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Preparing method for lauroyl arginine monohydrochloride

A technology of lauroyl arginine hydrochloride and arginine hydrochloride, which is applied in the chemical industry, can solve the problems of harsh storage conditions of raw materials, difficult purification of products, and easy hydrolysis of products, so as to facilitate large-scale production and technological progress Significant, overcoming the effect of easy hydrolysis

Inactive Publication Date: 2015-11-11
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Aiming at the above-mentioned technical problems in the prior art, the invention provides a kind of preparation method of lauroyl arginine hydrochloride, the preparation method of described this lauroyl arginine hydrochloride solves the problems in the prior art. The technical problems of the preparation method are that the product is easy to hydrolyze, the raw material storage conditions are harsh, the reaction temperature is high, and the product is not easy to purify

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] A preparation method of lauroyl arginine hydrochloride, specifically comprising the steps of:

[0029] L-arginine hydrochloride (2.0g) was dissolved in 30ml of chloroform, and 3.0ml of triethylamine was added with the addition funnel, then 2.2ml of lauroyl chloride was added dropwise with the addition funnel, stirred at 25°C for 10h, after the reaction was completed, Suction filtration, followed by rotary evaporation to remove the organic solvent to obtain a crude product, which was recrystallized with n-hexane to obtain 1.9 g of pure lauroyl arginine hydrochloride.

[0030] The L-arginine hydrochloride, alkali and lauroyl chloride used in the above condensation reaction are calculated in molar ratio, that is, L-arginine hydrochloride: alkali: lauroyl chloride is about 1:3:1.

[0031] The used organic solvent chloroform of above-mentioned condensation reaction is 13.8 times of the volume of lauroyl chloride.

Embodiment 2

[0033] A preparation method of lauroyl arginine hydrochloride, specifically comprising the steps of:

[0034] L-arginine hydrochloride (2.0g) was dissolved in 30ml of chloroform, and 2.0ml of triethylamine was added with the addition funnel, and then 2.2ml of lauroyl chloride was added dropwise with the addition funnel, and stirred at 25°C for 10h. After the reaction, Suction filtration, followed by rotary evaporation to remove the organic solvent to obtain a crude product, which was recrystallized with petroleum ether to obtain 1.9 g of pure lauroyl arginine hydrochloride.

[0035] The L-arginine hydrochloride used in the above-mentioned condensation reaction, alkali and lauroyl chloride are calculated by molar ratio, that is, L-arginine hydrochloride: alkali: lauroyl chloride is about 1:2:1;

[0036] The used organic solvent chloroform of above-mentioned condensation reaction is 13.8 times of the volume of lauroyl chloride.

Embodiment 3

[0038] A preparation method of lauroyl arginine hydrochloride, specifically comprising the steps of:

[0039] L-Arginine hydrochloride (2.0g) was dissolved in 30ml of dichloromethane, and 2.0ml of tributylamine was added with the addition funnel, then 2.2ml of lauroyl chloride was added dropwise with the addition funnel, stirred at 25°C for 10h, and the reaction was completed Finally, suction filtration, followed by rotary evaporation to remove the organic solvent to obtain the crude product, which was recrystallized with n-hexane to obtain 2.1 g of the pure product lauroyl arginine hydrochloride.

[0040] The L-arginine hydrochloride used in the above-mentioned condensation reaction, alkali and lauroyl chloride are calculated by molar ratio, that is, L-arginine hydrochloride: alkali: lauroyl chloride is about 1:2.3:1;

[0041] The used amount of the organic solvent dichloromethane used in the above condensation reaction is 13.8 times of the volume of lauroyl chloride.

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Abstract

The invention provides a preparing method for lauroyl arginine monohydrochloride. The preparing method includes the steps that L-arginine monohydrochloride, alkali and lauroyl chloride are weighed according to a weight ratio, the molar ratio of L-arginine monohydrochloride to alkali to lauroyl chloride is 1: 1-100: 1-100, and the alkali is carbonate, or bicarbonate, or acetate, or nitrogen heterocyclic amine or C3-C20 fatty amine; under the action of the alkali, the L-arginine monohydrochloride and the lauroyl chloride react in a condensation mode in first organic solvent for 1-24 h under the stirring condition, the temperature is controlled at minus 60 DEG C-100 DEG C, suction filtration, concentration and rotary evaporation are carried out on obtained reaction liquid to remove the organic solvent, and an obtained crude product is recrystallized with second organic solvent to obtain the lauroyl arginine monohydrochloride. The preparing method is moderate in reaction condition and easy to operate.

Description

technical field [0001] The invention belongs to the field of chemical industry, in particular to a kind of lauroyl arginine hydrochloride, specifically a kind of preparation method of lauroyl arginine hydrochloride. Background technique [0002] Lauroyl arginine ethyl ester hydrochloride is a food additive with a broad spectrum of anti-bacteria, yeast and mold activity, so it can be widely used as an effective preservative in the food industry; and lauroyl arginine Hydrochloride is a key intermediate for the synthesis of ethyl lauroyl arginine hydrochloride, and at the same time lauroyl arginine is a key impurity in the formulation of the process standard for ethyl lauroyl arginine hydrochloride, so It is of great significance to study the synthesis of lauroyl arginine hydrochloride. [0003] Patent EP1264591A2 uses L-arginine as a raw material, isopropanol and water as a mixed solvent, lauroyl chloride as an acylating agent, and aqueous sodium hydroxide as a base to synthe...

Claims

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Application Information

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IPC IPC(8): C07C279/36C07C277/08
Inventor 吴范宏吴闯汪忠华苏飞飞巫辅龙李丹丹
Owner SHANGHAI INST OF TECH
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