Hexanitrostilbene

Structural formula
General
Surname	Hexanitrostilbene
other names	HNS; 1,2-bis (2,4,6-trinitrophenyl) ethylene; 2,2 ', 4,4', 6,6'-hexanitrophenylethylene;
Molecular formula	C 14 H 6 N 6 O 12
External identifiers / databases
EC number	243-494-5
ECHA InfoCard	100.039.525
PubChem	253628
Wikidata	Q415410
properties
Molar mass	450.23 g mol −1
Physical state	firmly
Melting point	approx. 320 ° C
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 201
	P: ?
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Hexanitrostilbene (HNS) is a temperature-resistant explosive, which is used in particular for explosions in very hot oil deposits. HNS is less explosive than Hexogen (RDX), but has a higher melting point of approx. 320 ° C.

Extraction and presentation

The synthesis of HNS by reacting trinitrobenzyl chloride with alcoholic KOH was first described by Shipp.

properties

Light yellow orthorhombic crystals
Slightly soluble in acetone, methyl ethyl ketone, acetic acid 100%, dimethylformamide (DMF)
Moderately soluble in dimethyl sulfoxide (DMSO)
Can be recrystallized from HNO ₃ , acetone, dimethylformamide or nitrobenzene.
HNS is stable over a wide temperature range (from −200 ° C to 250 ° C) and is therefore also used as an explosive in space applications such as B. separating screws, etc. used.

Explosion parameters

The connection is particularly explosive when dry due to impact, friction, heat and other ignition sources and is subject to the Explosives Act .

Table with important explosion-relevant properties:
Oxygen balance	−67.5%
Nitrogen content	18.67%
Normal gas volume	893 l kg ⁻¹
Explosion heat	4056 kJ kg ⁻¹ (H ₂ O (l)) 3980 kJ kg ⁻¹ (H ₂ O (g))
Specific energy	975 kJ kg ⁻¹ (99.4 mt / kg)
Lead block bulge	30.1 cm ³ g ⁻¹
Sensitivity to impact	5 Nm
Rubbing sensitivity	Crackling from 235 N pin load
Detonation velocity	7,000 m / s

use

In military technology, a distinction is made between HNS-I, HNS-II, HNS-IV and HNS-V. These terms characterize the composition and particle properties of HNS. While HNS-I describes the HNS contaminated with hexanitrobibenzyl, HNS-II denotes recrystallized HNS with a purity of at least 98.50% by weight. HNS-IV identifies a material which is obtained by reprecipitating HNS-II and has a BET surface area of 5 to 25 m ² / g. Finally, HNS-V is HNS-IV which has been washed with DMSO and is free from DMF traces. HNS is mainly used in booster charges for explosive charges and in so-called Explosive-Foil-Initiator (EFI) detonators .

A content of 1% HNS in molten TNT prevents the formation of cracks upon solidification. Due to its low critical diameter of 0.4 mm, HNS can be used in metal-sheathed cutting cords. HNS is used together with hexanitroazobenzene CAS no. [19159-68-3] used in weak aluminum-encapsulated detonators, which can be stored up to 170 ° C.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k J. Köhler, R. Meyer, and A. Homburg: Explosivstoffe , tenth, completely revised edition. Wiley-VCH, Weinheim 2008, p. 167, ISBN 978-3-527-32009-7 .
↑ Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of 2,2 ', 4,4', 6,6'-hexanitrostilbene Template: link text check / apostrophe in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on July 19, 2019, is reproduced from a self-classification by the distributor .
↑ KG Shipp, J. Org. Chem. 29 , 2620 ( 1964 ); doi : 10.1021 / jo01032a034 .
↑ Roth, L .; Weller, U .: Hazardous Chemical Reactions , 65th supplement, ecomed-Verlag 2011.
↑ Explosives Act, Appendix I, List of Explosive Substances ( BGBl. 1975 I p. 853 ), to which the law is to be applied in full.
↑ BT Neyer, L. Cox, T. Stoutenborough, R. Tomasoski, HNS-IV Explosive Properties and Characterization Tests, AIAA2003-5138, Proceedings of 39th Joint Propulsion Conference, Huntsville, AL, July 2003 .
↑ Specification: MIL-E-82903 (OS).

[Explosivstoffe-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k J. Köhler, R. Meyer, and A. Homburg: Explosivstoffe , tenth, completely revised edition. Wiley-VCH, Weinheim 2008, p. 167, ISBN 978-3-527-32009-7 .

[2] Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of 2,2 ', 4,4', 6,6'-hexanitrostilbene Template: link text check / apostrophe in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on July 19, 2019, is reproduced from a self-classification by the distributor .

[3] KG Shipp, J. Org. Chem. 29 , 2620 ( 1964 ); doi : 10.1021 / jo01032a034 .

[Roth-Weller-4] Roth, L .; Weller, U .: Hazardous Chemical Reactions , 65th supplement, ecomed-Verlag 2011.

[SprengG-5] Explosives Act, Appendix I, List of Explosive Substances ( BGBl. 1975 I p. 853 ), to which the law is to be applied in full.

[6] BT Neyer, L. Cox, T. Stoutenborough, R. Tomasoski, HNS-IV Explosive Properties and Characterization Tests, AIAA2003-5138, Proceedings of 39th Joint Propulsion Conference, Huntsville, AL, July 2003 .

[7] Specification: MIL-E-82903 (OS).