The synthesis and characterization of 1-hydroxy-5-aminotetrazole and highly energetic azo-bis(l-hydroxy-tetrazole) and their ionic derivatives

摘要

In this contribution we report on the synthesis and characterization of energetic materials based on 1-hydroxy-5-aminotetrazole (1, which is obtained by the reaction of cyanogen bromide and hydroxyl amine. Oxidation with potassium permanganate yielded dipotassium 5,5'-azo-bis(tetrazole-l-oxide) which is stable up to temperatures of 280 °C. Protonation yielded highly energetic 5,5'-azo-bis(l-hydroxytetrazole) (2). This compound was reacted with several nitrogen-rich bases such as ammonia, hydrazine, hydroxylamine, and triaminoguanidine etc. to form energetic ionic derivatives with excellent properties as additives for explosive and propellant formulations. All derivatives were characterized by low temperature X-ray diffraction, NMR and vibrational spectroscopy, elemental analysis and differential scanning calorimetry. Heats of formation were calculated by CBS-4M electronic enthalpies. Detonation and propulsion data were computed by the EXPL05 code. In addition, all sensitivities towards impact (BAM drophammer), friction (BAM friction tester) and electrostatic discharge (OZM electrostatic discharge tester) were determined.