Preparation method of p-chlorophenylglycine

A technology of p-chlorophenylglycine and p-chlorobenzaldehyde is applied in the preparation of organic compounds, the preparation of cyanide reaction, chemical instruments and methods, etc. Low, avoids hazardous reagents, requires low-intensity effects on equipment

Inactive Publication Date: 2020-07-31
上海开荣化工科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this process is produced by the sodium cyanide method, which requires a large amount of sodium cyanide, which has high toxicity, high labor protection conditions, and great environmental pollution. The three wastes must be strictly treated.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] This embodiment provides a method for preparing p-chlorophenylglycine, which includes the following steps:

[0030] Step 1: Add the catalyst and p-chlorobenzaldehyde to the chloroform solution, and accelerate the dissolution of the catalyst and p-chloroformaldehyde in chloroform by shaking to make a mixed solution;

[0031] Step 2: Add the mixed solution made in step 1 to the sodium hydroxide solution and mix, and add liquid ammonia dropwise under stirring, and the time for the dropwise addition of liquid ammonia is 2h;

[0032] Step 3: After the dropwise addition of liquid ammonia is finished, add ammonium bicarbonate solution and react at room temperature for 8 hours;

[0033] Step 4. After the reaction, the reaction solution is concentrated by distillation and decolorization and filtration with activated carbon. The filtrate is adjusted to pH 6.0 with inorganic acid, and then cooled and filtered to obtain a crude product and mother liquor. The crude product is then subjected ...

Embodiment 2

[0039] This embodiment provides a method for preparing p-chlorophenylglycine, which includes the following steps:

[0040] Step 1: Add the catalyst and p-chlorobenzaldehyde to the chloroform solution, and accelerate the dissolution of the catalyst and p-chloroformaldehyde in chloroform by shaking to make a mixed solution;

[0041] Step two, add the mixed solution made in step one to the sodium hydroxide solution and mix, and add liquid ammonia dropwise under stirring, and the time for the dropwise addition of liquid ammonia is 4h;

[0042] Step 3: After the dropwise addition of liquid ammonia is finished, add ammonium bicarbonate solution and react at room temperature for 6 hours;

[0043] Step 4. After the reaction, the reaction solution is concentrated by distillation and decolorization and filtration with activated carbon. The filtrate is adjusted to pH 6.0 with inorganic acid, and then cooled and filtered to obtain a crude product and mother liquor. The crude product is then subjec...

Embodiment 3

[0049] This embodiment provides a method for preparing p-chlorophenylglycine, which includes the following steps:

[0050] Step 1: Add the catalyst and p-chlorobenzaldehyde to the chloroform solution, and accelerate the dissolution of the catalyst and p-chloroformaldehyde in chloroform by shaking to make a mixed solution;

[0051] Step two, add the mixed solution made in step one to the sodium hydroxide solution and mix, and add liquid ammonia dropwise under stirring, and the time for the dropwise addition of liquid ammonia is 4h;

[0052] Step 3: After the dropwise addition of liquid ammonia is completed, add ammonium bicarbonate solution and react at room temperature for 8 hours;

[0053] Step 4. After the reaction, the reaction solution is concentrated by distillation, and decolorized and filtered with activated carbon. The filtrate is adjusted to pH 6.0 with inorganic acid, and then cooled and filtered to obtain a crude product and mother liquor. The crude product is then subjected...

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Abstract

The invention provides a preparation method of p-chlorophenylglycine, which comprises the following steps: adding a mixed solution of a chloroform solution, a catalyst and p-chlorobenzaldehyde into asodium hydroxide solution, mixing, and dropwisely adding liquid ammonia while stirring for 2-6 hours; after finishing dropwise adding the liquid ammonia, adding an ammonium bicarbonate solution, and reacting for 5-10 hours at room temperature; after the reaction is finished, distilling and concentrating a reaction solution, decolorizing and filtering by using activated carbon, adjusting the pH value of a filtrate to 6.0 by using an inorganic acid, cooling and filtering to obtain a crude product and mother liquor, washing the crude product by using water, ethanol and diethyl ether, and drying to obtain a finished product p-chlorophenylglycine; wherein the catalyst is trioctyl methyl ammonium chloride; wherein the molar ratio of the p-chlorobenzaldehyde to the trioctyl methyl ammonium chloride to the chloroform to the sodium hydroxide to the ammonium bicarbonate is 1.0 : (0.02-0.38) : (1.5-2.5) : (6.0-10.0) : (0.03-0.07). The synthesis process is simple, raw materials are easy to obtain,the reaction is milder, and toxicity and pollution of cyanide are avoided.

Description

Technical field [0001] The present invention relates to the preparation field of chlorophenylglycine, in particular to a preparation method of p-chlorophenylglycine. Background technique [0002] P-Chlorophenylglycine (English: Chlorophenylglycine Chemical formula: C 8 H 8 CLNO 2 ) Is also known as DL-p-chlorophenylglycine. Its melting point is 220-230℃. It is a toxic substance and has irritating effects on the eyes, respiratory system and skin of the human body. The use of p-chlorophenylglycine requires wearing appropriate protective clothing. The main use is to synthesize drugs. [0003] The main methods for synthesizing p-chlorophenylglycine are biological and chemical methods. The chemical synthesis method mainly uses p-chlorobenzaldehyde, sodium cyanide and ammonium bicarbonate as raw materials, and first prepares p-chlorophenylhydantoin through Bucherer-Bergs reaction. Then, alkaline hydrolysis was carried out to obtain p-chlorophenylglycine. However, this process adopts th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/36C07C227/12C07C227/40
CPCC07C227/12C07C227/40C07C2531/02C07C229/36
Inventor 朱建永陈杰
Owner 上海开荣化工科技有限公司
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