Hexanitrostilbene: Difference between revisions

Hexanitrostilbene
Names
	Preferred IUPAC name 1,1′-[(E)-Ethane-1,2-diyl]bis(2,4,6-trinitrobenzene)
	Other names 1,2-bis-(2,4,6-trinitrophenyl)-ethylene; hexanitrodiphenylethylene, HNS
Identifiers
CAS Number	20062-22-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	10760172 ;
ECHA InfoCard	100.039.525
PubChem CID	253628;
UN number	0392; TNT mixtures: 0388, 0389
CompTox Dashboard (EPA)	DTXSID10864918 ;
	InChI InChI=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+ Key: LQXXGLZCVKSCEV-OWOJBTEDSA-N ; 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+ Key: LQXXGLZCVKSCEV-OWOJBTEDBF;
	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;
Properties
Chemical formula	C14H6N6O12
Molar mass	450.23 g/mol
Appearance	Yellow crystalline powder
Density	1.7 g/cm3
Melting point	316 °C (601 °F; 589 K)
Explosive data
Shock sensitivity	Low
Friction sensitivity	Low
Detonation velocity	7000 m/s
	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

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Latest revision as of 19:01, 30 January 2024

Hexanitrostilbene (HNS), also called JD-X, is an organic compound with the formula [(O₂N)₃C₆H₂CH]₂. It is a yellow-orange solid.^[1] It is used as a heat-resistant high explosive. It is slightly soluble (0.1 - 5 g/100 mL) in butyrolactone, DMF, DMSO, and 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.^[1] Because of its insensitivity but high explosive properties, HNS is used in space missions. It was the main explosive fill in the seismic source generating mortar ammunition canisters used as part of the Apollo Lunar Active Seismic Experiments.^[2]

Its heat of detonation is 4 kJ/g.^[3]

It was developed by Kathryn Grove Shipp at the U.S. Naval Ordnance Laboratory in the 1960s and has been improved on since then.^[4]

References

^ ^a ^b 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
^ NASA reference publication
^ Hexanitrostilbene and Its Properties^{[permanent dead link]}
^ Peter Golding, Asoka M. Jayaweera-Bandara, Henry Duffin, "Production of HNS" Patent 5023386. Filed: January 4, 1990.

[Ull-1] 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

[2] NASA reference publication

[3] Hexanitrostilbene and Its Properties^{[permanent dead link]}

[4] Peter Golding, Asoka M. Jayaweera-Bandara, Henry Duffin, "Production of HNS" Patent 5023386. Filed: January 4, 1990.

[1]

@@ Line 1: / Line 1: @@
+{{Short description|Heat-resistant high explosive}}
 {{chembox
+| verifiedrevid =
-| Watchedfields = changed
+| ImageFile = Hexanitrostilbene.
-| verifiedrevid = 400109776
-| ImageFile = Hexanitrostilbene.png
 | ImageSize = 200px
-| IUPACName = 1,3,5-Trinitro-2-[2-(2,4,6-trinitrophenyl)ethenyl]benzene
+|  = 1,---2-(2,4,6-)
-| OtherNames = 1,1'-(1,2-ethenediyl)bis[2,4,6-trinitrobenzene]; 1,2-bis-(2,4,6-trinitrophenyl)-ethylene; hexanitrodiphenylethylene
+| OtherNames = 1,2-bis-(2,4,6-trinitrophenyl)-ethylene; hexanitrodiphenylethylene
-| Section1 = {{Chembox Identifiers
+|Section1={{Chembox Identifiers
 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
 | ChemSpiderID = 10760172
@@ Line 15: / Line 15: @@
 | 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-])c1c(ccc(c1[N+]([O-])=O)[N+]([O-])=O)/C=C/c2ccc([N+]([O-])=O)c([N+]([O-])=O)c2[N+]([O-])=O
+| SMILES = O=N(O)(N(O)=O)N(O)=O)C=C(N(O)=O)(O)=O)N(O)=O
 }}
-| Section2 = {{Chembox Properties
+|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
@@ Line 28: / Line 29: @@
 | BoilingPt =
 | Solubility = }}
-| Section3 = {{Chembox Hazards
+|Section3={{Chembox Hazards
 | MainHazards =
 | FlashPt =
-| Autoignition = }}
+|  = }}
-| Section6 = {{Chembox Explosive
+|Section6={{Chembox Explosive
 | ShockSens = Low
 | FrictionSens = Low
-| ExplosiveV = 7000 [[metre per second|m/s]]
+|  = 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]].
-'''Hexanitrostilbene''' (HNS), also called '''JD-X''', is a heat resistant [[high explosive]] developed at the [[Naval Ordnance Laboratory]] in the 1960s. Other names include 1,1'-(1,2-ethenediyl)bis[2,4,6-trinitrobenzene]; 1,2-bis-(2,4,6-trinitrophenyl)-ethylene; hexanitrodiphenylethylene.
+==Production and use==
-It is commercially 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 very insensitive to impact. When casting TNT, HNS is added at 0.5% to form erratic micro-crystals within the TNT which prevent cracking.
+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]</ref>
-HNS was the main explosive fill in the Mortar grenades used as part of the Apollo Lunar Active Seismic Experiments.<ref>[http://www.lpi.usra.edu/lunar/documents/NASA%20RP-1036.pdf NASA reference publication]</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>
-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]</ref>
+==See also==
-''Solubility Information:'' (at room temperature in 100 ml of solvent)
+* [[TNT equivalent]]
-Acetone = Insoluble
+* [[RE factor]]
-Butyrolacetone = Slightly Soluble (0.1 - 5g)
-DMFA = Slightly Soluble (0.1 - 5g)
-DMSO = Slightly Soluble (0.1 - 5g)
-N-methyl-pyrrolidone = Slightly Soluble (0.1 - 5g)
 ==References==
@@ Line 63: / Line 58: @@
 [[Category:Explosive chemicals]]
-[[Category:Nitrobenzenes]]
+[[Category:]]
+[[Category:Stilbenoids]]
-{{Explosive-stub}}
-[[de:Hexanitrostilben]]
-[[fa:هگزانیترواستیلبن]]
-[[ja:ヘキサニトロスチルベン]]