Preparation method of epsilon-N lauroyl lysine

A technology of lauroyl lysine and lysine, which is applied to the preparation of carboxylic acid amides, the preparation of organic compounds, chemical instruments and methods, etc., which can solve the problems of low yield, many steps required for purification, and interference of by-product subsequent treatment Large and other problems, to achieve the effect of simple steps, increase reaction yield, and optimize synthesis steps

Pending Publication Date: 2020-09-29
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The purpose of the present invention is to provide a preparation method of ε-N lauroyl lysine, which solves the problem of low yield of ε-N lauroyl lysine prepared by amidation method in the prior art, large interference of by-products on subsequent treatment, There are many steps required for purification, etc., the preparation method of the present invention has simple steps, simple follow-up treatment, and high-purity products can be obtained

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

Examples

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Embodiment 1

[0026] A preparation method of ε-N lauroyl lysine, the specific preparation steps are as follows:

[0027] At 20°C, add 5g of lysine and 100mL of methanol to the flask, then add 15g of lauroyl chloride, adjust the pH value of the mixture to 9 with sodium hydroxide, stir and react for 2h, after the reaction stops, dilute the reaction solution with hydrochloric acid Adjust the pH value to 7, filter, wash the filtrate with 50mL of methanol, and filter again, then wash and filter the filtrate with methanol aqueous solution to obtain a high-purity product with a purity of >98.5%. Combine three methanol filtrates to be distilled, recover methanol, and then release time can continue to use.

Embodiment 2

[0029] A preparation method of ε-N lauroyl lysine, the specific preparation steps are as follows:

[0030] At 40°C, add 10g of lysine and 100mL of methanol to the flask, then add 20g of lauroyl chloride, adjust the pH of the mixture to 9 with potassium hydroxide, and stir for 2 hours. After the reaction stops, dilute the reaction solution with glacial acetic acid Adjust the pH value to 7, filter, wash the filtrate with 50mL of methanol, filter again, then wash and filter the filtrate with aqueous ethanol to obtain a high-purity product with a purity >98%, combine the methanol filtrate and aqueous ethanol twice to be distilled, After recycling, it can be used next time.

Embodiment 3

[0032] A preparation method of ε-N lauroyl lysine, the specific preparation steps are as follows:

[0033] At 50°C, add 10g of lysine and 300mL of methanol to the flask, then add 40g of lauroyl chloride, adjust the pH of the mixture to 10 with sodium hydroxide, and stir for 2 hours. After the reaction stops, adjust the pH of the reaction solution with hydrochloric acid Adjust the value to 8, filter, wash the filtrate in batches with 100mL methanol, filter again, wash and filter the filtrate with aqueous ethanol to obtain a high-purity product with a purity >99%, combine the methanol filtrate and aqueous ethanol to be distilled, and recover You can continue to use it next time.

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Abstract

The invention relates to a preparation method of epsilon-N lauroyl lysine. According to the preparation method, lysine or lysine salt and lauroyl chloride are used as raw materials. The method comprises the following specific steps: dissolving lysine in methanol to obtain a lysine methanol solution, dropwise adding lauroyl chloride at a certain temperature for an amidation reaction of lysine methanol solution, and adjusting the pH value of the mixed solution until the pH value is greater than 7 and less than or equal to 11; and after the reaction is finished, adjusting the pH value of the mixed solution to 7-9, and carrying out washing with methanol and an alcohol-water mixed solution sequentially to obtain a high-purity product. Compared with the prior art, the preparation method has theadvantages that only one step is needed for synthesis, subsequent treatment steps are simple, high temperature and high pressure are not needed in the reaction, a reaction solvent can be distilled, recovered and recycled, and the obtained product has high purity and good industrial production potential.

Description

technical field [0001] The invention relates to a preparation method of ε-N lauroyl lysine. Background technique [0002] ε-N lauroyl lysine is an amino acid derivative, the raw material is naturally renewable, with excellent performance, antibacterial, biodegradable and good skin affinity, etc. It is often used as a surface modifier and Additives for cosmetics. The common synthesis methods of ε-N lauroyl lysine include chemical method and enzymatic synthesis method, among which the cost of enzymatic synthesis method is high, and industrialization is relatively difficult. The existing chemical synthesis method may use metal ion chelation, and the waste liquid treatment is troublesome; Or high temperature and high pressure, which have higher requirements on equipment; or use group protection, although it can be synthesized precisely, but the cost is very high. [0003] Lysine is a basic amino acid with the chemical formula: [0004] [0005] Usually, the raw amino acid ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/02C07C233/47
CPCC07C231/02C07C233/47
Inventor 何怡静许虎君
Owner JIANGNAN UNIV
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