Synthesis and properties of hemifluorinated disodium alkanesulfonates

•Hemifluorinated dialkanesulfonate species were synthesized and characterized.•1H,1H,2H,2H-nonafluorohexyl iodide and diethylmalonate were used as starting materials.•NaH based alkylation and sultone ring opening reactions.•Lower critical micelle concentration values found than that of PFOS.

Perfluorobutyl substituted disodium alkanesulfonates derivatives were synthesized and characterized as alternative substances to perfluorooctanesulfonic acid (PFOS, 1), a well-known surfactant. 1H,1H,2H,2H-nonafluorohexyl iodide, diethyl malonate and sultones were used to prepare disodium sulfonates 2 and 3 in three synthetic steps. The surface tension behavior of 2 and 3 were studied and critical micelle concentration values were noted to be 2025 mg/L and 2052 mg/L, respectively, at room temperature.

Graphical abstractPerfluorobutyl substituted disodium alkanesulfonates derivatives were synthesized and characterized as alternative substances to perfluorooctanesulfonic acid (PFOS, 1), a well-known surfactant. 1H,1H,2H,2H-nonafluorohexyl iodide, diethyl malonate and sultones were used to prepare disodium sulfonates 2 and 3 in three synthetic steps. The surface tension behavior of 2 and 3 were studied and critical micelle concentration values were noted to be 2025 mg/L and 2052 mg/L, respectively, at room temperature.Figure optionsDownload full-size imageDownload as PowerPoint slide