Methyl nitrate

Methyl nitrate
Names
IUPAC name
Methyl nitrate
Other names
nitric acid, methyl ester
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.009.039
Properties
CH3NO3
Molar mass 77.04 g/mol
Appearance Liquid
Density 1.203 g/cm3, liquid
Melting point −82.3 °C (−116.1 °F; 190.8 K)[1]
Boiling point 64.6 °C (148.3 °F; 337.8 K) (explodes)[1]
Explosive data
Detonation velocity 7900 m s−1 [2]
Hazards
Main hazards Toxic, High Explosive
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Methyl nitrate is the methyl ester of nitric acid and has the chemical formula CH3NO3. It is a colourless volatile liquid that is explosive.

Synthesis

It can be produced by the condensation of nitric acid and methanol:[3]

CH3OH + HNO3 → CH3NO3 + H2O

Methyl nitrate can be produced on a laboratory or industrial scale either through the distillation of a mixture of methanol and nitric acid, or by the nitration of methanol by a mixture of sulfuric and nitric acids. The first procedure is not preferred due to the great explosion danger presented by the methyl nitrate vapour. The second procedure is essentially identical to that of making nitroglycerin. However, the process is usually run at a slightly higher temperature and the mixture is stirred mechanically on an industrial scale instead of with compressed air.

Explosive properties

Methyl nitrate is a sensitive explosive. When ignited it burns extremely fiercely with a gray-blue flame. Methyl nitrate is a very strong explosive, like Nitroglycerin, Ethylene glycol dinitrate, including other nitrate esters. The sensitivity of methyl nitrate to initiation by detonation is among the greatest known, with even a number one blasting cap, the lowest power available, producing a near full detonation of the explosive.

Despite the superior explosive properties of methyl nitrate, it has not received application as an explosive due mostly to its high volatility, which prevents it from being stored or handled safely. It was used as a rocket fuel by Germany in World War II, in a mixture containing 25% methanol, which was named "myrol". This mixture would evaporate at a constant rate and so its composition would not change over time. It presents a slight explosive danger (it is somewhat difficult to detonate) and does not detonate easily via shock.

Safety

As well as being an explosive, methyl nitrate is toxic and causes headaches when inhaled.

References

  1. 1 2 CRC Handbook of Chemistry and Physics, 64th ed. 1983. pp. C–376.
  2. ↑ Meyer, R.; Köhler, J.; Homberg, A. (2007). Explosives (pdf) (6th ed.). Wiley-VCH. p. 212. ISBN 978-3-527-31656-4.
  3. ↑ Black, A. P.; Babers, F. H. (1939). "Methyl nitrate". Organic Syntheses. 19: 64. ; Collective Volume, 2, p. 412
  • "Methyl nitrate". Webbook. NIST.
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