Phenyl‐Linked Alkyl Glycosides—A New Approach Towards Sugar‐Based Surfactants

ABSTRACT In response to technical challenges for the production of APG, a synthetic approach for phenyl‐linked alkyl glycosides was developed. The key feature of the concept is the separation of the glycosylation from the coupling of surfactant antipodes. This enables the reactions to run in homogenous solution. A series of surfactants was prepared, and their interfacial behavior was studied. The compounds varied in the connections between the aromatic ring and the hydrocarbon chain, on the one hand, and the spacer between the sugar head group and the phenyl linker on the other. High Krafft points, mismatching structurally related phenyl ethoxylate surfactants, suggest π‐stacking interaction as a possible source of limited water solubility. The coupling of the complementary surfactant domains via phenyl ether formation required temperatures exceeding the boiling point of low molecular weight alcohols, thereby requesting the use of ethylene‐oxide based solvents. Ethylene‐glycol linked surfactants suffered from intramolecular cyclization, leading to a low coupling yield.