Direct and one-pot conversion of polyguluronates and alginates into alkyl-L-guluronamide-based surfactant compositions

N. Sari-Chmayssem (1, 2) , F. Pessel (1) , Jean-Paul Guégan (1) , S. Taha (2) , H. Mawlawi (2) , Thierry Benvegnu (1)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 LU - Lebanese University [Beirut]

We describe here an efficient one-pot process for the synthesis of 100% bio-based L-guluronic acid based surfactant compositions as emulsion stabilizers, directly from L-polyguluronate or whole alginate, a renewable polysaccharide extracted from brown seaweeds. The transformation of these polymers into long-chain alkyl-L-guluronamides associated with D-mannuronamides when the alginate was used, has been achieved through the preparation of n-butyl uronate monosaccharide intermediates involving methane sulfonic acid-promoted hydrolysis, Fisher glycosylation and esterification reactions, followed by an in situ solvent-free aminolysis reaction with fatty amines.

Keywords: polyguluronates; alginates; surfactant composition

Domains: Chemical Sciences; Organic chemistry

N. Sari-Chmayssem, F. Pessel, Jean-Paul Guégan, S. Taha, H. Mawlawi, et al.. Direct and one-pot conversion of polyguluronates and alginates into alkyl-L-guluronamide-based surfactant compositions. Green Chemistry, 2016, 18 (24), pp.6573-6585. ⟨10.1039/c6gc01983h⟩. ⟨hal-01438116⟩