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Preparation method of epsilon-N-lauroyl lysine

A technology of lauroyl lysine and lauroyl lysine, which is applied in the field of preparation of ε-N-lauroyl lysine, can solve problems such as troublesome post-processing, inability to obtain high quality, etc. Simple process and clear reaction direction

Inactive Publication Date: 2012-08-01
ZHANGJIAGANG HUACHANG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The biggest disadvantage of the direct amidation of lysine is that the mixture of several compounds is obtained, and there are many side reactions, the post-processing is very troublesome, the yield is very low, and it is impossible or difficult to obtain high-quality ε-N-lauroyl lysine acid

Method used

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  • Preparation method of epsilon-N-lauroyl lysine
  • Preparation method of epsilon-N-lauroyl lysine
  • Preparation method of epsilon-N-lauroyl lysine

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preparation example Construction

[0015] ① Chelate preparation:

[0016] The preparation of chelate can be expressed as follows by chemical reaction equation:

[0017]

[0018] In the above formula, M 2+ Represents a divalent metal ion, which can be Ca 2 +, Mg 2+ 、Cu 2+ , Fe 2+ , Zn 2+ Wait. The compound of formula I is a chelate.

[0019] ② The chelate represented by formula I and lauroyl chloride carry out amidation reaction to obtain the compound of formula II.

[0020]

[0021] ③Acid hydrolysis of the compound of formula II to generate ε-N-lauroyl lysine (compound of formula III).

[0022]

Embodiment 1

[0025] In a reaction flask equipped with a stirrer, add CaCl 2 111g (1mol) and water, stir to dissolve, then add 292g (2mol) of L-lysine in batches, stir for 3 hours, adjust the pH to 8.0, dissolve the material in the bottle with salt water and cool to about -10°C, and start adding dropwise 218g (1mol) of lauroyl chloride was dropped within 2 hours. After the drop was completed, the reaction was continued at this temperature for 6 hours to obtain a white solid.

[0026] Add the white solid obtained above to 30wt% hydrochloric acid solution, stir at room temperature for 4 hours, filter to obtain the crude product, wash the crude product with purified water three times, and finally dry it to obtain a refined product with a melting point of 229-230°C, ε-N -Lauroyl lysine is 98.6% pure.

Embodiment 2

[0028] In a reaction flask equipped with a stirrer, add MgCl 2 95g (1mol) and water, stir to dissolve, then add 146g (1mol) of L-lysine in batches, stir for 3 hours, adjust the pH to 7.5, dissolve the material in the bottle with salt water and cool to about -5°C, and start adding dropwise 218g (1mol) of lauroyl chloride was dropped within 2 hours. After the drop was completed, the reaction was continued at this temperature for 8 hours to obtain a white solid.

[0029] Add the resulting white solid to 30 wt% hydrochloric acid solution, stir at room temperature for 5 hours, filter to obtain the crude product, wash the crude product with purified water three times, and finally dry it to obtain a refined product with a melting point of 229-230°C, ε-N- The purity of lauroyl lysine is 98.7%.

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Abstract

The invention relates to a preparation method of epsilon-N-lauroyl lysine. In the method, lysine or a salt thereof and lauroyl chloride are taken as raw materials. The method comprises the following steps of: making lysine or a salt thereof and a divalent metal ion form a chelate for protecting alpha-amino and carboxyl; undergoing an amidization reaction on the chelate and lauroyl chloride; and damaging a chelate structure through acid hydrolysis, and deprotecting alpha-amino and carboxyl to obtain the epsilon-N-lauroyl lysine. According to the method disclosed by the invention, an entire operating process is simple and convenient, reaction directional property is definite, a small quantity of side products are produced, high-purity epsilon-N-lauroyl lysine (more than or equal to 98.5 percent) can be obtained, and the obtained product can be applied in the field of cosmetics.

Description

technical field [0001] The invention relates to a preparation method of ε-N-lauroyl lysine. Background technique [0002] At present, the preparation methods of ε-N-lauroyl lysine mainly include the co-heating method of lauric acid and lysine, the dehydration method in an organic solvent with a high boiling point after the formation of a double salt between lauric acid and lysine, and the dehydration method of lauroyl chloride and lysine. Acid direct amidation, etc. There are many unfavorable factors in the above-mentioned several methods, wherein: the lauroyl lysine obtained by the co-heating method is a mixture, which contains ε-N-lauroyl lysine, α-N-lauroyl lysine, N, N-disubstituted lysine, etc., so it is difficult to obtain ε-N-lauroyl lysine with qualified purity, which limits the scope of use and cannot be applied to the cosmetics industry. The disadvantage of the organic solvent dehydration method is that a harmful solvent with a high boiling point is used in the s...

Claims

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Application Information

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IPC IPC(8): C07C233/47C07C231/12C07C231/02
Inventor 庞宝华叶爱英韦平和丁敬敏王平
Owner ZHANGJIAGANG HUACHANG PHARMA
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