Hexamethylene triperoxide diamine

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Image:Hexamethylene triperoxide diamine.png Hexamethylene triperoxide diamine
3,4,8,9,12,13-hexaoxa-1,6- diazabicyclo[4.4.4]tetradecane IUPAC name
Chemical formula	C₆H₁₂N₂O₆
Molecular mass	208.169 g/mol
Shock sensitivity	High
Friction sensitivity	High
Density	0.88 g/cm³
Explosive velocity	~4511 m/s
RE factor	?
Melting point	Decomposes at 75 °C
Autoignition temperature	N/A
Appearance	?
CAS number	283-66-9
PubChem	61101
SMILES	C1N2COOCN(COO1)COOC2

Hexamethylene triperoxide diamine, or HMTD is a high explosive organic chemical compound, first synthesised in 1885 by Legler<ref>Legler, L. Ber. 1885, 18, 3343-3351.</ref>. 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.<ref>Taylor, C. A.; Rinkenbach, W. H. Army Ordnance 1924. 5, 463-466</ref> However, it has since been superseded by even more stable compounds such as tetryl.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.<ref>"London bombers used everyday materials" Reuters, August 4, 2005, retrieved April 16, 2006</ref> The New York Times reported it as the planned explosive in the 2006 transatlantic aircraft plot. <ref>Van Natta Jr., Don, Elaine Sciolino, Stephen Grey. "In Tapes, Receipts and a Diary, Details of the British Terror Case", New York Times, 2006-08-27. Retrieved on 2006-10-12.</ref>

The easiest synthesis of HMTD involves unrestricted ingredients including hydrogen peroxide, citric acid or dilute sulfuric acid as a catalyst and Hexamine Fuel Tablets, which are available from camping supply stores or with military rations. Like other organic peroxides such as acetone peroxide, HMTD is an unstable compound that is sensitive to shock, friction, and heat. HMTD degrades too quickly for modern commercial and industrial applications, becoming useless in a matter of weeks. The compound is frequently suggested as a homemade explosive formulation with in-depth directions published in The Anarchist Cookbook.

Image:HMTD 3D.png