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Direct Conversion of Agarose into Alkyl Mono- and Disaccharide Surfactants Based on 3,6-Anhydro L- and D-Galactose Units

Abstract : 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 (andlt;27 mN m−1) and sunflower seed oil/water interfacial tensions (∼5 mN m−1) were obtained.
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https://hal.archives-ouvertes.fr/hal-03130460
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Submitted on : Thursday, September 16, 2021 - 2:14:12 PM
Last modification on : Thursday, September 16, 2021 - 2:14:16 PM

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Y. Wang, L. Renault, J.-P. Guégan, T. Benvegnu. Direct Conversion of Agarose into Alkyl Mono- and Disaccharide Surfactants Based on 3,6-Anhydro L- and D-Galactose Units. ChemistrySelect, Wiley, 2021, 6 (3), pp.389-395. ⟨10.1002/slct.202004542⟩. ⟨hal-03130460⟩

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