Design And Synthesis Of N-Acylamino Acids Surfactants

This paper designed a series of compounds. First, Williamson ether synthesis is carried out by the reactants of ethyl 4-bromobutanoate and phenol with different subst ituent (4-(1,1,3,3-Tetramethylbutyl) phenol and 4-Phenylphenol). Hydrolysis is next conduct to prepare a series of fatty acids. Then, the carboxylic acid (which is just ga ined) reacted with thionyl chloride to produce acyl chloride, which is finally reacted with amino acids (Glycine, Alanine, and Valine) to manufacture N-acyl amino acid su rfactants through Schotten-Baumann Condensation. Thus, the reacting technological con ditions are optimized for the Etherification, Acylation and Schotten-Baumann Condensa tion.Under these optimizing conditions, the ideal environment for each reaction is (1) Etherification:it should take DMF as solvent, keep reacting for 5h at 80℃, and mak e the mol ratio of POP:BBE=1:1.4. These conditions are met, the maximum yield ca n reach 83%; (2) Acylation:it should use thionyl chloride as solvent and chloride rea gent as well, keep the reacting for 2h at 70℃; (3) Schotten-Baumann Condensation:i t should take mol ratio of amino acids and acyl chloride 1:1, add acyl chloride at a speed of a drop per 6 seconds, which having a volume ratio 1:2 for THF solution o f Acryl chlorine with amino acid potassium and having 10% KOH solution as the rol e of bind the acid, control the reacting system value pH=9-10, acyl chloride was add ed at beneath 5℃, and then keep the reacting for 5 h at 0℃. After that, the product yield of N-acyl amino acid surfactants was 57.8-66.5%.The structures of these synthesized compounds are characterized by the methods of IR, MS and 1HNMR.