Original fluorinated surfactants potentially non-bioaccumulable

This minireview updates non-exhaustive recent strategies of synthesis of original fluorosurfactants potentially non-bioaccumulable. Various strategies have been focused on (i) the preparation of CF3–X–(CH2)n–SO3Na (with X = O, C6H4O or N(CF3) and n = 8–12), (ii) the oligomerization of hexafluoropropylene oxide (HFPO) to further synthesize oligo(HFPO)–CF(CF3)CO–RH (where RH stands for an hydrophilic chain); (iii) the telomerization of vinylidene fluoride (VDF) with 1-iodopentafluoroethane or 1-iodononafluorobutane to produce CnF2n+1–(VDF)2–CH2CO2R (n = 2 or 4, R = H or NH4), (iv) the radical telomerization of 3,3,3-trifluoropropene (TFP) with isoperfluoropropyliodide or diethyl hydrogenophosphonate to prepare (CF3)2CF(TFP)x–RH or CF3–CH2–CH2–(TFP)y–P(O)(OH)2, and (v) the radical cotelomerization of VDF and TFP, or their controlled radical copolymerization in the presence of (CF3)2CFI or a fluorinated xanthate. In most cases, the surface tensions versus the surfactant concentrations have been assessed. These above strategies led to various highly fluorinated (but yet not perfluorinated) telomers whose chemical changes enabled to obtain original surfactants as novel alternatives to perfluorooctanoic acid (PFOA), ammonium perfluorooctanoate (APFO), or perfluorooctylsulfonic acid (PFOS) regarded as bioaccumulable, persistent, and toxic.

The objective of this minireview concerns various strategies for synthesizing non-bioaccumulable alternatives to PFOA.Figure optionsDownload as PowerPoint slide