Method for catalytically synthesizing N-acylamino acid surfactant based on zirconium catalyst

An acylamino acid and surfactant technology, applied in the field of catalytic synthesis of fine chemicals, can solve the problems of low biodegradability, unsustainable resources, strong aquatic toxicity, etc., achieve high yield, simple steps, and avoid the synthesis process Effect

Active Publication Date: 2022-02-11
CHANGSHA PUJI BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Surfactants have been widely used in medicine, cosmetics, washing, lubricants, tertiary oil recovery and other fields, but traditional surfactants have low biodegradability, strong toxicity to aquatic organisms, and their raw materials come from unsustainable resources

Method used

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  • Method for catalytically synthesizing N-acylamino acid surfactant based on zirconium catalyst
  • Method for catalytically synthesizing N-acylamino acid surfactant based on zirconium catalyst
  • Method for catalytically synthesizing N-acylamino acid surfactant based on zirconium catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～41

[0035] The following examples 1 to 41 are based on lauric acid, myristic acid, palmitoleic acid, stearic acid or coconut oil, and glutamic acid or glutamate, glycine or glycinate, alanine or alanine , sarcosine or sarcosinate, methyl taurine or methyl taurine between the carboxyl-amino condensation reaction as an example to illustrate:

[0036] The N-acyl amino acid surfactants synthesized in the following examples are: glutamic acid compounds II-A~II-D, glycine compounds III-A~III-C, alanine compounds IV-A~II-B , sarcosine compounds Ⅴ-A~V-D, methyl taurine compounds VI-A~VI-C:

[0037]

[0038] where the R 1 , R 2 , R 3 , R 4 , R 5 It is undecyl, tridecyl, pentadecyl, 7-pentadecenyl, heptadecyl or 9-heptadecenyl.

Embodiment 1

[0040] Add catalyst bis(perfluorohexylsulfonate) zirconocene (0.0888g, 0.1mmol), lauric acid (2.000g, 10mmol), sodium glutamate (1.6911g, 10mmol) and acetone / Water (1:1) mixed solvent (30mL), reacted at 100°C for 24h, stopped the reaction, removed the solvent, added ethanol / petroleum ether mixed solvent to the solid compound, and crystallized for 24h to obtain sodium lauroyl glutamate with a yield of 85% .

Embodiment 2

[0042] A round bottom flask (100 mL) was charged with catalyst bis(perfluorohexylsulfonate) zirconocene (0.0888 g, 0.1 mmol), lauric acid (2.000 g, 10 mmol), disodium glutamate (1.9109 g, 10 mmol) and acetone / water mixed solvent (30mL), reacted at 100°C for 24h, stopped the reaction, removed the solvent and catalyst to obtain disodium lauroyl glutamate with a yield of 77%.

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Abstract

The invention discloses a method for catalytically synthesizing an N-acylamino acid surfactant based on a zirconium catalyst. According to the method, long-chain aliphatic carboxylic acid and amino acid and / or amino acid salt are subjected to condensation reaction under the catalytic action of bis (perfluorohexyl sulfonic acid) zirconocene to obtain the N-acylamino acid surfactant. The method has the advantages of simple operation, no need of acyl chloride intermediate conversion, no generation of high-salt wastewater, mild reaction conditions, high target product yield and wide functional group tolerance range.

Description

technical field [0001] The present invention relates to a kind of synthetic method of N-acyl amino acid surfactant, particularly a kind of using two (perfluorohexylsulfonic acid) zirconocene (Cp 2 Zr(OSO 2 C 6 f 13 ) 2 ) The method for catalyzing the N-acyl amino acid surfactant synthesized by condensation reaction of amino acid (or salt) and long-chain fatty carboxylic acid belongs to the technical field of catalytic synthesis of fine chemicals. Background technique [0002] Surfactants have been widely used in medicine, cosmetics, washing, lubricants, tertiary oil recovery and other fields, but traditional surfactants have low biodegradability, strong toxicity to aquatic organisms, and their raw materials come from unsustainable resources. With the proposal of environmental protection and sustainable development, the research and development of non-toxic, safe, biodegradable, biocompatible, mild, environmentally friendly, multi-functional and high-quality surfactants h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/47C07C233/49C07C231/02C07C309/15C07C303/22B01J31/22C09K23/22C09K23/24C09K23/28
CPCC07C231/02C07C303/22B01J31/2295B01J2531/0225B01J2531/48B01J2231/40C07C233/47C07C233/49C07C309/15Y02P20/584
Inventor 李今微喻名强
Owner CHANGSHA PUJI BIOTECH
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