Primary Nitramines Related to Nitroglycerine:
1-Nitramino-2,3-dinitroxypropane
and 1,2,3-Trinitraminopropane

 

Thomas ALTENBURG, Thomas M. KLAPÖTKE
and Alexander PENGER

Department Chemistry and Biochemistry,
Energetic Materials Research,
Ludwig-Maximilian University of Munich,
Butenandtstr. 5-13, D-81377 Munich, Germany


Abstract: The title compounds 1-nitramino-2,3-dinitroxypropane (NG-N1) and
1,2,3-trinitraminopropane (NG-N3) were formed by multi-step reaction from
the corresponding amine. Both compounds were fully characterized by means
of multinuclear NMR (1 H, 13 C, 14 N)
N), vibrational spectroscopy, elemental analysis
and mass spectrometry. For prediction of the energetic properties ∆Hc values are
determined by oxygen bomb calorimetry and validated by quantum theoretical
methods. Both compounds are superior in their performance data to nitroglycerine
(NG) and pentaerythritol tetranitrate (PETN). In comparison to nitroglycerine
the sensitivities towards mechanical stimuli is greatly reduced. X-ray diffraction
elucidated the molecular structure of both compounds. NG-N1 crystallizes in
the monoclinic space group P21 with a density of 1.799 g/cm³, NG-N3 in the
orthorhombic space group Pnma with a density of 1.783 g/cm³. The thermal
behavior and long term stabilities were checked using differential scanning
calorimetry and thermogravimetric measurements. NG-N1, shows for primary
nitramines, exceptional stability in the molten phase making this compound suitable
for melt-cast application (Tmp: 65 °C, Tdec: 170 °C).

Keywords: explosives, primary nitramine, nitroglycerin, structure
elucidation, thermostability