Synthesis and study of thermal stability of 3-nitro-1,2,4-triazole N-nitroxy-and N-azidomethyl derivatives

Целинский, И. В.; Tolstyakov, V. V.; Putis, S. M.; Мельникова, С. Ф.

doi:10.1007/s11172-009-0327-5

Cited by 12 publications

(6 citation statements)

References 2 publications

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“…Previously investigated materials based on N -nitroxyalkyl- and N -azidoalkyl-substituted nitro-based heterocycles − have been found to suffer from stability issues due to the inherent reactivity of the electrophilic ring. To mitigate the aforementioned safety concerns, the development of materials with heterocyclic Lewis basic character toward electrophilic energetic materials such as nitrocellulose (NC) and nitramines is desired.…”

Section: Introductionmentioning

confidence: 99%

Bis(1,2,4-oxadiazole)bis(methylene) Dinitrate: A High-Energy Melt-Castable Explosive and Energetic Propellant Plasticizing Ingredient

Johnson

Sabatini

Chávez

et al. 2018

Org. Process Res. Dev.

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Discussed herein is the synthesis of bis(1,2,4-oxadiazole)bis(methylene) dinitrate, determination of its crystal structure by X-ray diffractometry, calculations of its explosive performance, and sensitivity measurements. Steps taken to optimize the synthesis process and to improve yields of the dinitrate are also discussed. Bis(1,2,4-oxadiazole)bis(methylene) dinitrate has a calculated detonation pressure 50% higher than that of TNT. The dinitrate compound exhibits a relatively high decomposition temperature that is rarely observed for nitrate-based compounds. The dinitrate was found to have lower sensitivities to impact and friction compared with RDX. It is believed that intramolecular hydrogen bonding observed in the crystal lattice assists in the relatively high thermal stability and relatively low sensitivity of the material.

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Section: Introductionmentioning

confidence: 99%

Bis(1,2,4-oxadiazole)bis(methylene) Dinitrate: A High-Energy Melt-Castable Explosive and Energetic Propellant Plasticizing Ingredient

Johnson

Sabatini

Chávez

et al. 2018

Org. Process Res. Dev.

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“…The thermal stability of an energetic material is an important factor for its use and the desired decomposition temperature is above 473.15 K. For bis(5-amino-1,2,4-triazol-3-yl)methane (BATZM), the decomposition temperature is 566.15 K (Shreve & Charlesworth, 1956). It can be used as a precursor for the synthesis of bis-triazole-based energetic materials, such as bis(5-nitro-1,2,4-triazol-3-yl)methane (Bagal et al, 1970), bis(5-nitro-2-nitroxymethyl-1,2,4-triazol-3-yl)nitromethane (Tselinskii et al, 2009), bis(5-nitro-1,2,4-triazol-3-yl)nitromethane (Tselinskii et al, 2009), bis(5-nitro-1,2,4-triazol-3-yl)dinitromethane (Tselinskii et al, 2009), bis(5-nitrimino-1,2,4-triazol-3-yl)methane (Dippold et al, 2011) etc. In this article, BATZM was synthesized and its crystal structure is reported.…”

Section: Introductionmentioning

confidence: 99%

Crystal structure, thermodynamic properties and detonation characterization of bis(5-amino-1,2,4-triazol-3-yl)methane

Hong-ya

Yan

et al. 2020

Acta Crystallogr C

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Bis(5-amino-1,2,4-triazol-3-yl)methane (BATZM, C5H8N8) was synthesized and its crystal structure characterized by single-crystal X-ray diffraction; it belongs to the space group Fdd2 (orthorhombic) with Z = 8. The structure of BATZM can be described as a V-shaped molecule with reasonable chemical geometry and no disorder. The specific molar heat capacity (Cp,m ) of BATZM was determined using the continuous Cp mode of a microcalorimeter and theoretical calculations, and the Cp,m value is 211.19 J K−1 mol−1 at 298.15 K. The relative deviations between the theoretical and experimental values of Cp,m , HT – H 298.15K and ST – S 298.15K of BATZM are almost equivalent at each temperature. The detonation velocity (D) and detonation pressure (P) of BATZM were estimated using the nitrogen equivalent equation according to the experimental density; BATZM has a higher detonation velocity (7954.87 ± 3.29 m s−1) and detonation pressure (25.72 ± 0.03 GPa) than TNT.

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“…Bis(5-amino-1,2,4-triazol-3-yl)methane (BATZM) is an organic amine energetic material with a high decomposition temperature and a good detonation performance (Li et al, 2020). It can be used as a precursor for the synthesis of bistriazole-based energetic materials (Tselinskii et al, 2009;Dippold et al, 2011). We have investigated the changes that occur when BATZM is reacted with hydrochloric acid to and crystal structure of which are reported here.…”

Section: Introductionmentioning

confidence: 99%

Crystal structure, thermal properties and detonation characterization of bis(5-amino-1,2,4-triazol-4-ium-3-yl)methane dichloride

Hong-ya¹,

Yan²,

Ma³

et al. 2020

Acta Crystallogr C

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Bis(5-amino-1,2,4-triazol-4-ium-3-yl)methane dichloride (BATZM·Cl2 or C5H10N8 2+·2Cl−) was synthesized and crystallized, and the crystal structure was characterized by single-crystal X-ray diffraction; it belongs to the space group C2/c (monoclinic) with Z = 4. The structure of BATZM·Cl2 can be described as a V-shaped molecule with reasonable chemical geometry and no disorder, and its one-dimensional structure can be described as a rhombic helix. The specific molar heat capacity (Cp ,m) of BATZM·Cl2 was determined using the continuous C p mode of a microcalorimeter and theoretical calculations, and the Cp ,m value is 276.18 J K−1 mol−1 at 298.15 K. The relative deviations between the theoretical and experimental values of Cp ,m, HT – H 298.15K and ST – S 298.15K of BATZM·Cl2 are almost equivalent at each temperature. The detonation velocity (D) and detonation pressure (P) of BATZM·Cl2 were estimated using the nitrogen equivalent equation according to the experimental density; BATZM·Cl2 has a higher detonation velocity (7143.60 ± 3.66 m s−1) and detonation pressure (21.49 ± 0.03 GPa) than TNT. The above results for BATZM·Cl2 are compared with those of bis(5-amino-1,2,4-triazol-3-yl)methane (BATZM) and the effect of salt formation on them is discussed.

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Synthesis and study of thermal stability of 3-nitro-1,2,4-triazole N-nitroxy-and N-azidomethyl derivatives

Cited by 12 publications

References 2 publications

Bis(1,2,4-oxadiazole)bis(methylene) Dinitrate: A High-Energy Melt-Castable Explosive and Energetic Propellant Plasticizing Ingredient

Bis(1,2,4-oxadiazole)bis(methylene) Dinitrate: A High-Energy Melt-Castable Explosive and Energetic Propellant Plasticizing Ingredient

Crystal structure, thermodynamic properties and detonation characterization of bis(5-amino-1,2,4-triazol-3-yl)methane

Crystal structure, thermal properties and detonation characterization of bis(5-amino-1,2,4-triazol-4-ium-3-yl)methane dichloride

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