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3 Central European Journal of Energetic Materials

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Synthesis and Characterization of the Energetic Compounds Aminoguanidinium-, Triaminoguanidiniumand Azidoformamidinium Perchlorate

100%

Klapötke T. M. , Stierstorfer J.

Central European Journal of Energetic Materials

2008

tom Vol. 5, nr 1

13-30

Aminoguanidinium perchlorate (2, AGClO4) was formed by the reaction of aminoguanidinium bicarbonate (1) with aqueous perchloric acid solution. Triaminoguanidinium perchlorate (3, TAGClO4) was synthesized by nucleophilic attack of aqueous hydrazine solution on aminoguanidinium perchlorate under release of ammonia. The new and highly explosive azidoformamidinium perchlorate (4, AFClO4) was formed by the reaction of aminoguanidinium perchlorate with potassium nitrite under acidic conditions. The structures of the perchlorate salts in the crystalline state were determined using low temperature single crystal X-ray diffraction yielding monoclinic as well as orthorhombic structures. The compounds were characterized comprehensively using vibrational spectroscopy (IR and Raman), multinuclear (1H, 13C and 15N) NMR spectroscopy, elemental analysis and mass spectrometry. The thermal behavior as well as the decompositions were investigated using DSC (differential scanning calorimetry) and the heats of formation were calculated using heats of combustion determined by bomb calorimetric measurements. In addition, the sensitivities were evaluated using BAM methods (drophammer and friction tester), whereby the perchlorate salts are all sensitive towards impact as well as friction.

Highly Energetic Salts of 3,6-Bishydrazino-1,2,4,5-tetrazine

80%

Klapötke T. M. , Preimesser A. , Schedlbauer S. , Stierstorfer J.

Central European Journal of Energetic Materials

2013

tom Vol. 10, no. 2

151--170

3,6-Bishydrazino-1,2,4,5-tetrazine was synthesized as described by hydrazinolysis of 3,6-bis-(3,5-dimethylpyrazolyl)-1,2,4,5-tetrazine. Doubly protonated 1:1 and 1:2 salts of the highly energetic anions were synthesized. These are bishydrazinium-tetrazine dichloride dihydrate (1:2) (BHT-2HCl•2H2O) (2), bishydrazinium-tetrazine (5,5´-azotetrazolate) dihydrate (1:1) (BHT-ATz•2H2O) (3), bishydrazinium-tetrazine bis (3,5-dinitrotriazolate) dihydrate (1:2) (BHT(DNT)2•2H2O) (4), bishydrazinium-tetrazine bis (5-nitrotetrazolate) (1:2) (BHT(NT)2) (5), bishydrazinium-tetrazine (5,5´-bistetrazolate) dihydrate (1:1) (BHTBT•2H2O) (6), bishydrazinium-tetrazine bistetrazolylamine (1:1) (BHT-BTA) (7), bishydrazinium-tetrazine bis (3-amino-5-nitrotriazolate) (1:2) (BHT-(ANTA)2) (8) and bishydrazinium-tetrazine 4,4´,5,5´-tetranitro-2,2´-bisimidazolate (1:1) (9). Compounds 2-6 could be characterized by low temperature X-ray diffraction. All of the compounds were suffciently analyzed by 1H and {1H}13C and 14N NMR spectroscopy, elemental analysis (CHN), mass spectroscopy (FAB)) and vibrational spectroscopy (IR and Raman). The detonation parameters of the most promising candidates 5 and 9 in terms of energetic applications were calculated using the EXPLO5 V5.05 computer code. The energies of formation were calculated using CBS-4M electronic enthalpies and the atomization method. Furthermore, since all of the compounds are energetic materials, sensitivity tests towards impact (IS), friction (FS) and electrostatical discharge (ESD) were carried out. In addition their thermal stabilities were determined using a differential scanning calorimeter with a heating rate of 5 °C min-1.

Hydrazinium 5-Aminotetrazolate: an Insensitive Energetic Material Containing 83.72% Nitrogen

80%

Fischer N. , Klapötke T. M. , Scheutzow S. , Stierstorfer J.

Central European Journal of Energetic Materials

2008

tom Vol. 5, nr 3-4

3-18

Hydrazinium 5-aminotetrazolate (2) was synthesized via two facile routes. Both the reaction of 5-amino-1H-tetrazole (1) with hydrazine hydrate in aqueous solution and the reaction of 1 with diluted hydrazine solution in THF yield 2 in excellent purities and yields. 2 was characterized comprehensively by X-ray diffraction, IR, Raman and multinuclear NMR spectroscopy, mass spectrometry, elemental analysis and differential scanning calorimetry. The heat of formation was calculated (CMS-4M) using the atomization method to be 373 kJ mol-1. With this value and the X-ray density several detonation parameter (heats of explosion, detonation pressure, detonation velocity, explosion temperature) were calculated with the EXPLO5 computer software. An incredible high value (9516 m s-1) was obtained for the detonation velocity. Therefore experimentally tests to determine the velocity of detonation were performed. In addition the use of 2 in solid propellant compositions was calculated and tested in combination with oxidizers, e.g. ammonium dinitramide. Lastly the sensitivities towards impact, friction and electrostatic discharge were determined with the BAM drophammer, friction tester and an ESD machine.