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Title: Chemical tagging of chlorinated phenols for their facile detection and analysis by NMR spectroscopy

A derivatization method that employs diethyl (bromodifluoromethyl) phosphonate (DBDFP) to efficiently tag the endocrine disruptor pentachlorophenol (PCP) and other chlorinated phenols (CPs) along with their reliable detection and analysis by NMR is presented. The method accomplishes the efficient alkylation of the hydroxyl group in CPs with the difluoromethyl (CF2H) moiety in extremely rapid fashion (5 min), at room temperature and in an environmentally benign manner. The approach proved successful in difluoromethylating a panel of 18 chlorinated phenols, yielding derivatives that displayed unique 1H, 19F NMR spectra allowing for the clear discrimination between isomerically related CPs. Due to its biphasic nature, the derivatization can be applied to both aqueous and organic mixtures where the analysis of CPs is required. Furthermore, the methodology demonstrates that PCP along with other CPs can be selectively derivatized in the presence of other various aliphatic alcohols, underscoring the superiority of the approach over other general derivatization methods that indiscriminately modify all analytes in a given sample. The present work demonstrates the first application of NMR on the qualitative analysis of these highly toxic and environmentally persistent species.
Authors:
 [1] ;  [1]
  1. Lawrence Livermore National Laboratory (LLNL), Livermore, CA (United States)
Publication Date:
OSTI Identifier:
1182243
Report Number(s):
LLNL--JRNL-666745
Journal ID: ISSN 1618-2642
DOE Contract Number:
AC52-07NA27344
Resource Type:
Journal Article
Resource Relation:
Journal Name: Analytical and Bioanalytical Chemistry; Journal Volume: 407; Journal Issue: 13
Publisher:
Springer
Research Org:
Lawrence Livermore National Laboratory (LLNL), Livermore, CA (United States)
Sponsoring Org:
USDOE
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; 71 CLASSICAL AND QUANTUMM MECHANICS, GENERAL PHYSICS pentachlorophenol; endocrine disruptor; difluoromethylation; NMR