Water Solubility and Surface Property of Alkyl Di-/Tri-/Tetraoxyethyl β‑d‑Xylopyranosides

Alkyl di-/tri-/tetraoxyethyl β-d-xylopyranosides as derivatives of alkyl xylosides are a class of non-ionic sugar-based surfactants. They were stereoselectively synthesized by the Helferich method. Their properties including hydrophilic–lipophilic balance number, water solubility, surface property, foam property, emulsifying property, and thermotropic liquid crystal property were mainly investigated. The results showed that their water solubility decreased with increasing the alkyl chain length and increasing the number of the oligooxyethyl fragment. The critical micelle concentration had a monotonous decreasing trend with increasing the alkyl chain length. Nonyl di-/tri-/tetraoxyethyl β-d-xylopyranosides [−(OCH2CH2) m –, where m = 2, 3, and 4] exhibited the most excellent foaming ability and foam stability. In the n-octane/water system, dodecyl tetraoxyethyl β-d-xylopyranosides and tetradecyl tetraoxyethyl β-d-xylopyranosides had the strongest emulsion ability. In addition, some alkyl di-/tri-/tetraoxyethyl β-d-xylopyranosides had thermotropic liquid crystal properties. Such sugar-based surfactants, alkyl di-/tri-/tetraoxyethyl β-d-xylopyranosides, will be expected to develop for a variety of practical application.