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Using COSMOtherm to predict physicochemical properties of poly- and perfluorinated alkyl substances (PFASs)

Wang, Zhanyun, MacLeod, Matthew, Cousins, Ian T., Scheringer, Martin, Hungerbühler, Konrad·2011·Environmental Chemistry
DOI 10.1071/en10143
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Abstract

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. 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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Cited by

Sorted by citations

Metadata

Authors
Wang, Z., MacLeod, M., Cousins, I. T., Scheringer, M., & Hungerbühler, K.
Venue
Environmental Chemistry
Publisher
CSIRO Publishing
Published
2011-08-19
Volume
8
Issue
4
Pages
389-398
ISSN
  • 1448-2517
  • 1449-8979
DOI
10.1071/en10143
Cited by
267
References
7
Language
en
Licence
creativecommons.org/licenses/by-nc-nd/4.0/ (vor, 5015 d)

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