Atmospheric Chemistry of N-methyl Perfluorobutane Sulfonamidoethanol, C4F9SO2N(CH3)CH2CH2OH: Kinetics and Mechanism of Reaction with OH
Abstract
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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PFOS precursors transform to PFOS in air, water (including wastewater treatment), and soils.
“The transformation of PFOS-precursors to PFOS happens in air, water (including waste water treatment), and soils.”
From Short- and long-chain perfluoroalkyl substances in the water, suspended particulate matter, and surface sediment of a turbid river (2016) · cites this paper as D'eon et al., 2006
PFOS is known to be a final transformation product of some PFASs, including N-alkyl substituted perfluorooctane sulfonamides and N-ethyl perfluorooctane sulfonamido ethanol.
“This is because PFOS is known to be the final transformation product of some PFASs such as (N-alkyl substituted) perfluorooctane sulfonamides and N-ethyl perfluorooctane sulfonamido ethanol (D'eon et al., 2006;Benskin et al., 2012;Zhao et al., 2016).”
From Short- and long-chain perfluoroalkyl substances in the water, suspended particulate matter, and surface sediment of a turbid river (2016) · cites this paper as D'eon et al., 2006
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- Authors
- D'eon, J. C., Hurley, M. D., Wallington, T. J., & Mabury, S. A.
- Affiliations
- Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada M5S 3H6, Ford Motor Company, SRL 3083, P.O. Box 2053, Dearborn, Michigan, 48121-2053
- Ford Motor Company (United States) (US)
- Corresponding author
- Mabury, Scott A.
- Venue
- Environmental Science & Technology
- Publisher
- American Chemical Society (ACS)
- Published
- 2006-02-09
- Volume
- 40
- Issue
- 6
- Pages
- 1862-1868
- ISSN
- 0013-936X (ISSN-L)
- 1520-5851
- OpenAlex
- W1964637145
- Cited by
- 300
- References
- 18
- Citations by year
- 2026: 6 · 2025: 8 · 2024: 10 · 2023: 13 · 2022: 13 · 2021: 10 · 2020: 9 · 2019: 16 · 2018: 12 · 2017: 16 · 2016: 10 · 2015: 9 · 2014: 11 · 2013: 16 · 2012: 14
- FWCI
- 17.97
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Environmental Science & Technology (publishedVersion)
- PubMed (publishedVersion)
- Funders
- Natural Sciences and Engineering Research Council of Canada
- Topics
- Physical Sciences › Earth and Planetary Sciences › Atmospheric Science › Atmospheric chemistry and aerosols
- Physical Sciences › Earth and Planetary Sciences › Atmospheric Science › Atmospheric Ozone and Climate
- Physical Sciences › Environmental Science › Environmental Chemistry › Per- and polyfluoroalkyl substances research
- Keywords
- perfluorinated compounds, atmospheric chemistry, atmospheric lifetime, degradation products, PFBS, perfluorinated carboxylic acids, N-dealkylation, perfluorinated sulfonates
- MeSH terms
- Air Pollutants, Atmosphere, Fluorocarbons, Kinetics, Gas Chromatography-Mass Spectrometry, Sulfonamides, Sulfonic Acids, Trifluoroacetic Acid, Spectroscopy, Fourier Transform Infrared, Hydroxyl Radical
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