Ethyl nitrate

Not to be confused with nitroethane or ethyl nitrite.
Ethyl nitrate
Names
IUPAC name
Ethyl nitrate
Other names
Nitric acid ethyl ester
Identifiers
625-58-1 Yes
ChemSpider 11756 
Jmol-3D images Image
PubChem 12259
Properties
C2H5NO3
Molar mass 91.07 g/mol
Appearance colorless liquid
Density 1.10g/cm3
Melting point −102 °C (−152 °F; 171 K)
Boiling point 87.5 °C (189.5 °F; 360.6 K)
Decomposes
Hazards
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 4: Readily capable of detonation or explosive decomposition at normal temperatures and pressures. E.g., nitroglycerin Special hazards (white): no codeNFPA 704 four-colored diamond
3
2
4
Flash point −37 °C; −34 °F; 236 K
Explosive limits 4.1%-50%
Related compounds
Related Alkyl nitrates
Methyl nitrate
Ethylene glycol dinitrate
Isopropyl nitrate
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Ethyl nitrate is the ethyl ester of nitric acid and has the chemical formula C2H5NO3. It is a colourless, volatile, highly flammable liquid. It is used in organic synthesis and as an intermediate in the preparation of some drugs, dyes, and perfumes.

Ethyl nitrate is found in the atmosphere, where it can react with other gases to form smog. Originally thought to be a pollutant, formed mainly by the combustion of fossil fuels, recent analysis of ocean water samples reveal that in places where cool water rises from the deep, the water is saturated with alkyl nitrates, likely formed by natural processes.[1]

Preparation

Ethyl nitrate has been prepared by bubbling gaseous nitryl fluoride through ethanol at −10 °C.[2] The reaction was subsequently studied in detail.[3][4]


References

  1. ↑ S. Perkins (August 12, 2002). "Ocean yields gases that had seemed humanmade". Science News.
  2. ↑ G. Hetherington and R. L. Robinson (1954). "Nitryl fluoride as a nitrating agent". J. Chem. Soc.: 3512. doi:10.1039/JR9540003512.
  3. ↑ B. S. Fedorov and L. T. Eremenko (1997). "Nitration of alcohols by nitryl fluoride". Russian Chemical Bulletin 46 (5): 1022–1023. doi:10.1007/BF02496138.
  4. ↑ Explosives, 6th Edition, R. Meyer, J. Kohler, A. Homburg; page 125