large amount of sodium phenate, which needs to be washed with a large amount of chlorobenzene Purify, simultaneously this method washing mother liquor reclaims mechanically, and operation procedure is loaded down with trivial details; Document " SYNTHETIC COMMUNICATIONS, 27 (2i), 3729-3736 (1997) ", discloses under microwave condition, sodium phenoxide and sodium chloroacetate prepare sodium phenoxyacetate method, but this method has higher requirements on reaction equipment and conditions, and is also unfavorable for large-scale production

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  • Preparation method of sodium phenoxyacetate
  • Preparation method of sodium phenoxyacetate

Examples

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Embodiment 1

[0026] Add 282ml water in the 500ml reaction bottle, 28g sodium hydroxide, stir, preparation concentration is the sodium hydroxide solution of 9.0%, solid dissolves, and the exothermic heat of sodium hydroxide dissolution is obvious, is down to room temperature, adds 28.2g phenol (0.30mol), Add 37.8g of chloroacetic acid (0.40mol) to 80°C, keep it warm for 4 hours, stop heating, crystallize overnight at 30°C, filter with suction, and dry the obtained filter cake at 70°C (in specific implementation, vacuum can also be used) Drying method), 16.8g of white solid was obtained, and the yield was 32.2% (yield calculation formula=(moles of sodium phenoxyacetate / moles of phenol*100%, the same below), and the purity was 92.85% (using area normalization obtained by calculation, the same below).

[0027] (Column YMC 250*4.6, 5um, mobile phase 85% potassium dihydrogen phosphate, pH=3.5, adjusted by phosphoric acid, flow rate 1.5ml / min, column temperature 50°C, detection wavelength 220nm, ...

Embodiment 2

[0029] Add purified water 400ml in the 1000ml reaction flask, stir, add 88g (2.2mol) sodium hydroxide, the preparation concentration is the sodium hydroxide solution of 18%, treat that solid dissolves, be down to room temperature, add 75g (0.8mol) phenol, 76g ( 0.8mol) of chloroacetic acid, heated to 75°C, kept stirring for 2 hours, stopped heating, stirred at 30°C overnight for crystallization, a large amount of solids precipitated, filtered with suction, dried the obtained filter cake at 70°C for 8 hours, stopped drying, and obtained white The solid powder is 112g, the yield is 68.0%, and the purity is 99.14%.

Embodiment 3

[0031] Add 400ml of purified water in the 1000ml reaction bottle, stir, add 88g (2.2mol) sodium hydroxide, configure 18% sodium hydroxide solution (percentage concentration), after solid dissolves, be down to room temperature, add 75g (0.8mol) phenol, 95g (1.0mol) of chloroacetic acid, heated to 80°C, kept stirring for 3h, stopped heating, stirred at 28°C overnight, a large amount of solids precipitated, filtered with suction, dried the filter cake at 70°C for 8h, stopped drying, and obtained a white solid powder 122.0 g, the yield is 87.6%, and the purity is 99.32%.

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Abstract

The invention provides a preparation method of sodium phenoxyacetate. According to the sodium phenoxyacetate preparation method, phenol and chloroacetic acid are subjected to a heating reaction in a sodium hydroxide solution, cooling crystallization and one-step reaction are conducted to prepare sodium phenoxyacetate, and the obtained sodium phenoxyacetate is high in purity and yield. The method is simple to operate, safe in production, green, environment-friendly and suitable for large-scale production.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to a preparation method of a pharmaceutical intermediate sodium phenoxyacetate. technical background [0002] Sodium phenoxyacetate is an important chemical raw material, which can be used in food flavors and daily chemical flavor formulas, and can also be used as a fungicide. It is used to produce penicillin V, plant growth regulators, and pharmaceutical intermediates for various lipid-lowering drugs. , is widely used. [0003] Preparation of sodium phenoxyacetate mainly comprises at present: utilize phenol and sodium hydroxide to react sodium phenate, chloroacetic acid and sodium carbonate prepare sodium chloroacetate solution, then sodium phenoxide solution and sodium chloroacetate solution are mixed and reacted (as Chinese patent CN1044458A) , the method is complicated to operate, the solubility of sodium chloroacetate is low, and a large amount of solve...

Claims

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Application Information

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IPC IPC(8): C07C51/367C07C59/70C07C51/42
CPCC07C51/367C07C51/42C07C59/70
Inventor 岳永力沈艳阳饶经纬鲁飞林立陈冰张建
Owner ANQING ROUNDCARE PHARM CO LTD