Glucosamine, a carbohydrate derived from chitin, shows promise as a natural resource for the synthesis of glycolipid surfactants. Glucosamine has not been thoroughly explored as the hydrophilic basis of glycolipid surfactants but its structure makes it particularly interesting for use as a quaternary ammonium cationic surfactant. The synthesis of surfactants based on glucosamine requires i) protection of the sugar hydroxyl and amino groups, ii) attachment of a lipid chain (which can also be derived from renewable resources) at the anomeric carbon through O-glycosylation, and iii) deprotection of the hydroxyl groups. Conditions for the synthesis of these surfactants were chosen to minimize environmental impact (i.e., greener solvents, reactions at ambient temperature, etc.) Protection of the hydroxyl and amino groups of glucosamine has been completed and the glycosylation step of the protected sugar has been optimized. This nonionic amino glucoside is then converted into a quaternary ammonium cationic surfactant through methylation. The critical micelle concentration and average aggregate size for both the nonionic and cationic surfactants were determined through surface tensionmetry and dynamic light scattering, respectively. This work aims to establish a framework for a more sustainable, cost-effective and environmentally friendly synthetic method for these single-chain glycolipid surfactants, thereby, producing products with the potential to compete with surfactants derived from petroleum based sources.

Synthesis of glucosamine-based single chain nonionic and cationic surfactants

249th National Meeting (2015)

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