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Direct Conversion of Agarose into Alkyl Mono‐ and Disaccharide Surfactants Based on 3,6‐Anhydro L‐ and D‐Galactose Units
Author(s) -
Wang Yunhui,
Renault Louise,
Guégan JeanPaul,
Benvegnu Thierry
Publication year - 2021
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202004542
Subject(s) - chemistry , disaccharide , alkyl , dodecanol , galactose , agarose , organic chemistry , polymer chemistry , stereochemistry , chromatography
In this work, a new type of agaran‐derived non‐ionic surfactants has been prepared through the one‐pot transformation of agarose into 3,6‐anhydro L‐ and D‐galactose acetal monomers and dimers possessing one or two alkyl chains according to the cyclic or open form of the L‐ and D‐galactose units. The two steps process involves the butanolysis of agarose into butyl mono‐ and disaccharide 3,6‐anhydro L‐ and D‐galactose acetals promoted by the presence of Amberlyst‐15Dry, followed by the transacetalization with n ‐dodecanol using the same acid catalyst. The chemical structures of the alkyl mono‐ and disaccharide surfactants were fully characterized by 1D and 2D NMR experiments. Surface activities of these products in a pure form or as mixtures were investigated depending on their hydrophilicity/hydrophobicity and quite low values of superficial tensions (<27 mN m −1 ) and sunflower seed oil/water interfacial tensions (∼5 mN m −1 ) were obtained.