Synthesis, Characterization, and Properties of Acyl Glycine, Alanine, Valine, and Leucine Derived from Vegetable Oils and Beef Tallow

Changyao Liu; Yuzhao Wang; Lu Cui; Guiju Zhang; Baocai Xu

doi:10.3139/113.110695

Article

Synthesis, Characterization, and Properties of Acyl Glycine, Alanine, Valine, and Leucine Derived from Vegetable Oils and Beef Tallow

Changyao Liu , Yuzhao Wang , Lu Cui , Guiju Zhang and Baocai Xu

Published/Copyright: July 8, 2020

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From the journal Tenside Surfactants Detergents Volume 57 Issue 4

Abstract

In this study, 16 acylamino acid surfactants carrying glycine, alanine, valine, and leucine residues were synthesized in the desired yields in an environmentally friendly manner using vegetable oils and beef tallow as acyl donors. The quantitative compositional analyses of these surfactants were performed using HPLC/MS, and the results were consistent with the fatty acid compositions of the corresponding oils and tallow. Their CMC values, determined by surface tension measurements, generally increased with decreasing amino acid hydrophobicity and average chain lengths. Furthermore, all products showed a better detergency performance than sodium alcohol ether sulfate (NaAES) and the sodium soap derived from oils and tallow, suggesting that they can be potentially applied for the formulation of personal care products.

Kurzfassung

In dieser Studie wurden 16 Acylaminosäure-Tenside, die Glycin-, Alanin-, Valin- und Leucinreste tragen, unter Verwendung von Pflanzenölen und Rindertalg als Acyldonatoren in den gewünschten Ausbeuten umweltfreundlich synthetisiert. Die quantitative Analyse der Zusammensetzung dieser Tenside wurde mittels HPLC/MS durchgeführt, und die Ergebnisse stimmten mit den Fettsäurezusammensetzungen der entsprechenden Öle und des Rindertalgs überein. Ihre CMC-Werte, die durch Oberflächenspannungsmessungen bestimmt wurden, stiegen im Allgemeinen mit abnehmender Aminosäurehydrophobizität und der durchschnittlichen Kettenlänge an. Darüber hinaus zeigten alle Produkte eine bessere Reinigungsleistung als Natriumalkoholethersulfat (NaAES) und die aus Ölen und Talg gewonnene Natriumseife, was darauf hindeutet, dass diese Tenside potenziell für die Formulierung von Körperpflegeprodukten eingesetzt werden können.

Key words: Green synthesis; amino acid surfactants; vegetable oils; beef tallow; CMC

Stichwörter: Grüne Synthese; Aminosäure-Tenside; Pflanzliche Öle; Rindertalg; CMC

∗ Correspondence address Dr. Guiju Zhang and Dr. Baocai Xu School of Food and Chemical Engineering, Beijing Technology and Business University, No. 11, Fucheng Road, Haidian District, Beijing, P.R. China, 100048, E-Mail: zhangguiju@th.btbu.edu.cnxubaoc@btbu.edu.cn

Changyao Liu received her Ph.D. (2016) in chemistry from Rutgers University – New Brunswick. She is currently a faculty member of the School of Food and Chemical Engineering at Beijing Technology and Business University. Her research focuses on the synthesis and properties of surfactants.

Yuzhao Wang is a postgraduate student in applied chemistry in Beijing Technology and Business University. Her research interests are synthesis and properties of surfactants.

Lu Cui received an M.S. in applied chemistry from Beijing Technology and Business University. Her research interests are synthesis, properties and application of surfactants.

Guiju Zhang received a Ph.D. in organic chemistry from the Technical Institute of Physics and Chemistry, the Chinese Academy of Sciences. She is an associate professor in applied chemistry with research field in synthesis, properties and application of surfactants.

Baocai Xu received a Ph.D. in applied chemistry from Beijing Institute of Technology. He is a professor in applied chemistry with research field in synthesis, properties and application of surfactants.

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Received: 2018-08-29

Accepted: 2019-02-03

Published Online: 2020-07-08

Published in Print: 2020-07-15

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https://doi.org/10.3139/113.110695

Keywords for this article

Green synthesis; amino acid surfactants; vegetable oils; beef tallow; CMC