A Facile Synthesis of 3,3'-Dinitro-5,5'-Diamino-Bi-1,2,4-Triazole and Its Thermal Decomposition Study

Ma, Qing; Lu, Huanchang; Qu, Yanyang; Liao, Longyu; Li, Jinshan; Fan, Guijuan; Ya, Chen

doi:10.22211/cejem/69299

Cited by 6 publications

(4 citation statements)

References 35 publications

(13 reference statements)

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“…Organic compounds containing a core structural component of 1,2,4-triazole as the extremely good scaffold were reported to possess inter alia the important relevance as pharmaceutics in a common use from various therapeutic classes [2,3] as well as energetic materials [4][5][6][7][8][9][10][11][12][13][14][15][16][17]. There are some scientific papers focussed on the thermal properties of pharmacologically active molecules possessing the 1,2,4-triazole skeleton.…”

Section: Introductionmentioning

confidence: 99%

“…Studies of other researchers [4][5][6][7][8][9][10][11][12][13] were mainly focussed on the thermal properties and decomposition processes of various energetic materials with the 1,2,4-triazole skeleton. Another scientific investigations [14][15][16] were aimed at assessing the range of thermal stability, phase-transition and decomposition temperatures of nitrogen-rich energetic materials bearing in their hybrid structures the 1,2,4-triazole scaffold combined with an additional azole ring such as the 1,2,3-triazole, 1,2,4-triazole or 1,2,4-tetrazole. In turn, Yan et al [17] investigated the thermal properties of nitrogen-rich 1,2,4-triazole-1,2,4,5-tetrazine-1,2,4-triazole hybrids as highly stable energetic materials and identified their thermolysis products.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Thermal properties and decomposition mechanism of disubstituted fused 1,2,4-triazoles considered as potential anticancer and antibacterial agents

Worzakowska

Sztanke

2022

J Therm Anal Calorim

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Thermal resistance is a very important parameter when assessing the therapeutic usefulness of potential pharmaceutics. Therefore, the thermal behaviour and the decomposition mechanism in the atmosphere of helium and synthetic air of disubstituted fused 1,2,4-triazoles—which may be potential anticancer and antibacterial agents—were studied with a use of simultaneous thermal analysis: thermogravimetry/differential scanning calorimetry (TG/DTG/DSC) coupled online with Fourier transform infrared spectroscopy. It was confirmed that the thermal stability of the tested compounds is directly depended on their structure and thus on the number of chlorine atoms as substituents. The pyrolysis process of disubstituted fused 1,2,4-triazoles in inert conditions runs in two main, non-well-separated stages connected with the emission of NH3, HCN, acetonitrile, aromatics with an OH group, aromatics with a NH2 groups, H2O, CO2 and alkene fragments. However, the thermal stability of those compounds in synthetic air atmosphere is comparable or lower than their thermal stability in helium atmosphere. The decomposition of the tested compounds runs through at least three main stages, resulting in the emission of the same type of volatiles as in inert conditions plus the additional emission of CO and some carbonyl fragments for compounds with no or one chlorine atom as a substituent. The results indicate a simultaneous cleavage of C–N, N–N and C–O bonds during heating of the tested disubstituted fused 1,2,4-triazoles in inert conditions and additional combustion process of pre-formed residues in oxidative conditions.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Thermal properties and decomposition mechanism of disubstituted fused 1,2,4-triazoles considered as potential anticancer and antibacterial agents

Worzakowska

Sztanke

2022

J Therm Anal Calorim

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“…The results showed that decomposition temperature of these polymers is under 350 °C. Moreover, triazole linkages is present in many organic compounds requiring high temperatures for decomposition, such as 3,3′-dinitro-5,5′-diamino-bi-1,2,4-triazole, which decomposes at 275.5 °C with a heating rate of 5 K·min −1 [ 63 ]. In general, 1,2,3-triazole moiety decomposes at 300–400 °C [ 64 ], but the exact temperature of decomposition is always dependent on the structure of attached molecules because some moieties can decrease their stability.…”

Section: Deactivation Routes Of Diazonium-based Catalystsmentioning

confidence: 99%

Catalyst Design through Grafting of Diazonium Salts—A Critical Review on Catalyst Stability

Smołka,

Krukiewicz

2023

IJMS

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In the pursuit of designing a reusable catalyst with enhanced catalytic activity, recent studies indicate that electrochemical grafting of diazonium salts is an efficient method of forming heterogeneous catalysts. The aim of this review is to assess the industrial applicability of diazonium-based catalysts with particular emphasis on their mechanical, chemical, and thermal stability. To this end, different approaches to catalyst production via diazonium salt chemistry have been compared, including the immobilization of catalysts by a chemical reaction with a diazonium moiety, the direct use of diazonium salts and nanoparticles as catalysts, the use of diazonium layers to modulate wettability of a carrier, as well as the possibility of transforming the catalyst into the corresponding diazonium salt. After providing descriptions of the most suitable carriers, the most common deactivation routes of catalysts have been discussed. Although diazonium-based catalysts are expected to exhibit good stability owing to the covalent bond created between a catalyst and a post-diazonium layer, this review indicates the paucity of studies that experimentally verify this hypothesis. Therefore, use of diazonium salts appears a promising approach in catalysts formation if more research efforts can focus on assessing their stability and long-term catalytic performance.

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“…With increasing demands for high-energy-density materials (HEDMs), polynitro heterocyclic compounds have attracted considerable attention owing to their excellent detonation performances, good thermal stability, and low impact sensitivity. Recently, many polynitro heterocyclic compounds have been synthesized, such as 3,3′-dinitrimino-5,5′-bis(1 H -1,2,4-triazole) (DNABT), , 5,5′-dinitro-3,3′-bis-1,2,4-triazole (DNBT), 3,3′-dinitromethyl-5,5′-bis(1,2 H -1,2,4-triazole) (DNMBT), 5-(5-nitrimino-1,3 H -1,2,4-triazole-3-yl)-3-nitro-1 H -1,2,4-triazole (NNBT), 3,3′-dinitro-5,5′-bis-1,2,4-triazole-1,1′-diol (DNBTO), 1,1′-diamino-3,3′-dinitro-5,5-bis-1,2,4-triazole (DABNT), − 3,3′-diamino-4,4′-dinitramino-5,5′-bis-1,2,4-triazole (H 2 ANAT), and so on. These compounds possess aromatic ring skeletons and plenty of -NO 2 groups which can improve their stability and release more energy.…”

Section: Introductionmentioning

confidence: 99%

Density Functional Theory (DFT) Study on the Structures and Energetic Properties of Isomers of Tetranitro-bis-1,2,4-triazoles

Bao

Liu

et al. 2020

ACS Omega

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A series of isomers of tetranitro-bis-1,2,4-triazoles were designed, and their electronic structures, heats of formation, densities, detonation performances, thermal stabilities, and impact sensitivities were investigated by density functional theory (DFT). The structure and energetic properties of 1,3,5,7-tetranitro-1,3,5,7-tetrazocane (HMX) were also calculated at the same level. On comparing with the detonation velocity and pressure and bond dissociation energy (BDE) of HMX, it was found that four isomers (BT2, BT5, BT6, BT7) have higher detonation performances than HMX and three isomers (BT5, BT6, BT7) have better thermal stabilities than HMX. The calculated results of impact sensitivities indicated that all of the designed isomers have more sensitivity than HMX. The calculated results of energy gaps between the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) indicated that all of the designed isomers were more easily excited than HMX in the chemical reaction process. In particular, 3,3′,5,5′-tetranitro-1,1′-bis-1,2,4-triazoles (BT5) exhibited excellent detonation performances (9464 m s –1 , 39.44 GPa) and good thermal stability (BDE 256.81 kJ mol –1 ). The results indicated that the isomerization of tetranitro-bis-1,2,4-triazoles could improve their detonation performance or thermal stability and might lead to a promising isomer possessing both good performance and high thermal stability.

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A Facile Synthesis of 3,3'-Dinitro-5,5'-Diamino-Bi-1,2,4-Triazole and Its Thermal Decomposition Study

Cited by 6 publications

References 35 publications

Thermal properties and decomposition mechanism of disubstituted fused 1,2,4-triazoles considered as potential anticancer and antibacterial agents

Thermal properties and decomposition mechanism of disubstituted fused 1,2,4-triazoles considered as potential anticancer and antibacterial agents

Catalyst Design through Grafting of Diazonium Salts—A Critical Review on Catalyst Stability

Density Functional Theory (DFT) Study on the Structures and Energetic Properties of Isomers of Tetranitro-bis-1,2,4-triazoles

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