Hexamethylene triperoxide diamine

Chembox new
ImageFile = Hexamethylene triperoxide diamine.png ImageSize = 150px
IUPACName = 3,4,8,9,12,13-Hexaoxa-1,6-
diazabicyclo [4.4.4] tetradecane
OtherNames =
Section1 = Chembox Identifiers
CASNo = 283-66-9
PubChem = 61101
SMILES = 0
Section2 = Chembox Properties
Formula = C₆H₁₂N₂O₆
MolarMass = 208.17 g/mol
Appearance = White crystalline solid
Density = 0.88 g/cm³
MeltingPt = Decomposes at 75 °C
Ignites spontaneously at 133 °C
BoilingPt =
Solubility =
Section3 = Chembox Hazards
MainHazards =
FlashPt =
Autoignition =
Section6 = Chembox Explosive
ShockSens = High
FrictionSens = High
ExplosiveV = ~4511 m/s
REFactor =

Hexamethylene triperoxide diamine (HMTD) is a
high explosive organic chemical compound, first synthesised in 1885 by Legler. [cite journal | author = Legler, L. | journal = Chemische Berichte | year =1885 | volume =18 | pages =3343-3351 | doi = 10.1002/cber.188501802306
url = http://gallica.bnf.fr/ark:/12148/bpt6k90703s/f1537.chemindefer| title = Ueber Producte der langsamen Verbrennung des Aethyläthers ] The theorised structure lent itself well to acting as an initiating, or primary explosive. While still quite sensitive to shock and friction, it was relatively stable compared to other initiating explosives of the time, such as mercury fulminate, and proved to be relatively inexpensive and easy to synthesise. As such, it was quickly taken up as a primary explosive in mining applications. [Taylor, C. A.; Rinkenbach, W. H. "Army Ordnance" 1924. "5", 463-466] However, it has since been superseded by even more stable compounds such as tetryl.

Despite no longer being used in any official application, it remains a fairly popular home-made explosive and has been used in a large number of suicide bombings throughout the world, and was possibly used in the 7 July 2005 London bombings. [ [http://www.alertnet.org/thenews/newsdesk/L04442279.htm "London bombers used everyday materials"] Reuters, August 4, 2005, retrieved April 16, 2006] The "New York Times" reported it as the planned explosive in the 2006 transatlantic aircraft plot. [cite news|url=http://cryptome.org/nyt-ukterror.htm|title= In Tapes, Receipts and a Diary, Details of the British Terror Case|date=2006-08-27|accessdate=2006-10-12|publisher=New York Times|first=Don|last=Van Natta Jr.|coauthors=Elaine Sciolino, Stephen Grey]

Preparation and properties

HMTD may be prepared by the reaction of an aqueous solution of hydrogen peroxide and hexamine in the presence of citric acid or dilute sulfuric acid as a catalyst.

Like other organic peroxides such as acetone peroxide, HMTD is an unstable compound that is sensitive to shock, friction, and heat. This makes the substance extremely dangerous to manufacture. It also reacts with most common metals, which can lead to detonation. HMTD is very stable when pure (acid free) and does not quickly sublimate like its acetone counterparts.

References