Design, synthesis and surfactant properties of perfluorobutyl-based fluorinated sodium alkanesulfonates

Perfluorobutyl (C4) substituted linear C4-C4 ether linked tri-sodium sulfonate derivatives are designed, synthesized and characterized as alternative substances to perfluoroctanesulfonic acid (PFOS, 1), a well known surfactant used in various industrial and consumer products. The tri-sodium sulfonate was synthesized from commercially available octafluoro-1,4-diiodo butane as starting material in 9 steps using radical addition, Upjohn dihydroxylation and nucleophilic substitution reactions. Simultaneously, we have also synthesized di-branched C4-C4 perfluorobutyl alkyl mono-sodium sulfonate and di-sodium sulfonate. We have illustrated the surface tension behavior and calculated critical micelle concentration values for all three substances synthesized.