Sugar-based anionic surfactants: synthesis and micelle formation of sodium methyl 2-acylamido-2-deoxy-6-O-sulfo-D-glucopyranosides.
The following sequence of reactions has been employed to synthesize the title anionic surfactants: [chemical reaction: see text] where R=C7H15; C11H23; and C15H31, respectively, and Py refers to pyridine. Aggregation of the surfactants synthesized (predominantly alpha anomers) in water was studied at 40 degrees C by conductivity measurements. Increasing the chain length of R decreases the critical micelle concentration (CMC) and the degree of counter-ion dissociation. The dependence of the Gibbs free energy of micellization and CMC on the length of R is similar to other ionic surfactants, but the head-group, i.e., the sulfated sugar moiety is less hydrophilic than the structurally related group -(OCH2-CH2)2-OSO3-Na+, most probably because of intermolecular H-bonding in the micellar pseudo-phase
Bazito
R C
RC
Instituto de Química, Universidade de São Paulo, SP, Brazil.
El Seoud
O A
OA
D000838:Anions; D003847:Deoxyglucose / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D007851:Dodecanol / Q000737:chemistry; D005960:Glucosides / Q000138:chemical synthesis*; D000442:Octanols / Q000737:chemistry; D013501:Surface-Active Agents / Q000138:chemical synthesis*
D000838:Anions; D005960:Glucosides; D000442:Octanols; D013501:Surface-Active Agents; C438410:sodium methyl 2-acylamido-2-deoxy-6-O-sulfo-glucopyranoside; D007851:Dodecanol; D003847:Deoxyglucose