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Synthesis and Characterization of the Energetic Compounds Aminoguanidinium-, Triaminoguanidiniumand Azidoformamidinium Perchlorate

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Języki publikacji
EN
Abstrakty
EN
Aminoguanidinium perchlorate (2, AGClO4) was formed by the reaction of aminoguanidinium bicarbonate (1) with aqueous perchloric acid solution. Triaminoguanidinium perchlorate (3, TAGClO4) was synthesized by nucleophilic attack of aqueous hydrazine solution on aminoguanidinium perchlorate under release of ammonia. The new and highly explosive azidoformamidinium perchlorate (4, AFClO4) was formed by the reaction of aminoguanidinium perchlorate with potassium nitrite under acidic conditions. The structures of the perchlorate salts in the crystalline state were determined using low temperature single crystal X-ray diffraction yielding monoclinic as well as orthorhombic structures. The compounds were characterized comprehensively using vibrational spectroscopy (IR and Raman), multinuclear (1H, 13C and 15N) NMR spectroscopy, elemental analysis and mass spectrometry. The thermal behavior as well as the decompositions were investigated using DSC (differential scanning calorimetry) and the heats of formation were calculated using heats of combustion determined by bomb calorimetric measurements. In addition, the sensitivities were evaluated using BAM methods (drophammer and friction tester), whereby the perchlorate salts are all sensitive towards impact as well as friction.
Słowa kluczowe
Rocznik
Strony
13--30
Opis fizyczny
Bibliogr. 35 poz.
Twórcy
  • Department Chemistry and Biochemistry, Energetic Materials Research, Ludwig-Maximilian University of Munich, Butenandtstr. 5-13, D-81377 Munich, Germany, tmk@cup.uni-muenchen.de
Bibliografia
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  • [3] a) Urbansky E.T., Perchlorate as an Environmental Contaminant, Environmental Science and Polluting Research International, 2002, 9(3), 187-192. b) Hershman J.M., Perchlorate and Thyroid Function: What are the Environmental Issues?, Thyroid, 2005, 15(5), 427-431. c) Siglin C.J., Mattie D.R., Dodd D.E., Hildebrandt P.K., Baker W.H., A 90-day Drinking Water Toxicity Study in Rats of the Environmental Contaminant Ammonium Perchlorate, Toxicological Sciences, 2000, 57(1), 61-74.
  • [4] Köhler J., Mayer R., Explosivstoffe, VCH Verlagsgesellschaft, Weinheim, 9. Aufl., 1998, pp. 66-67.
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  • [6] a) Choi C.S., Prask H.J., Prince E., Crystal Structure of Ammonium Perchlorate AT 298, 78, and 10 Deg. K by Neutron Diffraction, J. Phys. Chem., 1974, 61(9), 3523-3529. b) Peyronel G., Pignedoli A., Three-Dimensional X-Ray Redetermination of the Crystal Structure of Ammonium Perchlorate, Acta Cryst., 1975, B32, 2052-2056. c) Choi C. S., Prask H.J., Ammonium Perchlorate: Reinvestigation of the Crystal Structure at 298 K, Acta Cryst., 1976, B32, 2919-2920.
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  • [11] a) Galvez-Ruiz J.C., Holl G., Karaghiosoff K., Klapötke T.M., Löhnwitz K., Mayer P., Nöth H., Polborn K., Rohbogner C.J., Suter M., Weigand J.J., Derivatives of 1,5-Diamino-1H-Tetrazole: A New Family of Energetic Heterocyclic-Based Salts, Inorg. Chem., 2005, 44, 4237-4253. b) Butler R.N., Duffy J.P., Bhradaigh E.P.N., McArdle P., Cunningham D., N-Methyl Quaternization of 2,5-Diaryltetrazoles and Reaction of the Tetrazolium Salts with Ethoxide Base, J. Chem. Res., 1994, 6, 216-217. c) Karaghiosoff K., Klapötke T.M., Mayer P., Sabate C.M., Penger A., Welch J.M., Energetic Salts of Methylated Aminotetrazoles, Inorg. Chem., 2007, in press.
  • [12] a) Pajak Z., Grottel M., Koziol A.E., Crystal Structure and Molecular Dynamics of Guanidinium Perchlorate, J. Chem. Soc., Faraday Trans., 2, 1982, 78, 1529-1538. b) Koziol A.E., Z. Kristallogr., 1984, 168(1-4), 313-315.
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  • [14] Martin A., Pinkerton A.A., Two Energetic Ionic Materials: The Biguanidium Perchlorates, Acta Cryst. C., 1996, 52, 1048-1052.
  • [15] AGClO4: Sauermilch W., Triaminoguanidine Nitrate, A Multilateral Effective Explosive. Explosivstoffe, 1964, 12(9), 197-199; TAGClO4: a) Matyushin Yu. N., Kon’kova T.S., Titova K.V., Rosolovskii V.Ya., Lebedev Yu.A., Enthalpies of Formation of Triaminoguanidinium Chloride, Nitrate, and Perchlorate, Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1982, 3, 498-501. b) Bedell S. F., U.S. patent, 1966, US 3293853.
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  • [22] Crystallographic data for the structure(s) have been deposited with the Cambridge Crystallographic Data Centre. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: int.code_(1223)336-033; e-mail for inquiry: fileserv@ccdc.cam.ac.uk; e-mail for deposition: deposit-@ccdc.cam.ac.uk).
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  • [24] Akella A., Keszler D.A., Aminoguanidinium Nitrate, ibid., 1994, C50, 1974-1976.
  • [25] Wiberg N., in: Lehrbuch der Anorganischen Chemie / Holleman-Wiberg, 101. Ed., de Gruyter, Berlin, 1995, p. 1842.
  • [26] a) Okaya Y., Pepinsky R., Crystal Structure of Triaminoguanidinium Chloride, (NH2.NH)3CCl, Acta Cryst., 1957, 10, 681-684. b) Bracuti A.J., Structure Refinement of 1,2,3-Triaminoguanidinium Chloride, CH9N6 +Cl-, ibid., 1983, C39, 1465-1467.
  • [27] Bracuti A.J., Crystal Structure of 1,2,3-Triaminoguanidinium Nitrate, ibid., 1979, B35, 760-761.
  • [28] Klapötke T.M., in: Moderne Anorganische Chemie, E. Riedel (Hrsg.), 2. Aufl., Walter de Gruyter, Berlin, New York 2003, pp. 84-86.
  • [29] Müller U., Bärnighausen H., Crystal Structure of Triazidocarboniumhexachloro-Antimonate, [C(N3)3]SbCl6, Acta Cryst., 1970, 26(B), 1671-1679.
  • [30] a) Geißler P., Klapötke T.M., Kroth H.J., 14N NMR Spectra of Covalent Halogen and Arsenic Azides: XN3 (X = Cl, Br, I), (CH3)nAs(N3)3-n (n = 0, 1, 2) and [As(N3)4]+, Spectroch. Acta., 1995, Part A, 51A(6), 1075-1078. b) Göbel M., Karaghiosoff K., Klapötke T.M., The First Structural Characterization of a Binary P-N Molecule: The Highly Energetic Compound P3N21, Angew. Chem., 2006, 118(3), 6183-6186; Angew, Chem. Int. Ed., 2006, 45, 6037-6040.
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  • [32] http://www.parrinst.com
  • [33] Impact: Insensitive > 40 J, less sensitive ≥ 35 J, sensitive ≥ 4, very sensitive ≤ 3 J; friction: Insensitive > 360 N, less sensitive = 360 N, sensitive < 360 N a. > 80 N, very sensitive ≤ 80 N, extreme sensitive ≤ 10 N; According to the UN Recommendations on the Transport of Dangerous Goods.
  • [34] http://www.bam.de/
  • [35] Geisberger G., Klapötke T.M., Stierstorfer J., Copper Bis(1-methyl-5-nitriminotetrazolate): A Promising New Primary Explosive, Eur. J. Inorg. Chem., 2007, 30, 4743-4750.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BAT1-0034-0041
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