Atmospheric Chemistry ofN-methyl Perfluorobutane Sulfonamidoethanol, C4F9SO2N(CH3)CH2CH2OH: Kinetics and Mechanism of Reaction with OH
Citations Over TimeTop 1% of 2006 papers
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.
Related Papers
- → Synthesis of Tri- and Tetrasubstituted Furans Catalyzed by Trifluoroacetic Acid(2000)62 cited
- → Trifluoroacetic acid prompted unexpected visible to NIR switching of ketoenamine-substituted triphenylamines(2023)7 cited
- → Carbamazepine trifluoroacetic acid solvate(2007)10 cited
- → Aziridination of alkenes using 3-amino-2-ethylquinazolin-4(3H)-one and lead tetra-acetate–trifluoroacetic acid(1989)13 cited