Chemical Engineering Journal, volume 467, pages 143527

The intramolecular integration of carbonyl and N-nitroamino groups to effectively balance the energy and sensitivity of N-nitroamino-functionalized bisazoles

Jinxiong Cai ¹

Jinya Zhang ¹

Jin Xiong ¹

Rui Lu ²

Fei Teng ¹

Qi Lai ¹

Ping Yin ^{1, 3}

Siping Pang ¹

Hide authors affiliations Show authors affiliations: 3 affiliations

School of Materials Science & Engineering, Beijing Institute of Technology, Beijing 100081, China |

Jingzhou Municipal Ecological Environment Information and Testing and Evaluation Center, Jingzhou 434000, China |

Beijing Institute of Technology Chongqing Innovation Center, Chongqing 401120, China |

Publication type: Journal Article

Publication date: 2023-07-01

Elsevier

Journal: Chemical Engineering Journal

Quartile SCImago

Quartile WOS

Impact factor: 15.1

ISSN: 13858947, 03009467

DOI: 10.1016/j.cej.2023.143527

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General Chemistry

General Chemical Engineering

Industrial and Manufacturing Engineering

Environmental Chemistry

Abstract

In this study, employing an innovative method by introducing the N-nitroamino groups into bis(1,2,4-oxadiazoles) skeleton for the first time, a fine balance between high detonation properties and mechanical stability of N-nitroamino-functionalized bisazoles was achieved. A novel compound N,N'-(5,5′-dioxo-[3,3′-bi(1,2,4-oxadiazole)]-4,4′(5H,5′H)-diyl)dinitramide (3) was synthesized using straightforward three-step synthetic routes. Compound 3 not only has a high crystal density of 1.932 g cm−3 at 296 K, but also competes well in impact and friction sensitivities of 10 J and 160 N among all reported energetic N-nitroamine analogues. Meanwhile, the energy level (detonation velocity: VD = 9106 m s−1; detonation pressure: P = 36.6 GPa) of 3 is much superior to that of benchmark explosive 1,3,5-trinitro-1,3,5-triazacyclohexane (RDX, VD = 8801 m s−1; P = 33.6 GPa) and approaches 1,3,5,7-tetranitro-1,3,5,7-tetrazocane (HMX, VD = 9144 m s−1; P = 39.2 GPa). Additionally, with a striking high density of 1.929 g cm−3, hydroxylammonium salt 8 (VD = 9507 m s−1; P = 40.1 GPa) exhibits a prominent detonation performance comparable to the ε-2,4,6.8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (ε-CL-20, VD = 9455 m s−1; P = 46.7 GPa). This work may give new insight into improving the mechanical stability of energetic materials and is beneficial for developing novel high-energy–density compounds with excellent overall performance.

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Cai J. et al. The intramolecular integration of carbonyl and N-nitroamino groups to effectively balance the energy and sensitivity of N-nitroamino-functionalized bisazoles // Chemical Engineering Journal. 2023. Vol. 467. p. 143527.

GOST all authors (up to 50) Copy

Cai J., Zhang J., Xiong J., Lu R., Teng F., Lai Q., Yin P., Pang S. The intramolecular integration of carbonyl and N-nitroamino groups to effectively balance the energy and sensitivity of N-nitroamino-functionalized bisazoles // Chemical Engineering Journal. 2023. Vol. 467. p. 143527.

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RIS Copy

TY - JOUR

DO - 10.1016/j.cej.2023.143527

UR - https://doi.org/10.1016/j.cej.2023.143527

TI - The intramolecular integration of carbonyl and N-nitroamino groups to effectively balance the energy and sensitivity of N-nitroamino-functionalized bisazoles

T2 - Chemical Engineering Journal

AU - Cai, Jinxiong

AU - Zhang, Jinya

AU - Xiong, Jin

AU - Lu, Rui

AU - Teng, Fei

AU - Lai, Qi

AU - Yin, Ping

AU - Pang, Siping

PY - 2023

DA - 2023/07/01 00:00:00

PB - Elsevier

SP - 143527

VL - 467

SN - 1385-8947

SN - 0300-9467

ER -

BibTex

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BibTex Copy

@article{2023_Cai,

author = {Jinxiong Cai and Jinya Zhang and Jin Xiong and Rui Lu and Fei Teng and Qi Lai and Ping Yin and Siping Pang},

title = {The intramolecular integration of carbonyl and N-nitroamino groups to effectively balance the energy and sensitivity of N-nitroamino-functionalized bisazoles},

journal = {Chemical Engineering Journal},

year = {2023},

volume = {467},

publisher = {Elsevier},

month = {jul},

url = {https://doi.org/10.1016/j.cej.2023.143527},

pages = {143527},

doi = {10.1016/j.cej.2023.143527}

}

Found error?

Publisher

Elsevier

Journal

Chemical Engineering Journal

Quartile SCImago

Quartile WOS

Impact factor

15.1

ISSN

13858947 (Print)
03009467 (Print)