Analysis of triacetone triperoxide (TATP) and TATP synthetic intermediates by electrospray ionization mass spectrometry

    Authors

    M. E. Sigman; C. D. Clark; T. Caiano;R. Mullen

    Comments

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    Abbreviated Journal Title

    Rapid Commun. Mass Spectrom.

    Keywords

    GAS CHROMATOGRAPHY/MASS SPECTROMETRY; CHEMICAL-IONIZATION; OZONOLYSIS; TETRAMETHYLETHYLENE; IDENTIFICATION; PEROXIDE; Chemistry, Analytical; Spectroscopy

    Abstract

    The explosive triacetone triperoxide (TATP) has been analyzed by electrospray ionization mass spectrometry (ESI-MS) on a linear quadrupole instrument, giving a 62.5 ng limit of detection in full scan positive ion mode. In the ESI interface with no applied fragmentor voltage the m/z 245 [TATP + Na](+) ion was observed along with m/z 215 [TATP + Na - C2H6](+) and 81 [(CH3)(2)CO + Na](+). When TATP was ionized by ESI with an applied fragmentor voltage of 75 V, ions at m/z 141 [C4H6O4 + Na](+) and 172 [C5H9O5 + Na](+) were also observed. When the precipitates formed in the synthesis of TATP were analyzed before the reaction was complete, a new series of ions was observed in which the ions were separated by 74 m1z units, with ions occurring at m1z 205, 279, 353, 427, 501, 575, 649 and 723. The series of evenly spaced ions is accounted for as oligomeric acetone carbonyl oxides terminated as hydroperoxides, [HOOC(CH3)(2){OOC(CH3)(2)}nOOH + Na](+) (n=1, 2...8). The ESI-MS spectra for this homologous series of oligoperoxides have previously been observed from the ozonolysis of tetramethylethylene at low temperatures. Precipitates from the incomplete reaction mixture, under an applied fragmentor voltage of 100V in ESI, produced an additional ion observed at m/z 99 [C2H4O3 + Na](+)(,) and a set of ions separated by 74 m/z units occurring at m/z 173, 247, 321, 395, 469 and 543, proposed to correspond to [CH3CO{OOC(CH3)(2)}(n) OOH + Na](+) (n = 1,2... 5). Support for the assigned structures was obtained through the analysis of both protiated and perdeuterated TATP samples. Copyright (c) 2007 John Wiley & Sons, Ltd.

    Journal Title

    Rapid Communications in Mass Spectrometry

    Volume

    22

    Issue/Number

    2

    Publication Date

    1-1-2008

    Document Type

    Article

    Language

    English

    First Page

    84

    Last Page

    90

    WOS Identifier

    WOS:000252678200002

    ISSN

    0951-4198

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