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Primary Explosives pp 157–166Cite as

Diazodinitrophenol

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Abstract

The 2-diazo-4,6-dinitrophenol (dinol, diazol, DDNP, DDNPh, or DADNPh) is the first-ever synthesized diazonium compound. Its synthesis is attributed to Griess [1] who prepared it by introducing nitric oxides into an alcoholic solution of 2-amino-4,6-dinitrophenol (picramic acid) [1, 2]. Its explosive character was, however, first reported more than 30 years later in 1892 by Lenze [3].

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References

  1. Griess, P.: Vorläufige Notiz über die Einwirkung von salpetriger Säure auf Aminitrophenylsäure. Annalen der Chemie und Pharmacie 106, 123–125 (1858)

    Article  Google Scholar 

  2. Griess, P.: Ueber eine neue Klasse organischer Verbindungen, welche Wasserstoff durch Stickstoff vertreten enthalten. Annalen der Chemie und Pharmacie 113, 200–217 (1860)

    Google Scholar 

  3. Urbański, T.: Chemie a technologie výbušin. SNTL, Praha (1959)

    Google Scholar 

  4. Bagal, L.I.: Khimiya i tekhnologiya iniciiruyushchikh vzryvchatykh veshchestv. Mashinostroenie, Moskva (1975)

    Google Scholar 

  5. Lowe-Ma, C.K., Nissar, R.A., Wilson, W.S.: Diazophenols – their structure and explosive properties, report AD-A197439. Naval Weapons Centrum, China Lake, USA (1987)

    Google Scholar 

  6. Holl, G., Klapötke, T.M., Polborn, K., Rienäcker, C.: Structure and bonding in 2-dizo-4,6-dinitrophenol (DDNP). Propellants, Explosives, Pyrotechnics 28, 153–156 (2003)

    Article  CAS  Google Scholar 

  7. Clark, L.V.: Diazodinitrophenol, a detonating explosive. J. Ind. Eng. Chem. 25, 663–669 (1933)

    Article  CAS  Google Scholar 

  8. Fedoroff, B.T., Sheffield O.E., Kaye S.M.: Encyclopedia of Explosives and Related Items. Picatinny Arsenal, New Jersey (1960–1983)

    Google Scholar 

  9. Meyer, R., Köhler, J., Homburg, A.: Explosives. Wiley-VCH Verlag GmbH, Weinheim (2002)

    Book  Google Scholar 

  10. Špičák, S., Šimeček, J.: Chemie a technologie třaskavin. Vojenská technická akademie Antonína Zápotockého, Brno, Czechoslovakia (1957)

    Google Scholar 

  11. Danilov, J.N., Ilyusin, M.A., Tselinsky, I.V.: Promyshlennye vzryvchatye veshchestva; chast I. Iniciiruyushchie vzryvshchatye veshchestva. Sankt-Peterburgskii gosudarstvennyi tekhnologicheskii institut, Sankt-Peterburg (2001)

    Google Scholar 

  12. Lowe-Ma, C.K., Nissan, R.A., Wilson, W.S., Houk, K.N., Wang, X.: Structure of diazophenols: 13C NMR spectroscopy, and molecular orbital studies. J. Chem. Res. (S), 214–215 (1988)

    Google Scholar 

  13. Urbański, T.: Chemistry and Technology of Explosives. PWN – Polish Scientific Publisher, Warszawa (1967)

    Google Scholar 

  14. Ficheroulle, H., Kovache, A.: Contribution à l`étude des explosifs d'amorçage. Mémorial des pouders 31, 7–27 (1949)

    CAS  Google Scholar 

  15. Military explosives. Report TM 9-1300-214, Washington DC (1984)

    Google Scholar 

  16. Dehn, W.M.: Process of increasing the sensitiveness and power of explosive compositions and product thereof. US Patent 1,428,011, 1922

    Google Scholar 

  17. Yamamoto, K.: Primary explosives. VIII. Photolysis of diazodinitrophenol. Chem. Abstr. 64, 3273d; CAN 3264:26627 (1966)

    Google Scholar 

  18. Kaiser, M., Ticmanis, U.: Thermal stability of diazodinitrophenol. Thermochim. Acta 250, 137–149 (1995)

    Article  CAS  Google Scholar 

  19. Tomlinson, W.R., Sheffield, O.E.: Engineering design handbook, explosive series of properties explosives of military interest. Report AMCP 706-177 (1971)

    Google Scholar 

  20. John, H.J., Yeager, C., Pile, D., Webb, T.: Non-toxic primer mix. US Patent 6,478,903 B1, 2002

    Google Scholar 

  21. Matyáš, R., Šelešovský, J., Musil, T.: Sensitivity to friction for primary explosives. J. Hazard. Mater. 213–214, 236–241 (2012)

    Google Scholar 

  22. Davis, T.L.: The Chemistry of Powder and Explosives. Wiley, New York (1943)

    Google Scholar 

  23. Henkin, H., McGill, R.: Rates of explosive decomposition of explosives. Ind. Eng. Chem. 44, 1391–1395 (1952)

    Article  CAS  Google Scholar 

  24. Garfield, F.M., Dreher, H.W.: Manufacture of diazodinitrophenol. US Patent 2,408,059, 1946

    Google Scholar 

  25. Strnad, J.: Primary explosives and pyrotechnics – lecture notes. Institute of Energetic Materials, University of Pardubice, Pardubice (1999)

    Google Scholar 

  26. Strnad, J.: Iniciační vlastnosti nejpoužívanějších třaskavin a vývoj nových metodik jejich měření. Dissertation thesis, Institute of Chemical Technology, Pardubice (1972)

    Google Scholar 

  27. Alexander, H.B.: Method of producing diazodinitrophanol and product thereof. US Patent 2,103,926, 1937

    Google Scholar 

  28. Hancock, R.S., Pritchett, L.C.: Method for producing diazodinitrophenol. US Patent 1,952,591, 1934

    Google Scholar 

  29. Babcock, L.W., Kenvil, N.J.: Diazodinitrophenol and the method of the preparation of the same. US Patent 2,155,579, 1939

    Google Scholar 

  30. Urbański, T., Szyc-Lewańska, K., Bednarczyk, M., Ejsmund, J.: On formation of 2,4-dinitro-6-diazoxide by oxidation of picramic acid. Bulletin de l'Académie polonaise des sciences Séries des sciences chimiques 8, 587–590 (1960)

    Google Scholar 

  31. Kaiser, H.E.: Percussion cap. US Patent 1,852,054, 1932

    Google Scholar 

  32. Lopata, F.G., Mei, G.C.: Non-toxic, non-corrosive rimfire cartridge. US Patent 4,674,409, 1987

    Google Scholar 

  33. Burns, J.E.: Ammunition. US Patent 1,862,295, 1932

    Google Scholar 

  34. Hagel, R., Redecker, K.: Sintox – a new, non-toxic primer composition by Dynamit Nobel AG. Propellants, Explosives, Pyrotechnics 11, 184–187 (1986)

    Article  CAS  Google Scholar 

  35. Jung, S.M., Lee, H.S., Son, J.W., Pak, C.H.: Non-toxic primer powder compositions for small-caliber ammunition. US Patent S 2005 224147, 2005

    Google Scholar 

  36. Tsukii, T., Kikuchi, S.: Explosive for riveting. Chem Abst 49, 10628 (1955)

    Google Scholar 

  37. Fronabarger, J.W., Williams, M.D.: Lead-free primers. US Patent 2009/0223401, 2009

    Google Scholar 

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  1. Faculty of Chemical Technology, University of Pardubice, Pardubice, Czech Republic

    Robert Matyáš & Jiří Pachman

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  1. Robert Matyáš
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  2. Jiří Pachman
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Matyáš, R., Pachman, J. (2013). Diazodinitrophenol. In: Primary Explosives. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-28436-6_6

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