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Simple synthesis process of 1-aminocyclopropane-1-carboxylic acid

A technology of alkylation cyclization and nitroacetate, applied in the field of simple synthesis of natural living amino acids, can solve the problems of high final product cost, low total yield, pollution of the environment, etc., and achieve green production procedures and simple equipment , large economic and social benefits

Active Publication Date: 2014-06-18
ZHANG JIA GANG VINSCE BIO PHARM
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  • Summary
  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

[0004] In the above route, the preparation of the starting raw material ethyl cyanoacetate in the first method will use metal cyanide, which is a highly toxic compound, pollutes the environment, and is very harmful to the health of operators; in the hydrolysis of 1-cyano-1 -When cyclopropanecarboxylic acid obtains 1-amino-carbonyl-1-cyclopropanecarboxylic acid, it is easy to obtain diacid by-products, resulting in low yield, high final product cost and no market competitiveness
The second method is only feasible in the laboratory. Raw and auxiliary materials are expensive in scale-up production, the reaction conditions are difficult to control, the total yield is extremely low, and there is no industrialization value.

Method used

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  • Simple synthesis process of 1-aminocyclopropane-1-carboxylic acid

Examples

Experimental program
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Effect test

Embodiment 1

[0015] Example 1 Synthesis of ethyl 1-nitrocyclopropane-1-carboxylate

[0016] In a 500 L stainless steel reactor, sequentially add 200 L of solvent methylene chloride, 40 kg of nitroacetate and 55 kg of 1,2-dibromoethane, 2.5 kg of catalyst anhydrous potassium carbonate, and slowly heat up to reflux , continue to control the temperature and react for 4-5 h, and monitor the complete reaction of the raw material nitroacetate by thin-layer chromatography, which is considered as the completion of the cyclization reaction. Lower the temperature to less than 10°C, add water to separate layers, and wash away the catalyst. The organic phase was separated, dried, and concentrated under reduced pressure to obtain 46.2 kg of ethyl 1-nitrocyclopropane-1-carboxylate intermediate.

Embodiment 2

[0017] Example 2 Synthesis of 1-nitrocyclopropane-1-carboxylic acid methyl ester

[0018] In a 500 L stainless steel reaction kettle, add 200 L of solvent dichloromethane, 40 kg of nitroethyl methyl ester and 42 kg of 1,2-dichloroethane, and 2.2 kg of catalyst anhydrous sodium carbonate in sequence, and slowly heat up to reflux , continue to control the temperature and react for 4-5 h, and monitor the complete reaction of the raw material nitroacetate by thin-layer chromatography, which is considered as the completion of the cyclization reaction. Lower the temperature to less than 10°C, add water to separate layers, and wash away the catalyst. The organic phase was separated, dried, and concentrated under reduced pressure to obtain 45.7 kg of ethyl 1-nitrocyclopropane-1-carboxylate intermediate.

Embodiment 3

[0019] Example 3 Synthesis of ethyl 1-aminocyclopropane-1-carboxylate

[0020] In a 500 L enamel reaction kettle, add 200 L of reaction solvent methanol and 45 kg of ethyl 1-nitrocyclopropane-1-carboxylate intermediate, stir to dissolve, cool the jacket to about 5 °C, and add dichloride in batches Tin is 70 kg, and the temperature is controlled at 15-20 °C, and the reaction is stirred for 3-4 h. The raw material 1-nitrocyclopropane-1-carboxylate intermediate basically disappears as monitored by thin-layer chromatography, and the reduction reaction is considered complete. Concentrate under reduced pressure to recover methanol, then add water and dichloromethane to extract twice, combine the organic phases, dry, and concentrate under reduced pressure to obtain 42.3 kg of crude 1-aminocyclopropane-1-carboxylate intermediate.

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Abstract

The invention relates to a synthesis process of 1-aminocyclopropane-1-carboxylic acid. According to the process, the 1-aminocyclopropane-1-carboxylic acid is synthesized from nitro acetate and 1,2-dihalo ethane through the reaction of alkylated cyclization, nitro reduction and carboxyl hydrolysis, and a high-content and high-purity product is obtained through carrying out separation, purification and crystallization after the reaction is ended. In the aspects of reagents and raw and auxiliary materials used during the reaction, both environment-friendliness and efficiency are taken into account. The process disclosed by the invention has the advantages of high atom economical efficiency, simple equipment and environment-friendly production procedure and has very large economic and social benefits.

Description

technical field [0001] The present invention relates to a kind of simple synthesis of natural active amino acid, specifically relates to synthesis raw material is nitroacetate, 1,2-dihalogenated ethane, involves reaction including alkylation reaction, hydrolysis reaction and reduction reaction, separation and purification can be A high content and high purity of 1-aminocyclopropane-1-carboxylic acid is obtained. Background technique [0002] 1-Aminocyclopropane-1-carboxylic acid, CAS number: 22059-21-8, English name: 1-aminocyclopropane-1-carboxylic acid, a natural non-protein amino acid, naturally occurring in various fruits, vegetables and crops Rice and wheat. The compound has a wide range of physiological and biological activities, such as the key regulation of plant growth, development and fruit under the catalysis of enzymes; it is also an important amino acid unit in the physiological process of fungi, microorganisms and insects; in human health, such as Senile dise...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/48C07C227/18
Inventor 彭学东张梅赵金召闫勇义
Owner ZHANG JIA GANG VINSCE BIO PHARM
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