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New Synthetic Methods for 4,4’,5,5’-Tetranitro-2,2’-bi- 1H-imidazole (TNBI)

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Języki publikacji
EN
Abstrakty
EN
Four new nitration methods for the synthesis of 4,4’,5,5’-tetranitro-2,2’- bi-1H-imidazole (TNBI) were examined. TNBI was synthesized by nitration of 2,2’-bi-imidazole (BI) with the following mixtures: (CH3CO)2O/HNO3, (CF3CO)2O/ HNO3, P4O10/HNO3 and H3PO4/P4O10/HNO3. Nitration of BI with a mixture of nitric acid and acetic anhydride leads to 4,4’-dinitro-bi-imidazole. The other nitrating conditions investigated gave TNBI in lower yields (6.0-22.4%). Crystallization of crude TNBI from wet ethanol/acetone gave TNBI as its dihydrate. The structures of BI and TNBI were characterized by 1H, 13C and 15N NMR spectroscopy and elemental analysis. Friction and impact sensitivity, detonability and detonation velocity were determined for pure TNBI dihydrate.
Rocznik
Strony
261--270
Opis fizyczny
Bibliogr. 14 poz., rys., tab.
Twórcy
autor
  • Military University of Technology, Faculty of New Technologies and Chemistry, 2 gen. S. Kaliskiego St., 00-908 Warsaw, Poland
autor
  • Military University of Technology, Faculty of New Technologies and Chemistry, 2 gen. S. Kaliskiego St., 00-908 Warsaw, Poland
Bibliografia
  • [1] Lehmstedt K., Organic Salts of Tetranitrobiimidazole and Methylation Products of Nitroimidazoles (in German), Liebigs Ann., 1933, 507, 213.
  • [2] Novikov S., Khmelnitskii L., Lebedev O., Sevastyanova V., Epishina L., Nitration of Imidazoles with Various Nitrating Agents, Chem. Heterocyc. Compd., 1970, 6, 503.
  • [3] Cromer D., Storm C., Structure of 2,2’-Bi-imidazole, Acta Crystallogr. C, 1990, C46, 1957.
  • [4] Damavarapu R., Jayasuriya K., Vladimroff T., Iyer S., 2,4-Dinitroimidazole – a Less Sensitive Explosive and Propellant Made by Thermal Rearrangement of Molten 1,4-Dinitroimidazole, US Patent 5387297, 1995.
  • [5] Cho S., Cho J., Goh E., Kim J., Synthesis and Characterization of 4,4’,5,5’-Tetranitro-2,2’-bi-1H-imidazole (TNBI), Propellants Explos. Pyrotech., 2005, 30, 445.
  • [6] Cho S., Cho J., Goh E., Kim J., Theoretical Studies on Molecular and Explosive Properties of 4,4′,5,5′-Tetranitro-2,2′-bi-1H-imidazole (TNBI), Propellants Explos. Pyrotech., 2006, 31, 33.
  • [7] Klapötke T., Preimesser A., Stierstoffer J., Energetic Derivatives of 4,4’,5,5’-Tetranitro-2,2’-bisimidazole, Z. Anorg. Allg. Chem., 2012, 638, 1278.
  • [8] Chavez D., Parrish D., Preston D., Mares I., Synthesis and Energetic Properties of 4,4’,5,5’-Tetranitro-2,2’-biimidazolate(N4BIM) Salts, Propellants Explos. Pyrotech., 2010, 35, 1-6.
  • [9] Steffens R., Schunack W., Formation of 1,1’-Bis(phenylmethyl)-2,2’-bi-imidazole-5,5’-dimethanol, Arch. Pharm., 1986, 319, 183.
  • [10] Silverstein R., Webster F., Kiemle D., Spectroscopic Identification of Organic Compounds, 7th ed., John Wiley & Sons Publ., New York, 2005.
  • [11] Melloni P., Dradi E., Logemann W., Synthesis and Antiprotozoal Activity of Methylnitro Derivatives of 2,2’-Bi-imidazole, J. Med. Chem., 1972, 15, 926.
  • [12] Weinheimer R., Proc. 18th Int. Pyrotechnics Seminar, 1992, Breckenridge, Colorado, US.
  • [13] Fried L.E., CHEETAH 1.39 – User’s Manual, Report UCRL-MA-117541, Lawrence Livermore National Laboratory, Los Alamos, USA, 1996.
  • [14] Hobbs M.L., Bauer M.R., Calibrating the BKW-EOS with a Large Product Species Data Base and Measured C-J Properties, The 10th Symposium (Int.) on Detonation, Boston, USA, 1994.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-858c72d7-edd0-4542-8178-0a39111a4d64
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