Atmospheric chemistry of N-methyl perfluorobutane sulfonamidoethanol, C4F9SO2N(CH3)CH2CH2OH: Kinetics and mechanism of reaction with OH
Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, CanadaEnvironmental Science and Technology (Impact Factor: 5.33). 03/2006; 40(6):1862-8. DOI: 10.1021/es0520767
Relative rate methods were used to measure the gas-phase reaction of N-methyl perfluorobutane sulfonamidoethanol (NMeFBSE) with OH radicals, giving k(OH + NMeFBSE) = (5.8 +/- 0.8) x 10(-12) cm3 molecule(-1) s(-1) in 750 Torr of air diluent at 296 K. The atmospheric lifetime of NMeFBSE is determined by reaction with OH radicals and is approximately 2 days. Degradation products were identified by in situ FTIR spectroscopy and offline GC-MS and LC-MS/MS analysis. The primary carbonyl product C4F9SO2N(CH3)CH2CHO, N-methyl perfluorobutane sulfonamide (C4F9SO2NH(CH3)), perfluorobutanoic acid (C3F7C(O)OH), perfluoropropanoic acid (C2F5C(O)OH), trifluoroacetic acid (CF3C(O)OH), carbonyl fluoride (COF2), and perfluorobutane sulfonic acid (C4F9SO3H) were identified as products. A mechanism involving the addition of OH to the sulfone double bond was proposed to explain the production of perfluorobutane sulfonic acid and perfluorinated carboxylic acids in yields of 1 and 10%, respectively. The gas-phase N-dealkylation product, N-methyl perfluorobutane sulfonamide (NMeFBSA), has an atmospheric lifetime (>20 days) which is much longer than that of the parent compound, NMeFBSE. Accordingly,the production of NMeFBSA exposes a mechanism by which NMeFBSE may contribute to the burden of perfluorinated contamination in remote locations despite its relatively short atmospheric lifetime. Using the atmospheric fate of NMeFBSE as a guide, it appears that anthropogenic production of N-methyl perfluorooctane sulfonamidoethanol (NMeFOSE) contributes to the ubiquity of perfluoroalkyl sulfonate and carboxylate compounds in the environment.
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- "Several typical neutral PFASs, such as fluorotelomer alcohols (FTOHs), fluorotelomer acrylates (FTAs), perfluorooctane sulfonamides (FOSAs) and perfluorooctane sulfonamidoethanols (FOSEs), are prone to release into the atmosphere and undergo long range atmospheric transport (LRAT) during their manufacture, use and disposal (Paul et al., 2009). These PFASs can degrade to, for example perfluorooctane sulfonate (PFOS) and perfluorooctanoate (PFOA), under the condition of $OH radicals initiated oxidation in the atmosphere (Butt et al., 2009; D'Eon et al., 2006). "
ABSTRACT: Dry deposition fluxes of 12 neutral poly-/perfluoroalkyl substances (PFASs) were estimated at Büsum located in northern German coast, and their gas/particle partition coefficients were predicted by employing the polyparameter linear free energy relationships (PP-LFERs). The gas deposition flux, particle deposition flux and total (gas + particle) flux of the 12 PFASs during sampling periods were 1088 ± 611, 189 ± 75 and 1277 ± 627 pg/(m(2) d), respectively. The gas deposition of PFASs played a key role during deposition to marine ecosystem. Sensitivity analysis showed that wind speed was the most sensitive parameter for gas deposition fluxes. Good agreements (within 1 log unit) were observed between the measured gas/particle partitioning data of PFASs and the predicted partition coefficients using PP-LFERs, indicating the model can reliably predict the gas/particle partitioning behaviors of atmospheric neutral PFASs. Copyright © 2015 Elsevier Ltd. All rights reserved.Environmental Pollution 07/2015; 202. DOI:10.1016/j.envpol.2015.03.029 · 4.14 Impact Factor
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- "Me-and EtFOSA, and Me-and EtFOSE). The high concentrations of the shorter chain compounds of PFBS and PFBA and their precursors found in this study possibly reflect the growing environmental occurrence of these compounds following increased production of MeFBSE, and other C 4 fluorocarbon products, following the industry phase out of perfluorooctanesulfonyl fluoride (POSF) (D'Eon et al., 2006 "
ABSTRACT: Per- and polyfluoroalkyl substances (PFAS) were measured systematically in a snowpack in northern Sweden to determine chemical behaviour during seasonal melt. Average PFAS concentrations were generally low, but displayed a wide range with median (range) concentrations of PFOA and PFOS of 66.5 pg L(-1) (ND-122) and 20.5 pg L(-1) (2.60-253) respectively. Average concentrations of the shorter chain, C4 and C5 perfluoroalkyl carboxylates (PFCAs) and perfluoroalkyl sulfonates (PFSAs), were ∼10-fold higher. Differences in the PFAS concentrations and profile were observed between surface snow and deeper layers, with evidence of PFAS migration to deeper snow layers as melt progressed. Chemical loads (ng m(-2)) for C4-9 PFCAs decreased gradually as melt progressed, but increased for C4, C6-8 PFSAs and the longer chain C10-12 PFCAs. This enrichment in the diminishing snowpack is an unusual phenomenon that will affect PFAS elution with meltwater and subsequent entry to catchment surface waters.Environmental Pollution 05/2014; 191C:190-198. DOI:10.1016/j.envpol.2014.04.032 · 4.14 Impact Factor
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- "In contrast, PFOS is the predominant compound in wildlife (Kannan et al., 2001a,b), which can be explained by its higher bioaccumulation potential, whereas PFOA has a higher water solubility (Brooke et al., 2004) and lower sorption potential to sediment (Higgins and Luthy, 2006). On the other hand, the PFOA concentrations are usually higher in open-ocean waters compared to PFOS, which can be explained by different amount of discharge into the aqueous environment , different sources (Prevedouros et al., 2006; Paul et al., 2009), different degradation process of the precursors (Ellis et al., 2004; D'Eon et al., 2006) and different physico-chemical characteristics. "
ABSTRACT: The spatial distribution of per- and polyfluoroalkyl compounds (PFCs) were investigated in coastal waters collected onboard research vessel Snow Dragon from the East to South China Sea in 2010. All samples were prepared by solid-phase extraction and analyzed using high performance liquid chromatography/negative electrospray ionization-tandem mass spectrometry (HPLC/(-)ESI-MS/MS). Concentrations of 9 PFCs, including C(4) and C(8) (PFBS, PFOS) perfluoroalkyl sulfonate (PFSAs), C(5)-C(9) and C(13) (PFPA, PFHxA, PFHpA, PFOA, PFNA, PFTriDA) perfluoroalkyl carboxylates (PFCAs), and N-ethyl perfluorooctane sulfonamide (EtFOSA) were quantified. The ΣPFC concentrations ranged from 133 pg/L to 3320 pg/L, with PFOA (37.5-1541 pg/L), PFBS (23.0-941 pg/L) and PFHpA (0-422 pg/L) as dominant compounds. Concentrations of PFCs were greater in coastal waters along Shanghai, Ningbo, Taizhou, Xiamen and along coastal cities of the Guangdong province compared to less populated areas along the east Chinese coast. Additionally, the comparison with other seawater PFC measurements showed lower levels in this study.Environmental Pollution 02/2012; 161:162-9. DOI:10.1016/j.envpol.2011.09.045 · 4.14 Impact Factor
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