A kind of preparation method of lipoamino acid compound based on deep eutectic solvent

A low eutectic solvent and amino acid technology, which is applied in the preparation of organic compounds, the preparation of carboxylic acid amides, chemical instruments and methods, etc. Stability and activity, the effect of simplifying the purification process

Active Publication Date: 2020-06-09
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, there are many by-products and low product synthesis efficiency.

Method used

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  • A kind of preparation method of lipoamino acid compound based on deep eutectic solvent
  • A kind of preparation method of lipoamino acid compound based on deep eutectic solvent
  • A kind of preparation method of lipoamino acid compound based on deep eutectic solvent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Weigh 25mM lauric acid and 25mM glycine respectively, and add 10ml natural deep eutectic solvent (choline chloride-glycerol) and 12.5mg lipase CALB into a 25ml reaction bottle. Then the reaction bottle was sealed and placed in a constant temperature water bath shaker at 60 ° C and 2000 rpm for 48 h.

[0034] After the reaction, take out the reaction bottle, add a large amount of water, shake vigorously, and then centrifuge at 10,000rpm for 10min. After centrifugation, vacuum filter to obtain a white solid, add methanol, and recrystallize the crude product twice to obtain a pure product with a purity of 98%. . The product yield was 50.49%.

[0035] pass Figure 5 It can be seen from the mass spectrometry in the product that there is no dipeptide, a common by-product in the synthesis of lipoamino acid, which has a high product yield and fewer by-products.

[0036] The cmc values ​​of several products were measured by conductivity method, and lauroyl glycine was 0.0044m...

Embodiment 2

[0038] Weigh 25mM lauric acid and 25mM glycine respectively, and add 10ml natural deep eutectic solvent (betaine-glycerol) and 12.5mg lipase CALB into a 25ml reaction bottle. Then the reaction bottle was sealed and placed in a constant temperature water bath shaker at 60 ° C and 2000 rpm for 48 h.

[0039] After the reaction, take out the reaction bottle, add a large amount of water, shake vigorously, and then centrifuge at 10,000rpm for 10min. After centrifugation, vacuum filter to obtain a white solid, add methanol, and recrystallize the crude product twice to obtain a pure product with a purity of 98%. . The final yield of the product was 43.98%.

Embodiment 3

[0041]Weigh 25mM lauric acid and 25mM glycine respectively, and add 10ml natural deep eutectic solvent (betaine-xylitol) and 12.5mg lipase CALB into a 25ml reaction bottle. Then the reaction bottle was sealed and placed in a constant temperature water bath shaker at 60 ° C and 2000 rpm for 48 h.

[0042] After the reaction, take out the reaction bottle, add a large amount of water, shake vigorously, and then centrifuge at 10,000rpm for 10min. After centrifugation, vacuum filter to obtain a white solid, add methanol, and recrystallize the crude product twice to obtain a pure product with a purity of 98%. . The final yield of the product is 38.97%.

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Abstract

The invention discloses a method for preparing lipoamino acid compounds based on a deep eutectic solvent, belonging to the field of organic synthesis. The preparation method of the invention uses fatty acids and amino acids as substrates and a deep eutectic solvent as a medium to directly prepare lipoamino acid surfactants under the catalysis of lipase CALB. The method of the present invention does not require the protection and deprotection of amino acids. Compared with the traditional chemical synthesis method, the invention has the advantages of greenness, safety, high selectivity and high yield, and has very important potential application value.

Description

technical field [0001] The invention relates to a method for preparing lipoamino acid compounds based on a deep eutectic solvent, belonging to the field of organic synthesis. Background technique [0002] Due to its unique properties, surfactants are often used in many aspects such as emulsifiers, thickeners, and defoamers in the food field. They are called "industrial monosodium glutamate" and have a great demand. In recent years, research on lipoamino acid surfactants has become a hot topic. Traditional lipoamino acid surfactants are mostly quaternary ammonium salts. Although they have good surface activity and antibacterial properties, they also have strong cytotoxicity, which limits their large-scale application in the food field. Compared with traditional surfactants, lipoamino acid surfactants are safer and have better application prospects in the food field. [0003] At present, most researches on the synthesis of lipoamino acid surfactants focus on chemical methods...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C231/02C07C233/47C07C277/08C07C279/22C12P13/02C12P13/00B01F17/22B01F17/28C09K3/00B01D19/04C09K23/22C09K23/28
Inventor 刘元法年彬彬曹晨李进伟徐勇将翟颖红
Owner JIANGNAN UNIV
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