View source for Hexanitrostilbene

{{Short description|Heat-resistant high explosive}}
{{chembox
| verifiedrevid = 444343776
| ImageFile = Hexanitrostilbene.svg
| ImageSize = 200px
| PIN = 1,1′-[(''E'')-Ethane-1,2-diyl]bis(2,4,6-trinitrobenzene)
| OtherNames = 1,2-bis-(2,4,6-trinitrophenyl)-ethylene; hexanitrodiphenylethylene, HNS
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10760172
| InChI = 1/C14H6N6O12/c21-15(22)9-5-3-7(11(17(25)26)13(9)19(29)30)1-2-8-4-6-10(16(23)24)14(20(31)32)12(8)18(27)28/h1-6H/b2-1+
| InChIKey = LQXXGLZCVKSCEV-OWOJBTEDBF
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C14H6N6O12/c21-15(22)9-5-3-7(11(17(25)26)13(9)19(29)30)1-2-8-4-6-10(16(23)24)14(20(31)32)12(8)18(27)28/h1-6H/b2-1+
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = LQXXGLZCVKSCEV-OWOJBTEDSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 20062-22-0
| PubChem = 253628 
| UNNumber = [[List of UN Numbers 0301 to 0400|0392]]<br/>''[[Trinitrotoluene|TNT]] mixtures:'' [[List of UN Numbers 0301 to 0400|0388]], [[List of UN Numbers 0301 to 0400|0389]]
| SMILES = O=N(=O)C1=CC(N(=O)=O)=C(/C=C/C2=C(N(=O)=O)C=C(N(=O)=O)C=C2N(=O)=O)C(N(=O)=O)=C1
}}
|Section2={{Chembox Properties
| Formula = C<sub>14</sub>H<sub>6</sub>N<sub>6</sub>O<sub>12</sub>
| MolarMass = 450.23 g/mol
| Appearance = Yellow crystalline powder
| Density = 1.7 [[gram|g]]/cm<sup>3</sup>
| MeltingPtC = 316
| BoilingPt = 
| Solubility = }}
|Section3={{Chembox Hazards
| MainHazards = 
| FlashPt = 
| AutoignitionPt = }}
|Section6={{Chembox Explosive
| ShockSens = Low
| FrictionSens = Low
| DetonationV = 7000 [[metre per second|m/s]]
| REFactor = }}
}}

'''Hexanitrostilbene''' (HNS), also called '''JD-X''', is an [[organic compound]] with the formula [(O<sub>2</sub>N)<sub>3</sub>C<sub>6</sub>H<sub>2</sub>CH]<sub>2</sub>.  It is a yellow-orange solid.<ref name=Ull>Jacques Boileau, Claude Fauquignon, Bernard Hueber and Hans H. Meyer "Explosives" in ''Ullmann's Encyclopedia of Industrial Chemistry'', 2009, Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a10_143.pub2}}</ref> It is used as a heat-resistant [[high explosive]].  It is slightly soluble (0.1 - 5 g/100 mL) in [[butyrolactone]], [[Dimethylformamide|DMF]], [[Dimethyl sulfoxide|DMSO]], and [[N-methylpyrrolidone|''N''-methylpyrrolidone]].

==Production and use==
It is produced by oxidizing [[trinitrotoluene]] (TNT) with a solution of [[sodium hypochlorite]]. HNS boasts a higher insensitivity to heat than TNT, and like TNT it is insensitive to impact. When casting TNT, HNS is added at 0.5% to form erratic micro-crystals within the TNT, which prevent cracking.<ref name=Ull/>  Because of its insensitivity but high explosive properties, HNS is used in space missions.  It was the main explosive fill in the [[Vibroseis|seismic source]] generating [[Mortar (weapon)|mortar ammunition]] canisters used as part of the [[Apollo Lunar Surface Experiments Package|Apollo Lunar Active Seismic Experiments]].<ref>[http://www.lpi.usra.edu/lunar/documents/NASA%20RP-1036.pdf NASA reference publication]</ref>

Its heat of detonation is 4 kJ/g.<ref>[http://publications.drdo.gov.in/gsdl/collect/defences/index/assoc/HASH0181/6881f845.dir/doc.pdf Hexanitrostilbene and Its Properties]{{Dead link|date=January 2020 |bot=InternetArchiveBot |fix-attempted=yes }}</ref>

It was developed by [[Kathryn Grove Shipp]] at the U.S. [[Naval Ordnance Laboratory]] in the 1960s and has been improved on since then.<ref>Peter Golding, Asoka M. Jayaweera-Bandara, Henry Duffin, "Production of HNS" Patent 5023386. Filed: January 4, 1990.</ref>

==See also==

* [[TNT equivalent]]
* [[RE factor]]

==References==
{{reflist}}

[[Category:Explosive chemicals]]
[[Category:Nitrobenzene derivatives]]
[[Category:Stilbenoids]]