Milliasseau Damien, Jeftić Jelena, Pessel Freddy, Plusquellec Daniel, Benvegnu Thierry
Univ. Rennes, CNRS, ISCR-UMR 6226, Ecole Nationale Supérieure de Chimie de Rennes, F-35000 Rennes, France.
SurfactGreen, 11 allée de Beaulieu, CS 50837, CEDEX 7, F-35708 Rennes, France.
Molecules. 2021 Mar 31;26(7):1956. doi: 10.3390/molecules26071956.
The present article describes the one-pot synthesis of double- and single-tailed surfactants by a cascade process that involves the hydrolysis/butanolysis of pectins into butyl galacturonate monosaccharides followed by transesterification/transacetalisation processes with fatty alcohols, and subsequent aqueous basic and acid treatments. The cascade mode allows the depolymerisation to proceed more efficiently, and the purification conditions are optimised to make the production of single-tailed surfactants more manufacturable. These products in a pure form or as mixtures with alkyl glycosides resulting from butanolysis and transglycosylation of pectin-derived hexoses, exhibit attractive surface-tension properties, especially for the -oleyl ᴅ-galactosiduronic acid products. In addition, a readily biodegradability and an absence of aquatic ecotoxicity are shown for the galacturonic acid derivatives possessing an oleyl alkyl chain at the anomeric position.
本文描述了通过级联过程一锅法合成双尾和单尾表面活性剂,该过程包括将果胶水解/丁醇解为丁基半乳糖醛酸单糖,随后与脂肪醇进行酯交换/缩醛交换过程,以及随后的碱性和酸性水处理。级联模式使解聚更有效地进行,并且优化了纯化条件以使单尾表面活性剂的生产更具可制造性。这些纯形式的产品或与果胶衍生的己糖经丁醇解和转糖基化产生的烷基糖苷的混合物,表现出吸引人的表面张力特性,特别是对于-油基ᴅ-半乳糖苷酸产品。此外,在异头位置具有油基烷基链的半乳糖醛酸衍生物显示出易于生物降解且不存在水生生态毒性。