Property Estimation of Per- and Polyfluoroalkyl Substances: A Comparative Assessment of Estimation Methods
Abstract
To accurately predict the environmental fate of per- and polyfluoroalkyl substances (PFAS), high-quality physicochemical property data are required. Because such data are often not available from experiments, assessment of the accuracy of existing property estimation models is essential. The quality of predicted physicochemical property data for a set of 25 PFAS was examined using COSMOtherm, EPI Suite, the estimation models accessible through the US Environmental Protection Agency's CompTox Chemicals Dashboard, and Linear Solvation Energy Relationships (LSERs) available through the UFZ-LSER Database. The results showed that COSMOtherm made the most accurate acid dissociation constant and air-water partition ratio estimates compared with literature data. The OPEn structure-activity/property Relationship App (OPERA; developed through the CompTox Chemicals Dashboard) estimates of vapor pressure and dry octanol-air partition ratios were the most accurate compared with other models of interest. Wet octanol-water partition ratios were comparably predicted by OPERA and EPI Suite, and the organic carbon soil coefficient and solubility were well predicted by OPERA and COSMOtherm. Acid dissociation of the perfluoroalkyl acids has a significant impact on their physicochemical properties, and corrections for ionization were included where applicable. Environ Toxicol Chem 2020;39:775-786. © 2020 SETAC.
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
For some PFAS, the only available values for physical and chemical properties are estimates derived from mathematical models such as QSAR models.
“In fact, for some PFAS, the only available values for physical and chemical properties are estimates derived from mathematical models, such as quantitative structure–activity relationship (QSAR) models [18], which can approximate the chemical and physical properties of compounds based on their chemical structure, rather values from direct measurements [19,20].”
From The EU’s Per- and Polyfluoroalkyl Substances (PFAS) Ban: A Case of Policy over Science (2023) · cites this paper as [20]
Available data suggest that both the melting temperature and melting enthalpy of PFAS increase with the length of the fluorinated carbon chain.
“Available data suggest that both the melting temperature and melting enthalpy of PFAS increase with the length of the fluorinated carbon chain [20,21].”
From The EU’s Per- and Polyfluoroalkyl Substances (PFAS) Ban: A Case of Policy over Science (2023) · cites this paper as [20]
Cites
US Environmental Protection Agency
Liu, X. (1998) · Choice Reviews Online · doi:10.5860/choice.35-4455 · Cited by 5,887 · see citing works
Klamt, A. (1995) · The Journal of Physical Chemistry · doi:10.1021/j100007a062 · Cited by 4,194 · see citing works
Refinement and Parametrization of COSMO-RS
Klamt, A., Jonas, V., Bürger, T., & Lohrenz, J. C. W. (1998) · The Journal of Physical Chemistry A · doi:10.1021/jp980017s · Cited by 1,998 · see citing works
Fast solvent screening via quantum chemistry: COSMO‐RS approach
Eckert, F., & Klamt, A. (2002) · AIChE Journal · doi:10.1002/aic.690480220 · Cited by 1,831 · see citing works
The CompTox Chemistry Dashboard: a community data resource for environmental chemistry
Williams, A. J., Grulke, C., Edwards, J., McEachran, A. D., Mansouri, K., Baker, N., Patlewicz, G. Y., Shah, I., Wambaugh, J. F., Judson, R., et al. (2017) · Journal of Cheminformatics · doi:10.1186/s13321-017-0247-6 · Cited by 1,164 · see citing works
Determination of sets of solute descriptors from chromatographic measurements
Abraham, M. H., Ibrahim, A., & Zissimos, A. M. (2004) · Journal of Chromatography A · doi:10.1016/j.chroma.2003.12.004 · Cited by 942 · see citing works
Bidleman, T. F. (1988) · Environmental Science & Technology · doi:10.1021/es00169a002 · Cited by 872 · see citing works
OPERA models for predicting physicochemical properties and environmental fate endpoints
Mansouri, K., Grulke, C., Judson, R., & Williams, A. J. (2018) · Journal of Cheminformatics · doi:10.1186/s13321-018-0263-1 · Cited by 635 · see citing works
Rayne, S., & Forest, K. (2009) · Journal of Environmental Science and Health, Part A · doi:10.1080/10934520903139811 · Cited by 475 · see citing works
The p <i>K</i> <sub>a</sub> Values of PFOA and Other Highly Fluorinated Carboxylic Acids
Goss, K.-U. (2008) · Environmental Science & Technology · doi:10.1021/es702192c · Cited by 471 · see citing works
The National Institute of Environmental Health Sciences
Mody, V. V., & Ray, S. D. (2014) · Elsevier eBooks · doi:10.1016/b978-0-12-386454-3.00341-9 · Cited by 407 · see citing works
Prediction of Solubility of Drugs and Other Compounds in Organic Solvents
Abraham, M. H., Smith, R. E., Luchtefeld, R., et al. (2009) · Journal of Pharmaceutical Sciences · doi:10.1002/jps.21922 · Cited by 344 · see citing works
Applications of Polyparameter Linear Free Energy Relationships in Environmental Chemistry
Endo, S., & Goss, K. (2014) · Environmental Science & Technology · doi:10.1021/es503369t · Cited by 302 · see citing works
Nguyen, T. H., Goss, K., & Ball, W. P. (2005) · Environmental Science & Technology · doi:10.1021/es048839s · Cited by 277 · see citing works
Wang, Z., MacLeod, M., Cousins, I. T., Scheringer, M., & Hungerbühler, K. (2011) · Environmental Chemistry · doi:10.1071/en10143 · Cited by 272 · see citing works
Burns, D. C., Ellis, D. A., Li, H., McMurdo, C. J., & Webster, E. M. (2008) · Environmental Science & Technology · doi:10.1021/es802047v · Cited by 270 · see citing works
Dalahmeh, S., Tirgani, S., Komakech, A. J., Niwagaba, C. B., & Ahrens, L. (2018) · Science of The Total Environment · doi:10.1016/j.scitotenv.2018.03.024 · Cited by 262 · see citing works
Chen, H., Yao, Y., Zhao, Z., Wang, Y., Wang, Q., Ren, C., Wang, B., Sun, H., Alder, A. C., & Kannan, K. (2018) · Environmental Science & Technology · doi:10.1021/acs.est.8b00544 · Cited by 261 · see citing works
Predicting the Partitioning Behavior of Various Highly Fluorinated Compounds
Arp, H. P. H., Niederer, C., & Goss, K. (2006) · Environmental Science & Technology · doi:10.1021/es060744y · Cited by 250 · see citing works
Goss, K. (2005) · Fluid Phase Equilibria · doi:10.1016/j.fluid.2005.04.006 · Cited by 212 · see citing works
Bhhatarai, B., & Gramatica, P. (2010) · Environmental Science & Technology · doi:10.1021/es101181g · Cited by 182 · see citing works
Armitage, J. M., Schenker, U., Scheringer, M., Martin, J. W., MacLeod, M., & Cousins, I. T. (2009) · Environmental Science & Technology · doi:10.1021/es901448p · Cited by 181 · see citing works
Bao, J., Liu, W., Liu, L., Jin, Y., Dai, J., Ran, X., Zhang, Z., & Tsuda, S. (2010) · Environmental Science & Technology · doi:10.1021/es102610x · Cited by 175 · see citing works
Lei, Y. D., Wania, F., Mathers, D., & Mabury, S. A. (2004) · Journal of Chemical & Engineering Data · doi:10.1021/je049949h · Cited by 138 · see citing works
The Partition Behavior of Fluorotelomer Alcohols and Olefins
Goss, K., Bronner, G., Harner, T., Hertel, M., & Schmidt, T. C. (2006) · Environmental Science & Technology · doi:10.1021/es060004p · Cited by 135 · see citing works
Winkens, K., Giovanoulis, G., Koponen, J., Vestergren, R., Berger, U., Karvonen, A. M., Pekkanen, J., Kiviranta, H., & Cousins, I. T. (2018) · Environment International · doi:10.1016/j.envint.2018.06.009 · Cited by 127 · see citing works
Card, M. L., Gomez‐Alvarez, V., Lee, W.-H., Lynch, D. G., Orentas, N., Titcombe, M., Wong, E. M., & Boethling, R. S. (2017) · Environmental Science Processes & Impacts · doi:10.1039/c7em00064b · Cited by 109 · see citing works
Lorenzo, M., Campo, J., Morales‐Suárez‐Varela, M., & Picó, Y. (2018) · The Science of The Total Environment · doi:10.1016/j.scitotenv.2018.07.304 · Cited by 96 · see citing works
Solubility and Sorption by Soils of 8:2 Fluorotelomer Alcohol in Water and Cosolvent Systems
Liu, J., & Lee, L. (2005) · Environmental Science & Technology · doi:10.1021/es051125c · Cited by 91 · see citing works
Vapor Pressure and Intramolecular Hydrogen Bonding in Fluorotelomer Alcohols
Krusic, P. J., Marchione, A. A., Davidson, F., Kaiser, M. A., Kao, C.-P. C., Richardson, R. E., Botelho, M. A., Waterland, R. L., & Buck, R. C. (2005) · The Journal of Physical Chemistry A · doi:10.1021/jp0502961 · Cited by 91 · see citing works
Determination of Acidity Constants of Perfluoroalkanoic Acids
Moroi, Y., Yano, H., Shibata, O., & Yonemitsu, T. (2001) · Bulletin of the Chemical Society of Japan · doi:10.1246/bcsj.74.667 · Cited by 83 · see citing works
Effect of Fluorotelomer Alcohol Chain Length on Aqueous Solubility and Sorption by Soils
Liu, J., & Lee, L. (2007) · Environmental Science & Technology · doi:10.1021/es070228n · Cited by 82 · see citing works
Robson, M. G. (2014) · 142nd APHA Annual Meeting and Exposition (November 15 - November 19, 2014) · Cited by 70 · see citing works
Liu, S., Lu, Y., Xie, S., Wang, T., Jones, K. C., & Sweetman, A. J. (2015) · Environment International · doi:10.1016/j.envint.2015.08.007 · Cited by 68 · see citing works
Kutsuna, S., & Hori, H. (2008) · Atmospheric Environment · doi:10.1016/j.atmosenv.2008.09.008 · Cited by 57 · see citing works
Li, H., Ellis, D., & Mackay, D. (2007) · Journal of Chemical & Engineering Data · doi:10.1021/je600556d · Cited by 54 · see citing works
Kong, X., Liu, W., He, W., Xu, F., Koelmans, A. A., & Mooij, W. M. (2018) · Environmental Pollution · doi:10.1016/j.envpol.2018.02.026 · Cited by 49 · see citing works
Partitioning of Fluorotelomer Alcohols to Octanol and Different Sources of Dissolved Organic Carbon
Carmosini, N., & Lee, L. (2008) · Environmental Science & Technology · doi:10.1021/es800263t · Cited by 47 · see citing works
Expanding the Applicability of Multimedia Fate Models to Polar Organic Chemicals
Breivik, K., & Wania, F. (2003) · Environmental Science & Technology · doi:10.1021/es034454i · Cited by 44 · see citing works
Prediction of soil sorption coefficients with a conductor-like screening model for real solvents
Klamt, A., Eckert, F., & Diedenhofen, M. (2002) · Environmental Toxicology and Chemistry · doi:10.1002/etc.5620211206 · Cited by 41 · see citing works
Determination of the Octanol−Air Partition Coefficients (KOA) of Fluorotelomer Alcohols
Thuens, S., Dreyer, A., Sturm, R., Temme, C., & Ebinghaus, R. (2007) · Journal of Chemical & Engineering Data · doi:10.1021/je700522f · Cited by 40 · see citing works
Wang, Z., Scheringer, M., MacLeod, M., et al. (2012) · Environmental Pollution · doi:10.1016/j.envpol.2012.03.037 · Cited by 40 · see citing works
Physicochemical Properties of 8-2 Fluorinated Telomer B Alcohol
Kaiser, M. A., Cobranchi, D. P., Kao, C.-P. C., Krusic, P. J., Marchione, A. A., & Buck, R. C. (2004) · Journal of Chemical & Engineering Data · doi:10.1021/je034222z · Cited by 38 · see citing works
Dreyer, A., Langer, V., & Ebinghaus, R. (2009) · Journal of Chemical & Engineering Data · doi:10.1021/je900082g · Cited by 33 · see citing works
Mechanisms of Neutral and Anionic Surfactant Sorption to Solid-Phase Microextraction Fibers
Haftka, J. J. H., Hammer, J., & Hermens, J. L. M. (2015) · Environmental Science & Technology · doi:10.1021/acs.est.5b02901 · Cited by 33 · see citing works
Wang, Z., Xie, Z., Möller, A., Mi, W., Wolschke, H., & Ebinghaus, R. (2015) · Environmental Pollution · doi:10.1016/j.envpol.2015.03.029 · Cited by 26 · see citing works
Melting Point and Aqueous Solubility Determination of 2H-Hexadecafluoro-2-decenoic Acid (C10F16H2O2)
Fischer-Drowos, S. G., Betz, L. R., DiBussolo, J. M., et al. (2007) · Journal of Chemical & Engineering Data · doi:10.1021/je0603628 · Cited by 3 · see citing works
Martin, J., Moussaoui, S. E., & Asuero, A. G. (2018) · Cited by 1 · see citing works
Flagged first, then by citations
Cited by
Sorted by citations
De Silva, A. O., Armitage, J. M., Bruton, T. A., Dassuncao, C., Heiger-Bernays, W., Hu, X. C., Kärrman, A., Kelly, B., Ng, C., Robuck, A., et al. (2020) · Environmental Toxicology and Chemistry · doi:10.1002/etc.4935 · Cited by 835 · see citing works
Sima, M. W., & Jaffé, P. R. (2021) · Science of The Total Environment · doi:10.1016/j.scitotenv.2020.143793 · Cited by 242 · see citing works
D’Ambro, E. L., Pye, H. O. T., Bash, J. O., Bowyer, J., Allen, C., Efstathiou, C., Gilliam, R. C., Reynolds, L., Talgo, K., & Murphy, B. N. (2021) · Environmental Science & Technology · doi:10.1021/acs.est.0c06580 · Cited by 145 · see citing works
The EU’s Per- and Polyfluoroalkyl Substances (PFAS) Ban: A Case of Policy over Science
Spyrakis, F., & Dragani, T. A. (2023) · Toxics · doi:10.3390/toxics11090721 · Cited by 78 · see citing works
Colnot, T., & Dekant, W. (2022) · Archives of Toxicology · doi:10.1007/s00204-022-03336-9 · Cited by 9 · see citing works
- Authors
- Lampic, A., & Parnis, J. M.
- Affiliations
- Trent University (CA)
- Corresponding author
- Parnis, J. Mark
- ORCID
- Parnis, J. Mark
- Venue
- Environmental Toxicology and Chemistry
- Publisher
- Oxford University Press (OUP)
- Published
- 2020-02-05
- Volume
- 39
- Issue
- 4
- Pages
- 775-786
- ISSN
- 0730-7268 (ISSN-L)
- 1552-8618
- OpenAlex
- W3004760718
- Cited by
- 52
- References
- 49
- Citations by year
- 2026: 8 · 2025: 3 · 2024: 7 · 2023: 17 · 2022: 10 · 2021: 5 · 2020: 2
- FWCI
- 3.15
- Type
- journal article
- Language
- en
- Open access
- closed
- Licence
- Locations
- Environmental Toxicology and Chemistry (publishedVersion)
- PubMed (publishedVersion)
- Funders
- Natural Sciences and Engineering Research Council of Canada (RGPIN-2016-03-65, RGPIN‐2016‐03‐65)
- Topics
- Physical Sciences › Environmental Science › Environmental Chemistry › Per- and polyfluoroalkyl substances research
- Physical Sciences › Computer Science › Computational Theory and Mathematics › Computational Drug Discovery Methods
- Physical Sciences › Environmental Science › Health, Toxicology and Mutagenesis › Toxic Organic Pollutants Impact
- Keywords
- per- and polyfluoroalkyl substances, PFAS, physicochemical property prediction, COSMOtherm, EPI Suite, CompTox Chemicals Dashboard, linear solvation energy relationships, acid dissociation constants, octanol-air partition coefficient, octanol-water partition coefficient, vapor pressure, soil organic carbon partition coefficient, solubility, ionization corrections, environmental fate prediction, model accuracy comparison
- MeSH terms
- Alkanes, Environmental Monitoring, Environmental Pollutants, Hydrocarbons, Fluorinated, Models, Chemical, Solubility, Thermodynamics, United States, United States Environmental Protection Agency, Molecular Structure, Quantitative Structure-Activity Relationship
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
