HMX

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For other uses, see HMX (disambiguation).
HMX
IUPAC name

Octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine

Identifiers
CAS number 2691-41-0 YesY
PubChem 17596
ChemSpider 16636 YesY
ChEBI CHEBI:33176 YesY
Jmol-3D images {{#if:C1N(CN(CN(CN1[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-]|Image 1
Properties
Molecular formula C4H8N8O8
Molar mass 296.155 g/mol
Density 1.91 g/cm3, solid
Melting point 276–286 °C
Explosive data
Shock sensitivity Low
Friction sensitivity Low
Explosive velocity 9100 m/s
RE factor 1.70
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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.[1]

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.

Production

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.[2]

Applications

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.[3] 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.

During World War II, under the code name Aunt Jemima, HMX was mixed with flour and used by Chinese guerrillas to disrupt the Japanese invasion and occupation of China. The mixture could easily pass for regular flour, thereby passing checkpoints without detection. It could even be cooked into pancakes without exploding and eaten without poisoning anyone. Uneaten pancakes or unused dough could still be used later for its original explosive purposes. In China during WWII, 15 tons of the "Aunt Jemima" HMX mixture was used. None was ever "discovered" by the Japanese.[4]

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.

Toxicity

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.[5]

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.[2][6] HMX is considered the least toxic amongst TNT and RDX.[7] Remediating HMX contaminated water supplies has proven to be successful.[8]

Biodegredation

Both wild and transgenic plants can phytoremediate explosives from soil and water. [9]

See also

Notes

  1. ↑ Cooper, Paul W., Explosives Engineering, New York: Wiley-VCH, 1996. ISBN 0-471-18636-8
  2. ↑ 2.0 2.1 John Pike (1996-06-19). "Nitramine Explosives". Globalsecurity.org. Retrieved 2012-05-24. 
  3. ↑ WE Bachmann, JC Sheehan (1949). "A New Method of Preparing the High Explosive RDX1". Journal of the American Chemical Society, 1949 (5):1842–1845.
  4. ↑ Weird Warfare episode on History Channel, air date 4-6-2011
  5. ↑ "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. <http://www.epa.gov/iris/subst/0311.htm>.
  6. ↑ "Fact Sheets". Mmr-iagwsp.org. Retrieved 2012-05-24. 
  7. ↑ "Information Bridge: DOE Scientific and Technical Information - Sponsored by OSTI". Osti.gov. Retrieved 2012-05-24. 
  8. ↑ Newell, Charles. "Treatment of RDX & HMX Plumes Using Mulch Biowalls." ESTCP Project ER-0426. 2008.
  9. ↑ 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. PMID 22996005. 

References

  • Cooper, Paul W., Explosives Engineering, New York: Wiley-VCH, 1996. ISBN 0-471-18636-8
  • Urbanski, Tadeusz. Chemistry and Technology of Explosives. Vol. III., Warszawa: Polish Scientific Publishers, 1967
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