Nitrogen-rich salts based on polyamino substituted N,N′-azo-1,2,4-triazole: a new family of high-performance energetic materials

Liu, Wei; Li, Sheng‐Hua; Li, Yuchuan; Yang, Yuzhang; Yu, Yi; Pang, Siping

doi:10.1039/c4ta03016h

Cited by 54 publications

(25 citation statements)

References 39 publications

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“…1,1ʹ-Azobis-1,2,3-triazole ( 1 ) and 4,4ʹ-azobis-1,2,4-triazole ( 2 ) were prepared according to literature procedures [13, 14]. The sample purities were > 0.99 (w/w).…”

Section: Materials and Methodologymentioning

confidence: 99%

“…The title compounds 1,1ʹ-azobis-1,2,3-triazole ( 1 ) and 4,4ʹ-azobis-1,2,4-triazole ( 2 ) show remarkable properties, such as high enthalpies of formation, high melting points, and relatively high stabilities [5, 13, 14, 17]. In order to rationalize this unexpected behavior of the two compounds, it is necessary to study their thermal decompositions and pyrolyses.…”

Section: Introductionmentioning

confidence: 99%

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Thermogravimetric analysis, kinetic study, and pyrolysis–GC/MS analysis of 1,1ʹ-azobis-1,2,3-triazole and 4,4ʹ-azobis-1,2,4-triazole

Jia

Zhang

et al. 2018

Chemistry Central Journal

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BackgroundIn general, the greater the number of directly linked nitrogen atoms in a molecule, the better its energetic performance, while the stability will be accordingly lower. But 1,1ʹ-azobis-1,2,3-triazole (1) and 4,4ʹ-azobis-1,2,4-triazole (2) show remarkable properties, such as high enthalpies of formation, high melting points, and relatively high stabilities. In order to rationalize this unexpected behavior of the two compounds, it is necessary to study their thermal decompositions and pyrolyses. Although a great deal of research has been focused on the synthesis and characterization of energetic materials with 1 and 2 as the backbone, a complete report on their fundamental thermodynamic parameters and thermal decomposition properties has not been published.MethodsThermogravimetric–differential scanning calorimetry were used to obtain the thermal decomposition data of the title compounds. Kissinger and Ozawa–Doyle methods, the two selected non-isothermal methods, are presented for analysis of the solid-state kinetic data. Pyrolysis–gas chromatography/mass spectrometry was used to study the pyrolysis process of the title compounds.ResultsThe DSC curves show that the thermal decompositions of 1 and 2 are at different heating rates involved a single exothermic process. The TG curves provide insight into the total weight losses from the compounds associated with this process. At different pyrolysis temperatures, the compositions and types of the pyrolysis products differ greatly and the pyrolysis reaction at 500 °C is more thorough than 400 °C.ConclusionsApparent activation energies (E) and pre-exponential factors (lnA/s−1) are 291.4 kJ mol−1 and 75.53 for 1; 396.2 kJ mol−1 and 80.98 for 2 (Kissinger). The values of E are 284.5 kJ mol−1 for 1 and 386.1 kJ mol−1 for 2 (Ozawa–Doyle). The critical temperature of thermal explosion (Tb) is evaluated as 187.01 °C for 1 and 282.78 °C for 2. The title compounds were broken into small fragment ions under the pyrolysis conditions, which then might undergo a multitude of collisions and numerous other reactions, resulting in the formation of C2N2 (m/z 52), etc., before being analyzed by the GC/MS system.Electronic supplementary materialThe online version of this article (10.1186/s13065-018-0381-x) contains supplementary material, which is available to authorized users.

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“…1,1ʹ-Azobis-1,2,3-triazole ( 1 ) and 4,4ʹ-azobis-1,2,4-triazole ( 2 ) were prepared according to literature procedures [13, 14]. The sample purities were > 0.99 (w/w).…”

Section: Materials and Methodologymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Thermogravimetric analysis, kinetic study, and pyrolysis–GC/MS analysis of 1,1ʹ-azobis-1,2,3-triazole and 4,4ʹ-azobis-1,2,4-triazole

Jia

Zhang

et al. 2018

Chemistry Central Journal

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“…A series of new polynitrogen compounds with growing number of catenated nitrogen atoms have been synthesized through the oxidative coupling reaction of the N-NH 2 moiety of the heterocycles [1][2][3][4][5][6][7][8][9]. More importantly, with their similar structures and experimental data, such compounds offer a unique opportunity to theoretically study the relationship between structure and thermal stability, and verify its validity.…”

Section: Introductionmentioning

confidence: 98%

“…Nevertheless, the poor thermal stability makes it difficult to explore the limit to the number of the catenated nitrogen atoms experimentally, and greatly reduces their efficiency as HEDMs [1][2][3][4][5][6][7][8][9][10][11][12][13][14].…”

Section: Introductionmentioning

confidence: 99%

The stability and decomposition mechanism of the catenated nitrogen compounds

Zhao

Zhang

et al. 2015

J Mol Model

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Through theoretical calculation and experimental data, the decomposition mechanism of the N,N'-azo azole poly-nitrogen compounds were obtained. The compounds with the decomposition caused by the rupture of the -N-N=N-N- bridge are more stable than the ones with the ring-opening decomposition mechanisms. The catenated -N-N=N-N- bridge can strengthen the stability of the nitrogen chain. Preventing the hybridization change of the N atom where the ring-opening reaction occurs is essential for the nitrogen chain elongation on the ring system. Moreover, the introduction of energetic substituents like nitro group can further improve the performances of poly-nitrogen compounds; and such a modification should be based on a stable poly-nitrogen backbone.

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“…The creation of a rather long chain of catenated nitrogen atoms by the attachment of an azo group to the nitrogen atoms of heteroaromatic rings generates unique properties in the synthesis material. Furthermore, in contrast to the toxicity of many azobenzene-based compounds, these high-nitrogen azo compounds are nontoxic and harmless [24,25]. Recently, Liu et al [24] reported a new family of nitrogen-rich energetic salts based on 3,3′-diamino-4,4′-azo-1,2,4-triazole containing an N-N′-azo linkage and these salts exhibited excellent thermal stabilities, high detonation properties and reasonable sensitivities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Physical and Chemical Properties of Hypergolic Chemicals such as N,N,N-Trimethylhydrazinium and 1-Ethyl-4-Methyl-1,2,4-Triazolium Salts

Kim

Son

et al. 2015

Applied Sciences

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Nitrogen-rich salts based on polyamino substituted N,N′-azo-1,2,4-triazole: a new family of high-performance energetic materials

Abstract: A new family of high performance, nitrogen-rich energetic salts containing N,N′-azo linkage were synthesized through the protonation of 3,3′-diamino-4,4′-azobis-1,2,4-triazole.

Cited by 54 publications

References 39 publications

Thermogravimetric analysis, kinetic study, and pyrolysis–GC/MS analysis of 1,1ʹ-azobis-1,2,3-triazole and 4,4ʹ-azobis-1,2,4-triazole

Thermogravimetric analysis, kinetic study, and pyrolysis–GC/MS analysis of 1,1ʹ-azobis-1,2,3-triazole and 4,4ʹ-azobis-1,2,4-triazole

The stability and decomposition mechanism of the catenated nitrogen compounds

Synthesis and Physical and Chemical Properties of Hypergolic Chemicals such as N,N,N-Trimethylhydrazinium and 1-Ethyl-4-Methyl-1,2,4-Triazolium Salts

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