Diazodinitrophenol

Diazodinitrophenol
Diazonium structure	Non-radical diazo structure
Names
	Preferred IUPAC name 6-Diazo-2,4-dinitrocyclohexa-2,4-dien-1-one
Identifiers
CAS Number	4682-03-5 ;
3D model (JSmol)	Interactive image;
Abbreviations	DDNP
ChemSpider	4576415 ;
ECHA InfoCard	100.022.849
EC Number	225-134-9;
PubChem CID	5463880;
UNII	CV76O0RICT ;
CompTox Dashboard (EPA)	DTXSID00884100 ;
	InChI InChI=1S/C6H2N4O5/c7-8-4-1-3(9(12)13)2-5(6(4)11)10(14)15/h1-2H Key: IUKSYUOJRHDWRR-UHFFFAOYSA-N ;
	SMILES [N]=[N]=C(C=C([N+]([O-])=O)C=C1[N+]([O-])=O)C1=O;
Properties
Chemical formula	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)
Solubility in water	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). verify (what is ?) Infobox references

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]

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,^[update] 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

1 2 3 4 5 Matyáš, Robert; Pachman, Jiří (2013). "Chapter 6: Diazodinitrophenol". Primary Explosives. Berlin, Germany: Springer Verlag. pp. 157–166. ISBN 978-3-642-28436-6.
↑ Military Explosives (Report). September 1984. pp. 7-9 – 7-11. TM 9-1300-214.
↑ 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.
↑ (Urbański, 1967), p. 202.
↑ (Urbański, 1967), p. 204.
↑ 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].
↑ 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.
1 2 Clark, L. V. (June 1933). "Diazodinitrophenol, a Detonating Explosive". Industrial & Engineering Chemistry. 25 (6): 663–669. doi:10.1021/ie50282a021. ISSN 0019-7866.
↑ 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.
↑
See:
- (Urbański, 1967), p. 202.
- H. Kast, Spreng- und Zündstoffe [Explosives and Detonators] (Braunschweig, Germany: Friedrich Vieweg & Sohn, 1921), pp. 433, 426.
↑
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.

[Matyas2013-1] 1 2 3 4 5 Matyáš, Robert; Pachman, Jiří (2013). "Chapter 6: Diazodinitrophenol". Primary Explosives. Berlin, Germany: Springer Verlag. pp. 157–166. ISBN 978-3-642-28436-6.

[USArmy1984-2] Military Explosives (Report). September 1984. pp. 7-9 – 7-11. TM 9-1300-214.

[3] 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.

[4] (Urbański, 1967), p. 202.

[5] (Urbański, 1967), p. 204.

[6] 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].

[7] 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.

[Clark1933-8] 1 2 Clark, L. V. (June 1933). "Diazodinitrophenol, a Detonating Explosive". Industrial & Engineering Chemistry. 25 (6): 663–669. doi:10.1021/ie50282a021. ISSN 0019-7866.

[9] 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.

[10] See:
(Urbański, 1967), p. 202.

H. Kast, Spreng- und Zündstoffe [Explosives and Detonators] (Braunschweig, Germany: Friedrich Vieweg & Sohn, 1921), pp. 433, 426.

[mwyQ] (Urbański, 1967), p. 202.

[mwyg] H. Kast, Spreng- und Zündstoffe [Explosives and Detonators] (Braunschweig, Germany: Friedrich Vieweg & Sohn, 1921), pp. 433, 426.

[11] 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.

[mw0Q] 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.

[mw0w] 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.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

This page was redesigned at the edge.

History

Structure

Synthesis

References