Using COSMOtherm to predict physicochemical properties of poly- and perfluorinated alkyl substances (PFASs)
Zhanyun Wang A , Matthew MacLeod B , Ian T. Cousins B , Martin Scheringer A C and Konrad Hungerbühler A
+ Author Affiliations
- Author Affiliations
A Institute for Chemical and Bioengineering, Swiss Federal Institute of Technology, ETH Zurich, CH-8093 Zurich, Switzerland.
B Department of Applied Environmental Science (ITM), Stockholm University, SE-10691 Stockholm, Sweden.
C Corresponding author. Email: scheringer@chem.ethz.ch
Environmental Chemistry 8(4) 389-398 https://doi.org/10.1071/EN10143
Submitted: 24 December 2010 Accepted: 1 March 2011 Published: 19 August 2011
Journal Compilation © CSIRO Publishing 2011 Open Access CC BY-NC-ND
Environmental context. Poly- and perfluorinated alkyl substances (PFASs) include a wide range of individual compounds that are used in many consumer products, but only a few physicochemical property data are available for these chemicals. Here we provide estimates of physicochemical properties (vapour pressure, water solubility, etc.) of 130 individual PFASs derived with a quantum-chemical model. Our results provide insight into the effect of molecular structure on the properties of PFASs and a basis for estimating the environmental partitioning and fate of PFASs.
Abstract. Recently, there has been concern about the presence of poly- and perfluorinated alkyl substances (PFASs) in the environment, biota and humans. However, lack of physicochemical data has limited the application of environmental fate models to understand the environmental distribution and ultimate fate of PFASs. We employ the COSMOtherm model to estimate physicochemical properties for 130 individual PFASs, namely perfluoroalkyl acids (including branched isomers for C4–C8 perfluorocarboxylic acids), their precursors and some important intermediates. The estimated physicochemical properties are interpreted using structure-property relationships and rationalised with insight into molecular interactions. Within a homologous series of linear PFASs with the same functional group, both air–water and octanol–water partition coefficient increase with increasing perfluorinated chain length, likely due to increasing molecular volume. For PFASs with the same perfluorinated chain length but different functional groups, the ability of the functional group to form hydrogen bonds strongly influences the chemicals’ partitioning behaviour. The partitioning behaviour of all theoretically possible branched isomers can vary considerably; however, the predominant isopropyl and monomethyl branched isomers in technical mixtures have similar properties as their linear counterparts (differences below 0.5 log units). Our property estimates provide a basis for further environmental modelling, but with some caveats and limitations.
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