Effect of Fluorotelomer Alcohol Chain Length on Aqueous Solubility and Sorption by Soils

Fluorotelomer alcohols (FTOHs) are a group of polyfluorinated alkyl chemicals that have been widely studied as precursors to perfluorocarboxylates such as perfluorooctanoic acid and for which knowledge on their fate in soils is sparse. The solubility and sorption by soil of the homologous 4:2 to 10:2 FTOHs were measured in water or cosolvent/water solutions. For the smaller 4:2 and 6:2 FTOHs, solubility and sorption could be measured adequately in aqueous systems although transformation was apparent even in γ-irradiated and autoclaved systems. Sorption coefficients estimated by measuring both sorbed and solution-phase concentrations were not significantly affected by the biotransformation process. The use of cosolvents was employed for probing the behavior of the longer-chain FTOHs with limited aqueous solubility. A single log-linear correlation between aqueous solubility and modified McGowan molar volumes resulted for the n-alkanols and FTOHs. Soil organic carbon (OC) consistently appeared to be the key soil property influencing sorption of the FTOHs while the perfluorocarbon chain length was the dominant structural feature influencing solubility and sorption. Each CF2 moiety decreased the aqueous solubility by ∼0.78 log units (compared to 0.60 log units for each CH2 addition in hydrogenated primary alcohols), and increased OC-normalized sorption coefficients (K oc) by ∼0.87 log units. Good log−log linear correlations between K oc and both octanol−water partition coefficients and solubility were observed for the FTOHs.