Cited by 300Atmospheric chemistry and aerosolsAtmospheric Ozone and ClimatePer- and polyfluoroalkyl substances research

Atmospheric Chemistry of N-methyl Perfluorobutane Sulfonamidoethanol, C4F9SO2N(CH3)CH2CH2OH: Kinetics and Mechanism of Reaction with OH

D'eon, Jessica C., Hurley, Michael D., Wallington, Timothy J., Mabury, Scott A.·2006·Environmental Science & Technology

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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Crossref · 10.1021/es0520767

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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
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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