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Diazodinitrophenol : ウィキペディア英語版
Diazodinitrophenol

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Diazodinitrophenol (DDNP) was the first diazo compound produced; it was subsequently used to make dyes and explosives. It forms yellow crystals in pure form; however, the color of impure forms may vary from dark yellow to green to dark brown.〔Robert Matyáš and Jiří Pachman, ''Primary Explosives'' (Berlin, Germany: Springer Verlag, 2013), (Chapter 6: Diazodinitrophenol, pp. 157-166 ) ; see p. 159.〕 It is soluble in acetic acid, acetone, concentrated hydrochloric acid, most non-polar solvents and is slightly soluble in water.〔Tadeus Urbański with Marian Jurecki and Sylvia Laverton, trans., ''Chemistry and Technology of Explosives'' (Oxford, England: Permagon Press, 1967), vol. 3, (pp. 201-204; ) see especially p. 202.〕

A solution of cold sodium hydroxide may be used to destroy it.〔(Urbański, 1967), p. 202.〕 DDNP may be desensitized by immersing it in water, as it does not react in water at normal temperature. It is less sensitive to impact but more powerful than mercury fulminate and almost as powerful as lead azide.〔(Urbański, 1967), p. 204.〕 The sensitivity of DDNP to friction is much less than that of mercury fulminate, but it is approximately that of lead azide.
DDNP is used with other materials to form priming mixtures, particularly where a high sensitivity to flame or heat is desired. DDNP is often used as an initiating explosive in propellant primer devices and is a substitute for lead styphnate in what are termed "non-toxic" (lead free) priming explosive compositions.
== History ==

Diazodinitrophenol was first prepared in 1858 by the German chemist Peter Griess.〔Peter Griess (1858) ("Vorläufige Notiz über die Einwirkung von salpetriger Säure auf Amidinitro- und Aminitrophenylsäure," ) (Preliminary notice of the reaction of nitrous acid with picramic acid and aminonitrophenol], ''Annalen der Chemie und Pharmacie'', 106 : 123-125.〕 It was among the first diazo compounds and for a long time thereafter it was
used as a starting material for dyes.〔L. V. Clark (1933) "Diazodinitrophenol, a detonating explosive," ''Industrial & Engineering Chemistry'', 25 (6) : 663-669.〕 Although Griess had mentioned in 1859 that diazodinitrophenol exploded upon heating,〔P. Griess (1859) ("On new nitrogenous derivatives of the phenyl- and benzoyl-series," ) ''Proceedings of the Royal Society of London'', 9 : 594-597 ; see especially p. 595.〕 it was not until 1892 that diazodinitrophenol was first used as an explosive – when Wilhelm Will〔For biographical information about Wilhelm Will, see Wilhelm Will in German Wikipedia (in German).〕 and Friedrich Lenze, German chemists at the ''Militär-Versuchsamt'' (military research office) in Spandau, Germany, began to investigate azides as potential initiators of explosives.〔See:
* (Urbański, 1967), p. 202.
* H. Kast, ''Spreng- und Zündstoffe'' (and Detonators ) (Braunschweig, Germany: Friedrich Vieweg & Sohn, 1921), (pp. 433 ), 426.〕 The research was conducted secretly; however, after a fatal accident, the work was discontinued.〔See:
* Guy B. Taylor and W. C. Cope (1917) "Initial priming substances for high explosives," Technical Paper 162, Bureau of Mines, U. S. Dept. of the Interior, 32 pages; (see p. 7. )
* Will, W. (1914) ("Der Fortschritt in der Auslösung der explosiblen Systeme und sein Einfluss auf die Sprengstoffindustrie" ) (Progress in the triggering of explosive systems and its influence on the explosives industry), ''Zeitschrift für das gesamte Schieß- und Sprengstoffwesen'', 9 : 52-53.〕

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