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Experimental pKa Determination for Perfluorooctanoic Acid (PFOA) and the Potential Impact of pKa Concentration Dependence on Laboratory-Measured Partitioning Phenomena and Environmental Modeling

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    Article

    Experimental pKa Determination for Perfluorooctanoic Acid (PFOA) and the Potential Impact of pKa Concentration Dependence on Laboratory-Measured Partitioning Phenomena and Environmental Modeling
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    Department of Chemistry, Centre for Environmental Modelling and Chemistry (CEMC), and Worsfold Water Quality Centre, Trent University, 1600 West Bank Drive, Peterborough, Ontario, K9J 7B8 Canada
    * Corresponding author e-mail: [email protected]; tel: (705) 748 1011, ext 7898; fax: (705) 748 1625.
    §Worsfold Water Quality Centre.
    †Department of Chemistry.
    ‡Centre for Environmental Modelling and Chemistry (CEMC).
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    Environmental Science & Technology

    Cite this: Environ. Sci. Technol. 2008, 42, 24, 9283–9288
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    https://doi.org/10.1021/es802047v
    Published November 7, 2008
    Copyright © 2008 American Chemical Society
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    Abstract

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    An accurately measured equilibrium acid dissociation constant (pKa) is essential for understanding and predicting the fate of perfluorocarboxylic acids (PFCAs) in the environment. The aqueous pKa of perfluorooctanoic acid (PFOA) has been determined potentiometrically using a standard water−methanol mixed solvent approach and was found to be 3.8 ± 0.1. The acidity of PFOA is thus considerably weaker than its shorter-chain PFCA homologues. This was attributed to differences in molecular and electronic structure, coupled with solvation effects. The pKa of PFOA was suppressed to ∼2.3 at higher concentrations because of the aggregation of perfluorooctanoate (PFO). Often, PFCA partion coefficients are determined at concentrations above those found in the environment. Thus, it was suggested that a pKa correction factor, which accounts for this concentration-dependent shift in acid/base equilibrium, should be applied to PFCA partition efficients before they are implemented in environmental fate models. A pKa of 3.8 ± 0.1 suggests that a considerable concentration of the PFCA exists as the neutral species in the aqueous environment, for example, in typical Ontario rainwater, it is ∼17%. Transport, fate, and partitioning models have often ignored the presence this species completely. The environmental dissemination of PFCAs could, in part, be explained by considering the role of the neutral species.

    Copyright © 2008 American Chemical Society

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    Additional materials and methodology describing mixed solvent titrations, the investigation of sorption, and 1H and 19F NMR spectroscopy. This material is available free of charge via the Internet at. http://pubs.acs.org.

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    Cite this: Environ. Sci. Technol. 2008, 42, 24, 9283–9288
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