Method for crystallizing N-carbamylglutamic acid with mixed acid

A carbamoylglutamic acid and crystallization technology, which is applied in the field of mixed acid crystallization N-carbamylglutamic acid, can solve the problems of reduced yield, low solubility of salt compounds, and low purity of NCG crude products, and achieves improved The effect of purity

Active Publication Date: 2016-05-25
南京恒通医药开发有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are certain defects in this method: (1) the salt compounds produced after acidification are not highly soluble in water; (2) single acidification with concentrated hydrochloric acid will cause the same ion effect, resulting in sodium chloride or potassium chloride with the product during crystallization. Precipitate together, the purity of the obtained NCG crude product is not high, although the product purity has been improved by recrystallization, the yield has decreased

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] (1) Using the preparation method of N-carbamoylglutamic acid disclosed by the patent publication number CN101168518A, fully mix 1mol glutamic acid, 1mol potassium cyanate, and 1mol potassium hydroxide to obtain a mixture, and dissolve the mixture in 250mL Place in distilled water at room temperature (20-25°C) for 16-20 hours to obtain 250 mL of N-carbamoylglutamic acid reaction solution with a concentration of 558.3 ​​g / L;

[0027] (2) At a temperature of 20°C, add 75mL concentrated hydrochloric acid (37% mass fraction) and 75mL concentrated nitric acid (69.8% mass fraction) to acidify the reaction solution obtained in step (1) in sequence, and the pH of the solution reaches 3;

[0028] (3) Place the solution obtained in step (2) in a refrigerator at 0-4°C overnight to crystallize;

[0029] (4) Suction filtration, and the obtained solid was vacuum-dried at 70°C for 24 hours to obtain the crude product of N-carbamoylglutamic acid with a primary yield of 81.33% and a puri...

Embodiment 2

[0033] (1) Using the N-carbamylglutamic acid preparation method disclosed by the patent publication number CN101440042B, weigh 1mol of glutamic acid, 1mol of ammonium formate and 3mol of sodium hydroxide, and oxidize the weighed glutamic acid and hydroxide Dissolve sodium in 0.5L distilled water, stir, then add weighed ammonium formate to the obtained mixture, stir thoroughly, and reflux at 110°C for 30 minutes to obtain 500mL of N-carbamoylglutamine with a concentration of 401.45g / L Acid reaction solution;

[0034] (2) At a temperature of 45°C, add 167mL (2mol) concentrated hydrochloric acid (mass fraction 37%) and 125mL (2mol) concentrated nitric acid (mass fraction 69.8%) in sequence to acidify the reaction solution obtained in step (1), and the solution pH to 3;

[0035] (3) Place the solution obtained in step (2) in a refrigerator at 0-4°C overnight to crystallize;

[0036] (4) Suction filtration, and the obtained solid was vacuum-dried at 70°C for 24 hours to obtain th...

Embodiment 3

[0042](1) Using the N-carbamoylglutamic acid published in the article reported by Liu Yaqian et al. Acid preparation method: add 300mL distilled water, 1mol potassium cyanate, and 1mol potassium hydroxide to 1mol glutamic acid, mix well, heat to dissolve the solid, and stir and react at 65°C for 2 hours to obtain 300mL glutamic acid with a concentration of 649.5g / L N-carbamoylglutamic acid reaction solution;

[0043] (2) At a temperature of 30°C, add 75mL of concentrated hydrochloric acid (37% by mass fraction) and 75mL of concentrated sulfuric acid (98% by mass) in order to acidify the reaction solution obtained in step (1), and the pH of the solution reaches 1;

[0044] (3) Place the solution obtained in step (2) in a refrigerator at 0-4°C overnight to crystallize;

[0045] (4) Suction filtration, and the obtained solid was vacuum-dried at 70°C for 24 hours to obtain the crude product of N-carbamoylglutamic acid with a primary yield of 90.53% and a purity of 92.09%.

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Abstract

The invention discloses a method for crystallizing N-carbamylglutamic acid with mixed acid. According to the method, two or more types of acid are sequentially added to an N-carbamylglutamic acid reaction solution for acidification; an obtained solution stands still at the temperature of 0-4 DEG C and stays overnight, and crystallization is conducted; suction filtration is conducted, obtained solid is dried, and a crude product of the N-carbamylglutamic acid is obtained. The acid is two or more of concentrated hydrochloric acid, concentrated nitric acid, concentrated sulfuric acid, concentrated phosphoric acid and other types of inorganic acid. Compared with an acidification method with a single type of acid, the method for crystallizing N-carbamylglutamic acid with mixed acid has the advantages that the mixed acid acidification reaction liquid is adopted, and the common ion effect caused by single acid acidification can be avoided, so that precipitation of sodium salt along with a product is avoided, crystallization purity of the product, namely the N-carbamylglutamic acid is effectively improved, and the maximum one-time crystallization purity of the product can reach 98.3%.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a method for crystallizing N-carbamylglutamic acid with mixed acid. Background technique [0002] Arginine is an essential amino acid for young mammals. Since the arginine provided by breast milk and the pup's own synthesis cannot meet its nutritional needs, it must be provided additionally. For adult animals, arginine is a conditionally essential amino acid. For poultry, because there is no carbamoyl phosphate synthase in the mitochondria, arginine cannot be synthesized endogenously through the ornithine cycle, and it needs to be ingested in the feed. However, arginine has a high price and has an antagonistic effect with lysine and histidine, so it has not been widely used as a feed additive in animal production. [0003] Recently, an endogenous arginine synthesis agent, N-carbamylglutamate (NCG), has appeared on the market. It is an analog of N-acetylglutamate an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C273/18C07C275/16
CPCC07C273/1863C07C273/189C07C275/16
Inventor 曹飞李文惠武红丽汤智群洪伟鸣陆辉
Owner 南京恒通医药开发有限公司
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