Selecting reliable physicochemical properties of perfluoroalkyl and polyfluoroalkyl substances (PFASs) based on molecular descriptors

Kim, Minhee; Li, Loretta Y.; Grace, John R.; Yue, Changtao

doi:10.1016/j.envpol.2014.11.008

Cited by 82 publications

(35 citation statements)

References 58 publications

(100 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…for PFOS as for their suggested pK a ranges. This indicated that at least the maximum values of K AW which were suggested by Kim et al [37] would be not supported by our measurement.…”

Section: Estimation Of Pk a From Observed D Awcontrasting

confidence: 72%

See 1 more Smart Citation

<i>In situ</i> measurement-based partitioning behavior of perfluoroalkyl acids in the atmosphere

Kim

Kannan

2019

Environmental Engineering Research

View full text Add to dashboard Cite

Environmental fate of ionizable organic pollutants such as perfluoroalkyl acids (PFAAs) are of increasing interest but has not been well understood because of uncertain values for parameters related with atmospheric interphase partitioning behavior. In the present study, not only the values for air-water partition coefficient (K AW) and dissociation constant (pK a) of PFAAs were induced by adjusting to in situ measurements of air-water distribution coefficient between vapor phase and rainwater but also gas-particle partition coefficients were also estimated using three-phase partitioning model of ionizable organic pollutants, in situ measurements of PFAAs in aerosol and air vapor phase, and obtained parameter values. The pK a values of PFAAs we obtained were close to the minimum values suggested in literature except for perfluorooctane sulfonic acids, and COSMOtherm-modeled K AW values were assessed to more appropriate among suggested values. When applying parameter values we obtained, it was predicted that air particle-associated fate and transport of PFAAs could be negligible and PFAAs could distribute ubiquitously along the transection from urban to rural region by pH-dependent phase transfer in air. Our study is expected to have some implications in prediction of the environmental redistribution of other ionizable organic compounds

show abstract

“…for PFOS as for their suggested pK a ranges. This indicated that at least the maximum values of K AW which were suggested by Kim et al [37] would be not supported by our measurement.…”

Section: Estimation Of Pk a From Observed D Awcontrasting

confidence: 72%

“…(COSMOtherm) to 0.57 (EPI Suite) for PFOA and -2.40 (COSMOtherm) to -0.35 (EPI Suite) for PFOS. Recently, Kim et al [37] who used molar volume as a molecular descriptor suggested K AW values greater than 10 times than the maximum values suggested by previous QSAR-based models ( Table 2).…”

Section: Estimation Of Pk a From Observed D Awmentioning

confidence: 80%

<i>In situ</i> measurement-based partitioning behavior of perfluoroalkyl acids in the atmosphere

Kim

Kannan

2019

Environmental Engineering Research

View full text Add to dashboard Cite

show abstract

“…Nevertheless, it has been reported that the partition coefficient (Kow, for octanol-water) for PFUnDA is higher than that for the other PFASs we studied, thus some PFUnDA could be partitioning into the lipid compartment (Jing et al, 2009; Kim et al, 2015). However in these data, changes in BMI were unrelated to PFAS concentration in the second pregnancy and the change in BMI, when added to the model shown in table 4, did not predict PFAS concentration (data not shown).…”

Section: Discussionmentioning

confidence: 62%

Reliability of perfluoroalkyl substances in plasma of 100 women in two consecutive pregnancies

Papadopoulou

Haug

Sabaredzovic

et al. 2015

Environmental Research

View full text Add to dashboard Cite

The potential toxicity of background exposure to perfluoroalkyl substances (PFASs) is currently under active investigation. Such investigations typically rely on a single measure of PFAS concentration, yet the longer-term reliability of a single measure has not been well characterized, especially among reproductive-aged women. Our aim was to investigate the association between PFAS plasma concentrations of 100 women in two consecutive pregnancies and explore changes in plasma concentration related to reproductive factors. The women in our study were enrolled in the Norwegian Mother and Child Cohort Study (MoBa) from 2003 to 2009. About half of them breastfed exclusively for 6 months and the rest of the participants did not breastfeed between the two consecutive pregnancies (median time between pregnancies: 18 months). Maternal blood was collected at mid-pregnancy and plasma was analyzed for 10 PFASs. Statistical analyses were restricted to 6 PFASs that were quantifiable in more than 80% of the samples. We estimated the correlation between repeated PFAS measurements, the percentage change between pregnancies and the effect of several reproductive factors in multivariate linear regression models of PFAS concentration in the second pregnancy. The Pearson correlation coefficient between repeated PFAS measurements was, for perfluorooctane sulfonate (PFOS), 0.80; perfluorooctanoate (PFOA), 0.50; perfluorohexane sulfonate (PFHxS), 0.74; perfluorononanoate (PFNA), 0.39; perfluoroundecanoate (PFUnDA), 0.71; and perfluorodecanoate (PFDA), 0.60. Adjustment for maternal age, delivery year, and time and breastfeeding between pregnancies did not substantially affect the observed correlations. We found 44-47% median reductions in the concentrations of PFOS, PFOA and PFHxS between pregnancies, while the change in concentrations between pregnancies was smaller and more variable for PFNA, PFUnDA and PFDA. The variation in plasma concentrations in the second pregnancy was mainly accounted for by the concentration in the first pregnancy; for PFOS, PFOA, and PFNA, breastfeeding also accounted for a substantial proportion. In conclusion, we found the reliability of PFAS measurements in maternal plasma to be moderate to high, and in these data, several factors, especially breastfeeding, were related to plasma concentrations.

show abstract

“…For example, Bhhatarai and Gramatica conducted an extensive QSPR analysis for PFAS, and showed that aqueous solubility, vapor pressure, and critical micelle concentration (CMC) were all well described by simple QSPR models. Similarly, Kim et al (2015) demonstrated the effectiveness of simple QSPR models for estimating vapor pressures, aqueous solubilities, octanol/water partition coefficients, air/water partition coefficients, and octanol/air partition coefficients of PFAS. Lyu et al (2018) successfully applied QSPR analysis to air-water interfacial adsorption coefficients for a homologous series of perfluoroalkyl carboxylates.…”

Section: Introductionmentioning

confidence: 91%

“…Extensive research has demonstrated that a wide range of organic compounds undergo adsorption at air-water interfaces (e.g., Karger et al, 1971; (QSPR) analysis methods can be used to provide empirical-based estimates. This approach is widely used for the estimation of many phase-transfer (partition) coefficients, and it has been applied to PFAS (e.g., Gabriel et al, 1996;Bhhatarai and Gramatica, 2011;Kim et al, 2015;Lyu et al, 2018). For example, Bhhatarai and Gramatica conducted an extensive QSPR analysis for PFAS, and showed that aqueous solubility, vapor pressure, and critical micelle concentration (CMC) were all well described by simple QSPR models.…”

Section: Introductionmentioning

confidence: 99%

The influence of molecular structure on the adsorption of PFAS to fluid-fluid interfaces: Using QSPR to predict interfacial adsorption coefficients

Brusseau

2019

Water Research

111

View full text Add to dashboard Cite

Per-and poly-fluoroalkyl substances (PFAS) are emerging contaminants of critical concern for human health risk. Assessing exposure risk requires a thorough understanding of the transport and fate behavior of PFAS in the environment. Adsorption to fluid-fluid interfaces, which include airwater, OIL-water, and air-OIL interfaces (where OIL represents organic immiscible liquid), is a potentially significant retention process for PFAS transport. Fluid-fluid interfacial adsorption coefficients (K i) are required for use in transport modeling and risk characterization, yet these data are currently not available for the vast majority of PFAS. Surface-tension and interfacial-tension data sets collected from the literature were used to determine interfacial adsorption coefficients for 42 individual PFAS. The PFAS evaluated comprise homologous series of perfluorocarboxylates and perfluorosulfonates, branched perfluoroalkyls, polyfluoroalkyls, alcohol PFAS, and nonionic PFAS. The K i values vary across eight orders of magnitude, and are a function of molecular structure. The results of quantitative-structure/property-relationship (QSPR) analysis demonstrate that a model employing molar volume (V m) as a descriptor provides robust predictions of log K i values for air-water interfacial adsorption of the wide range of PFAS. The model also produced good predictions for a limited set of data for OIL-water interfacial adsorption. The predictive capability of the QSPR model for a wide range of PFAS with greatly varying structures reflects the fact that molar volume provides a reasonable representation of the influence of molecular size on cavity formation/destruction in solution, and thus the hydrophobic-interaction driving force for interfacial adsorption. The QSPR model presented herein provides a means to incorporate the fluid-fluid interfacial adsorption process into transport characterization and risk assessment of PFAS in the environment. This will be particularly relevant for determining PFAS mass flux in the Publisher's Disclaimer: This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final citable form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain.

show abstract

Selecting reliable physicochemical properties of perfluoroalkyl and polyfluoroalkyl substances (PFASs) based on molecular descriptors

Cited by 82 publications

References 58 publications

<i>In situ</i> measurement-based partitioning behavior of perfluoroalkyl acids in the atmosphere

<i>In situ</i> measurement-based partitioning behavior of perfluoroalkyl acids in the atmosphere

Reliability of perfluoroalkyl substances in plasma of 100 women in two consecutive pregnancies

The influence of molecular structure on the adsorption of PFAS to fluid-fluid interfaces: Using QSPR to predict interfacial adsorption coefficients

Contact Info

Product

Resources

About