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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  • Abstract
  • Description
  • Claims
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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

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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