Direct and one-pot conversion of polyguluronates and alginates into alkyl-l-guluronamide-based surfactant compositionsElectronic supplementary information (ESI) available: 1H NMR, 13C (JMod) of guluronate monomers 1-3 and fractions enriched in α or β furanosides or pyranosides in the d-mannuronamide or l-guluronamide series, isolated after silica gel column chromatography of the GulC4N12, GulC4N18, AlgC4N12 and AlgC4N18 compositions. See DOI: 10.1039/c6gc01983h
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We describe here an efficient one-pot process for the synthesis of 100% bio-based
-guluronic acid based surfactant compositions as emulsion stabilizers, directly from
-polyguluronate or whole alginate, a renewable polysaccharide extracted from brown seaweeds. The transformation of these polymers into long-chain alkyl-
-guluronamides associated with
-mannuronamides when the alginate was used, has been achieved through the preparation of
-butyl uronate monosaccharide intermediates involving methane sulfonic acid-promoted hydrolysis, Fisher glycosylation and esterification reactions, followed by an
solvent-free aminolysis reaction with fatty amines.
One-pot transformation of
-polyguluronates or alginates into 100% bio-based surfactants proceeded efficiently to provide novel long-chain alkyl-
-mannuronamide compositions as emulsion stabilizers.