Synthesis and Degradation of Hexamethylene Triperoxide Diamine (HMTD)

Jimmie C. Oxley, James L. Smith, Matthew Porter, Lindsay McLennan, Kevin Colizza, Yehuda Zeiri, Ronnie Kosloff, Faina Dubnikova

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

The synthesis and decomposition of hexamethylene triperoxide diamine (HMTD) were studied. Mechanisms were proposed based on isotopic labeling and mass spectral interpretation of both condensed phase products and head-space products. Formation of HMTD from hexamine appeared to proceed from dissociated hexamine as evident from scrambling of the 15N label when synthesis was carried out with equal molar labeled/unlabeled hexamine. Decomposition of HMTD was considered with additives and in the presence and absence of moisture. In addition to mass spectral interpretation, density functional theory (DFT) was used to calculate energy differences of transition states and the entropies of intermediates along different possible decomposition pathways. HMTD is destabilized by water and citric acid making purification following initial synthesis essential in order to avoid unanticipated violent reaction.

Original languageEnglish
Pages (from-to)334-350
Number of pages17
JournalPropellants, Explosives, Pyrotechnics
Volume41
Issue number2
DOIs
StatePublished - 1 Apr 2016

Keywords

  • Decomposition mechanisms
  • Head-space products
  • Hexamethylene triperoxide diamine (HMTD)
  • Isotopic labels
  • Synthesis

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