A guiding simulation research on developing promising energetic materials

Liu, Min-Hsien; Cheng, Ken-Fa; Chen, Cheng; Hong, Yaw‐Shun

doi:10.1002/qua.21894

Cited by 4 publications

(2 citation statements)

References 14 publications

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“…Besides, experimental research on high-energy explosives is not only risky, but requires time and financial commitments. We were motivated, based upon past experience, [15][16][17][18][19] to conduct various reactions and obtain results through theoretical computation. Furthermore, quantum chemical theory calculation was used to analyze the kinetic energy barriers and to identify a more beneficial route for the reaction.…”

Section: Introductionmentioning

confidence: 99%

A Computational Study of Reaction Routes of 1,3,3‐trinitroazetidine (TNAZ) Synthesis

Liu

Cheng

Yen

2015

J Chinese Chemical Soc

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This study performs simulation modeling of the synthesis of 1,3,3-trinitro azetidine (TNAZ), a high-energy compound. Based on the experimental nitromethane and 1,3-dihalo-2-propanol raw material methods in the latest literature, we suggest reasonable reaction mechanisms. Using quantum mechanical theory, i.e., electronic density functional theory (DFT) B3LYP/6-31G(d,p) in the Gaussian 09 program, we have completed optimization work for all species in related reaction stages and obtained energy barrier data, which are used to identify the most feasible reaction pathways. Nitromethane has been used to react with formaldehyde through an ionic-type transition to produce 2,2-dinitro-1,3-propandiol, followed by reaction with hydrogen bromide to produce 1,3-dibromo-2,2-dinitro propane, then further react with a tertiary amine to produce 1-tertiary amino-3,3-dinitro azetidine, and subsequently nitrate to obtain TNAZ. Substituent effects of some atomic groups have been found during synthesis modeling, and a total activation energy of 1386.6 kJ/mol needs to be conquered in order to complete the reaction. Furthermore, from synthesis modeling using the 1,3-dihalo-2-propanol raw material method, the suggested reaction routes could be bromination of glycerol to 1,3-dibromo-2-propanol, followed by reaction with nitromethane to undergo amination, and further cyclization, oxidation, oximization, and nitration in sequence to produce the target product TNAZ. An overall 1163.5 kJ/mol energy barrier needs to be overcome in this part of the computation.

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Section: Introductionmentioning

confidence: 99%

A Computational Study of Reaction Routes of 1,3,3‐trinitroazetidine (TNAZ) Synthesis

Liu

Cheng

Yen

2015

J Chinese Chemical Soc

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“…Previously, we performed the successful synthesis and simulation of high‐energy explosives . In this study, we performed theoretical simulations of the newly developed, high‐energy TNTA explosive.…”

Section: Introductionmentioning

confidence: 99%

Comparative theoretical synthesis of high-energy density materials 2,4,6-trinitro-1,3,5-triazine

Cheng

Liu

2014

Int. J. Quantum Chem.

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In this study, the optimal synthetic route for 2,4,6‐trinitro‐1,3,5‐triazine (TNTA) was investigated. The synthesis of TNTA was performed using cyanamide (H2NCN) as a starting material. In the first stage, a radical addition reaction was used to generate melamine, which is the precursor of TNTA. In addition, a gaseous nitration reaction using nitrogen dioxide radicals (•NO2) as the nitration agent was used to gradually induce radical substitutions to convert dicyandiamide (H2NCN)2 to melamine (H2NCN)3. Additional nitration steps lead to triaminocyanide and, ultimately, TNTA. In addition, nitryl cyanide (O2NCN) was also tested as a starting material for radical addition to generate dinitryl cyanide (O2NCN)2, trinitryl cyanide (O2NCN)3, and, finally, TNTA. The activation energy barrier in each of the reaction steps as well as the various synthetic routes were compared to provide insight into the design of more feasible routes for the synthesis of TNTA. © 2014 Wiley Periodicals, Inc.

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2‐(Dinitromethylene)‐1‐nitro‐1, 3‐diazacyclopentane‐Based Energetic Salts

Song

Zhou

Cao

et al. 2012

Zeitschrift anorg allge chemie

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Energetic salts that contain nitrogen‐rich cations and the 2‐(dinitromethyl)‐3‐nitro‐1, 3‐diazacyclopent‐1‐ene anion were synthesized in high yield by direct neutralization reactions. The resulting salts were fully characterized by multinuclear NMR spectroscopy (1H and 13C), vibrational spectroscopy (IR), elemental analysis, density and differential scanning calorimetry (DSC), and elemental analysis. Additionally, the structures of the ammonium (1) and isopropylideneaminoguanidinium (9) 2‐(dinitromethyl)‐3‐nitro‐1, 3‐diazacyclopent‐l‐ene salts were confirmed by single‐crystal X‐ray diffraction. Solid‐state 15N NMR spectroscopy was used as an effective technique to further determine the structure of some of the products. The densities of the energetic salts paired with organic cations fell between 1.50 and 1.79 g·cm–3 as measured by a gas pycnometer. Based on the measured densities and calculated heats of formation, detonation pressures and velocities were calculated using Explo 5.05 and found to to be 25.2–35.5 GPa and 7949–9004 m·s–1, respectively, which make them competitive energetic materials.

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A guiding simulation research on developing promising energetic materials

Cited by 4 publications

References 14 publications

A Computational Study of Reaction Routes of 1,3,3‐trinitroazetidine (TNAZ) Synthesis

A Computational Study of Reaction Routes of 1,3,3‐trinitroazetidine (TNAZ) Synthesis

Comparative theoretical synthesis of high-energy density materials 2,4,6-trinitro-1,3,5-triazine

2‐(Dinitromethylene)‐1‐nitro‐1, 3‐diazacyclopentane‐Based Energetic Salts

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