Methyl nitrate

From Sciencemadness Wiki
Jump to: navigation, search
Methyl nitrate
Names
IUPAC name
Methyl nitrate
Systematic IUPAC name
Methyl nitrate
Other names
Nitrooxy-methane
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
–2023.6 kJ/kg
Hazards
Safety data sheet None
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.

While they have similar names, methyl nitrate is NOT nitromethane (CH3NO2).

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

Due to its high sensitivity, methyl nitrate is not sold and has to be made in situ.

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! Use it as quickly as possible

Disposal

Small amounts of methyl nitrate can be detonated in a safe area.

For a chemical, safer method, methyl nitrate should be first diluted in an alcohol, then very carefully and slowly, a diluted solution of NaOH in alcohol is added dropwise, while keeping the solution cooled at low temperature. This route should not be performed unless the person knows how the reaction will proceed.

References

  1. http://www.orgsyn.org/demo.aspx?prep=CV2P0412
  2. Journal of Physical Chemistry; vol. 93; 13; (1989); p. 5162 - 5165
  3. International Journal of Chemical Kinetics; vol. 46; nb. 9; (2014); p. 501 - 511
  4. Journal of Physical Chemistry; vol. 85; nb. 9; (1981); p. 1126 - 1132
  5. Zhurnal Organicheskoi Khimii, vol. 4, (1968), p. 1893 - 1899, 1829 - 1833
  6. http://pubs.acs.org/doi/abs/10.1021/j100125a016
  7. International Journal of Chemical Kinetics; vol. 28; nb. 4; (1996); p. 299 - 306
  8. http://onlinelibrary.wiley.com/doi/10.1002/hlca.193501801137/abstract
  9. Chem. Zentralbl.; vol. 103; nb. II; (1932); p. 2032

Relevant Sciencemadness threads