Biodegradation of Perfluorinated Compounds

Parsons, John R.; Sáez, M.; Dolfing, Jan; Voogt, P. de

doi:10.1007/978-0-387-78444-1_2

Cited by 128 publications

(131 citation statements)

References 63 publications

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“…Biotransformation processes of polyfluoroalkyl precursors in microbial and animal models generally initiate from the hydrocarbon part of the molecular structures, due to the high carbon-fluorine bond energy (450 KJ/mol) [22]. For example, biotransformation of fluorotelomer-based substances often involves cleavage of functional groups (e.g., ester, ether, urethane) to form FTOHs, which are then further converted to FT aldehyde (FTAL), FT unsaturated carboxylic acids (FTUCAs), FT ketone and FT secondary alcohol (sFTOH), and x:3 fluorotelomer acids (F(CF2)nCH2CH2COOH, n = 3-7) [23,24].…”

Section: Introductionmentioning

confidence: 99%

Methodology for studying biotransformation of polyfluoroalkyl precursors in the environment

Ruan

Lin

Wang

et al. 2015

TrAC Trends in Analytical Chemistry

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A B S T R A C TBiotransformation of polyfluoroalkyl precursors contributes in part to the perfluoroalkyl carboxylates and sulfonates detected in the global environment and biota. Robust sample preparation and sensitive analytical techniques for maximum analyte recovery are essential to identify and to quantify biotransformation products often present at low levels in environmental matrices and experimental systems. This critical review covers current sample-preparation and analytical methods, including extraction, concentration, clean-up and derivatization, mass spectrometry coupled to gas or liquid chromatography, and radioisotope labeling and tracking techniques. We also critically review methodologies for molecular structural elucidation and in-silico prediction of potential transformation products. We describe current knowledge gaps and challenges in studying novel alternative polyfluoroalkyl substances. We discuss future trends on utilizing advanced analytical techniques.

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Section: Introductionmentioning

confidence: 99%

Methodology for studying biotransformation of polyfluoroalkyl precursors in the environment

Ruan

Lin

Wang

et al. 2015

TrAC Trends in Analytical Chemistry

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“…They have been found in the environment and biota all over the world, including in remote regions, [2] and also in human food items. [3] Certain PFASs are suspected of having high persistence, [4,5] potential for bioaccumulation, [6][7][8][9] and toxicity, [10,11] but there is still an incomplete understanding of their sources, transport and ultimate fate in the environment.…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2011

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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.Abstract. 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 C 4 -C 8 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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“…[9] However, their biotic and abiotic degradation pathways are thus far only marginally known. [10,11] In Canada and Europe, some PFASs, notably perfluorooctane sulfonate (PFOS) are under restrictions for meeting criteria of persistent organic pollutants (POPs) that are controlled under the Stockholm convention (see http://chm.pops.int/Programmes/New%20POPs/ The%209%20new%20POPs/tabid/672/language/en-US/Default. aspx, accessed November 2012).…”

Section: Introductionmentioning

confidence: 99%

Experimental hydrophobicity parameters of perfluorinated alkylated substances from reversed-phase high-performance liquid chromatography

et al. 2012

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Environmental context. Perfluorinated compounds are synthetic chemicals shown to be present in the blood of humans. To study how these contaminants get into our blood requires a good understanding of their physicochemical properties. We describe an alternative way to obtain values for how perfluorinated compounds distribute between water and fatty phases (mimicking e.g. gut content and gut wall), which is essential information for modelling and understanding the environmental fate of these chemicals.Abstract. Capacity factors of perfluorinated alkylated substances were obtained from isocratic reversed-phase highperformance liquid chromatography-mass spectrometry experiments at different organic modifier strengths of the mobile phase. The resulting capacity factor v. modifier strengths plots were extrapolated to obtain capacity factors at 100 % water (k 0 ) that can serve as indicators of the hydrophobicity of the perfluorinated acids. Values of log k 0 were shown to increase linearly with the number of CF 2 units in the fluorinated alkyl chain.

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Biodegradation of Perfluorinated Compounds

Cited by 128 publications

References 63 publications

Methodology for studying biotransformation of polyfluoroalkyl precursors in the environment

Methodology for studying biotransformation of polyfluoroalkyl precursors in the environment

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

Experimental hydrophobicity parameters of perfluorinated alkylated substances from reversed-phase high-performance liquid chromatography

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