Design and synthesis of energetic materials towards high density and positive oxygen balance by N-dinitromethyl functionalization of nitroazoles

Zhao, Xiaojing; Li, S. H.; Wang, Yuqing; Li, Y. C.; Zhao, Fengqi; Pang, Siping

doi:10.1039/c6ta01501h

Cited by 148 publications

(66 citation statements)

References 41 publications

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“…The n NHx and n Ar are equal to zero in our system. We can see that the values of I sp are increased from A1 to F and all of them are higher than that of CL-20, the result is caused by the gradually rising HOFs along with the increase of nitrogen contents [28]. The large I sp values mean that they all have greater energy efficiency than CL-20 as energetic materials.…”

Section: Full Papermentioning

confidence: 87%

Effect of Nitrogen-Doping on Detonation and Stability Properties of CL-20 Derivatives from a Theoretical Viewpoint

Hao

Chi

Tian

et al. 2017

Prop., Explos., Pyrotech.

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Six nitrogen‐doping CL‐20 derivatives were designed and investigated as energetic materials at B3LYP/6‐31G** level based on the density functional theory method. Results show that nitrogen‐doping derivatives exhibit high crystal densities (1.98∼2.18 g cm−3) and positive heats of formation (451.68∼949.68 kJ mol−1). Among nitrogen‐doping derivatives, 2,4,6,8,10,12‐hexanitro‐2,4,6,8,9,10,12‐heptaazaisowurtzitane(A1), 2,4,6,8,10,12‐hexanitro‐2,3,4,6,8,9,10,12‐octaazaisowurtzitane(B1) and 2,4,6,8,10,12‐hexanitro‐1,2,3,4,6,8,9,10,12‐nonaazaisowurtzitane(C1) possess better detonation velocity and pressure than CL‐20, and A1 gives the best performance (DK‐J•A1=9.6 km s−1; PK‐J•A1=43.07 GPa). Moreover, the specific impulse, brisance, and power of N‐doping CL‐20 derivatives are also higher than that of CL‐20. The thermal stability and sensitivity of nitrogen‐doping molecules were analyzed via the bond dissociation energy (BDE), the characteristic height (h50) and electrostatic sensitivity (EES). The results indicate that the stability of A1, B1 and 2,4,6,8,10,12‐hexanitro‐1,2,3,4,6,7,8,9,10,12‐decaazaisowurtzitane(D1) is comparable with that of CL‐20. Considering detonation performance and stability, A1 and B1 may be promising candidates as energetic materials with superior detonation performance and favorable stability.

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Section: Full Papermentioning

confidence: 87%

Effect of Nitrogen-Doping on Detonation and Stability Properties of CL-20 Derivatives from a Theoretical Viewpoint

Hao

Chi

Tian

et al. 2017

Prop., Explos., Pyrotech.

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“…Li and Pang have reported characterization of 5-nitro-2-nitratomethyl-1,2,3,4-tetrazole for its synthesis [2]. Zhao and co-workers synthesized N-dinitromethyl-5-nitrotetrazoles, N-dinitromethyl-3-nitro-1,2,4-triazole, and N-dinitromethyl-3-nitropyrazole [14]. It is important to use suitable ab initio or density functional theory (DFT) as well as empirical methods for this purpose.…”

Section: Introductionmentioning

confidence: 99%

Introducing Novel Tetrazole Derivatives as High Performance Energetic Compounds for Confined Explosion and as Oxidizer in Solid Propellants

Keshavarz

Abadi

Esmaeilpour

et al. 2017

Propellants Explo Pyrotec

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This paper introduces five novel high-nitrogen content (N > 50%) tetrazole derivatives with desirable physicothermal properties, high detonation and combustion performance as well as suitable sensitivities with respect to external stimuli electric spark and heat. Suitable density functional theory (DFT) and empirical methods were used to predict their crystal density, melting point, condensed phase heat of formation, enthalpy of fusion, Gibbs free energy of formation, velocity of detonation, detonation pres-sure, Gurney velocity, heat of detonation, power (strength), brisance, impact sensitivity, electric spark sensitivity, heat sensitivity and specific impulse. Two compounds 5,5'-[(1Z,5Z)-3,4-dinitrohexaaza-1,5-diene-1,6-diyl]bis(1-nitro-1Htetrazole) and 3,3',7,7'-tetranitro-3,3a,3',3'a-tetrahydro-7H,7'H-6,6'-bitetrazolo [1,5-e]pentazine as compared to the other new derivatives can be introduced as high performance explosives for confined explosion and oxidizers in solid propellants.Keywords: Tetrazole derivative · High-nitrogen content material · High performance · Physicothermal property 2 Materials and Methods For prediction of crystalline densities of the new compounds 1 to 5, a new method on the basis of DFT at the B3LYP/6-31G(d,p) with the Gaussian program package was used [22,23]. The best available new and reliable empirical [a] M.

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“…[10][11][12][13][14][15][16][17][18] More importantly,t he chemical energy in high-nitrogen heterocyclic energetic materials is not only generated by oxidation of the carbonb ackboned uring the explosion process but also arisesf rom cleavagea nd recombination of abundantC ÀN, NÀ N, and N=Nb onds. As ar esult, extensive efforts have been appliedt o the developmento fn ew high-performance energetic materials basedo nh igh-nitrogen heterocyclic skeletons because of their advantageous properties, such as high-energy (NÀN, N=N, and CÀNb onds) and more positive heats of formation.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of gem‐Dinitromethylated and Fluorodinitromethylated Derivatives of 5,5′‐Dinitro‐bis‐1,2,4‐triazole as Promising High‐Energy‐Density Materials

Huang

Tian

et al. 2017

Chemistry A European J

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gem-Dinitromethylated and fluorodinitromethylated 5,5'-dinitro-3,3'-bis-1,2,4-triazole (DNBT) (2 and 3) along with seven ionic derivatives 4-9, were synthesized and characterized by NMR and IR spectroscopies, elemental analysis, single-crystal X-ray diffraction (XRD), and differential scanning calorimetry (DSC). XRD revealed that compounds 2 and 3 crystallized in the monoclinic P2 /n space group and compound 5 crystallized in the monoclinic P2 /c space group. The physicochemical properties of the as-synthesized compounds 2-9 were investigated and the results indicated that compounds 3, 6, and 7 exhibited a good balance between high energy and low sensitivity, demonstrating their potential as new high-energy-density materials (HEDMs). The proposed synthetic strategy for introducing gem-dinitromethyl and fluorodinitromethyl groups into the DNBT framework to prepare materials with high energy and low sensitivity suitable for HEDMs looks promising.

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Design and synthesis of energetic materials towards high density and positive oxygen balance by N-dinitromethyl functionalization of nitroazoles

Abstract: The top of the pyramid of tetrazole-based CHNO energetic materials for density and OB: N-dinitromethyl functionalization is a new N-functionalized strategy for the synthesis of highly dense and oxygen-rich energetic materials.

Cited by 148 publications

References 41 publications

Effect of Nitrogen-Doping on Detonation and Stability Properties of CL-20 Derivatives from a Theoretical Viewpoint

Effect of Nitrogen-Doping on Detonation and Stability Properties of CL-20 Derivatives from a Theoretical Viewpoint

Introducing Novel Tetrazole Derivatives as High Performance Energetic Compounds for Confined Explosion and as Oxidizer in Solid Propellants

Synthesis of gem‐Dinitromethylated and Fluorodinitromethylated Derivatives of 5,5′‐Dinitro‐bis‐1,2,4‐triazole as Promising High‐Energy‐Density Materials

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