Convenient synthesis of energetic polynitro materials including (NO2)3CCH2CH2NH3-salts via Michael addition of trinitromethane.
The nucleophilic Michael addition of nitroform with acrylamide creates a variety of energetic products. Several interesting compounds with a trinitromethyl group were synthesized, among them salts containing the trinitropropylammonium cation, [(NO2)3CCH2CH2NH3]X. Owing to their positive oxygen balance, the suitability of these compounds as potential high-energy dense oxidizers (HEDOs) in energetic formulations was investigated and discussed. Furthermore, numerous important and reactive compounds for the continuing synthesis of molecules with a high oxygen balance are presented. All compounds were fully characterized, including multinuclear NMR spectroscopy, vibrational analysis (IR, Raman), elemental analysis, as well as single crystal X-ray diffraction. Thermal stabilities were studied using differential scanning calorimetry and sensitivity data against friction, impact and electrostatic discharge were collected. The energies of formation were calculated using Gaussian 09 and energetic properties, such as the specific impulse and detonation velocity, were predicted with the EXPLO5 (V6.02) computer code.
Department of Chemistry, Ludwig-Maximilian University of Munich, Butenandtstr. 5-13 (D), 81377 Munich, Germany. tmk@cup.uni-muenchen.de.
Quirin J
QJ
Axthammer
Thomas M
TM
Klapötke
Burkhard
B
Krumm
Regina
R
Scharf
Cornelia C
CC
Unger