Estimation of the Acid Dissociation Constant of Perfluoroalkyl Carboxylic Acids through an Experimental Investigation of their Water-to-Air Transport
The acid dissociation constants (pK as) of perfluoroalkyl carboxylic acids (PFCAs) have been the subject of discussion in the literature; for example, values from −0.2 to 3.8 have been suggested for perfluorooctanoic acid (PFOA). The dissociated anionic conjugate bases of PFCAs have negligible air–w...
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| Published in | Environmental science & technology Vol. 47; no. 19; pp. 11032 - 11039 |
|---|---|
| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
Washington, DC
American Chemical Society
01.10.2013
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| Subjects | |
| Online Access | Get full text |
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| Abstract | The acid dissociation constants (pK as) of perfluoroalkyl carboxylic acids (PFCAs) have been the subject of discussion in the literature; for example, values from −0.2 to 3.8 have been suggested for perfluorooctanoic acid (PFOA). The dissociated anionic conjugate bases of PFCAs have negligible air–water partition coefficients (K AWs) and do not volatilize from water. The neutral acids, however, have relatively high K AWs and volatilization from water has been demonstrated. The extent of volatilization of PFCAs in the environment will depend on the water pH and their pK a. Knowledge of the pK as of PFCAs is therefore vital for understanding their environmental transport and fate. We investigated the water-to-air transfer of PFCAs in a novel experimental setup. We used ∼1 μg L–1 of PFCAs in water (above environmental background concentrations but below the concentration at which self-association occurs) at different water pH (pH 0.3 to pH 6.9) and sampled the PFCAs volatilized from water during a 2-day experiment. Our results suggest that the pK as of C4–11 PFCAs are <1.6. For PFOA, we derived a pK a of 0.5 from fitting the experimental measurements with a volatilization model. Perfluoroalkane sulfonic acids were not volatilized, suggesting that their pK as are below the investigated pH range (pK a <0.3). |
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| AbstractList | The acid dissociation constants (pKas) of perfluoroalkyl carboxylic acids (PFCAs) have been the subject of discussion in the literature; for example, values from -0.2 to 3.8 have been suggested for perfluorooctanoic acid (PFOA). The dissociated anionic conjugate bases of PFCAs have negligible air-water partition coefficients (KAWs) and do not volatilize from water. The neutral acids, however, have relatively high KAWs and volatilization from water has been demonstrated. The extent of volatilization of PFCAs in the environment will depend on the water pH and their pKa. Knowledge of the pKas of PFCAs is therefore vital for understanding their environmental transport and fate. We investigated the water-to-air transfer of PFCAs in a novel experimental setup. We used ∼1 μg L(-1) of PFCAs in water (above environmental background concentrations but below the concentration at which self-association occurs) at different water pH (pH 0.3 to pH 6.9) and sampled the PFCAs volatilized from water during a 2-day experiment. Our results suggest that the pKas of C4-11 PFCAs are <1.6. For PFOA, we derived a pKa of 0.5 from fitting the experimental measurements with a volatilization model. Perfluoroalkane sulfonic acids were not volatilized, suggesting that their pKas are below the investigated pH range (pKa <0.3).The acid dissociation constants (pKas) of perfluoroalkyl carboxylic acids (PFCAs) have been the subject of discussion in the literature; for example, values from -0.2 to 3.8 have been suggested for perfluorooctanoic acid (PFOA). The dissociated anionic conjugate bases of PFCAs have negligible air-water partition coefficients (KAWs) and do not volatilize from water. The neutral acids, however, have relatively high KAWs and volatilization from water has been demonstrated. The extent of volatilization of PFCAs in the environment will depend on the water pH and their pKa. Knowledge of the pKas of PFCAs is therefore vital for understanding their environmental transport and fate. We investigated the water-to-air transfer of PFCAs in a novel experimental setup. We used ∼1 μg L(-1) of PFCAs in water (above environmental background concentrations but below the concentration at which self-association occurs) at different water pH (pH 0.3 to pH 6.9) and sampled the PFCAs volatilized from water during a 2-day experiment. Our results suggest that the pKas of C4-11 PFCAs are <1.6. For PFOA, we derived a pKa of 0.5 from fitting the experimental measurements with a volatilization model. Perfluoroalkane sulfonic acids were not volatilized, suggesting that their pKas are below the investigated pH range (pKa <0.3). The acid dissociation constants (pKₐs) of perfluoroalkyl carboxylic acids (PFCAs) have been the subject of discussion in the literature; for example, values from −0.2 to 3.8 have been suggested for perfluorooctanoic acid (PFOA). The dissociated anionic conjugate bases of PFCAs have negligible air–water partition coefficients (KAWs) and do not volatilize from water. The neutral acids, however, have relatively high KAWs and volatilization from water has been demonstrated. The extent of volatilization of PFCAs in the environment will depend on the water pH and their pKₐ. Knowledge of the pKₐs of PFCAs is therefore vital for understanding their environmental transport and fate. We investigated the water-to-air transfer of PFCAs in a novel experimental setup. We used ∼1 μg L–¹ of PFCAs in water (above environmental background concentrations but below the concentration at which self-association occurs) at different water pH (pH 0.3 to pH 6.9) and sampled the PFCAs volatilized from water during a 2-day experiment. Our results suggest that the pKₐs of C₄–₁₁ PFCAs are <1.6. For PFOA, we derived a pKₐ of 0.5 from fitting the experimental measurements with a volatilization model. Perfluoroalkane sulfonic acids were not volatilized, suggesting that their pKₐs are below the investigated pH range (pKₐ <0.3). The acid dissociation constants (pKas) of perfluoroalkyl carboxylic acids (PFCAs) have been the subject of discussion in the literature; for example, values from -0.2 to 3.8 have been suggested for perfluorooctanoic acid (PFOA). The dissociated anionic conjugate bases of PFCAs have negligible air-water partition coefficients (KAWs) and do not volatilize from water. The neutral acids, however, have relatively high KAWs and volatilization from water has been demonstrated. The extent of volatilization of PFCAs in the environment will depend on the water pH and their pKa. Knowledge of the pKas of PFCAs is therefore vital for understanding their environmental transport and fate. We investigated the water-to-air transfer of PFCAs in a novel experimental setup. We used ~1 mu g L-1 of PFCAs in water (above environmental background concentrations but below the concentration at which self-association occurs) at different water pH (pH 0.3 to pH 6.9) and sampled the PFCAs volatilized from water during a 2-day experiment. Our results suggest that the pKas of C4-11 PFCAs are <1.6. For PFOA, we derived a pKa of 0.5 from fitting the experimental measurements with a volatilization model. Perfluoroalkane sulfonic acids were not volatilized, suggesting that their pKas are below the investigated pH range (pKa <0.3). The acid dissociation constants (pK as) of perfluoroalkyl carboxylic acids (PFCAs) have been the subject of discussion in the literature; for example, values from −0.2 to 3.8 have been suggested for perfluorooctanoic acid (PFOA). The dissociated anionic conjugate bases of PFCAs have negligible air–water partition coefficients (K AWs) and do not volatilize from water. The neutral acids, however, have relatively high K AWs and volatilization from water has been demonstrated. The extent of volatilization of PFCAs in the environment will depend on the water pH and their pK a. Knowledge of the pK as of PFCAs is therefore vital for understanding their environmental transport and fate. We investigated the water-to-air transfer of PFCAs in a novel experimental setup. We used ∼1 μg L–1 of PFCAs in water (above environmental background concentrations but below the concentration at which self-association occurs) at different water pH (pH 0.3 to pH 6.9) and sampled the PFCAs volatilized from water during a 2-day experiment. Our results suggest that the pK as of C4–11 PFCAs are <1.6. For PFOA, we derived a pK a of 0.5 from fitting the experimental measurements with a volatilization model. Perfluoroalkane sulfonic acids were not volatilized, suggesting that their pK as are below the investigated pH range (pK a <0.3). The acid dissociation constants (pKas) of perfluoroalkyl carboxylic acids (PFCAs) have been the subject of discussion in the literature; for example, values from -0.2 to 3.8 have been suggested for perfluorooctanoic acid (PFOA). The dissociated anionic conjugate bases of PFCAs have negligible air-water partition coefficients (KAWs) and do not volatilize from water. The neutral acids, however, have relatively high KAWs and volatilization from water has been demonstrated. The extent of volatilization of PFCAs in the environment will depend on the water pH and their pKa. Knowledge of the pKas of PFCAs is therefore vital for understanding their environmental transport and fate. We investigated the water-to-air transfer of PFCAs in a novel experimental setup. We used ~1 μg L-1 of PFCAs in water (above environmental background concentrations but below the concentration at which self-association occurs) at different water pH (pH 0.3 to pH 6.9) and sampled the PFCAs volatilized from water during a 2-day experiment. Our results suggest that the pKas of C4-11 PFCAs are <1.6. For PFOA, we derived a pKa of 0.5 from fitting the experimental measurements with a volatilization model. Perfluoroalkane sulfonic acids were not volatilized, suggesting that their pKas are below the investigated pH range (pKa <0.3). [PUBLICATION ABSTRACT] The acid dissociation constants (pKas) of perfluoroalkyl carboxylic acids (PFCAs) have been the subject of discussion in the literature; for example, values from -0.2 to 3.8 have been suggested for perfluorooctanoic acid (PFOA). The dissociated anionic conjugate bases of PFCAs have negligible air-water partition coefficients (KAWs) and do not volatilize from water. The neutral acids, however, have relatively high KAWs and volatilization from water has been demonstrated. The extent of volatilization of PFCAs in the environment will depend on the water pH and their pKa. Knowledge of the pKas of PFCAs is therefore vital for understanding their environmental transport and fate. We investigated the water-to-air transfer of PFCAs in a novel experimental setup. We used ∼1 μg L(-1) of PFCAs in water (above environmental background concentrations but below the concentration at which self-association occurs) at different water pH (pH 0.3 to pH 6.9) and sampled the PFCAs volatilized from water during a 2-day experiment. Our results suggest that the pKas of C4-11 PFCAs are <1.6. For PFOA, we derived a pKa of 0.5 from fitting the experimental measurements with a volatilization model. Perfluoroalkane sulfonic acids were not volatilized, suggesting that their pKas are below the investigated pH range (pKa <0.3). The acid dissociation constants (pK(a)s) of perfluoroalkyl carboxylic acids (PFCAs) have been the subject of discussion in the literature; for example, values from -0.2 to 3.8 have been suggested for perfluorooctanoic acid (PFOA). The dissociated anionic conjugate bases of PFCAs have negligible air-water partition coefficients (K(AW)s) and do not volatilize from water. The neutral acids, however, have relatively high K(AW)s and volatilization from water has been demonstrated. The extent of volatilization of PFCAs in the environment will depend on the water pH and their pK(a). Knowledge of the pK(a)s of PFCAs is therefore vital for,understanding their environmental transport and fate. We investigated the water-to-air transfer of PFCAs in a novel experimental setup. We used similar to 1 mu g L-1 of PFCAs in water (above environmental background concentrations but below the concentration at which self-association occurs) at different water pH (pH 0.3 to pH 6.9) and sampled the PFCAs volatilized from water during a 2-day experiment. Our results suggest that the pK(a)s of C4-11 PFCAs are <1.6. For PFOA, we derived a pK(a) of 0.5 from fitting the experimental measurements with a volatilization model. Perfluoroalkane sulfonic acids were not volatilized, suggesting that their pK(a)s are below the investigated pH range (pK(a) <0.3). |
| Author | Cousins, Ian T Berger, Urs Vierke, Lena |
| AuthorAffiliation | Leuphana University Lüneburg Department of Applied Environmental Science (ITM) Federal Environment Agency, Section for Chemicals Institute of Sustainable and Environmental Chemistry Stockholm University |
| AuthorAffiliation_xml | – name: Leuphana University Lüneburg – name: Stockholm University – name: Department of Applied Environmental Science (ITM) – name: Institute of Sustainable and Environmental Chemistry – name: Federal Environment Agency, Section for Chemicals |
| Author_xml | – sequence: 1 givenname: Lena surname: Vierke fullname: Vierke, Lena email: Lena.Vierke@uba.de – sequence: 2 givenname: Urs surname: Berger fullname: Berger, Urs – sequence: 3 givenname: Ian T surname: Cousins fullname: Cousins, Ian T |
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| Snippet | The acid dissociation constants (pK as) of perfluoroalkyl carboxylic acids (PFCAs) have been the subject of discussion in the literature; for example, values... The acid dissociation constants (pKas) of perfluoroalkyl carboxylic acids (PFCAs) have been the subject of discussion in the literature; for example, values... The acid dissociation constants (pKₐs) of perfluoroalkyl carboxylic acids (PFCAs) have been the subject of discussion in the literature; for example, values... The acid dissociation constants (pK(a)s) of perfluoroalkyl carboxylic acids (PFCAs) have been the subject of discussion in the literature; for example, values... |
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| SubjectTerms | Acidity Acids Air Applied sciences Atmospheric pollution Biological and physicochemical phenomena carboxylic acids Carboxylic Acids - chemistry Chemical compounds dissociation Earth sciences Earth, ocean, space Engineering and environment geology. Geothermics Estimating techniques Exact sciences and technology Experiments Fluorocarbons - chemistry Natural water pollution partition coefficients perfluorooctanoic acid Pollutants physicochemistry study: properties, effects, reactions, transport and distribution Pollution Pollution, environment geology sulfonic acids Volatilization Water - chemistry Water Pollutants, Chemical - chemistry Water treatment and pollution |
| Title | Estimation of the Acid Dissociation Constant of Perfluoroalkyl Carboxylic Acids through an Experimental Investigation of their Water-to-Air Transport |
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