Diazodinitrophenol

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Diazodinitrophenol
Diazodinitrophenol.svg
Diazodinitrophenol-3D-balls-2.png
Diazodinitrophenol.jpg
Names
Preferred IUPAC name
6-Diazo-2,4-dinitrocyclohexa-2,4-dien-1-one
Identifiers
3D model (JSmol)
AbbreviationsDDNP
ChemSpider
ECHA InfoCard 100.022.849 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 225-134-9
PubChem CID
UNII
  • InChI=1S/C6H2N4O5/c7-8-4-1-3(9(12)13)2-5(6(4)11)10(14)15/h1-2H X mark.svgN
    Key: IUKSYUOJRHDWRR-UHFFFAOYSA-N X mark.svgN
  • [N]=[N]=C(C=C([N+]([O-])=O)C=C1[N+]([O-])=O)C1=O
Properties
C6H2N4O5
Molar mass 210.105 g·mol−1
Insoluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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. [1] It is soluble in acetic acid, acetone, concentrated hydrochloric acid, like most non-polar solvents and is slightly soluble in water. [2]

A solution of cold sodium hydroxide may be used to destroy it. [3] 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. [4] 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. [5]

History

Diazodinitrophenol was first prepared in 1858 by the German chemist Peter Griess. [6] It was among the first diazo compounds and for a long time thereafter it was used as a starting material for dyes. [7] Although Griess had mentioned in 1859 that diazodinitrophenol exploded upon heating, [8] it was not until 1892 that diazodinitrophenol was first used as an explosive – when Wilhelm Will [9] 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]

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<span class="mw-page-title-main">Mercury(II) fulminate</span> Chemical compound

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 formula is identical, has a different atomic arrangement; the cyanate and fulminate anions are isomers.

<span class="mw-page-title-main">Detonator</span> Small explosive device used to trigger a larger explosion

A detonator is a device used to make an explosive or explosive device explode. Detonators come in a variety of types, depending on how they are initiated and details of their inner working, which often involve several stages. Types of detonators include non-electric and electric. Non-electric detonators are typically stab or pyrotechnic while electric are typically "hot wire", exploding bridge wire or explosive foil.

<span class="mw-page-title-main">Lead styphnate</span> Chemical compound

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The Griess test is an analytical chemistry test which detects the presence of nitrite ion in solution. One of its most important uses is the determination of nitrite in drinking water. The Griess diazotization reaction, on which the Griess reagent relies, was first described in 1858 by Peter Griess. The test has also been widely used for the detection of nitrates, which are a common component of explosives, as they can be reduced to nitrites and detected with the Griess test.

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Phenyl azide is an organic compound with the formula C6H5N3. It is one of the prototypical organic azides. It is a pale yellow oily liquid with a pungent odor. The structure consists of a linear azide substituent bound to a phenyl group. The C−N=N angle is approximately 120°. It was discovered in 1864 by Peter Griess by the reaction of ammonia and phenyldiazonium.

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Lead(II) thiocyanate is a compound, more precisely a salt, with the formula Pb(SCN)2. It is a white crystalline solid, but will turn yellow upon exposure to light. It is slightly soluble in water and can be converted to a basic salt (Pb(CNS)2·Pb(OH)2 when boiled. Salt crystals may form upon cooling. Lead thiocyanate can cause lead poisoning if ingested and can adversely react with many substances. It has use in small explosives, matches, and dyeing.

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References

  1. Robert Matyáš and Jiří Pachman, Primary Explosives (Berlin, Germany: Springer Verlag, 2013), Chapter 6: Diazodinitrophenol, pp. 157-166; see p. 159.
  2. Tadeusz 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.
  3. (Urbański, 1967), p. 202.
  4. (Urbański, 1967), p. 204.
  5. Courtney, Elya; Courtney, Amy; Peter David Summer; Courtney, Michael (2014). "Performance testing of lead free primers: Blast waves, velocity variations, and environmental testing". arXiv: 1410.6390 [physics.pop-ph].
  6. 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.
  7. L. V. Clark (1933) "Diazodinitrophenol, a detonating explosive," Industrial & Engineering Chemistry, 25 (6) : 663-669.
  8. 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.
  9. For biographical information about Wilhelm Will, see Wilhelm Will in German Wikipedia (in German).
  10. See:
    • (Urbański, 1967), p. 202.
    • H. Kast, Spreng- und Zündstoffe [Explosives and Detonators] (Braunschweig, Germany: Friedrich Vieweg & Sohn, 1921), pp. 433, 426.
  11. See: