Editing Lead styphnate

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 447123478
| ImageFile = Bleistyphnat.png
| ImageSize = 
| PIN = Lead(II) 2,4,6-trinitrobenzene-1,3-bis(olate)
| OtherNames = Lead 2,4,6-trinitrobenzene-1,3-diolate<br />Lead 2,4,6-trinitro-''m''-phenylene dioxide<br />1,3-Benzenediol, 2,4,6-trinitro-, lead(2+) salt (1:1)<br />Lead tricinate<br />Lead trinitroresorcinate<br />Tricinat<ref>ECHA, European Chemicals Agency {{cite web |url=http://echa.europa.eu/documents/10162/13638/svhc_supdoc_lead_styphnate_en.pdf |title=Support document for identification of lead styphnate as a substance of very high concern because of its CMR properties |accessdate=2014-10-17 |url-status=dead |archiveurl=https://web.archive.org/web/20141022103059/http://echa.europa.eu/documents/10162/13638/svhc_supdoc_lead_styphnate_en.pdf |archivedate=2014-10-22 }}</ref>
|Section1 = {{Chembox Identifiers
 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
 | ChemSpiderID = 55674
 | SMILES = c1c(c(c(c(c1[N+](=O)[O-])[O-])[N+](=O)[O-])[O-])[N+](=O)[O-].[Pb+2]
 | InChI = 1/C6H3N3O8.Pb/c10-5-2(7(12)13)1-3(8(14)15)6(11)4(5)9(16)17;/h1,10-11H;/q;+2/p-2
 | InChIKey = WETZJIOEDGMBMA-NUQVWONBAY
 | StdInChI_Ref = {{stdinchicite|changed|chemspider}}
 | StdInChI = 1S/C6H3N3O8.Pb/c10-5-2(7(12)13)1-3(8(14)15)6(11)4(5)9(16)17;/h1,10-11H;/q;+2/p-2
 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
 | StdInChIKey = WETZJIOEDGMBMA-UHFFFAOYSA-L
 | CASNo_Ref = {{cascite|correct|??}}
 | CASNo = 15245-44-0
 | UNII_Ref = {{fdacite|correct|CAS}}
 | UNII = 0T8SE91KOP
 | CASNoOther = <!-- deleted CAS numbers 4219-19-6, 6594-85-0, 59286-40-7, 63918-97-8 -->
 | PubChem = 61789
 | EC_number = 239-290-0
 | UNNumber = 0130
 }}
|Section2 = {{Chembox Properties
 | Formula = C<sub>6</sub>HN<sub>3</sub>O<sub>8</sub>Pb
 | MolarMass = 450.288 g/mol
 | Appearance = 
 | Density = 3.06 to 3.1 g cm<sup>−3</sup>
 | MeltingPt = 
 | BoilingPt = 
 | Solubility = 
 }}
|Section3 = {{Chembox Explosive
 | ShockSens = High
 | FrictionSens = High
 | DetonationV = 5200 m/s
 | REFactor = 
 }}
|Section4 = {{Chembox Hazards
 | ExternalSDS = [http://msds.chem.ox.ac.uk/LE/lead_styphnate.html Oxford MSDS]
| GHSPictograms = {{GHS01}}{{GHS07}}{{GHS08}}{{GHS09}}
| GHSSignalWord = danger
| HPhrases      = {{HPhrases|H200|H302|H332|H360Df|H373|H410}}
| PPhrases      = {{PPhrases|}}
| GHS_ref       = <ref>GHS: [https://gestis.dguv.de/data?name=490561 GESTIS 490561]</ref>
 | FlashPt = 
 | NFPA-H = 4
 | NFPA-F = 0
 | NFPA-R = 3
 | AutoignitionPtC = 330
 | AutoignitionPt_notes = 
 }}
}}

'''Lead styphnate''' (lead 2,4,6-[[resorcinol|trinitroresorcinate]], C<sub>6</sub>HN<sub>3</sub>O<sub>8</sub>Pb ), whose name is derived from [[styphnic acid]], is an [[explosive]] used as a component in [[primer (firearm)|primer]] and [[detonator]] mixtures for less sensitive [[secondary explosive]]s.  Lead styphnate is only slightly soluble in [[water]] and [[methanol]].<ref name=":0"/> Samples of lead styphnate vary in color from yellow to gold, orange, reddish-brown, to brown. Lead styphnate is known in various polymorphs, hydrates, and basic salts. Normal lead styphnate monohydrate, monobasic lead styphnate, tribasic lead styphnate dihydrate, and pentabasic lead styphnate dehydrate as well as α, β [[polymorphism (materials science)|polymorphs]] of lead styphnate exist.

Lead styphnate forms six-sided crystals of the [[monohydrate]] and small rectangular crystals.  Lead styphnate is particularly sensitive to fire and the discharge of [[static electricity]]. Long thin crystals are particularly sensitive. Lead styphnate does not react with other metals and is less sensitive to shock and friction than [[Mercury(II) fulminate|mercury fulminate]] or [[Lead(II) azide|lead azide]].  It is stable in storage, even at elevated temperatures. As with other [[lead]]-containing compounds, lead styphnate is toxic owing to [[Heavy metal (chemistry)|heavy metal]] poisoning.

==Preparation==
Lead styphnate (or, as it was then called, trinitro-orcinate) was discovered along with many other thrinitroresorcinate salts by British chemist [[John Stenhouse]] in 1871, the synthesis route involving action of trinitroresorcinol on [[lead acetate]].<ref>{{Cite book |last=Matyáš |first=Robert |url=https://books.google.com/books?id=wfJHAAAAQBAJ&pg=PA138 |title=Primary Explosives |last2=Pachman |first2=Jiří |date=2013-03-12 |publisher=Springer Science & Business Media |isbn=978-3-642-28436-6 |language=en}}</ref><ref>{{Cite book |last=Stenhouse |first=J. |url=http://archive.org/details/philtrans04851702 |title=Contributions to the History of Orcin.--No. I. Nitro-Substitution Compounds of the Orcins |date=March 1871 |publisher=Royal Society of London}}</ref>

In 1919, Austrian chemist Edmund von Herz first established a preparation of anhydrous normal lead styphnate by the reaction of magnesium styphnate with lead acetate in the presence of [[nitric acid]].<ref>{{cite journal|author=J.R. Payne|title=Thermochmistry of lead styphnate|journal=Thermochimica Acta |year=1994|doi=10.1016/0040-6031(94)85003-8|volume=242|pages=13–21}}</ref><ref name=":0">{{citation | last1=Boileau | first1=Jacques | last2=Fauquignon | first2=Claude | last3=Hueber | first3=Bernard | last4=Meyer | first4=Hans H. | title=Ullmann's Encyclopedia of Industrial Chemistry | chapter=Explosives | publisher=Wiley-VCH Verlag GmbH & Co. KGaA | publication-place=Weinheim, Germany | date=2009-04-15 | doi=10.1002/14356007.a10_143.pub2| isbn=978-3527306732 }}</ref>

:{C<sub>6</sub>N<sub>3</sub>O<sub>8</sub>}MgH<sub>2</sub>O + Pb(CH<sub>3</sub>CO<sub>2</sub>)<sub>2</sub>   →   {C<sub>6</sub>N<sub>3</sub>O<sub>8</sub>}PbH<sub>2</sub>O  + Mg(CH<sub>3</sub>CO<sub>2</sub>)<sub>2</sub>

==Structure==
Normal lead styphnate exists as α and β polymorphs, both being monoclinic crystals. The lead centres are seven-coordinate and are bridged via oxygen bridges. The water molecule is coordinated to the metal and is also hydrogen-bonded to the anion. Many of the Pb-O distances are short, indicating some degree of covalency. The styphnate ions lie in approximately parallel
planes linked by Pb atoms.<ref>{{cite journal|author=Pierce-Butler, M.A.|title=The structure of the lead salt of 2,4,6-trinitro-1,3-benzenediol monohydrate (alpha-polymorph)|journal=Acta Crystallogr.|year=1984|doi=10.1107/S0108270184003036|volume=40|pages=63–65}}</ref><ref>{{cite journal|author=Pierce-Butler, M.A.|title=Structures of the barium salt of 2,4,6-trinitro-1,3-benzenediol monohydrate and the isomorphous lead salt (beta-polymorph)|journal=Acta Crystallogr.|year=1982|doi=10.1107/S0567740882010966|volume=38|issue=12|pages=3100–3104}}</ref>

==Properties==
Lead styphnate's heat of formation is −835 kJ mol<sup>−1</sup>. The loss of water leads to the formation of a sensitive anhydrous material with a density of 2.9 g cm<sup>−3</sup>. The variation of colors remains unexplained.<ref>{{cite book|author1=Robert Matyáš |author2=Ji í Pachman |title=Primary Explosives|publisher=Springer Science & Business Media|year=2013|doi=10.1007/978-3-642-28436-6|isbn=978-3-642-28435-9 |s2cid=199492549 }}</ref> Lead styphnate has a detonation velocity of 5.2&nbsp;km/s and an explosion temperature of 265–280&nbsp;°C after five seconds.<ref>{{cite journal|author1=Hyman Henkin |author2=Russell McGill |title=Rates of Explosive Decomposition of Explosives. Experimental and Theoretical Kinetic Study as a Function of Temperature|journal=Ind. Eng. Chem.|year=1952|doi=10.1021/ie50510a054|volume=44|issue=6 |pages=1391–1395}}</ref>
<!-- something messed up here:{C<sub>6</sub>N<sub>3</sub>O<sub>8</sub>}PbH<sub>2</sub>O  →   Pb(CN)<sub>2</sub>  +   4 CO<sub>2</sub>  +  1/2 H<sub>2</sub>  +  H<sub>2</sub>O-->

==Applications==
Lead styphnate is mainly used in small arms [[ammunition]] for military and commercial applications. It serves as a [[primary explosive]] used in firearms primers, which will ignite upon a simple impact.<ref>{{cite journal|author=Gray, Theodore |title=Flash Bang|journal=Popular Science |year=2009|url=http://www.periodictable.com/PopSci/2009/10/01/index.html}}</ref> It is similarly used in blank cartridges for [[powder-actuated]] nail guns. Lead styphnate is also used as primer in microthrusters for small satellite stationkeeping.<ref>{{cite journal|author=Daniel W. Youngner|title=MEMS Mega-pixel Micro-thruster Arrays for Small Satellite Stationkeeping|journal=Honeywell Technology 14th Annual/USU Conference on Small Satellites|year=2000|url=http://alfven.princeton.edu/publications/youngner-ssc-2000|display-authors=etal|access-date=2016-10-18|archive-date=2021-03-10|archive-url=https://web.archive.org/web/20210310033937/https://alfven.princeton.edu/publications/youngner-ssc-2000|url-status=dead}}</ref>

==References==
<references />

==External links==
*[https://web.archive.org/web/20080111154608/http://www.npi.gov.au/database/substance-info/profiles/50.html National Pollutant Inventory - Lead and Lead Compounds Fact Sheet]

[[Category:Lead(II) compounds]]
[[Category:Explosive chemicals]]
[[Category:Nitrobenzene derivatives]]
[[Category:Phenolates]]