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The Partition Behavior of Fluorotelomer Alcohols and Olefins
Abstract
In this paper we present a number of equilibrium partition constants for fluorotelomer alcohols and olefins among them data for air/water and octanol/air partitioning. These data are typically required for environmental fate modeling. Our data deviate substantially from those in the literature. A comprehensive check for consistency and plausibility strongly suggests that the data published here are correct. As a consequence the fluorotelomer alcohols will sorb much more to organic phases and have a smaller tendency to remain in the water phase than expected based on previous data. The presented partition data also allow us to derive descriptors for the various kinds of specific (e.g., H-bonds) and nonspecific (e.g., van der Waals) intermolecular interactions thatthe compounds can undergo. These descriptors can be used in polyparameter linear free energy relationships (pp-LFER) in orderto predict a large variety of other partition coefficients (e.g., air/solvent, solvent/ water) as well as the temperature dependence of their air/ water partitioning. The experimental and theoretical approach that we present here can serve as a general example for what needs to be done in order to ensure high quality physicochemical data for organic pollutants.
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Previous studies have shown that A values for 4:2, 6:2, and 8:2 FTOHs are higher than those of nonfluorinated alkyl alcohols and that B has the opposite relationship.
“previous studies have shown that A values for 4:2, 6:2, and 8:2 FTOHs are higher than those of nonfluorinated alkyl alcohols and that B has the opposite relationship.9,11,12”
From Intermolecular Interactions, Solute Descriptors, and Partition Properties of Neutral Per- and Polyfluoroalkyl Substances (PFAS) (2023) · cites this paper as [11]
Goss et al. determined solute descriptors for four fluorotelomer alcohols (FTOHs) and four fluorotelomer olefins (FTOs).
“In the past, Goss et al.11 determined solute descriptors for four fluorotelomer alcohols (FTOHs) and four fluorotelomer olefins (FTOs).”
From Intermolecular Interactions, Solute Descriptors, and Partition Properties of Neutral Per- and Polyfluoroalkyl Substances (PFAS) (2023) · cites this paper as [11]
L was updated from the reported values using literature data for nonpolar GC columns (squalane, SPB-Octyl, and Apolane) because small influences of polar interactions on log k could be taken into account with the values of S and A for PFAS.
“L was also updated from the reported values18 in this iterative calculation using the literature data for nonpolar GC columns (squalane, SPB-Octyl,18 and Apolane)11 because small influences of polar interactions on log k, which were not considered in the previous studies,11,18 could be taken into account with the values of S and A for PFAS.”
From Intermolecular Interactions, Solute Descriptors, and Partition Properties of Neutral Per- and Polyfluoroalkyl Substances (PFAS) (2023) · cites this paper as [11]
Sorption of PFAS such as telomers can be relatively large, due primarily to organic-carbon partitioning associated with hydrophobic interactions.
“For example, the sorption of PFAS such as the telomers can be relatively large, due primarily to organic-carbon partitioning associated with hydrophobic interactions (e.g., Liu and Lee, 2005, Goss et al., 2006).”
From Assessing the potential contributions of additional retention processes to PFAS retardation in the subsurface (2018) · cites this paper as Goss et al., 2006
H values for other PFAS, such as fluorotelomer alcohols (FTOHs) and fluorotelomer olefins, are quite large, ranging approximately 0.05-4 and 100-10,000, respectively.
“Conversely, H values for other PFAS, such as fluorotelomer alcohols (FTOHs) and fluorotelomer olefins are quite large, ranging approximately 0.05–4 and 100–10,000, respectively (Goss et al., 2006, Ding and Peijnenburg, 2013).”
From Assessing the potential contributions of additional retention processes to PFAS retardation in the subsurface (2018) · cites this paper as Goss et al., 2006
Reported Kaw values for a single compound differ between studies by up to a factor of 130.
“Some of the reported values, however, differ between the studies by up to a factor of 130 for a single compound.”
Three studies measured Kaw for 3 or 4 fluorotelomer alcohols (FTOHs).
“Three studies measured Kaw for 3 or 4 fluorotelomer alcohols (FTOHs).7−9”
The VPR-HS measurement for Kaw could result in substantial errors if the mass balance assumption does not hold true, as was experimentally demonstrated before.
“This measurement was conducted for a comparison purpose because the VPR-HS measurement for Kaw could result in substantial errors if the mass balance assumption does not hold true, as was experimentally demonstrated before.8”
Only a few scientific articles have reported direct measurements of Kaw for PFAS with a perfluorocarbon chain length of 4 or more.
“There have been only a few scientific articles that reported direct measurements of Kaw for PFAS with a perfluorocarbon chain length of 4 or more.”
Various researchers derived Kaw from the saturated vapor pressure relative to the aqueous solubility (VP/S) to fill the data gap.
“To fill the huge data gap, various researchers derived Kaw from the saturated vapor pressure relative to the aqueous solubility (VP/S).8,9,12,13”
Kaw values for five PFAS were directly measured using a standard VPR-HS method.
“Kaw values for five PFAS were directly measured using a standard VPR-HS method, as in the literature.7,8”
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Metadata
- Authors
- Goss, K.-U., Bronner, G., Harner, T., Hertel, M., & Schmidt, T. C.
- Venue
- Environmental Science & Technology
- Publisher
- American Chemical Society (ACS)
- Published
- 2006-04-08
- Volume
- 40
- Issue
- 11
- Pages
- 3572-3577
- ISSN
- 0013-936X
- 1520-5851
- Cited by
- 126
- References
- 0
- Language
- en
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