Preparation of Heat Resistant and Insensitive Explosives by Vicarious Nucleophilic Substitution (VNS) in Polinitroaromatic Compounds

• Autorzy: Szala M. , Jończyk A. , Skupiński W.
• Języki publikacji: EN

Abstrakty

EN

Reaction of vicarious nucleophilic substitution (VNS) of hydrogen was applied for preparation of 1,3,5-triamino-2,4,6-trinitrobenzene (TATB) in a twostep process. Using this approach 3-amino-2,4,6'2'4 6' -hexanitrostilbene (MNHNS) and new 2,6-bis(3-amino-2,4,6-trinitrophenyl)-3,5-dinitropyridine (DAPYX) were obtained.

Słowa kluczowe

EN

DATB; HNS; PYX; amination; vicarious nucleophilic substitution; 3-amino-2,4,6,2'4'6'-hexanitrostilbene; 2,6-bis(3-amino-2,4,6-trinitrophenyl)-3,5- dinitropyridine

• Czasopismo: Central European Journal of Energetic Materials
• Rocznik: 2005
• Tom: Vol. 2, nr 2
• Strony: 15--27
• Opis fizyczny: Bibliogr. 21 poz.

Twórcy

autor

Szala M.

autor

Jończyk A.

autor

Skupiński W.

• Faculty of Chemistry, Warsaw University of Technology, 3 Noakowskiego Str., 00-664 Warszawa, Poland,

Bibliografia

• [1] Agrawal J. P., Recent Trends in High-Energy Materials, Prog. Energ. Combust. Sci., 1998, 24, l.
• [2] Bellamy A. J., Ward S. J., A New Synthetic Route to 1,3,5- Triamino-2,4,6-trinitrobenzene - TATB, Propellants, Explos., Pyrotech., 2002, 27, 49.
• [3] Goliński l, Mąkosza M., Viacarious Nuckeophilic Substitution of Hydrogen in Nitoaromatic Compounds, Tetrahedron Lett., 1978,3495.
• [4] Mąkosza M., Winiarski l, Viacarious Nuckeophilic Substitution of Hydrogen, Acc. Chem. Res., 1987,20,282.
• [5] Nasielski-Hinkens R., Kotel l, Lecloux T., Nasielski l, 5-Aminp-6-nitroquinoxalines from 6-Nitroquinoxalinesby the Amination Reaction with Hydroxylamine, Synth. Commun., 1989,19,511.
• [6] Bakke J. M., Svensen H., Trevisan R., Selective Vicarious Nucleophilic Amination of 3-Nitropyridines,J. Chem. Soc., Perkin Trans l, 2001,367.
• [7] Katritzky A. R., Laurenzo K. S., Direct Amination ofNitrobenzenes by Vicarious Nucleophilic Substitution,J. Org. Chem., 1986, 51, 5039.
• [8] Pagoria P. F., Mitchell A. M., Schmidt R. D., l, l, l ,Trimethylhydraziniumiodide a Novel Highly Reactive Reagent for Amination via Vicarious Nucleophilic Substitution ofHydrogen, J. Org. Chem., 1996, 61, 2934.
• [9] Mąkosza M., Białecki M., Nitroaryloamines via the Vicarious Nucleophilic Substitution of Hydrogens: Amination, Alkyloamination and Aryloamination of Nitroarenes with Sulfenamides, J. Org. Chem., 1998,63,4878.
• [10] Pagoria P. F.,Lee G. S., Mitchell A. R., Schmidt R. D., A Review ofEnergetic Materials Synthesis, Thermochimica Acta, 2002,384, 187.
• [11] Mitchel A. R., Pagoria F., Schmidt R. D.,Viacarious Nuckeophilic Substitution to Prepare 1,3,5- Triamino-2,4,6-trinitrobenzene, Pat. USA 5569783 (1996).
• [12] Mitchel A. R., Pagoria F., Schmidt R. D., Viacarious Nuckeophilic Substitution Using 4-Amino-1,2,4-triazole or O-alkylhydroxylamine to Prepare 1,3-Diamino-2,4,6-trinitrobenzene, Pat. USA 5 633 406 (1997).
• [13] Mitchel A. R., Pagoria F., Schmidt R. D., Amination of Electrophi1ic Aromatic Compounds by Viacarious Nuckeophilic Substitution Pat. USA 6069277 (2000).
• [14] Cetner W. P., Preparatyka materiałów wybuchowych i produktów pośrednich. Wydawnictwa WAT, Warszawa 1974.
• [15] Malesa M., Skupiński w., Jamroz M., Separation ofAmrnonium Dinitroamine from Reaction Mixture, Prope/lants, Explos., Pyrotech., 1999, 24, l.
• [16] Poradnik Fizykochemiczny, WNT, Warszawa 1974.
• [17] Urbański T., Chemistry and Technology oj Explosives, Pergamon Press Ltd., New York 1964.
• [18] Bailey A., Bellerby J. M., Kinioch S. A., The Identification of Bonding Agends for TATBIHTPB Polymer Bonded Explosives,Phil. Trans R. Soc. Land, A., 1992,339,321.
• [19] Mayer R., Explosives, VCH, Milnich 1987.
• [20] Pawłowski w., Badania nad Technologią Otrzymywania Materiału Wybuchowego 2,6-Bis(aminopikrylo)-3,5-dinitropirydyny(PYX), Politechnika Warszawska 2002.
• [21] Allen C. F. H., Bell A., 4-Amino-1 ,2,4-triazole, Org., Synth., 1944,24,12.