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Article Dans Une Revue Advanced Sustainable Systems Année : 2021

Direct Conversion of Alginate Oligo- and Polysaccharides into Biodegradable and Non-Ecotoxic Anionic Furanic Surfactants-An Experimental and Mechanistic Study

Résumé

A series of novel anionic furanic surfactants characterized by the presence of a couple of lipophilic chains acetal-linked to a sodium 2-furoate head group, are prepared by the conversion of oligo-alginates or alginate to butyl 5-(dibutoxymethyl)-2-furoate, followed by the introduction of fatty alkyl chains containing 7 to 18 carbon atoms and the release of the carboxylate function. A plausible mechanism for the unexpected formation of butyl 5-(dibutoxymethyl)-2-furoate is proposed through a study based on both experimental results and density functional calculations. One-pot processes involving hydrolysis, butanolysis, dehydration, transesterification, transacetalization, and saponification reactions, are successfully developed to provide furan-type surfactants under conditions that respect the principles of green chemistry. The surface activities of these products in a pure form or as a mixture are evaluated and quite low values of superficial tensions (<25 mN m(-1)) and foaming properties are obtained depending on the alkyl chain length. In addition, a readily biodegradability and an absence of aquatic ecotoxicity are shown for a surfactant composition based on sodium 5-(dioctyloxymethyl)-2-furoate.
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Dates et versions

hal-03281345 , version 1 (27-10-2022)

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Louise Renault, Rémi Marchal, Boris Le Guennic, Xavier Roussel, Pierre-Yves Divet, et al.. Direct Conversion of Alginate Oligo- and Polysaccharides into Biodegradable and Non-Ecotoxic Anionic Furanic Surfactants-An Experimental and Mechanistic Study. Advanced Sustainable Systems, 2021, 5 (7), pp.2100108. ⟨10.1002/adsu.202100108⟩. ⟨hal-03281345⟩
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