Structural and kinetic regularities of thermal decomposition of gem-trinitromethylazoles in the liquid phase

Stepanov, R. S.; Kruglyakova, L. A.; Astakhov, A. M.

doi:10.1134/s1070363207110151

Cited by 11 publications

(9 citation statements)

References 2 publications

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“…Kinetic parameters obtained in the study (red circles) along with literature data for trinitroethylamine , and trinitroethylnitramine species, , trinitromethyltriazines, and tetranitromethane. , The line corresponds to the linear fit of data for trinitroethylnitramine-based compounds. The red symbols indicate the present study data for noncatalytic primary reaction of 1 , 2 , and 3 .…”

Section: Discussionmentioning

confidence: 99%

Delving into Autocatalytic Liquid-State Thermal Decomposition of Novel Energetic 1,3,5-Triazines with Azido, Trinitroethyl, and Nitramino Groups

et al. 2020

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Thermal decomposition of 1,3,5-triazines with azido, trinitroethyl, and nitramino groups, the three important energetic functionalities, has been studied with a range of thermal analysis tools. The involved compounds melt under heating with the following mass loss and heat and gas release in the course of thermal decomposition. Model-fitting kinetic analysis resulted in formal reaction schemes with two general stages. In case of the least energetic 6-azido-2,4-bis(2,2,2-trinitroethylamino)-1,3,5-triazine, the first reaction is a first-order reaction followed by a thirdorder reaction. Alternatively, for 6-azido-2,4-bis(2,2,2-trinitroethylnitramino)-1,3,5-triazine and 2,4,6-tris(2,2,2-trinitroethylnitramino)-1,3,5-triazine, the first step comprises the autocatalytic reaction. The activation energy for the first decomposition step drops from 141 to 122 kJ mol −1 due to the inductive influence of a β-nitramino group. The second general reaction for all species obeys the third-order reaction model with activation energies in the range 112−126 kJ mol −1 . On the basis of the analysis of the kinetic data and temporal behavior of the evolved gases, a similar primary decomposition channel, the homolytic cleavage of a C− NO 2 bond, has been proposed for all investigated substances.

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Section: Discussionmentioning

confidence: 99%

Delving into Autocatalytic Liquid-State Thermal Decomposition of Novel Energetic 1,3,5-Triazines with Azido, Trinitroethyl, and Nitramino Groups

et al. 2020

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“…A relation has been found between the rate of thermal decomposition and nature of the substituent in the benzene ring. Effects of solvent and temperature on thermal decomposition of substituted tetrazoles have been revealed.We have earlier shown that decomposition mechanism and thermal stability of energetic compounds based on 5-R-2-methyltetrazoles strongly depends on the nature of the R substituent [1][2][3]. Extending these studies, herein we report on thermal decomposition of compounds I-VIII aiming to reveal a quantitative relationship between the tetrazoles reactivity and nature of the substituent in the 5-phenyl ring.…”

mentioning

confidence: 84%

Substituent effect on the rate of thermal decomposition of 5-(R-phenyl)-2-methyl-1,2,3,4-tetrazoles

Stepanov

Kruglyakova

2015

Russ J Gen Chem

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Thermal decomposition of substituted 2-methyl-5-phenyltetrazoles in solution has been studied by manometric method with chromatographic determination of the evolved nitrogen. A relation has been found between the rate of thermal decomposition and nature of the substituent in the benzene ring. Effects of solvent and temperature on thermal decomposition of substituted tetrazoles have been revealed.We have earlier shown that decomposition mechanism and thermal stability of energetic compounds based on 5-R-2-methyltetrazoles strongly depends on the nature of the R substituent [1][2][3]. Extending these studies, herein we report on thermal decomposition of compounds I-VIII aiming to reveal a quantitative relationship between the tetrazoles reactivity and nature of the substituent in the 5-phenyl ring.

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“…The commonly acceptedm odel for the thermal decomposition of nitroaliphatics involves CÀNO 2 homolysis as the initial step. [40,45,46] This suggestion was verifiedi nt he case of compound 5 by mass spectrometry,t he mass spectrum of which has peaks that correspond to the loss of one and two nitro groups,w hich give rise to signals with m/z values of 454 (MÀNO 2 )a nd 408 (MÀ2NO 2 ). Despite understanding the initial step of the thermolysis sequence, the subsequentp rocess is complicated by rapid secondary reactions.…”

Section: Decomposition Studymentioning

confidence: 96%

“…Likely,t he self-acceleration is from the submelting of the sample. [40] The similarity of the kinetic data of self-acceleration (k 2 )t ot he decomposition kinetic data of the related compound 4-trinitromethyl-2-methyl-1,2,3-triazole in the liquid state [45] favors this assumption.…”

Section: Decomposition Studymentioning

confidence: 98%

“…There is an approximate 25-to 35-foldd ifferencei nt he decomposition rate constants of compound 5 in the molten versus the solidp hases.T he kinetic parameters for the decompositiono fc ompound 5 in al iquid state, namely,t he preexponent (10 12.95 )a nd activation energy( E a = 118.3 kJ mol À1 or 28.3 kcal mol À1 ), are similar to the parameters found for the decomposition of other trinitromethyl azoles. [45]…”

Section: Combustion Studymentioning

confidence: 99%

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Oxygen‐Rich 1,2,4‐Triazolo[3,4‐d]‐1,2,4‐triazolo[3,4‐f]furazano[3,4‐b]pyrazines as Energetic Materials

et al. 2016

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Oxygen-Rich 1,2,4-Triazolo [3,4-d]-1,2,4-triazolo[3,4-f]furazano [3,4b]pyrazines as Energetic Materials Aleksei B. Sheremetev,* [a] Vecheslav L. Korolev, [a] AleksandrA.P otemkin, [a, b] Abstract: Ac onvenient one-pot synthesis of 5,10-bis(trinitromethyl)-(5)a nd 5,10-bis(fluorodinitromethyl)furazano[3,4e]di([1,2,4]triazolo)[4,3-a:3',4'-c]pyrazines (6)b ye mploying the reaction of 5,6-dichlorofurazano[3,4-b]pyrazine with 5-(trinitromethyl)-and 5-(1-fluoro-1,1-dinitromethyl)tetrazoles, respectively,w as developed. The protocol was carriedo ut under mild conditions at am oderate temperature and over short reaction times to synthesize the products in excellent yields. For the first time, thesep olynitromethyl-substituted compounds, whichm ay have potential use as explosive and propellant materials,h ave been fully characterized. The burningr ate of compound 5 was shown to be slightly superior to that of 2,4,6,8,10,12-hexanitrohexaazaisowurtzitane (CL-20).[a] Prof. A. B. Sheremetev,V .L.Korolev,A .A.P otemkin, N.

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Structural and kinetic regularities of thermal decomposition of gem-trinitromethylazoles in the liquid phase

Cited by 11 publications

References 2 publications

Delving into Autocatalytic Liquid-State Thermal Decomposition of Novel Energetic 1,3,5-Triazines with Azido, Trinitroethyl, and Nitramino Groups

Delving into Autocatalytic Liquid-State Thermal Decomposition of Novel Energetic 1,3,5-Triazines with Azido, Trinitroethyl, and Nitramino Groups

Substituent effect on the rate of thermal decomposition of 5-(R-phenyl)-2-methyl-1,2,3,4-tetrazoles

Oxygen‐Rich 1,2,4‐Triazolo[3,4‐d]‐1,2,4‐triazolo[3,4‐f]furazano[3,4‐b]pyrazines as Energetic Materials

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