Misplaced Pages

Hexamethylene triperoxide diamine

Article snapshot taken from[REDACTED] with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.

This is an old revision of this page, as edited by Beetstra (talk | contribs) at 15:47, 23 February 2011 (Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChEMBL.). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Revision as of 15:47, 23 February 2011 by Beetstra (talk | contribs) (Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChEMBL.)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff)
Hexamethylene triperoxide diamine
Names
IUPAC names 3,4,8,9,12,13-Hexaoxa-1,6-
diazabicyclotetradecane
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H12N2O6/c1-7-2-11-13-5-8(4-10-9-1)6-14-12-3-7/h1-6H2Key: HMWPNDNFTFSCEB-UHFFFAOYSA-N
  • InChI=1/C6H12N2O6/c1-7-2-11-13-5-8(4-10-9-1)6-14-12-3-7/h1-6H2Key: HMWPNDNFTFSCEB-UHFFFAOYAC
SMILES
  • C1N2COOCN(COO1)COOC2
Properties
Chemical formula C6H12N2O6
Molar mass 208.17 g/mol
Appearance White crystalline solid
Density 0.88 g/cm
Melting point Decomposes at 75 °C
Ignites spontaneously at 133 °C
Explosive data
Shock sensitivity High
Friction sensitivity High
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Hexamethylene triperoxide diamine (HMTD) is a high explosive organic compound, first synthesised in 1885 by Legler. 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. However, it has since been superseded by even more stable compounds such as tetryl.

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.

No peroxide has found practical use as an explosive, a consequence of the weak oxygen– oxygen bond leading to poor thermal and chemical stability and a high sensitivity to impact. HMTD is a more powerful initiating explosive than mercury fulminate but its poor thermal and chemical stability prevents its use in detonators.

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 sublime like its acetone counterparts.

Terrorism

Ahmed Ressam, the al-Qaeda Millennium Bomber, used HMTD as one of the components in the explosives that he prepared to bomb Los Angeles International Airport on New Year's Eve 1999/2000; the explosives could have produced a blast 40x greater than that of a devastating car bomb.

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. The New York Times reported it as the planned explosive in the 2006 transatlantic aircraft plot.

References

  1. Legler, L . (1885). "Ueber Producte der langsamen Verbrennung des Aethyläthers". Berichte der deutschen chemischen Gesellschaft. 18: 3343–3351. doi:10.1002/cber.188501802306.
  2. Taylor, C. A.; Rinkenbach, W. H. Army Ordnance 1924. 5, 463-466
  3. Hodgson,Robert ; Agrawal,Jai P. (2007). Organic Chemistry of Explosives. Wiley. p. 414.{{cite book}}: CS1 maint: multiple names: authors list (link)
  4. U.S. Court of Appeals for the Ninth Circuit (2 February 2010). "U.S. v. Ressam" (PDF). Retrieved 27 February 2010.
  5. "Complaint; U.S. v. Ressam" (PDF). NEFA Foundation. December 1999. Retrieved 26 February 2010.
  6. "London bombers used everyday materials" Reuters, 4 August 2005, retrieved 16 April 2006
  7. Van Natta, Don, Jr. (28 August 2006). "Details Emerge in British Terror Case". The New York Times. Retrieved 7 February 2009. {{cite news}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)CS1 maint: multiple names: authors list (link)

Categories:
Hexamethylene triperoxide diamine Add topic