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Diazodinitrophenol

Chemical compound From Wikipedia, the free encyclopedia

Diazodinitrophenol (DDNP) was one of the first diazonium or diazo compounds ever produced;[1]: 157  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.[1]: 159  It is soluble in acetic acid, acetone, concentrated hydrochloric acid, like most non-polar solvents and is slightly soluble in water.[3]

Quick facts Names, Identifiers ...
Diazodinitrophenol
Skeletal formula
Diazonium structure
Ball-and-stick model
Non-radical diazo structure
Names
Preferred IUPAC name
6-Diazo-2,4-dinitrocyclohexa-2,4-dien-1-one
Identifiers
3D model (JSmol)
Abbreviations DDNP
ChemSpider
ECHA InfoCard 100.022.849 Edit this at Wikidata
EC Number
  • 225-134-9
UNII
  • InChI=1S/C6H2N4O5/c7-8-4-1-3(9(12)13)2-5(6(4)11)10(14)15/h1-2H X markN
    Key: IUKSYUOJRHDWRR-UHFFFAOYSA-N X markN
  • [N]=[N]=C(C=C([N+]([O-])=O)C=C1[N+]([O-])=O)C1=O
Properties[1][2]
C6H2N4O5
Molar mass 210.105 g·mol−1
Appearance Yellow crystals
Density
  • 1.71–1.72 g/cm−3 (pure)
  • 1.63–1.65 g/cm−3 (technical grade)
Melting point 157–158 °C (315–316 °F; 430–431 K) (with decomposition)
0.8 g/L (25 °C)
Solubility Soluble in acetone, acetic acid, nitrobenzene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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A solution of cold sodium hydroxide may be used to destroy it.[4] 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.[5] 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 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.[6]

History

Diazodinitrophenol was first prepared in 1858 by the German chemist Peter Griess.[7] It was among the first diazo compounds and for a long time thereafter it was used as a starting material for dyes.[8] Although Griess had mentioned in 1859 that diazodinitrophenol exploded upon heating,[9] it was not until 1892 that diazodinitrophenol was first used as an explosive – when Wilhelm Will [de] and Friedrich Lenze, German chemists at the Militär-Versuchsamt (military research office) in Spandau, Germany, began to investigate azides as potential initiators of explosives.[10] The research was conducted secretly. After a fatal accident, the work was discontinued.[11]

Structure

As of 2013, its exact bonding and structure was still unclear. It has variously been described as a diazonium compound or diazo compound.[1]: 157–158 

Synthesis

DDNP can be synthesized by the reaction of nitrous acid with picramic acid.[8][1]: 162 

References

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