Difference between revisions of "Methyl nitrate"
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| − | | Name =Methyl nitrate | + | | Name = Methyl nitrate |
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| − | | SystematicName =Methyl nitrate | + | | SystematicName = Methyl nitrate |
| − | | OtherNames = | + | | OtherNames = Nitrooxy-methane |
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| − | | OtherCompounds = [[ | + | | OtherCompounds = [[Nitric acid]]<br>[[Ethyl nitrate]]<br>[[Ethylene glycol dinitrate]]<br>[[Nitroglycerin]] |
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| − | '''Methyl nitrate''' is a chemical compound with the formula CH<sub>3</sub>NO<sub>3</sub>. It is the methyl ester of nitric acid. | + | '''Methyl nitrate''' is a chemical compound with the formula '''CH<sub>3</sub>NO<sub>3</sub>'''. It is the methyl ester of [[nitric acid]]. |
| + | |||
| + | While they have similar names, methyl nitrate is NOT [[nitromethane]] (CH<sub>3</sub>NO<sub>2</sub>). | ||
==Properties== | ==Properties== | ||
===Chemical=== | ===Chemical=== | ||
| − | Methyl nitrate is a strong explosive, sensitive, that burns with a blue-grayish flame | + | Methyl nitrate is a strong explosive, sensitive, that burns with a blue-grayish flame. |
===Physical=== | ===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/cm<sup>3</sup>. | 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/cm<sup>3</sup>. | ||
| + | |||
| + | ===Explosive=== | ||
| + | Methyl nitrate is a sensitive explosive, with a detonation velocity of 6300 m/s, slightly below that of [[Trinitrotoluene|TNT]]. | ||
==Availability== | ==Availability== | ||
| − | + | Due to its high sensitivity, methyl nitrate is not sold and has to be made in situ. | |
==Preparation== | ==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. | 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]].<ref>http://www.orgsyn.org/demo.aspx?prep=CV2P0412</ref> Nitrogen dioxide can also be used.<ref>Journal of Physical Chemistry; vol. 93; 13; (1989); p. 5162 - 5165</ref> | + | A safer way involved the nitration of methanol with a mixture of [[nitric acid]] and [[sulfuric acid]], aka [[nitrating mixture]].<ref>http://www.orgsyn.org/demo.aspx?prep=CV2P0412</ref> Nitrogen dioxide can also be used instead.<ref>Journal of Physical Chemistry; vol. 93; 13; (1989); p. 5162 - 5165</ref> |
Oxidizing [[nitromethane]] with [[nitrogen dioxide]] in an inert atmosphere will also yield methyl nitrate.<ref>International Journal of Chemical Kinetics; vol. 46; nb. 9; (2014); p. 501 - 511</ref> The same process also works with oxygen and [[sulfur dioxide]].<ref>Journal of Physical Chemistry; vol. 85; nb. 9; (1981); p. 1126 - 1132</ref> | Oxidizing [[nitromethane]] with [[nitrogen dioxide]] in an inert atmosphere will also yield methyl nitrate.<ref>International Journal of Chemical Kinetics; vol. 46; nb. 9; (2014); p. 501 - 511</ref> The same process also works with oxygen and [[sulfur dioxide]].<ref>Journal of Physical Chemistry; vol. 85; nb. 9; (1981); p. 1126 - 1132</ref> | ||
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[[Methyl iodide]] can be used instead of methanol, though this reaction must take place at -10 °C.<ref>Zhurnal Organicheskoi Khimii, vol. 4, (1968), p. 1893 - 1899, 1829 - 1833</ref> | [[Methyl iodide]] can be used instead of methanol, though this reaction must take place at -10 °C.<ref>Zhurnal Organicheskoi Khimii, vol. 4, (1968), p. 1893 - 1899, 1829 - 1833</ref> | ||
| − | The reaction of chloroethane with [[nitrogen monoxide]] and [[chlorine]] at 21.9 °C yields methyl nitrate, [[nitromethane]] and carbon oxides.<ref>http://pubs.acs.org/doi/abs/10.1021/j100125a016</ref> | + | The reaction of chloroethane with [[nitric oxide|nitrogen monoxide]] and [[chlorine]] at 21.9 °C yields methyl nitrate, [[nitromethane]] and carbon oxides.<ref>http://pubs.acs.org/doi/abs/10.1021/j100125a016</ref> |
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.<ref>International Journal of Chemical Kinetics; vol. 28; nb. 4; (1996); p. 299 - 306</ref> | 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.<ref>International Journal of Chemical Kinetics; vol. 28; nb. 4; (1996); p. 299 - 306</ref> | ||
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===Storage=== | ===Storage=== | ||
| − | Do not store methyl nitrate! | + | Do not store methyl nitrate! Use it as quickly as possible. |
===Disposal=== | ===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== | ==References== | ||
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[[Category:Contact poisons]] | [[Category:Contact poisons]] | ||
[[Category:Things that can kill you very quickly]] | [[Category:Things that can kill you very quickly]] | ||
| + | [[Category:Liquids]] | ||
Latest revision as of 17:46, 15 February 2020
| 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 | |
| Std enthalpy of
formation (ΔfH |
–2023.6 kJ/kg |
| Hazards | |
| Safety data sheet | None |
| Related compounds | |
| Related compounds
|
Nitric acid Ethyl nitrate 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).
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
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
- ↑ 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
