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Hexamethylene triperoxide diamine

Structural formula
Surname Hexamethylene triperoxide diamine
other names
  • 1,6-diaza-3,4,8,9,12,13-hexaoxa
    bicyclo [4,4,4] tetradecane (IUPAC)
  • HMTD
Molecular formula C.6H12N2O6
CAS number 283-66-9
Brief description crystalline, white solid
Molar mass 208.1 g mol−1
Physical state firmly
density 1.57 g cm−3

poorly soluble in acetone and water

safety instructions
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions.

Hexamethylene triperoxide diamine, often as HMTD abbreviated, is an organic compound, an amine with 3 peroxy groups. According to the IUPAC nomenclature, the compound is called 1,6-diaza-3,4,8,9,12,13-hexaoxabicyclo [4,4,4] tetradecane.


Hexamethylene triperoxide diamine was first produced in 1885 by L. Legler in Dresden from ammonia and lamp acid.[1] In 1900, Baeyer and Villiger succeeded in preparing it from ammonium sulfate, formaldehyde and hydrogen peroxide. Conway Freiherr von Girsewald from Berlin-Halensee applied for a patent as an initial explosive in 1912 and developed a synthesis method that is still used today.

Extraction and presentation

It is represented according to the process first described in 1912 by reacting hexamethylenetetramine with hydrogen peroxide and citric acid as a catalyst. Better yields at a higher reaction rate are obtained with hydrochloric acid instead of citric acid or by using the hexamethylenetetramine salt of hydrochloric acid.


Pure hexamethylene triperoxide diamine is a crystalline, white solid. The compound is only sparingly soluble in water and most organic solvents. Like most organic peroxides, it is very unstable; water that is already hot leads to the decomposition of the peroxide. Dried hexamethylene triperoxide diamine is extremely unstable; exposure to shock, heat, friction or sparks can lead to explosive decomposition. When pressure is applied with metal spatulas or other hard objects, the peroxide regularly explodes.

Educational energy −1610.6 kJ / kg
Enthalpy of formation −1729.7 kJ / kg
Oxygen balance −92,2 %
Nitrogen content 13,46 %
Normal gas volume 1247 l / kg
Explosion heat 3369 kJ / kg (H2O (l))
3128 kJ / kg (H2O (g))
Specific energy 855 kJ / kg (87.2 mt / kg)
Lead block bulge 330 cm3 (similar to picric acid)
Deflagration point 200 ° C (decomposition from 149 ° C, explosion from 130 ° C possible)
Detonation velocity 4500-5100 m / s
Sensitivity to impact 0.6 Nm


HMTD was tested as an initial explosive for less sensitive explosives and proved to be superior to mercury fulminate. In open accumulation, it only evaporates in larger quantities (a few grams), while it will readily detonate if it is only slightly enclosed or even pressed. However, it has not found any practical use because it is heat-sensitive and unstable to moisture. It is less sensitive to impact than many other initial explosives, but it has a considerable explosive power and in the sand test it crushes about 2.5 to three times more sand than mercury fulminate. HMTD explodes at the so-called Drop hammer test already with a 2 kg drop hammer from a height of 10 cm.

safety instructions

Hexamethylene triperoxide diamine is an initial explosive and therefore particularly explosive. An explosion can occur through ignition sources or mechanical effects such as friction or impact, but also through exposure to radiation (e.g. UV radiation or sunlight), through drying or contact with other chemical compounds, especially with metals, or through their own decomposition products over a longer period of time Storage. Great caution and care must be exercised when handling and special precautions must be taken. It is also explosive when stored under water, but decomposes slowly even at room temperature.

Dealing with more than the smallest amounts is irresponsible, as the risk of a spontaneous reaction is omnipresent.


HMTD is subject to explosives law (in particular the authorization requirement of § 7 and 27 Explosives Act, provided that no exceptions for research and teaching according to the 1st Ordinance to the Explosives Act apply).


  • Alfred Stettbacher: The guns and explosives., 2nd edition Leipzig 1933
  1. L. Legler, Ber. 1885, 18, 3343-3351

Categories: Explosive substances | Amine | Peroxide | explosive