A strategy for stabilizing of N8 type energetic materials by introducing 4-Nitro-1,2,3-Triazole scaffolds

被引：17
|
作者：
Feng, Shangbiao [1 ,2 ]
Li, Yunlu [1 ,2 ]
Lai, Qi [2 ]
Cai, Jinxiong [2 ]
Wang, Zhe [2 ]
Yin, Ping [1 ,2 ]
He, Chunlin [1 ,2 ]
Pang, Siping [2 ]
机构：
[1] Beijing Inst Technol Chongqing Innovat Ctr, Chongqing 401120, Peoples R China
[2] Beijing Inst Technol, Sch Mat Sci & Engn, Beijing 100081, Peoples R China
来源：
CHEMICAL ENGINEERING JOURNAL | 2022年 / 430卷
基金：
中国国家自然科学基金;
关键词：
PERFORMANCE; COMPOUND;
D O I：
10.1016/j.cej.2021.133181
中图分类号：
X [环境科学、安全科学];
学科分类号：
08 ; 0830 ;
摘要：
A series of multi-functionalized 4-nitro-1,2,3-triazole based C-N linked biheterocyclic energetic compounds were synthesized using CDI (1,1'-carbonyldiimidazole) induced dehydrative cyclization. Among these energetic analogues, the representative compounds 2 and 6 exhibit great potential as melt-castable explosive (2: T-m = 72 degrees C , T-d = 231 degrees C) and high-performance insensitive energetic material (6: d = 1.82 g cm(-3) , D = 8688 m s(-1) , IS > 40 J), respectively. More importantly, employing THA (O-tosylhydroxylamine) and SDIC(sodium dichloroisocyanurate), functionalized N8-branched compound (F-N8B, (E)-1,2-bis(4,5'-dinitro-2'H-[2,4'-bi(1,2,3-triazol)]-2'-yl)diazene) was synthesized via N-amination and oxidative azo coupling. In comparison to previously reported N8 type of energetic compounds, F-N8B exhibits improved impact sensitivity and friction sensitivity (IS = 7 J, FS = 72 N).
引用
收藏
页数：9
相关论文
共 50 条
  • [1] A strategy for stabilizing of N8 type energetic materials by introducing 4-Nitro-1,2,3-Triazole scaffolds
    Feng, Shangbiao
    Li, Yunlu
    Lai, Qi
    Cai, Jinxiong
    Wang, Zhe
    Yin, Ping
    He, Chunlin
    Pang, Siping
    [J]. Chemical Engineering Journal, 2022, 430
  • [2] Sensitive Energetics from the N-Amination of 4-Nitro-1,2,3-Triazole
    Wozniak, Dominique R.
    Salfer, Benjamin
    Zeller, Matthias
    Byrd, Edward F. C.
    Piercey, Davin G.
    [J]. CHEMISTRYOPEN, 2020, 9 (08): : 806 - 811
  • [3] Density functional analysis of a decomposition of 4-nitro-1,2,3-triazole through the evolution of N-2
    Politzer, P
    Grice, ME
    Seminario, JM
    [J]. INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY, 1997, 61 (03) : 389 - 392
  • [4] N-Alkylation of 4-nitro-1,2,3-triazole revisited. Detection and characterization of the N3-ethylation product, 1-ethyl-5-nitro-1,2,3-triazole
    Voitekhovich, Sergei V.
    Gaponik, Pavel N.
    Lyakhov, Alexander S.
    Filipova, Juliya V.
    Sukhanova, Anna G.
    Sukhanov, Gennady T.
    Ivashkevich, Oleg A.
    [J]. TETRAHEDRON LETTERS, 2009, 50 (21) : 2577 - 2579
  • [5] Acid Catalyzed tert-Butylation and Tritylation of 4-Nitro-1,2,3-triazole: Selective Synthesis of 1-Methyl-5-nitro-1,2,3-triazole via 1-tert-Butyl-4-nitro-1,2,3-triazole
    Filippova, Yuliya V.
    Sukhanova, Anna G.
    Voitekhovich, Sergei V.
    Matulis, Vadim E.
    Sukhanov, Gennady T.
    Grigoriev, Yury V.
    Ivashkevich, Oleg A.
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2012, 49 (04) : 965 - 968
  • [6] STRUCTURAL BASIS OF THE IMPACT SENSITIVITIES OF 1-PICRYL-1,2,3-TRIAZOLE, 2-PICRYL-1,2,3-TRIAZOLE, 4-NITRO-1-PICRYL-1,2,3-TRIAZOLE, AND 4-NITRO-2-PICRYL-1,2,3-TRIAZOLE
    STORM, CB
    RYAN, RR
    RITCHIE, JP
    HALL, JH
    BACHRACH, SM
    [J]. JOURNAL OF PHYSICAL CHEMISTRY, 1989, 93 (02): : 1000 - 1007
  • [7] Mass spectrometric study of substituted 5- or 4-nitro-1,2,3-triazole 1-oxides
    Godovikova T.I.
    Karpenko N.F.
    Vozchikova S.A.
    Ignat'eva E.L.
    [J]. Chemistry of Heterocyclic Compounds, 2002, 38 (12) : 1475 - 1479
  • [8] REACTIONS OF 4-NITRO-1,2,3-TRIAZOLE WITH ALKYLATING-AGENTS AND COMPOUNDS, CONTAINING ACTIVATED MULTIPLE BONDS
    VERESHCHAGIN, LI
    KUZNETSOVA, NI
    KIRILLOVA, LP
    SHCHERBAKOV, VV
    SUKHANOV, GT
    GAREEV, GA
    [J]. KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1986, (07): : 932 - 935
  • [9] Introduction of an N-Amino Group onto 4-(Tetrazol-5-yl)-5-nitro-1,2,3-triazole: A Strategy for Enhancing the Density and Performance of Energetic Materials
    Huang, Xun
    Zhao, Pinxu
    Huang, Haifeng
    Yang, Jun
    [J]. SYNLETT, 2024,
  • [10] Modulating Lectin Inhibition with N-Glycosyl-1,2,3-triazole Scaffolds
    Azcune, Itxaso
    Balentova, Eva
    Sagartzazu-Aizpurua, Maialen
    Ignacio Santos, J.
    Miranda, Jose I.
    Fratila, Raluca M.
    Aizpurua, Jesus M.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (12) : 2434 - 2444
12345