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{{Unreferenced|date=December 2009}}
{{Chembox {{Chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 392483295
| Watchedfields = changed
⚫ |ImageFile=Diazodinitrophenol.svg
⚫ | verifiedrevid = 427437931
|ImageSize=150px
| ImageFileL1 = 2-Diazo-4,6-dinitrophenol.svg
⚫ |IUPACName=6-Diazo-2,4-dinitrocyclohexa-2,4-dien-1-one
| ImageSizeL1 = 150
⚫ |OtherNames=
| ImageAltL1 = Skeletal formula
| ImageFileR1 = Diazodinitrophenol-3D-balls-2.png
| ImageSizeR1 = 160
| ImageAltR1 = Ball-and-stick model
⚫ | ImageFile2 = Diazodinitrophenol.jpg
| ImageSize2 = 300
⚫ | PIN=6-Diazo-2,4-dinitrocyclohexa-2,4-dien-1-one
⚫ | OtherNames=
|Section1={{Chembox Identifiers |Section1={{Chembox Identifiers
| Abbreviations = DDNP | Abbreviations = DDNP
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=4682-03-5 | CASNo=4682-03-5
⚫ | PubChem=5463880
| UNII_Ref = {{fdacite|changed|FDA}}
⚫ | SMILES= C1(=O)C(=N=N)CC(=O)CC1(=O)
| EINECS = 225-134-9 | UNII = CV76O0RICT
⚫ | PubChem=5463880
⚫ | SMILES= ==C(C=C(()=O)C=C1()=O)C1=O
| EINECS = 225-134-9
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 4576415
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C6H2N4O5/c7-8-4-1-3(9(12)13)2-5(6(4)11)10(14)15/h1-2H
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = IUKSYUOJRHDWRR-UHFFFAOYSA-N
}} }}
|Section2={{Chembox Properties |Section2={{Chembox Properties
| C=6|H=2|N=4|O=5
| Formula=C<sub>6</sub>H<sub>2</sub>N<sub>4</sub>O<sub>5</sub>
| Appearance=
| MolarMass=210.10 g/mol
| Appearance= | Density=
| Density= | MeltingPt=
| MeltingPt= | BoilingPt=
⚫ | Solubility=Insoluble
| BoilingPt=
⚫ | Solubility=Insoluble
}} }}
|Section3={{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPt= | FlashPt=
| AutoignitionPt =
| Autoignition=
}} }}
}} }}


'''Diazodinitrophenol''' ('''DDNP''') was the first ] 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.<ref>Robert Matyáš and Jiří Pachman, ''Primary Explosives'' (Berlin, Germany: Springer Verlag, 2013), ; see p. 159.</ref> It is soluble in ], ], concentrated ], like most non-polar solvents and is slightly soluble in ].<ref>Tadeusz Urbański with Marian Jurecki and Sylvia Laverton, trans., ''Chemistry and Technology of Explosives'' (Oxford, England: Permagon Press, 1967), vol. 3, ; see especially p. 202.</ref>
'''Diazodinitrophenol''' ('''DDNP''') is a yellowish brown ]. It is soluble in ], ], concentrated ], and most non-polar solvents but is insoluble in ].
⚫ A solution of cold ] 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 ] and ]. The sensitivity of DDNP to friction is much less than that of mercury fulminate, but it is approximately that of lead azide.


⚫ A solution of cold ] may be used to destroy it.<ref>(Urbański, 1967), p. 202.</ref> 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 ] and almost as powerful as ].<ref>(Urbański, 1967), p. 204.</ref> 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 ], particularly where a high sensitivity to flame or heat is desired. DDNP is often used as an ] in ] primer devices and is a substitute for ] in what are termed "non-toxic" (lead free) priming explosive compositions.


{{multiple image
==See also==
| align = center
* ]
| direction =
| width = 238
| image1 =
| alt1 = 2
| caption1 =
| image2 =
| alt2 = 3
| caption2 =
| image3 =
| alt3 = 4
| footer = Sensitivity of DDNP compared to other primary explosives and PETN.
}}

⚫ DDNP is used with other materials to form ], particularly where a high sensitivity to flame or heat is desired. DDNP is often used as an ] in ] primer devices and is a substitute for ] 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.<ref>{{cite arXiv |eprint=1410.6390|ref=Courtney|last1=Courtney|first1=Elya|title=Performance testing of lead free primers: Blast waves, velocity variations, and environmental testing|last2=Courtney|first2=Amy|author3=Peter David Summer|last4=Courtney|first4=Michael|class=physics.pop-ph|year=2014}}</ref>

==History==

Diazodinitrophenol was first prepared in 1858 by the German chemist ].<ref>Peter Griess (1858) (Preliminary notice of the reaction of nitrous acid with picramic acid and aminonitrophenol), ''Annalen der Chemie und Pharmacie'', '''106''' : 123-125.</ref> It was among the first ] compounds and for a long time thereafter it was
used as a starting material for dyes.<ref>L. V. Clark (1933) "Diazodinitrophenol, a detonating explosive," ''Industrial & Engineering Chemistry'', '''25''' (6) : 663-669.</ref> Although Griess had mentioned in 1859 that diazodinitrophenol exploded upon heating,<ref>P. Griess (1859) ''Proceedings of the Royal Society of London'', '''9''' : 594-597; see especially p. 595.</ref> it was not until 1892 that diazodinitrophenol was first used as an explosive – when Wilhelm Will<ref>For biographical information about Wilhelm Will, see ] in German Misplaced Pages (in German).</ref> and Friedrich Lenze, German chemists at the ''Militär-Versuchsamt'' (military research office) in Spandau, Germany, began to investigate azides as potential initiators of explosives.<ref>See:
* (Urbański, 1967), p. 202.
* H. Kast, ''Spreng- und Zündstoffe'' (Braunschweig, Germany: Friedrich Vieweg & Sohn, 1921), , 426.</ref> The research was conducted secretly. After a fatal accident, the work was discontinued.<ref>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;
* Will, W. (1914) (Progress in the triggering of explosive systems and its influence on the explosives industry), ''Zeitschrift für das gesamte Schieß- und Sprengstoffwesen'', '''9''' : 52-53.</ref>

==Synthesis==
DDNP can be synthesized by the reaction of ] with ] in ].<ref>{{cite journal | last=Clark | first=L. V. | title=Diazodinitrophenol, a Detonating Explosive | journal=Industrial & Engineering Chemistry | volume=25 | issue=6 | date=1933 | issn=0019-7866 | doi=10.1021/ie50282a021 | pages=663–669}}</ref>

==References==
{{reflist}}


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Latest revision as of 14:15, 9 December 2024

Diazodinitrophenol
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name 6-Diazo-2,4-dinitrocyclohexa-2,4-dien-1-one
Identifiers
CAS Number
3D model (JSmol)
Abbreviations DDNP
ChemSpider
ECHA InfoCard 100.022.849 Edit this at Wikidata
EC Number
  • 225-134-9
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H2N4O5/c7-8-4-1-3(9(12)13)2-5(6(4)11)10(14)15/h1-2HKey: IUKSYUOJRHDWRR-UHFFFAOYSA-N
SMILES
  • ==C(C=C(()=O)C=C1()=O)C1=O
Properties
Chemical formula C6H2N4O5
Molar mass 210.105 g·mol
Solubility in water Insoluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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, concentrated hydrochloric acid, like most non-polar solvents and is slightly soluble in water.

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 and almost as powerful as lead azide. 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.

History

Diazodinitrophenol was first prepared in 1858 by the German chemist Peter Griess. 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.

Synthesis

DDNP can be synthesized by the reaction of nitric acid with picramic acid in ethanol.

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 .
  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 Misplaced Pages (in German).
  10. See:
    • (Urbański, 1967), p. 202.
    • H. Kast, Spreng- und Zündstoffe (Braunschweig, Germany: Friedrich Vieweg & Sohn, 1921), pp. 433, 426.
  11. See:
  12. Clark, L. V. (1933). "Diazodinitrophenol, a Detonating Explosive". Industrial & Engineering Chemistry. 25 (6): 663–669. doi:10.1021/ie50282a021. ISSN 0019-7866.
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