Abstract
Tetrazoles are chemical compounds characterized by a doubly unsaturated five-membered ring containing four nitrogen atoms and one carbon atom. The tetrazole ring usually exists in two tautomeric forms, 1H and 2H:
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsReferences
Fedoroff, B.T., Sheffield, O.E., Kaye, S.M.: Encyclopedia of Explosives and Related Items. Picatinny Arsenal, New Jersey (1960–1983)
Bagal, L.I.: Khimiya i tekhnologiya iniciiruyushchikh vzryvchatykh veshchestv. Mashinostrojenije, Moskva (1975)
Matushin, Y.N., Lebedev, V.P.: Thermochemical properties of mononitroderivates of azoles and oxadiazoles. In: Proceedings of 28th International Annual Conference of ICT, pp. 98/1–98/10, Karlsruhe, 1997
Bates, L.R., Jenkins, J.M.: Search for new detonators. In: Proceedings of International Conference on Research in Primary Explosives, pp. 14/1–14/18, Waltham Abbey, England, 1975
Chen, Z.X., Xiao, H., Yang, S.: Theoretical investigation on the impact sensitivity of tetrazole derivates and their metal salts. Chem. Phys. 250, 243–248 (1999)
Haskins, P.J.: Electronic structure of some explosives and its relationship to sensitivity In: Jenkins, J.M., White, J.R. (eds.) International Conference on Research of Primary Explosives, vol. 1, pp. 6/1–6/28, Waltham Abbey (1975)
Avanesov, D.C.: Praktikum po fiziko-khimicheskim icpytaniyam vzryvchatykh veshchectv. Gosudarstbennoe izdatelstvo oboronnoi promyshlennosti, Moskva (1959)
Ilyushin, M.A., Tselinskii, I.V., Sudarikov, A.M.: Razrabotka komponentov vysokoenergicheskikh kompozitsii. SPB:LGU im. A. S. Pushkina – SPBGTI(TU), Sankt-Peterburg (2006)
Hoffman, K.A., Roth, R.: Aliphatische Diazosalze. Berichte der deutschen chemischen Gesellschaft 43, 682–688 (1910)
Patinkin, S.H., Horwitz, J.P., Lieber, E.: The structure of tetracene. J. Am. Chem. Soc. 77, 562–567 (1955)
Duke, J.R.C.: X-ray crystal and molecular structure of “tetrazene”, (“tetracene”), C2H8N10O. Chem. Commun. 1, 2–3 (1971)
Davis, T.L.: The Chemistry of Powder and Explosives. Wiley, New York (1943)
Krauz, C.: Technologie výbušin. Vědecko-technické nakladatelství, Praha (1950)
Špičák, S., Šimeček, J.: Chemie a technologie třaskavin. Vojenská technická akademie Antonína Zápotockého, Brno (1957)
Rinkenbach, W.H., Burton, O.E.: Explosive characteristics of tetracene. Army Ordonance 12, 120–123 (1931)
Meyer, R., Köhler, J., Homburg, A.: Explosives. Wiley-VCH, Weinheim (2002)
Danilov, J.N., Ilyushin, M.A., Tselinskii, I.V.: Promyshlennye vzryvchatye veshchestva; chast I. Iniciiruyushchie vzryvshchatye veshchestva. Sankt-Peterburgskii gosudarstvennyi tekhnologicheskii institut, Sankt-Peterburg (2001)
Urbański, T.: Chemistry and Technology of Explosives. Pergamon, Oxford (1984)
Wallbaum, R.: Sprengtechnische Eigenschaften und Lagerbeständigkei der wichtigsten Initialsprengstoffe. Zeitschrift für das gesamte Schiess- und Sprengstoffwesen 34, 161–163 (1939)
Tomlinson, W.R., Sheffield, O.E.: Engineering Design Handbook, Explosive Series of Properties Explosives of Military Interest. Report AMCP 706-177, 1971
Matyáš, R., Šelešovský, J., Musil, T.: Sensitivity to friction for primary explosives. J. Hazard. Mater. 213–214, 236–241 (2012)
Urbański, T.: Chemistry and Technology of Explosives. PWN—Polish Scientific Publisher, Warszawa (1967)
Lieber, E., Smith, G.B.L.: The chemistry of aminoguanidine and related substances. Chem. Rev. 25, 213–271 (1939)
Hagel, R., Redecker, K.: Sintox—a new, non-toxic primer composition by Dynamit Nobel AG. Propellants Explosives Pyrotechnics 11, 184–187 (1986)
Brede, U., Hagel, R., Redecker, K.H., Weuter, W.: Primer compositions in the course of time: From black powder and SINOXID to SINTOX compositions and SINCO booster. Propellants Explosives Pyrotechnics 21, 113–117 (1996)
Nesveda, J., Brandejs, S., Jirásek K.: Non toxic and non-corrosive ignition mixtures. WO Patent 01/21558, 2001
Whelan, D.J., Spear, R.J., Read, R.W.: The thermal decomposition of some primary explosives as studied by differential scanning calorimetry. Thermochim. Acta 80, 149–163 (1984)
Mihina, J.S., Herbst, R.M.: The reaction of nitriles with hydrazonic acid: Synthesis of monosubstituted tetrazoles. J. Org. Chem. 15, 1082–1092 (1950)
Thiele, J.: Ueber Nitro- und Aminoguanidin. Justus Liebigs Annalen der Chemie 270, 1–63 (1892)
Bates, L.R., Jenkins, J.M.: Salts of 5-Substituted Tetrazole: Part 2: Metallic Salts and Complexes of Tetrazole 5-Aminotetrazole, 5-Phenyltetrazole, and 5-Methyltetrazole. Report AD 727350. Explosives Research and Development Establishment, Waltham Abbey (1970).
Taylor, F.: Primary Explosive Research. Report NAVORD 2800, Naval Ordinance, 1953
Benson, F.R.: The chemistry of the tetrazoles. Chem. Rev. 41, 1–61 (1947)
Hantzsch, A., Vagt, A.: Ueber das sogenannte Diazoguanidin. Justus Liebigs Annalen der Chemie 314, 339–369 (1901)
Arient, J., Vobořil, I.: Způsob přípravy 5-aminotetrazolu. CS Patent 190,055, 1979
Stollé, R.: Zur Kenntnis des Amino-5-tetrazols. Berichte der deutschen chemischen Gesellschaft 62, 1118–1126 (1929)
Stollé, R., Schick, E.: Verfahren zur Darstellung von Aminotetrazol. DE Patent 426,343, 1926
Daugherty, N.A., Brubaker, C.H.J.: Complexes of copper(II) and some 5-substituted tetrazoles. J. Am. Chem. Soc. 83, 3779–3782 (1961)
Rittenhouse, C.T.: Di-silver aminotetrazole perchlorate. US Patent 3,663,553, 1972
Karaghiosoff, K., Klapötke, T.M., Sabaté, C.M.: Energetic silver salt with 5-aminotetrazole ligands. Chemistry 15, 1164–1176 (2009)
Bates, L.R., Jenkins, J.M.: Production of 5-nitrotetrazole salts. US Patent 4,094,879, 1978
Bates, L.R., Jenkins, J.M.: Improvements in or relating to production of 5-nitrotetrazole salts. GB Patent 1,519,796, 1978
Bates, L.R.: The potential of tetrazoles in initiating explosives systems. In: Proceedings of 13th Symposium on Explosives and Pyrotechnics, pp. III1–III10, 1986
Koldobskii, G.I., Soldatenko, D.S., Gerasimova, E.S., Khokhryakova, N.R., Shcherbinin, M.B., Lebedev, V.P., Ostrovskii, V.A.: Tetrazoles: XXXVI. Synthesis, structure, and properties of 5-nitrotetrazole. Russ. J. Org. Chem. 33, 1771–1783 (1997)
Khmelnitskii, L.I.: Spravochnik po vzryvchatym veshchestvam. Voennaya ordena Lenina i ordena Suvorova Artilleriiskaya inzhenernaya akademiya imeni F. E, Dzerzhinskogo, Moskva (1962)
Herz, E.: C-nitrotetrazole compounds. US Patent 2,066,954, 1937
Gilligan, W.H., Kamlet, M.J.: Synthesis of Mercuric 5-nitrotetrazole. Report NSWC/WOL TR 76-146. Navel Surface Weapons Center, Silver Spring, MD (1976)
Hirlinger, J., Fronabarger, J., Williams, M., Armstrong, K., Cramer, R.J.: Lead azide replacement program. In: Proceedings of NDIA, Fuze Conference, Seattle, Washington, April 5-7, 2005
Fronabarger, J., Sanborn, W.B., Bichay, M.: An investigation of some alternatives to lead based primary explosive. In: Proceedings of 37th AIAA 2001-3633; Joint Propulsion Conference and Exhibit, pp. 1–9, Salt Lake City, Utah, 2001
Fronabarger, J.W., Williams, M.D., Sanborn, W.B.: Lead-free primary explosive composition and method of preparation. US Patent 2009/0069566 A1, 2009
Fronabarger, J.W., Williams, M.D., Sanborn, W.B.: Lead-free primary explosive composition and method of preparation. WO Patent 2008/048351 A2, 2008
Klapötke, M., Sabaté, C.M., Welch, J.M.: Alkali metal 5-nitrotetrazolate salts: prospective replacements for service lead(II) azide in explosive initiators. Dalton Trans. 6372–6380 (2008)
Millar, R.W.: Lead-free Initiator Materials for Small Electro-explosive Devices for Medium Caliber Munitions. Report QinetiQ/FST/CR032702/1.1, QINETIQ Ltd, Farnborough, 2003
Harris, A.D., Herber, R.H., Jonassen, H.B., Wertheim, G.K.: Complexes of iron(II) and some 5-substituted tetrazoles. J. Am. Chem. Soc. 85, 2927–2930 (1963)
Brown, M.E., Swallowe, G.M.: The thermal decomposition of the silver(I) and mercury(II) salts of 5-nitrotetrazole and of mercury(II) fulminate. Thermochim. Acta 49, 333–349 (1981)
Blay, N.J., Rapley, R.J.: The testing of primary explosives for stability and compatibility In: Jenkins, J.M., White, J.R. (eds.) Proceedings of the International Conference on Research in Primary Explosives, vol. 3, pp. 20/1–20/19, Waltham Abbey (1975)
Redman, L.D., Spear, R.J.: Mercuric 5-Nitrotetrazole, a Possible Replacement for Lead Azide in Australian Ordnance. Part 1. An Assessment of Preparation Methods. Report MRL-R-901, Department of Defense, Material Research Laboratories, Ascot Vale, 1983
Klapötke, M., Sabaté, C.M.: Less sensitive transition metal salts of the 5-nitrotetrazolate anion. Cent. Eur. J. Energetic Mater. 7, 161–173 (2010)
Lee, K., Coburn, M.D.: Binary eutectics formed between ammonium nitrate and amine salts of 5-nitrotetrazole I. Preparation and initial characterization. J. Energetic Mater. 1, 109–122 (1983)
Scott, C.L.: Mercuric 5-nitrotetrazole as a lead azide replacement. In: Proceedings of the International Conference on Research in Primary Explosives, vol. 2, pp 15/1-15/23 Waltham Abbey, (1975)
Hirlinger, J.M.: Investigating alternative “green” primary explosives. In: Proceedings of NDIA 39th Annual Gun & Ammunition Missiles & Rockets Conference & Exhibition, Baltimore, MD, 2004
Gilligan, W.H., Kamlet, M.J.: Method of preparing the acid copper salt of 5-nitrotetrazole. US Patent 4,093,623, 1978
Hirlinger, J.M., Bichay, M.: New Primary Explosives Development for Medium Caliber Stab Detonators. Report SERDP PP-1364, US Army ARDEC, 2004
Talawar, M.B., Agrawal, A.P., Asthana, S.N.: Energetic co-ordination compounds: Synthesis, characterization and thermolysis studies on bis-(5-nitro-2H-tetrazolato-N 2)tetraammine cobalt(III) perchlorate (BNCP) and its new transition metal (Ni/Cu/Zn) perchlorate analogues. J. Hazard. Mater. 120, 25–35 (2005)
Spear, R.J., Elischer, P.P.: Studies of stab initiation. Sensitization of lead azide by energetic sensitizers. Aust. J. Chem. 35, 1–13 (1982)
Lee, K., Coburn, M.D.: Ethylenediamine salt of 5-nitrotetrazole and preparation. US Patent 4,552,598, 1985
McGuchan, R.: Improvements in primary explosive compositions and their manufacture. In: Proceedings of 10th Symposium on Explosives and Pyrotechnics, San Francisco, 1979
Glover, D.J.: Analysis of Mercuric 5-nitrotetrazole. Report NSWC/WOL/TR 77-71. Naval Surface Weapon Center, Silver Spring, MD (1977)
Fronabarger, J.W., Williams, M.D.: Preparation of lead-free primary explosive. US Patent 2010/0280254 A1, 2010
Scott, C., Leopold, H.S.: Single chemical electric detonator. US Patent 3,965,951, 1976
Tompa, A.S.: Thermal stability of an explosive detonator. Thermochim. Acta 80, 367–377 (1984)
Scott, C.L., Leopold, H.S.: Stab-initiated explosive device containing a single explosive charge. US Patent 4,024,818, 1977
Duguet, J.: Priming composition which is sensitive to percussion and a method for preparing it. US Patent 4,566,921, 1986
Hagel, R., Bley, U.: Anzündmittel. DE Patent 10,221,044, 2002
Piechowicz, T.: Les explosifs d`amorcage nouveaux et leurs applications spatiales. In: Proceedings of Utilisation des éléments pyrotechniques et explosifs dans les systèmes spatiaux; Colloque International, pp. 99–104, Tarbes, 1968
Henry, R.A., Finnegan, W.G.: An improved procedure for the deamination of 5-aminotetrazole. J. Am. Chem. Soc. 76, 290–291 (1954)
Taylor, G.W.C., Jenkins, J.M.: Progress toward primary explosives on improved stability. In: Proceedings of 3rd Symposium on Chemical Problems Connected with the Stability of Explosives, pp. 43–46, Ystad, 1973
Stierstorfer, J., Klapötke, T.M., Hammerl, A., Chapman, R.D.: 5-Azido-1H-tetrazole—Improved synthesis, crystal structure and sensitivity data. Zeitschrift für anorganische und allgemeine Chemie 634, 1051–1057 (2008)
Lieber, E., Levering, D.R.: The reaction of nitrous acid with diaminoguanidine in acetic acid media. Isolation and structure proof of reaction products. J. Am. Chem. Soc. 73, 1313–1317 (1951)
Friedrich, W.: Spreng- und Zündstoffe. DE Patent 695,254, 1940
Rathsburg, H.: Explosive compound for primers and detonators. US Patent 1,511,771, 1924
Friedrich, W., Flick, K.: Verfahren zur Herstellung von Tetrazylazid bzw. seinen Salzen. DE Patent 719,135, 1942
Marsh, F.D.: Cyanogen azide. J. Org. Chem. 37, 2966–2969 (1972)
Klapötke, T.M., Stierstorfer, J.: The CN -7 anion. J. Am. Chem. Soc. 131, 1122–1134 (2009)
Hammerl, A., Klapötke, T.M., Noth, H., Warchhold, M.: Synthesis, structure, molecular orbital and valence bond calculations for tetrazole azide, CHN7. Propellants Explosives Pyrotechnics 28, 165–173 (2003)
Rathsburg, H.: Initial primers and a process for their manufacture. GB Patent 185,555, 1921
Thiele, J., Ingle, H.: Ueber einige Derivate des Tetrazols. Justus Liebigs Annalen der Chemie 287, 233–265 (1895)
Thiele, J.: Ueber Isocyantetrabromid. Berichte der deutschen chemischen Gesellschaft 26, 2645–2647 (1893)
Thiele, J., Marais, J.T.: Tetrazolderivate aus Diazotetrazotsäure. Justus Liebigs Annalen der Chemie 273, 144–160 (1893)
Hammerl, A., Holl, G., Klapötke, T.M., Mayer, P., Noth, H., Piotrowski, H., Warchhold, M.: Salts of 5,5′-azotetrazolate. Eur. J. Inorg. Chem. 834–845 (2002)
Reddy, G.O., Chatterjee, A.K.: A thermal study of the salts of azotetrazole. Thermochim. Acta 66, 231–244 (1983)
Thiele, J.: Ueber Azo- und Hydrazoverbindungen des Tetrazols. Justus Liebigs Annalen der Chemie 303, 57–75 (1898)
Singh, R.P., Verma, R.D., Meshri, D.T., Shreeve, J.N.M.: Energetic nitrogen-rich salts and ionic liquids. Angew. Chem. 45, 3584–3601 (2006)
Pierce-Butler, M.A.: Structure of bis[hydroxolead(III)] 5,5′-azotetrazolediide. Acta Crystallogr. B 38, 2681–2683 (1982)
Mayants, A.G., Vladimirov, V.N., Razumov, N.M., Shlyanochnikov, V.A.: Razlozhenie solei azotetrazola v kislykh sredakh. Zhurnal organicheskoi khimii 27, 2450–2455 (1991)
Hiskey, M.A., Goldman, N., Stine, J.R.: High-nitrogen energetic materials derived from azotetrazolate. J. Energetic Mater. 16, 119–127 (1998)
Taylor, G.W.C., Thomas, A.T.: Improvements in the manufacture of lead azotetrazole. GB Patent 986,631, 1965
Rathsburg, H.: Manufacture of detonating compositions. US Patent 1,580,572, 1926
Stollé, R., Roser, O.: Abkömmlinge des Amino-5-tetrazols. Journal für praktische Chemie 139, 63–64 (1934)
Friederich, W.: Disruptive or brisant explosive composition. US Patent 2,170,943, 1939
Author information
Authors and Affiliations
Rights and permissions
Copyright information
© 2013 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Matyáš, R., Pachman, J. (2013). Tetrazoles. In: Primary Explosives. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-28436-6_8
Download citation
DOI: https://doi.org/10.1007/978-3-642-28436-6_8
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-28435-9
Online ISBN: 978-3-642-28436-6
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)