Challenging the limits of the oxygen balance of a pyrazole ring

Wenjin Zhang; Yiling Yang; Yuchuan Wang; Teng Fei; Yu Wang; Chenghui Sun; Siping Pang

doi:10.1016/j.cej.2022.138609

Challenging the limits of the oxygen balance of a pyrazole ring

Wenjin Zhang, Yiling Yang, Yuchuan Wang, Teng Fei, Yu Wang, Chenghui Sun^*, Siping Pang

^*Corresponding author for this work

School of Material Science and Engineering

Beijing Institute of Technology

Research output: Contribution to journal › Article › peer-review

31 Citations (Scopus)

Abstract

3,4,5-Trinitropyrazole was successfully functionalized with the trinitromethyl group to give 1-trinitromethyl-3,4,5-trinitropyrazole (3), which was structurally characterized by IR, NMR, elemental analysis, and single-crystal X-ray diffraction. Compound 3 exhibits a super-high density (2.006 g cm⁻³ at 170 K, 1.964 g cm⁻³ at 296 K), excellent oxygen balance (+18.1 %), and good thermal stability (160 ℃). With X-ray data and quantum computing, the intermolecular interactions of 3 was carefully studied to investigate its structure–property relationship. The high density, excellent oxygen balance, good thermal stability, along with its green feature (chloride free) make compound 3 a potential replacement for ammonium perchlorate (AP) and ammonium dinitramide (ADN) in solid propellants.

Original language	English
Article number	138609
Journal	Chemical Engineering Journal
Volume	451
DOIs	https://doi.org/10.1016/j.cej.2022.138609
Publication status	Published - 1 Jan 2023

Keywords

1-trinitromethyl-3,4,5-trinitropyrazole
Diazoacetone
Green energetic oxidiser material
High crystal density
Thermal stability

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10.1016/j.cej.2022.138609

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title = "Challenging the limits of the oxygen balance of a pyrazole ring",

abstract = "3,4,5-Trinitropyrazole was successfully functionalized with the trinitromethyl group to give 1-trinitromethyl-3,4,5-trinitropyrazole (3), which was structurally characterized by IR, NMR, elemental analysis, and single-crystal X-ray diffraction. Compound 3 exhibits a super-high density (2.006 g cm−3 at 170 K, 1.964 g cm−3 at 296 K), excellent oxygen balance (+18.1 %), and good thermal stability (160 ℃). With X-ray data and quantum computing, the intermolecular interactions of 3 was carefully studied to investigate its structure–property relationship. The high density, excellent oxygen balance, good thermal stability, along with its green feature (chloride free) make compound 3 a potential replacement for ammonium perchlorate (AP) and ammonium dinitramide (ADN) in solid propellants.",

keywords = "1-trinitromethyl-3,4,5-trinitropyrazole, Diazoacetone, Green energetic oxidiser material, High crystal density, Thermal stability",

author = "Wenjin Zhang and Yiling Yang and Yuchuan Wang and Teng Fei and Yu Wang and Chenghui Sun and Siping Pang",

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year = "2023",

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doi = "10.1016/j.cej.2022.138609",

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T1 - Challenging the limits of the oxygen balance of a pyrazole ring

AU - Zhang, Wenjin

AU - Yang, Yiling

AU - Wang, Yuchuan

AU - Fei, Teng

AU - Wang, Yu

AU - Sun, Chenghui

AU - Pang, Siping

PY - 2023/1/1

Y1 - 2023/1/1

N2 - 3,4,5-Trinitropyrazole was successfully functionalized with the trinitromethyl group to give 1-trinitromethyl-3,4,5-trinitropyrazole (3), which was structurally characterized by IR, NMR, elemental analysis, and single-crystal X-ray diffraction. Compound 3 exhibits a super-high density (2.006 g cm−3 at 170 K, 1.964 g cm−3 at 296 K), excellent oxygen balance (+18.1 %), and good thermal stability (160 ℃). With X-ray data and quantum computing, the intermolecular interactions of 3 was carefully studied to investigate its structure–property relationship. The high density, excellent oxygen balance, good thermal stability, along with its green feature (chloride free) make compound 3 a potential replacement for ammonium perchlorate (AP) and ammonium dinitramide (ADN) in solid propellants.

AB - 3,4,5-Trinitropyrazole was successfully functionalized with the trinitromethyl group to give 1-trinitromethyl-3,4,5-trinitropyrazole (3), which was structurally characterized by IR, NMR, elemental analysis, and single-crystal X-ray diffraction. Compound 3 exhibits a super-high density (2.006 g cm−3 at 170 K, 1.964 g cm−3 at 296 K), excellent oxygen balance (+18.1 %), and good thermal stability (160 ℃). With X-ray data and quantum computing, the intermolecular interactions of 3 was carefully studied to investigate its structure–property relationship. The high density, excellent oxygen balance, good thermal stability, along with its green feature (chloride free) make compound 3 a potential replacement for ammonium perchlorate (AP) and ammonium dinitramide (ADN) in solid propellants.

KW - 1-trinitromethyl-3,4,5-trinitropyrazole

KW - Diazoacetone

KW - Green energetic oxidiser material

KW - High crystal density

KW - Thermal stability

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DO - 10.1016/j.cej.2022.138609

M3 - Article

AN - SCOPUS:85135915077

SN - 1385-8947

VL - 451

JO - Chemical Engineering Journal

JF - Chemical Engineering Journal

M1 - 138609

ER -

Challenging the limits of the oxygen balance of a pyrazole ring

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Keywords

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