Synthesis and Degradation of Hexamethylene Triperoxide Diamine (HMTD)

Authors

Jimmie C. Oxley, University of Rhode Island
James L. Smith, University of Rhode Island
Matthew Porter, University of Rhode Island
Lindsay McLennan, University of Rhode Island
Kevin Colizza, University of Rhode Island
Yehuda Zeiri, Ben-Gurion University of the Negev
Ronnie Kosloff, Hebrew University of Jerusalem
Faina Dubnikova, Hebrew University of Jerusalem

Document Type

Article

Date of Original Version

4-1-2016

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.

Publication Title, e.g., Journal

Propellants, Explosives, Pyrotechnics

Volume

41

Issue

2

Citation/Publisher Attribution

Oxley, Jimmie C., James L. Smith, Matthew Porter, Lindsay McLennan, Kevin Colizza, Yehuda Zeiri, Ronnie Kosloff, and Faina Dubnikova. "Synthesis and Degradation of Hexamethylene Triperoxide Diamine (HMTD)." Propellants, Explosives, Pyrotechnics 41, 2 (2016): 334-350. doi: 10.1002/prep.201500151.