Preparation method of ethyl lauroyl arginate hydrochloride

A technology of lauroyl arginine ethyl ester hydrochloride and arginine hydrochloride, which is applied to the preparation of organic compounds, organic chemical methods, skin care preparations, etc., and can solve the problem of low content and purity and water removal Low efficiency, poor crystal form and other problems, to achieve the effect of high product purity, good crystallization effect, and easy removal

Inactive Publication Date: 2017-10-24
WUHAN JASON BIOTECH CO LTD
View PDF9 Cites 12 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method uses arginine hydrochloride instead as a raw material, and the cost is lower, which is beneficial to industrialized production, but the reaction is carried out in a strong alkali aqueous solution, and lauroyl chloride is easily hydrolyzed into lauric acid under alkaline aqueous conditions, and lauroyl arginine The crystal form of ethyl acetate hydrochloride is not good in water, and the wet product after centrifugation contains a large amount of water, and the remaining raw materials and impurities produced during the reaction process include arginine, ethyl arginine, ethyl laurate and sodium chloride etc. will remain in the product with water, resulting in low content and purity of the product (purity is only about 90%), plus lauroyl arginine ethyl ester hydrochloride has a melting point of 50-58°C and is separated from water Lauroyl arginine ethyl ester hydrochloride will melt when the temperature is slightly higher when it is dried, and the water removal efficiency is very low at low temperature, so it is difficult to dry

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of ethyl lauroyl arginate hydrochloride
  • Preparation method of ethyl lauroyl arginate hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] 60kg of water and 60kg of acetone were sequentially pumped into the 200L reactor, 21kg of arginine hydrochloride was added into the reactor, stirred and dissolved, the temperature was lowered to 5°C, and the pH value was adjusted to 10 with 20wt% sodium hydroxide aqueous solution. Add 21.9kg of lauroyl chloride dropwise to the system, and at the same time add 20wt% sodium hydroxide aqueous solution dropwise to keep the pH at 10 and the temperature at 5°C. After the addition of lauroyl chloride is completed, stir for 2 hours and use 6mol / L Adjust the pH to 7 with hydrochloric acid, centrifuge, and dry to obtain lauroyl arginine. Put the obtained lauroyl arginine into a 200L reactor, add 100kg of ethanol, 11.9kg of thionyl chloride, reflux for 5 hours, evaporate the ethanol under reduced pressure to obtain a crude product, add 150kg of ethyl acetate to the reactor, and add 5wt% of 30kg of sodium bicarbonate aqueous solution, stirred evenly, left to stand for stratificatio...

Embodiment 2

[0040] Pump 60kg of water and 70kg of ethyl acetate into the 200L reaction kettle in sequence, add 21kg of arginine hydrochloride into the reaction kettle, stir and dissolve, cool down to 10°C, and use 20wt% sodium carbonate aqueous solution to adjust the pH value to 9 , add 21.9kg of lauroyl chloride dropwise to the system, and at the same time add dropwise 20wt% sodium carbonate aqueous solution to keep the pH at 9 and the temperature at 10°C. After the addition of lauroyl chloride is completed, stir for 5 hours and use 6mol / L Adjust the pH to 5 with hydrochloric acid, centrifuge, and dry to obtain lauroyl arginine. Put the obtained lauroyl arginine into a 200L reactor, add 80kg of ethanol, 13kg of thionyl chloride, react at 30°C for 9 hours, evaporate the ethanol under reduced pressure to obtain a crude product, add 150kg of butyl acetate into the reactor, and add 10wt% 30kg of aqueous sodium carbonate solution, stirred evenly, allowed to stand for stratification, discarded...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

PropertyMeasurementUnit
melting pointaaaaaaaaaa
Login to view more

Abstract

The invention discloses a preparation method of ethyl lauroyl arginine hydrochloride, which belongs to the technical field of organic synthesis. The method comprises: reacting L-arginine hydrochloride with lauroyl chloride in a mixed solvent composed of water and organic solvent A, after the reaction is completed, adjusting the pH value to 5-9, centrifuging and drying to obtain lauroyl arginine; React lauroyl arginine with ethanol and thionyl chloride, and evaporate to dryness to obtain the crude product after the reaction is completed; dissolve the crude product in organic solvent B, add alkaline aqueous solution to adjust the pH value to 5-8, stir, stand still, and take The organic layer was cooled to crystallize, centrifuged and dried to obtain the refined product of ethyl lauroyl arginate hydrochloride. The preparation method provided by the invention has the advantages of simple operation, few by-products, easy separation, easy drying and easy crushing, etc., and the main impurities in the product are effectively removed during the preparation process, and high-purity fine particle lauroyl arginine B can be obtained. Ester hydrochloride, suitable for large-scale production, the product is widely used in food and cosmetic industries.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a preparation method of ethyl lauroyl arginine hydrochloride, in particular to a preparation method of ethyl lauroyl arginine hydrochloride which can be used as a preservative for food and cosmetics . Background technique [0002] Lauroyl arginine ethyl ester hydrochloride is a new type of antibacterial agent. According to research, lauroyl arginine ethyl ester hydrochloride has a strong effect on Gram-negative and Gram-positive bacteria, yeast and mold. antibacterial effect. Its mechanism of action is that ethyl lauroyl arginate hydrochloride is a cationic surfactant, which can affect the negatively charged membrane protein and enzymatic mechanism in the bacterial cell membrane, change the permeability of the cell membrane, and achieve the effect of inhibiting microorganisms. The effect of growing or inactivating microorganisms. [0003] Lauroyl arginine ethyl ester hydrochlo...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07C277/08C07C279/14A23L3/3526A61K8/44A61Q19/00
CPCC07C277/08A23L3/3526A23V2002/00A61K8/44A61K2800/10A61K2800/524A61Q19/00C07B2200/13
Inventor 李海亮张进军李健雄刘兵程哲超
Owner WUHAN JASON BIOTECH CO LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap