|Jmol-3D images||Image 1|
|Molar mass||296.155 g/mol|
|Density||1.91 g/cm3, solid|
|Melting point||276–286 °C|
|Explosive velocity||9100 m/s|
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
|(what is: / ?)|
HMX, also called octogen, is a powerful and relatively insensitive nitroamine high explosive, chemically related to RDX. Like RDX, the compound's name is the subject of much speculation, having been variously listed as High Melting eXplosive, Her Majesty's eXplosive, High-velocity Military eXplosive, or High-Molecular-weight rdX.
The molecular structure of HMX consists of an eight-membered ring of alternating carbon and nitrogen atoms, with a nitro group attached to each nitrogen atom. Because of its high molecular weight, it is one of the most potent chemical explosives manufactured, although a number of newer ones, including HNIW and ONC, are more powerful.
HMX is more complicated to manufacture than most explosives and this confines it to specialist applications. It may be produced by nitration of hexamine in the presence of acetic anhydride, paraformaldehyde and ammonium nitrate. RDX produced using the Bachmann Process usually contains 8–10% HMX.
Also known as cyclotetramethylene-tetranitramine, tetrahexamine tetranitramine, or octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine, HMX was first made in 1930. In 1949 it was discovered that HMX can be prepared by nitrolysis of RDX. Nitrolysis of RDX is performed by dissolving RDX in a 55% HNO3 solution, followed by placing the solution on a steambath for about six hours. HMX is used almost exclusively in military applications, including as the detonator in nuclear weapons, in the form of polymer-bonded explosive, and as a solid rocket propellant.
HMX is used in melt-castable explosives when mixed with TNT, which as a class are referred to as "octols". Additionally, polymer-bonded explosive compositions containing HMX are used in the manufacture of missile warheads and armor-piercing shaped charges.
HMX is also used in the process of perforating the steel casing in oil and gas wells. The HMX is built into a shaped charge that is detonated within the wellbore to punch a hole through the steel casing and surrounding cement out into the hydrocarbon bearing formations. The pathway that is created allows formation fluids to flow into the wellbore and onward to the surface.
At present, the information needed to determine if HMX causes cancer is insufficient. Due to the lack of information, EPA has determined that HMX is not classifiable as to its human carcinogenicity.
The available data on the effects on human health of exposure to HMX are limited. HMX causes CNS effects similar to those of RDX, but at considerably higher doses. In one study, volunteers submitted to patch testing, which produced skin irritation. Another study of a cohort of 93 workers at an ammunition plant found no hematological, hepatic, autoimmune, or renal diseases. However, the study did not quantify the levels of exposure to HMX.
HMX exposure has been investigated in several studies on animals. Overall, the toxicity appears to be quite low. HMX is poorly absorbed by ingestion. When applied to the dermis, it induces mild skin irritation but not delayed contact sensitization. Various acute and subchronic neurobehavioral effects have been reported in rabbits and rodents, including ataxia, sedation, hyperkinesia, and convulsions. The chronic effects of HMX that have been documented through animal studies include decreased hemoglobin, increased serum alkaline phosphatase, and decreased albumin. Pathological changes were also observed in the animals' livers and kidneys. No data are available concerning the possible reproductive, developmental, or carcinogenic effects of HMX. HMX is considered the least toxic amongst TNT and RDX. Remediating HMX contaminated water supplies has proven to be successful.
Both wild and transgenic plants can phytoremediate explosives from soil and water. 
- 4,4’-Dinitro-3,3’-diazenofuroxan (DDF)
- Heptanitrocubane (HNC)
- Octanitrocubane (ONC)
- RE factor
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- John Pike (1996-06-19). "Nitramine Explosives". Globalsecurity.org. Retrieved 2012-05-24.
- WE Bachmann, JC Sheehan (1949). "A New Method of Preparing the High Explosive RDX1". Journal of the American Chemical Society, 1949 (5):1842–1845.
- "Octahydro-1,3,5,7-tetranitro-1,3,5,7-tetr... (HMX) (CASRN 2691-41-0) | IRIS | US EPA." EPA. Environmental Protection Agency, n.d. Web. 15 Nov. 2012.
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- Newell, Charles. "Treatment of RDX & HMX Plumes Using Mulch Biowalls." ESTCP Project ER-0426. 2008.
- Panz K; Miksch K (December 2012). "Phytoremediation of explosives (TNT, RDX, HMX) by wild-type and transgenic plants". Journal of Environmental Management 113: 85–92. doi:10.1016/j.jenvman.2012.08.016. PMID 22996005.