N-Trinitroethyl-substituted azoxyfurazan: high detonation performance energetic materials

Yu, Qingbo; Wang, Zhixin; Yang, Hongwei; Wu, Bo; Lin, Qiuhan; Ju, Xue‐Hai; Lu, Chunmei

doi:10.1039/c5ra03230j

Cited by 26 publications

(14 citation statements)

References 98 publications

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“…Along with energetic salts several neutral energetic compounds, namely N , N ′‐bis(2,2,2‐trinitroethyl)‐3,3′‐diamino‐4,4′‐azoxyfurazan 154 and N , N ′‐bis(2,2,2‐trinitroethyl)‐3,3′‐dinitramino‐4,4′‐azoxyfurazan 155 were recently synthesized . Their synthesis involves a Mannich reaction of 3,3′‐diamino‐4,4′‐azoxyfurazan 120 with 2,2,2‐trinitroethanol (TNE) followed by nitration of formed Mannich base 154 (Scheme ).…”

Section: Alliance Of 125‐oxadiazole Ringsmentioning

confidence: 99%

1,2,5‐Oxadiazole‐Based High‐Energy‐Density Materials: Synthesis and Performance

2019

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This Review covers the synthesis and performance of the most promising 1,2,5-oxadiazole-based high-energy density materials (HEDMs). These materials comprise a 1,2,5-oxadiazole subunit as a key structural motif linked to various acyclic explosophoric groups or to nitrogen-rich and nitrogen-oxygen azoles: 1,2,4triazole, tetrazole, 1,2,4-and 1,3,4-oxadiazoles. Energetic alliances of two and more 1,2,5-oxadiazole rings linked directly or through heteroatom spacers are also presented. Particular attention is devoted to the installation of different explosophores: nitro, nitramino, azo, azoxy, dinitromethyl, trinitroethyl moieties and their combination. Promising environmentally benign energetic materials with high detonation velocity and pressure, and outstanding insensitivity are summarized. Overall, the presented materials may be considered as next-generation high-performance energetic materials that are superior to commonly used traditional explosives (TNT, PETN, RDX, HMX).

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Section: Alliance Of 125‐oxadiazole Ringsmentioning

confidence: 99%

1,2,5‐Oxadiazole‐Based High‐Energy‐Density Materials: Synthesis and Performance

2019

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“…IR (ATR, cm −1 ): 3017 (w), 2974 (w), 2895 (w), 1795 (m), 1764 (m), 1582 (s), 1444 (w), 1410 (w), 1390 (m), 1330 (m), 1265 (m), 1297 (s), 1169 (m), 1125 (s), 1057 (m), 958 (w), 877 (w), 855 (m), 817 (m), 794 (m), 776 (s), 639 (m), 599 (m), 572 (w), 541 (m), 435 (w). Raman (1064 nm, 800 mW, cm −1 ): 3005 (16), 2960 (39), 1798 (9), 1786 (15), 1767 (9), 1611 (32), 1445 (11), 1410 (12), 1391 (24), 1356 (38), 1305 (32), 1265 (11), 1171 (7), 1093 (6), 1051 (16), 1005 (7), 959 (9), 928 (13), 895 (7), 877 (8), 858 (101), 822 (5), 801 (7), 781 (6), 681 (4), 643 (8), 602 (4), 543 (16), 436 (15), 412 (39), 374 (66), 298 (9), 284 (13) Nitraminodiacetic Acid. Method A.…”

Section: ■ Conclusionmentioning

confidence: 99%

Oxygen-Rich Bis(trinitroethyl esters): Suitable Oxidizers as Potential Ammonium Perchlorate Replacements

et al. 2020

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In the area of solid rocket propellants, research efforts are ongoing to find suitable oxidizers as ammonium perchlorate (AP) replacements. On the one hand, AP's performance data are excellent; on the other hand, AP and its combustion products lead to health and environmental issues. Herein, the nitraminodiacetic acid bis(2,2,2-trinitroethyl ester) (NABTNE) is presented as a green AP alternative and is compared to the bis(trinitroethyl ester) of malonic acid (MaBTNE). Simple syntheses based on economic starting materials furnished both compounds, with NABTNE having a positive oxygen balance (according to CO), a density of 1.84 g cm −3 (@T = −118 °C), and a decomposition point of 180 °C. The density of MaBTNE (δ = 1.81 g cm −3 @T = −147 °C) and the thermal stability (T dec = 157 °C) are also advantageous. NABTNE as a moderately sensitive and the most promising derivative was shown to be of good stability toward long-term storage. Moreover, mixtures for a potential application in solid rocket formulations were calculated using EXPLO5 (V 6.03).

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“…N-hydroxymethyl group can be reacted with trinitromethane to obtain more powerful trinitro derivative, and a lot of trinitro derivatives were synthesized by this method [30]. However, after reaction with trinitromethane in methanol by the reported method [31], N-methoxymethyl derivative 2 without trinitro group was obtained in 78 % yield.…”

Section: Synthesismentioning

confidence: 99%

An Unexpected Method to Synthesize Fluorinated Derivative of ANPZ

Huang

Guo

et al. 2019

Propellants Explo Pyrotec

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Nucleophilic reaction of ANPZ (2,6-diamino-3,5-dinitropyrazine) with formaldehyde was researched for the first time to synthesize its N-hydroxymethyl derivative. With further modification, ether derivative and fluorinated derivative of ANPZ were obtained by an unexpected reaction pathway. The physical properties of new derivatives were also determined by experimental and theoretical methods, which indicate that fluorinated functionalization can be easily introduced by this unexpected method to improve the integrated performance of energetic materials.

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N-Trinitroethyl-substituted azoxyfurazan: high detonation performance energetic materials

Abstract: An N-nitrated trinitroethylamino azoxyfurazan derivative reported here possesses oxygen balance of near zero (+2.5%) and exhibits outstanding properties (ΔfHm, 962.1 kJ mol−1; D, 9458 m s−1; P, 41.2 GPa).

Cited by 26 publications

References 98 publications

1,2,5‐Oxadiazole‐Based High‐Energy‐Density Materials: Synthesis and Performance

1,2,5‐Oxadiazole‐Based High‐Energy‐Density Materials: Synthesis and Performance

Oxygen-Rich Bis(trinitroethyl esters): Suitable Oxidizers as Potential Ammonium Perchlorate Replacements

An Unexpected Method to Synthesize Fluorinated Derivative of ANPZ

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