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Preparation and Characterization of Cationic Energetic Salts of 5-Amino-3-[(2,4,6-trinitrophenyl)amino]-1H-1,2,4-triazole (APATO)

Šarlauskas Jonas, Tamulienė Jelena

Central European Journal of Energetic Materials

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2022

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Vol. 19, no. 3

311--325

EN

The synthesis and properties of some 5-amino-3-[(2,4,6-trinitrophenyl) amino]-1H-1,2,4-triazole (APATO) cationic salts are described. A detailed structure of one of the salts obtained, 5-amino-3-[(2,4,6-trinitrophenyl)amino]-1H-1,2,4-triazol-4-ium perchlorate (APATO·HClO4) was characterized using low temperature (173 K) single crystal X-ray diffraction: orthorhombic yellow block, space group ‘Pbc21’, crystal density at 173 K (calculated) and at 293 K (pycnom.) were 1.863 and 1.840 g/cm3, respectively. The APATO salts were characterized by spectroscopic methods and thermal analysis. Preliminary computer calculated energetic characteristics showed that the synthesized salts possess increased energetic characteristics, superior in comparison to the TNT. The APATO perchlorate salt may deserve special attention as a thermostable HEDM.

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Oxygen-containing Tetrazole Salts of 3-Hydrazino-4-amino-1,2,4-triazole (HATr): Nitrogen-rich Ionic Materials with High Thermal Stability

Wu J.-T., Zhang J.-G., Yin X., Li T., Wu L., Zhang Z.-B.

Central European Journal of Energetic Materials

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2017

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Vol. 14, no. 1

217--232

EN

Energetic salts of doubly-protonated 3-hydrazino-4-amino-1,2,4-triazole (2-4), and mono-protonated 3-hydrazino-4-amino-1,2,4-triazole (5-7), have been prepared in high yields from the corresponding oxygen-containing tetrazoles by (i) reaction of free acids and neutral 3-hydrazino-4-amino-1,2,4-triazole, or (ii) metathesis reactions of 3-hydrazinium-4-amino-1H-1,2,4-triazolium di-chloride with the silver salts of the corresponding oxygen-containing tetrazoles. All of these energetic salts were fully characterized by single-crystal X-ray diffraction, FT-IR and DSC measurements. All of the structures are dominated by extensive hydrogen bonds due to amino groups, hydrazino groups and oxygen atoms in the molecules. These salts exhibit good thermal stability, especially the salt 3-hydrazinium-4-amino-1H-1,2,4-triazolium 1H,1’H-5,5’-bitetrazole-1,1’-diolate (4), which exhibits a measured onset of decomposition temperature of 237 °C. Quantum chemical calculations, carried out using the Gaussian 03 suite of programs and based on the experimental densities were used to calculate the detonation pressures and velocities of all of the salts.

3

Energetic Nitrogen-rich Salts

Wu J.-W., Zhang J.-G., Zhang T.-L., Yang L.

Central European Journal of Energetic Materials

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2015

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Vol. 12, no. 3

417--437

EN

Energetic salts as a unique class of energetic materials have recently been investigated widely, since they possess advantages over their atomically similar nonionic analogues – they tend to exhibit lower vapor pressures, higher densities and better thermal stabilities. Furthermore, these salts are readily improved upon by the appropriate combination of different cations and anions. Over the last twenty years, our group has continued to synthesize and study novel ionic energetic materials. Here, we have summarized all of the series of nitrogen-rich energetic salts. This review gives an overview of the various studies dealing with synthetic aspects and some of the physicochemical properties of ionic compounds that are based on ammonia, guanidine, semicarbazide, carbohydrazide, tetrazine, tetrazole, triazole and imidazole. In addition, their potential applications in the fields of explosives and propellants are discussed. We hope these investigations will be helpful in providing a wider insight for future research in the area of energetic salts.

4

Preparation, Structure and Kinetic Analysis of the Thermal Behavior of Some Energetic Salts of 3-Hydrazino-4-amino-1,2,4-triazole

Wu J. T., Zhang J. G., Sun M., Yin X., Zhang T. L.

Central European Journal of Energetic Materials

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2013

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Vol. 10, no. 4

481--493

EN

As a key research objective for low melting explosives and propellants, energetic salts have received worldwide attention. 3-Hydrazino-4-amino-1,2,4triazole (HATr) is an important high-nitrogen compound (73.65% N) with good stability. This paper focuses on the energetic salts which were formed between HATr and picric acid (PA) or 2,4,6-trinitroresorcinol (TNR). Single crystals of HATr·PA and HATr·TNR·H2O were grown and their crystal structures determined at low temperature. They both belong to the monoclinic system, P21/n space group. The thermal characteristics of the two target salts were investigated using DSC and TG-DTG. In addition, the non-isothermal decomposition kinetics, heats of combustion and sensitivity have also been investigated. The detonation pressures (P) and detonation velocities (D) of the salts have been calculated using the K-J equations. The results indicated that both salts have certain potential applications as gunpowder and propellant materials.

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

Klapötke T. M., Stierstorfer J.

Central European Journal of Energetic Materials

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2008

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Vol. 5, nr 1

13-30

EN

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.