A Stepwise Strategy for the Synthesis of HMX from 3,7‐Dipropionyl‐1,3,5,7‐Tetraazabicyclo[3.3.1]Nonane

Zhang, Yu; Xu, Zhen-Lin; Ruan, Jian; Wang, Xiaolong; Zhang, Luyao; Luo, Jun

doi:10.1002/prep.201800193

Cited by 9 publications

(8 citation statements)

References 35 publications

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“…They are also easily functionalized with explosophoric substituents. However, commonly used high performing compounds such as 2,4,6-Triamino-1,3,5-trinitrobenzene (TATB) and Octahydro-1,3,5,7-tetranitro-1,3,5,7tetrazocine (HMX) benefit from consistently improved syntheses with high yield [1,2], and as economic viability ultimately determines the adoption of a new material, there is a strong need for the next generation of energetics to utilize inexpensive and commercially available precursors with a simple overall synthetic scheme and high yields competitive with benchmark materials.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of the energetic 5,7‐diamino‐2‐nitro‐1,2,4‐triazolo[1,5‐a]‐1,3,5‐triazine

Roux,

Zeller,

Byrd

et al. 2023

Propellants Explo Pyrotec

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The energetic compound 5,7‐diamino‐2‐nitro‐1,2,4‐triazolo[1,5‐a]‐1,3,5‐triazine (ANTT) was synthesized through the selective nitration of 2,5,7‐triamine‐1,2,4‐triazolo[1,5‐a]‐1,3,5‐triazine (TTT). This facile synthetic strategy yields a highly insensitive energetic nitrogen bicycle with potential for further functionalization. ANTT was chemically characterized by NMR, IR, and single crystal X‐Ray crystallography. Its energetic sensitivities (impact, friction) were experimentally determined, and its energetic performances were calculated for the first time.

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Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of the energetic 5,7‐diamino‐2‐nitro‐1,2,4‐triazolo[1,5‐a]‐1,3,5‐triazine

Roux,

Zeller,

Byrd

et al. 2023

Propellants Explo Pyrotec

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“…NMR spectra of both the control and irradiated samples of PATO in dry dimethyl sulfoxide (DMSO) were identical, with broad peaks at 8.43 (1H), 9.01 (2H), 10.50 (1H), and 13.90 (1H), consistent with the literature values. 39 PBX 9501 samples with and without Irganox 1010 stabilizers were dissolved in DMSO (with no remaining particulates) and all the control and irradiated sample spectra were identical, with a large singlet for HMX at 6.05 ppm (8H, CH 2 ) 43 and a range of singlets and multiplets observed between 1.2 and 7.4 ppm for the binder system, consistent with the literature values. 44−46 The full 1 H NMR results for PETN, PATO, and both PBX 9501 samples are provided in the Supporting Information.…”

Section: ■ Introductionmentioning

confidence: 99%

Effects of Low-Level Gamma Radiation on Common Nitroaromatic, Nitramine, and Nitrate Ester Explosives

et al. 2022

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The aging of high explosives in an ionizing radiation field is not well understood, and little work has been done in the low dose and low dose rate regime. In this study, four explosives were exposed to low-level gamma irradiation from a 137Cs source: PETN, PATO, and PBX 9501 both with and without the Irganox 1010 stabilizer. Post-irradiation analysis included GC–MS of the headspace gas, SEM of the pellets and powder, NMR spectroscopy, DSC analysis, impact sensitivity tests, and ESD sensitivity tests. Overall, no significant change to the materials was seen for the dose and dose rate explored in this study. A small change in the 1H NMR spectrum of PETN was observed and SEM and ESD results suggest a surface energy change in PATO, but these differences are minor and do not appear to have a substantial impact on the handling safety.

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“…The development of high-energy and low-sensitivity materials has attracted increasing attention due to their important applications in aerospace technology and national defense. − In the synthesis of high-energy compounds, the nitrification step is essential and important. For example, nitrification constitutes key steps in the synthesis of 1,3,5-trinitro-1,3,5-triazacyclohexane (RDX), 1,3,5,7-tetranitro-1,3,5,7-tetraazacyclooctane (HMX), and other energetic compounds . Besides these traditional high-energy compounds, in recent years, many new energetic compounds based on pyridazine, tetrazole, and furoxan frameworks have been developed. − For developing these energetic compounds, nitrification was also used to improve the energy.…”

Section: Introductionmentioning

confidence: 99%

“…1−3 In the synthesis of high-energy compounds, the nitrification step is essential and important. For example, nitrification constitutes key steps in the synthesis of 1,3,5-trinitro-1,3,5triazacyclohexane (RDX), 4 1,3,5,7-tetranitro-1,3,5,7-tetraazacyclooctane (HMX), 5 and other energetic compounds. 6 Besides these traditional high-energy compounds, in recent years, many new energetic compounds based on pyridazine, tetrazole, and furoxan frameworks have been developed.…”

Section: Introductionmentioning

confidence: 99%

Self-Assembly of Nitrogen-Rich Heterocyclic Compounds with Oxidants for the Development of High-Energy Materials

Zheng

Chen

et al. 2021

ACS Appl. Mater. Interfaces

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The development of energetic materials with high energy and low sensitivity has attracted immense interests due to their widespread applications in aerospace technology and national defense. In this work, a promising self-assembly strategy was developed to prepare three high-energy materials (1–3) through the introduction of oxidant molecules into the crystal voids of the parent materials. The structures of these new materials were comprehensively examined by infrared spectroscopy, nuclear magnetic resonance (NMR) spectroscopy, and single-crystal X-ray diffraction. In these materials, three unique layer structures with hcb, sql, and interrupted sql topologies were observed, which were formed by the fused-ring-based energetic components. Windows with hexagonal, square, and rectangular structures were observed within these layer structures, which were occupied by H2O2, NO3 –, and ClO4 –, respectively. Oxidant molecules interacted with parent molecules via hydrogen bonds to form crystal structures of these materials. Moreover, the energetic property of these materials was estimated by computing methods. The calculation results revealed that these self-assembly materials exhibit excellent energetic properties. The highest energetic performance was observed for compound 3. The detonation velocity, detonation pressure, and specific impulse values were up to 9339 m·s–1, 42.5 GPa, and 308 s, respectively, which were greater than those of HMX. Furthermore, these materials exhibited good sensitivity, which was closely related to their unique crystal structures. The high performance of these materials indicated that the self-assembly strategy should be a promising method for the development of novel energetic materials.

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A Stepwise Strategy for the Synthesis of HMX from 3,7‐Dipropionyl‐1,3,5,7‐Tetraazabicyclo[3.3.1]Nonane

Cited by 9 publications

References 35 publications

Synthesis and characterization of the energetic 5,7‐diamino‐2‐nitro‐1,2,4‐triazolo[1,5‐a]‐1,3,5‐triazine

Synthesis and characterization of the energetic 5,7‐diamino‐2‐nitro‐1,2,4‐triazolo[1,5‐a]‐1,3,5‐triazine

Effects of Low-Level Gamma Radiation on Common Nitroaromatic, Nitramine, and Nitrate Ester Explosives

Self-Assembly of Nitrogen-Rich Heterocyclic Compounds with Oxidants for the Development of High-Energy Materials

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