Methyl nitrate
| Names | |
|---|---|
| IUPAC name
Methyl nitrate
| |
| Systematic IUPAC name
Methyl nitrate | |
| Properties | |
| CH3NO3 | |
| Molar mass | 77.04 g/mol |
| Appearance | Colorless liquid |
| Density | 1.203 g/cm3 |
| Melting point | −82.3 °C (−116.1 °F; 190.8 K) |
| Boiling point | 64.6 °C (148.3 °F; 337.8 K) |
| Poorly soluble in water | |
| Thermochemistry | |
| Std enthalpy of
formation (ΔfH |
–2023.6 kJ/kg |
| Hazards | |
| Related compounds | |
| Related compounds
|
Nitric acid Ethylene glycol dinitrate Nitroglycerin |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Methyl nitrate is a chemical compound with the formula CH3NO3. It is the methyl ester of nitric acid.
Contents
Properties
Chemical
Methyl nitrate is a strong explosive, sensitive, that burns with a blue-grayish flame.
Physical
Methyl nitrate is a colorless liquid, poorly soluble in water. It freezes at −82.3 °C and boils at 64.6 °C. Methyl nitrate has a density of 1.203 g/cm3.
Explosive
Methyl nitrate is a sensitive explosive, with a detonation velocity of 6300 m/s, slightly below that of TNT.
Availability
Methyl nitrate is too dangerous to be sold.
Preparation
Although methyl nitrate can be produced through the distillation of a mixture of methanol and nitric acid, this is extremely dangerous as methyl nitrate vapors may explode.
A safer way involved the nitration of methanol with a mixture of nitric acid and sulfuric acid, aka nitrating mixture.[1] Nitrogen dioxide can also be used instead.[2]
Oxidizing nitromethane with nitrogen dioxide in an inert atmosphere will also yield methyl nitrate.[3] The same process also works with oxygen and sulfur dioxide.[4]
Methyl iodide can be used instead of methanol, though this reaction must take place at -10 °C.[5]
The reaction of chloroethane with nitrogen monoxide and chlorine at 21.9 °C yields methyl nitrate, nitromethane and carbon oxides.[6]
Oxidizing di-tert-butyl ether with oxygen, nitrogen monoxide and chlorine at 21.9 °C produces carbon monoxide, nitromethane, methyl nitrate and tert-butyl acetate. The process also works at 1020 mbar under irradiation.[7]
The electrolysis of sodium acetate and sodium nitrate in acetic acid at 20 °C can also yield methyl nitrate.[8]
Reacting methyl bisulfate with nitric acid will also produce methyl nitrate.[9]
Projects
- Make blasting cap
- Make myrol (75% CH3NO3, 25%CH3OH)
Handling
Safety
Methyl nitrate is sensible to shock and may explode if struck. This property is greatly increased by its volatility. It is also toxic and, like in the case of nitroglycerin, it will cause headaches if inhaled.
Storage
Do not store methyl nitrate!
Disposal
Methyl nitrate can be safely destroyed with a base, at low temperature.
References
- ↑ http://www.orgsyn.org/demo.aspx?prep=CV2P0412
- ↑ Journal of Physical Chemistry; vol. 93; 13; (1989); p. 5162 - 5165
- ↑ International Journal of Chemical Kinetics; vol. 46; nb. 9; (2014); p. 501 - 511
- ↑ Journal of Physical Chemistry; vol. 85; nb. 9; (1981); p. 1126 - 1132
- ↑ Zhurnal Organicheskoi Khimii, vol. 4, (1968), p. 1893 - 1899, 1829 - 1833
- ↑ http://pubs.acs.org/doi/abs/10.1021/j100125a016
- ↑ International Journal of Chemical Kinetics; vol. 28; nb. 4; (1996); p. 299 - 306
- ↑ http://onlinelibrary.wiley.com/doi/10.1002/hlca.193501801137/abstract
- ↑ Chem. Zentralbl.; vol. 103; nb. II; (1932); p. 2032
