5-Perfluoroalkyl bicyclic amide acetals

Lewis, Terry W.

doi:10.1016/s0022-1139(00)81520-1

Cited by 6 publications

(3 citation statements)

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“…The syntheses of MeFOAE and EtFOAE by using an ester precursor was roughly adapted from Lewis. 16 Methanol (4.0 mmol) and triethylamine (4.0 mmol) were added to a round-bottom flask and cooled in an ice bath. Perfluorooctanoyl chloride (4.0 mmol) was added dropwise with continuous stirring.…”

Section: ■ Experimental Detailsmentioning

confidence: 99%

“…15 Lewis synthesized the trifluoromethyl analogue of MeFOAE for use in a synthetic reaction to produce cyclic amide acetals, but no further characterizations or links to sulfonamide chemistry were given. 16 The most relevant find was an internal 3M report by Seacat in which MeFOA (referred to as MePFOAA) was orally dosed in rats and found to hydrolyze to PFOA in vivo. 17 Although this study was performed in 2004, the MeFOA material was synthesized in 2000.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Several monosubstituted amides including MeFOA and EtFOA were synthesized and analyzed with regards to their surfactant properties . Lewis synthesized the trifluoromethyl analogue of MeFOAE for use in a synthetic reaction to produce cyclic amide acetals, but no further characterizations or links to sulfonamide chemistry were given . The most relevant find was an internal 3M report by Seacat in which MeFOA (referred to as MePFOAA) was orally dosed in rats and found to hydrolyze to PFOA in vivo .…”

Section: Introductionmentioning

confidence: 99%

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Polyfluorinated Amides as a Historical PFCA Source by Electrochemical Fluorination of Alkyl Sulfonyl Fluorides

Jackson

Mabury

2012

Environ. Sci. Technol.

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Polyfluorinated amides (PFAMs) are a class of compounds produced as byproducts of polyfluorinated sulfonamide synthesis by electrochemical fluorination (ECF). We measured four PFAM derivatives of perfluorooctanoic acid (PFOA) in a wide range of compounds, experimental materials, and commercial products synthesized by ECF. Initial screening was performed using headspace solid phase microextraction gas chromatography mass spectrometry (SPME-GC-MS), and quantification using in-house synthesized standards was accomplished with GC-MS using positive chemical ionization. Two monosubstituted PFAMs, N-methylperfluorooctanamide (MeFOA) and N-ethylperfluorooctanamide (EtFOA), were detected in the majority of materials that were analyzed. Two disubstituted PFAMs, N-methyl-N-(2-hydroxyethyl)perfluorooctanamide (MeFOAE) and N-ethyl-N-(2-hydroxyethyl)perfluorooctanamide (EtFOAE), were not detected in any sample, likely because they were never synthesized. The concentrations of PFAMs in the sulfonamide compounds under study ranged from 12 to 6736 μg/g, suggesting their historical importance as PFCA precursors. In each case, branched isomers for PFAMs were detected, providing further support for their link to an ECF source. A hydrolysis study performed at pH 8.5 showed no degradation of EtFOA to PFOA after 8 days due to the stability of the amide bond. The environmental fate of PFAMs is suggested to be volatilization to the atmosphere followed by oxidation by hydroxyl radical with a predicted lifetime of 3-20 days. Subsequent PFAM exposure to biota will likely lead to enzymatic hydrolysis of the amide linkage to give a PFCA. Human exposure to PFAMs may have contributed to the presence of branched PFOA isomers in blood by serving as an indirect source. The decline in PFOA concentrations in human blood is consistent with a significant drop in PFAM production concurrent with the POSF phase-out in 2000-2001.

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Section: ■ Experimental Detailsmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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