Metody syntezy i właściwości fizykochemiczne 2,4,6,8,10,12-heksanitro-2,4,6,8,10,12-heksaazaizowurcytanu (HNIW)

• Autorzy: Borkowski J. , Czerwińska M.

Warianty tytułu

EN

The methods of synthesis and physicochemical properties of 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (HNIW)

• Języki publikacji: PL

Abstrakty

EN

Explosives have a very rich history of its creation. This history dates back to the ninth century, when the Chinese invented a black powder. In the end of the twentieth century, the first nitroamine polycyclic cage structure was obtained. The representative of this group is 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaizowurtzitane (HNIW, Cl-20). HNIW has recently been the subject of an interest as one of the strongest explosive material. As nitroamine, HNIW is compared to the other energetic materials: RDX i HMX [1, 2]. Researchers [5, 6] showed, that it is possible to replace a variety of typical explosives by HNIW and thanks to that obtain compositions with higher densities, heat of explosion and higher velocity of detonation. In the published papers [7-13, 16] there were presented six polymorphs of HNIW: αβγδε with specific stabilities and structural characteristics. Unfortunately, there is no a direct method of obtaining HNIW. There are at least four steps needed to obtain HNIW. The first step is the synthesis of HBIW [20-22]. The next one is debenzylation reaction of HBIW [20-29] in order to remove the benzyl groups. The third step is removal of the two other benzyl groups and replace them by nitroso, formyl or acetyl groups [20, 24, 30, 32]. In the final step there is a nitration of HNIW precursors [31-37]. The HNIW seems to be a promising explosive and it can replace other currently used energetic materials. However, using HNIW is limited due to the complicated and expensive technology of its production. Therefore, research groups carried out new syntheses of HNIW to eliminated these problem. In this article, review of the literature on the physicochemical properties and synthetic methods for HNIW were presented. The basic physical and explosive parameters of HNIW were summarized. The spatial structure was presented and polymorphs of HNIW were characterized. The methods for obtaining HNIW and intermediate products needed for its preparation were described. The methods of preparation of different HNIW polymorphs were also given.

Słowa kluczowe

PL

Cl-20; HNIW; synteza; właściwości chemiczne; właściwości wybuchowe

EN

CL-20; HNIW; synthesis; chemical properties; explosive properties

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Wiadomości Chemiczne
• Rocznik: 2013
• Tom: [Z] 67, 1-2
• Strony: 93--109
• Opis fizyczny: Bibliogr. 56 poz., rys., schem., tab.

Twórcy

autor

Borkowski J.

• Wojskowy Instytut Techniczny Uzbrojenia, Zakład Badań Środków Bojowych, ul. Prym. St. Wyszyńskiego 7, 05-220 Zielonka

autor

Czerwińska M.

• Wojskowy Instytut Techniczny Uzbrojenia, Zakład Badań Środków Bojowych, ul. Prym. St. Wyszyńskiego 7, 05-220 Zielonka

Bibliografia

• [1] A. Koutsospyros, C. Christodoulatos, N. Panikov, O. Malcheva, P. Karakaya, S. Nicolich, Water. Air. Soil Pollut., 2004, 4, 459.
• [2] A.E.D.M. Van der Heijden, R.H.B. Bouma, Cryst. Growth Des., 2004, 4(5), 999.
• [3] M. Qasim, B. Flemming, L. Hansen, Proc. of Current Trends Computers in Chem., 2001, 184.
• [4] R.L. Simpson, P.A. Urtiew, D.L. Ornellas, G.L. Moody, K.J. Scribner, D.M. Hoffman, Propell. Explos. Pyrot., 1997, 22, 249.
• [5] S. Cudziło, A. Maranda, J. Nowaczewski, R. Trębiński, W. Trzciński, Wojskowe materiały wybuchowe, Wyd. Politech. Częstoch., 2000.
• [6] www.detonator.com, 2006.
• [7] M.F. Foltz, C.L. Coon, F. Gracia, A.L. Nichols III, Propell. Explos. Pyrot., 1994, 19, 19.
• [8] T.P. Russell, P.J. Miller, G.J. Piermarini, S. Block, J. Phys. Chem., 1992, 96(13), 5509.
• [9] T.P. Russell, P.J. Miller, G.J. Piermarini, S. Block, J. Phys. Chem., 1993, 97, 1993.
• [10] J. Lin, T.B. Brill, Propell. Explos. Pyrot., 2007, 32, 326.
• [11] V. Thome, P.B. Kempa, M. Herrman, Proc. 32nd Int. Annual conference of ICT, Karlsruhe, 2007, 157/1.
• [12] E.H. Johnston, R.W. Eugene, US Patent 5874574 A, 1999.
• [13] U.R. Nair, R. Sivabalan, G.M. Gore, M. Geetha, S.N. Asthana, H. Singh, Combust. Explo. Shock+, 2005, 41(2), 121.
• [14] J.A. Ciezak, T.A. Jenkins, Z. Liu, Propell. Explos. Pyrot., 2007, 32(6), 472.
• [15] D.C. Sorescu, B.M. Rice, D.L. Thompson, J. Phys.Chem., 1999, 103, 989.
• [16] A.T. Nielsen, M.L. Chan, K.J. Kraeutle, C.K. Lowe-Ma, R.A. Hollins, M.P. Nadler, R.A. Nissan, W.P. Norris, D.J. Vanderah, R.Y. Yee, NWC-TP-8020, 1989.
• [17] N.V. Chukanov, B.L. Korsounskii, T.S. Larikova, V.V. Nadelko, 30th Int. Ann. Conf. ICT, Karlsruhe, 1999, 64.
• [18] J. Li, T.B. Brill, Propell. Explos. Pyrot., 2007, 32(4), 326.
• [19] J.J. Tan, G.F. Ji, X.R. Chen, Z. Li, Physica B, 2011, 406, 2925.
• [20] A.T. Nielsen, R.A. Nissan, D.J. Vanderah, Tetrahedron, 1998, 54(39), 11793.
• [21] J. Huiping, X. Yongjiang, et all, , Energetic Materials, 1999, 42(2).
• [22] A.T. Nielsen, A.P. Chafin, R.A. Nissan, D.J. Vanderah, et. all., J. Org. Chem., 1990, 55(5), 1459.
• [23] A.L. Cambell, D.R. Pilipausleas, I.K. Khama, R.A. Rhodes, Tetrahedron Lett., 1987, 28(21), 2331.
• [24] T. Kodama, M. Tojo, M. Ikeda, PCT Int. Appl., 1996, WO 23, 792.
• [25] T. Kodama, Japanese Patents, JP 06321962, C.A.122, 265409j, 1995.
• [26] R.B. Wardle, W.W. Edwards, PTC Patents, WO 20785, Thiokol, 1997.
• [27] T. Kodama, N. Ishihara, H. Minoura, N. Mijake, S. Yamamatsu, PCT Japanese Patents, JP 004644, WIPO Patents Application WO 019328, 1999.
• [28] P. Bescond, H. Graindorge, H. Mace, European Patents EP 913374 A1, Poudres and Explosifs, 1998.
• [29] J.A. Bellamy, Tetrahedron, 1995, 51(16), 4711.
• [30] R.B. Wardle, W.W. Edwards, US Patents 5739325, 1998.
• [31] Y. Ou, Y. Xu, B. Chen, L. Liu, C. Wang, 26th Int. Pyrotech. Semin., 1999, 406.
• [32] A.J. Belamy, P. Goede, N.V. Latypov, U. Wellmar, Org. Process Res. Dev., 2000, 4(3), 156.
• [33] P. Maksimowski , A. Fabijańska , J. Adamiak, Propell. Explos. Pyrot., 2010, 35, 353.
• [34] A.J. Sanderson, K. Warner, R.B. Wardle, Alliant Techsystems Inc., WIPO Patent Application, WO 052011, 2000.
• [35] R.B. Wardle, J.C. Hinshaw, Cordant Technologies Inc., US 6,147,209, 2000.
• [36] S. Rao, D. Reddy, D. Rajagopal, et.all., 31st Int. Ann. Conf. ICT, Karlsruhe, 2000, 108/1.
• [37] H.Y. Chung , H.S. Kil, I. Choi, et.all., J. Heterocycl. Chem., 2000, 37(6), 1647.
• [38] W.G. Qiu, S.S. Chen, Y.Z. Yu, Chin. J. Chem., 1999, 17(5), 554.
• [39] M. Duda, praca dyplomowa, Politech. Warszawska, 2002.
• [40] Y. Ou, H. Jia, Y. Xu, B. Chen, G. Fan, L. Liu, F.P. Zheng, Z. Pan, C. Wang, Sci. China, Ser. B, 1999, 42(2), 217.
• [41] A.T. Nielsen, US Patent 5693794, 1997.
• [42] C. Wang, Y. Ou, B. Chen, Beijing Ligong Daxue Xuebao, 2000, 20 (4), 521.
• [43] Y.X. Ou, Y.J. Xu, B.R. Chen, L.H. Liu, C. Wang, Chin. J. Org. Chem., 2000, 20(4), 556.
• [44] R.S. Hamilton, A.J. Sanderson, R.B. Wardle, K.F. Warner, 31st Int. Ann. Conf. ICT, Karlsruhe, 2000, 21/1.
• [45] A.J. Bellamy, Combust. Explo. Shock+, 2005, 109/1.
• [46] S. Jin, Q. Shu, S. Chen, Y. Shi, Propell. Explos. Pyrot., 2007, 32(6), 468.
• [47] J.Q. Liu, S.H. Jin, Q.H. Shu, H.X. Lu, Chin. J. Energ. Mater., 2006, 14(5), 346.
• [48] S. Kawabe, H. Miya, T. Kodama, N. Miyake, PCT Int. Appl., WO 9805666 A1, 1998.
• [49] A.J. Sanderson, K.F. Warner, R.B. Wardle, PCT Int. Appl., WO 2000052011, 2000.
• [50] S. Torry, A. Cunliffe, 31st Int. Ann. Conf. ICT, Karlsruhe, 2000, 107/1.
• [51] R.G. Duddu, P.R. Dave, US Patent 6,015,898, 2000.
• [52] J.Q. Liu, Y.X. Ou, Y.F. Wang, Z. Meng, X.G. Wu, Binggong Xuebao/Acta Armamentarii, 2007, 28(1), 122.
• [53] S.H. Jin, M.C. Zhai, J.Q. Liu, C.M. Zheng, S.S. Chen, Q.C. Song, Hanneng Cailiao/ Chin. J. Energ. Mater., 2006, 14(3), 165.
• [54] P. Bescond, H. Graindorge, H. Mace, US Patent 5973149, 1999.
• [55] A.K. Mandal, C.S. Pant, S.M. Kasar, T. Soman, J. Energ. Mater, 2009, 27, 231.
• [56] R. Meyer, J. Kohler, A. Homburg, Explosives, Sixth Edition, Wiley-VCH, 2007.