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Simultaneous and Practical Difluoromethylation of Triclosan, 2,4,6-Trichlorophenol and Pentachlorophenol in Soils for their Qualitative Detection by Electron Ionization GC-MS

Simultaneous and Practical Difluoromethylation of Triclosan, 2,4,6-Trichlorophenol and... AbstractThe extremely rapid (30 seconds) and practical derivatization of three environmentally relevant chlorinated phenols (CPs): triclosan, 2,4,6-trichlorophenol and pentachlorophenol for their qualitative detection by GC-MS is presented. The method involves the use of the eco-friendly difluoromethylating agent diethyl (bromodifluoromethyl) phosphonate (DBDFP) and results in the efficient tagging of the hydroxyl group in the phenols with the difluoromethyl (CF2H) moiety. Moreover, the protocol is carried out at ambient temperature and thus eliminates the heating involved with more conventional methods such as silylation. Another important facet of the derivatization is its biphasic nature, allowing for the specific tagging of phenolic species that are present in water or in an organic matrix. The derivatization yields difluoromethylated ether versions of the phenols with enhanced detectability by EI-GC-MS and as a way of demonstrating the robustness of the protocol, the three CPs were derivatized and unequivocally identified when spiked in three different types of soils: Virginia type A soil, Ottawa Sand and Nebraska EPA soil at a 1 μg g-1 concentration each. The protocol offers a fast way of derivatizing these types of phenols since no prior, separate sample preparation or extraction steps are needed. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Analytical Chemistry Letters Taylor & Francis

Simultaneous and Practical Difluoromethylation of Triclosan, 2,4,6-Trichlorophenol and Pentachlorophenol in Soils for their Qualitative Detection by Electron Ionization GC-MS

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Simultaneous and Practical Difluoromethylation of Triclosan, 2,4,6-Trichlorophenol and Pentachlorophenol in Soils for their Qualitative Detection by Electron Ionization GC-MS

Abstract

AbstractThe extremely rapid (30 seconds) and practical derivatization of three environmentally relevant chlorinated phenols (CPs): triclosan, 2,4,6-trichlorophenol and pentachlorophenol for their qualitative detection by GC-MS is presented. The method involves the use of the eco-friendly difluoromethylating agent diethyl (bromodifluoromethyl) phosphonate (DBDFP) and results in the efficient tagging of the hydroxyl group in the phenols with the difluoromethyl (CF2H) moiety. Moreover, the...
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Publisher
Taylor & Francis
Copyright
This material is published by permission of the Lawrence Livermore National Laboratory, operated by the Lawrence Livermore National Security (LLNS) for the US Department of Energy under Contract No. [DE-AC52-07NA27344]. The US Government retains for itself, and others acting on its behalf, a paid-up, non-exclusive, and irrevocable worldwide license in said article to reproduce, prepare derivative works, distribute copies to the public, and perform publicly and display publicly, by or on behalf of the Government
ISSN
2230-7532
eISSN
2229-7928
DOI
10.1080/22297928.2017.1282326
Publisher site
See Article on Publisher Site

Abstract

AbstractThe extremely rapid (30 seconds) and practical derivatization of three environmentally relevant chlorinated phenols (CPs): triclosan, 2,4,6-trichlorophenol and pentachlorophenol for their qualitative detection by GC-MS is presented. The method involves the use of the eco-friendly difluoromethylating agent diethyl (bromodifluoromethyl) phosphonate (DBDFP) and results in the efficient tagging of the hydroxyl group in the phenols with the difluoromethyl (CF2H) moiety. Moreover, the protocol is carried out at ambient temperature and thus eliminates the heating involved with more conventional methods such as silylation. Another important facet of the derivatization is its biphasic nature, allowing for the specific tagging of phenolic species that are present in water or in an organic matrix. The derivatization yields difluoromethylated ether versions of the phenols with enhanced detectability by EI-GC-MS and as a way of demonstrating the robustness of the protocol, the three CPs were derivatized and unequivocally identified when spiked in three different types of soils: Virginia type A soil, Ottawa Sand and Nebraska EPA soil at a 1 μg g-1 concentration each. The protocol offers a fast way of derivatizing these types of phenols since no prior, separate sample preparation or extraction steps are needed.

Journal

Analytical Chemistry Letters – Taylor & Francis

Published: Jan 2, 2017

Keywords: Triclosan; Pentachlorophenol; Derivatization; Difluoromethylation; GC-MS

References

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  • On the Need and Speed of Regulating Triclosan and Triclocarban in the United States
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  • Analysis of twenty phenolic compounds in human urine: hydrochloric acid hydrolysis, solid-phase extraction based on K2CO3 -treated silica, and gas chromatography tandem mass spectrometry
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  • GC-MS determination of parabens, triclosan and methyl triclosan in water by in situ derivatisation and stir-bar sorptive extraction
  • Trimethylsilyldiazomethane: a safe non-explosive, cost effective and less-toxic reagent for phenol derivatization in GC applications
  • Chemical tagging of chlorinated phenols for their facile detection and analysis by NMR spectroscopy
  • Diethyl bromodifluoromethylphosphonate: a highly efficient and environmentally benign difluorocarbene precursor