Title

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

Authors

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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