Synthesis of n-isomers: Native and deuterium-labelled short-chain perfluoroalkane sulfonamide derivatives

D. Jérémy Liwara*, Anton Pavlov, Craig Mckenzie, Jon E. Johansen, Pim E.G. Leonards, Sicco Brandsma, Jacob de Boer, Huiling Liu

*Corresponding author for this work

Research output: Contribution to JournalArticleAcademicpeer-review

Abstract

Perfluorooctane sulfonamide derivatives have been extensively used by industry for their surfactant properties and as building blocks for other perfluoroalkyl substances (PFAS). Due to their environmental impact and their potential degradation to other harmful PFAS, short-chain sulfonamide derivatives alternatives were introduced. However, these are now also suspected to be present in different environmental matrices and there is a lack of labelled and unlabelled reference standards to perform analyses. To address this gap, 40 native and deuterium labelled short-chain perfluoroalkane sulfonamide derivatives were synthesized, utilizing commercial perfluoroalkane sulfonyl fluoride as starting materials. All products were synthesized and then purified to obtain linear n-isomer reference standards. NMR, GC-FID-MS and LC-MS techniques were used for product identification and purity assessment. Recrystallization method was developed to selectively isolate the n-isomer from the isomer mixtures, thereby providing valuable reference and internal standards for environmental and toxicological investigations.

Original languageEnglish
Article number110311
Pages (from-to)1-13
Number of pages13
JournalJournal of Fluorine Chemistry
Volume278
Early online date6 Aug 2024
DOIs
Publication statusPublished - Aug 2024

Bibliographical note

Publisher Copyright:
© 2024

Keywords

  • Internal standards
  • n-isomers
  • Per- and polyfluoroalkyl substances
  • Reference standards
  • Short-chain perfluoroalkane sulfonamide derivatives

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