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. It is soluble in acetic acid,

acetone Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour. Acetone is miscib ...

, concentrated

hydrochloric acid Hydrochloric acid, also known as muriatic acid, is an aqueous solution of hydrogen chloride. It is a colorless solution with a distinctive pungent smell. It is classified as a strong acid Acid strength is the tendency of an acid, symbol ...

, most non-polar solvents and is slightly soluble in

water Water (chemical formula ) is an Inorganic compound, inorganic, transparent, tasteless, odorless, and Color of water, nearly colorless chemical substance, which is the main constituent of Earth's hydrosphere and the fluids of all known living ...

. A solution of cold sodium hydroxide may be used to destroy it. 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 Mercury(II) fulminate, or Hg(CNO)2, is a primary explosive. It is highly sensitive to friction, heat and shock and is mainly used as a trigger for other explosives in percussion caps and detonators. Mercury(II) cyanate, though its chemical formu ...

and almost as powerful as

lead azide Lead(II) azide is an inorganic compound. More so than other azides, is explosive. It is used in detonators to initiate secondary explosives. In a commercially usable form, it is a white to buff powder. Preparation and handling Lead(II) azid ...

. The sensitivity of DDNP to friction is much less than that of mercury fulminate and 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 Lead styphnate (lead 2,4,6- trinitroresorcinate, C6HN3O8Pb ), whose name is derived from styphnic acid, is an explosive used as a component in primer and detonator mixtures for less sensitive secondary explosives. Lead styphnate is only slightly ...

in what are termed "green" or "non-toxic" (lead free) priming explosive compositions. Lead free primers have been judged as inadequate for service use in firearms due to weak and uneven initiation compared to lead based primers.

History

Diazodinitrophenol was first prepared in 1858 by the German chemist

Peter Griess Johann Peter Griess (6 September 1829 – 30 August 1888) was an industrial chemist and an early pioneer of organic chemistry. Griess was influential in the formation of modern dyes, first formulating the diazotization reaction of arylamines. Li ...

. It was among the first diazo compounds and for a long time thereafter it was used as a starting material for dyes. Although Griess had mentioned in 1859 that diazodinitrophenol exploded upon heating, it was not until 1892 that diazodinitrophenol was first used as an explosive – when Wilhelm Will and Friedrich Lenze, German chemists at the ''Militär-Versuchsamt'' (military research office) in Spandau, Germany, began to investigate azides as potential initiators of explosives. The research was conducted secretly. 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.

References

{{reflist Explosive chemicals Nitrobenzenes Diazo compounds Ketones