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

21 Scopus citations


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
Issue number2
StatePublished - 1 Apr 2016


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

ASJC Scopus subject areas

  • General Chemistry
  • General Chemical Engineering


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