Thermal decomposition peculiarities and combustion behavior of nitropyrazoles

Sinditskii, Valery P.; Smirnov, Sergei; Egorshev, V.Y.; Chernyi, A. N.; Шкинева, Т. К.; Палысаева, Надежда В.; Suponitsky, Kyrill Yu.; Далингер, И. Л.

doi:10.1016/j.tca.2017.02.019

Cited by 33 publications

(24 citation statements)

References 46 publications

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“…The FRDX decomposition experiments under isothermal conditions were carried out in thin-walled glass manometers of the compensation type (the Bourdon glass gauge) in the temperature range 110-130°C following the standard procedure. [18] The ratio of the mass of the sample to the volume of the reaction vessel (m/V) is about 10 À 3 g/cm 3 . Gas evolution rate increases with time (see the Supporting Information, Figure S1).…”

Section: 68-trinitro-4578-tetrahydro-6h-furazano-[34-f]-135-mentioning

confidence: 99%

Furazan‐Fused Azacyclic Nitramines: Influence of Structural Features on the Combustion and the Thermolysis

et al. 2020

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The combustion behavior and thermal stability of 4,6,8-trinitro-4,5,7,8-tetrahydro-6H-furazano[3,4-f]-1,3,5-triazepine (FRDX) and 1,4,5,8-tetranitrodifurazano[3,4-c][3,4-h]tetraazadecaline (FTNAD) were investigated and compared with analogs, where the furazan ring is substituted with CH 2 or C=O units. It has been shown that the furazan-fused unit reduces the thermal stability of azacyclic nitramines, probably due to the weakening of the NÀ NO 2 bond. The burning rates of FRDX and FTNAD are determined by the kinetics of heat release in the melt. There is the peculiar effect of the furazan unit on the burning rate: according to thermocouple measurements, the unit increases the volatility of cyclic nitramines and reduces the temperature of the burning surface, which should lead to a decrease in the burning rate, but on the other hand, it simultaneously increases the rate of heat release in the melt, and as a result, the burning rate increases rather than falls.

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Section: 68-trinitro-4578-tetrahydro-6h-furazano-[34-f]-135-mentioning

confidence: 99%

Furazan‐Fused Azacyclic Nitramines: Influence of Structural Features on the Combustion and the Thermolysis

et al. 2020

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“… 46 The heat of formation of the parent ring of a10 was calculated to be 164.56 kJ mol −1 by Bo, 47 much lower than that of a10 (949.87 kJ mol −1 ) substituted by two –NHNO 2 . The heat of formation of the compound with the same parent ring as a2–a9 but with two –NO 2 substituted at the carbon atom of pyrazole was reported to be 550.84 kJ mol −1 , 48 significantly lower than those of the eight compounds (a2–a9) with the same parent ring, indicating the energetic characteristics of the –NHNO 2 and –ONO 2 substituents.…”

Section: Resultsmentioning

confidence: 96%

A property-oriented adaptive design framework for rapid discovery of energetic molecules based on small-scale labeled datasets

Xie

Liu

et al. 2021

RSC Adv.

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“…Salts I – III and cocrystal IV all do not have a melting process, and they directly decompose with temperatures of 140.6 °C ( I ), 148.2 °C ( II ), 203.4 °C ( III ), and 181.9 °C ( IV ), respectively. Practically, the first step of DNP decomposition proceeds without heat release at 230–260 °C, with a loss of one NO 2 group . In any event, HH, ED, AG, and U all make the DNP prone to decomposition, demonstrating that salt formation and cocrystallization can be used as a strategy to modulate the thermal stability.…”

Section: Resultsmentioning

confidence: 99%

Origins of Salt Formation and Cocrystallization: A Combined Experimental and Theoretical Study

Yang

Yin

Gong

et al. 2020

Crystal Growth & Design

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Three DNP (3,4-dinitropyrazole) salts and one DNP cocrystal were synthesized and characterized by IR, elemental analysis, and single-crystal X-ray diffraction. DSC analysis shows that hydrazine hydrate (HH), ethanediamine (ED), aminoguanidine (AG), and urea (U) all make DNP prone to decomposition, demonstrating that salt formation and cocrystallization are two strategies to modulate the thermal stability and the coformers play a vital role in the performance of the target products. Hirshfeld surfaces suggest that O•••H close contacts make the greatest contribution to the stabilization of I− IV. Electrostatic potential and pK a values give a reasonable explanation that DNP forms salts I−III with HH, ED, and AG, while it forms cocrystal IV with U. The hydrogen-bonding interactions were evaluated by the quantum theory of atoms-in-molecules (AIM) and the independent gradient model (IGM), further revealing that DNP and U prefer to form a cocrystal, rather than a salt or as the individual compounds. The systematic experimental and theoretical work gives a clear comparison of the salt and cocrystal formation processes and explains their origins on the atomic scale, which can prompt the development of the design and synthesis of new salts and cocrystals.

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Thermal decomposition peculiarities and combustion behavior of nitropyrazoles

Cited by 33 publications

References 46 publications

Furazan‐Fused Azacyclic Nitramines: Influence of Structural Features on the Combustion and the Thermolysis

Furazan‐Fused Azacyclic Nitramines: Influence of Structural Features on the Combustion and the Thermolysis

A property-oriented adaptive design framework for rapid discovery of energetic molecules based on small-scale labeled datasets

Origins of Salt Formation and Cocrystallization: A Combined Experimental and Theoretical Study

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