Ethyl nitrate
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| Names | |
|---|---|
| IUPAC name 1-Nitrosooxyethane | |
| Preferred IUPAC name Ethyl nitrate | |
| Other names Nitric acid ethyl ester | |
| Identifiers | |
3D model (JSmol) | |
| ChemSpider | |
| ECHA InfoCard | 100.009.913 |
PubChem CID | |
| UNII | |
CompTox Dashboard (EPA) | |
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| Properties | |
| C2H5NO3 | |
| Molar mass | 91.066 g·mol−1 |
| Appearance | colorless liquid |
| Odor | sweet |
| Density | 1.10g/cm3 |
| Melting point | −102 °C (−152 °F; 171 K) |
| Boiling point | 87.5 °C (189.5 °F; 360.6 K) |
| soluble | |
| Hazards | |
| NFPA 704 (fire diamond) | |
| 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 otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Ethyl nitrate is the ethyl ester of nitric acid and has the chemical formula C2H5NO3. It is a colourless, volatile, explosive, and extremely flammable liquid. It is used in organic synthesis with use as a nitrating agent and as an intermediate in the preparation of some drugs, dyes, and perfumes.[1] Like nitroglycerin, it's a vasodialator.
Ethyl nitrate is found in the atmosphere, where it can react with other gases to form smog. The pollutant was originally thought to have been formed mainly by the combustion of fossil fuels. However 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.[2]
Preparation
[edit]Ethyl nitrate has been prepared by bubbling gaseous nitryl fluoride through ethanol at −10 °C.[3] The reaction was subsequently studied in detail.[4][5]
Ethyl nitrate can be prepared by nitrating ethanol with fuming nitric acid or a mixture of concentrated sulfuric and nitric acids. Urea should be added to remove any nitrous acid and prevent explosion.[6] Further purifying by distillation carries a risk of explosion.[7]
A nucleophilic substitution reaction of ethyl halides and silver nitrate can also yield ethyl nitrate. Again, purification poses explosion risks.
Chemical reactions
[edit]Ethyl nitrate can be reduced with stannous chloride to form hydroxylammonium chloride, though product separation is somewhat difficult.[8]
Explosive properties
[edit]Ethyl nitrate is a sensitive explosive that is prone to detonating upon impact or high temperatures, though is less so than methyl nitrate. It has a detonation velocity of 6,010 m/s,[9] and is therefore a high explosive.
References
[edit]- ^ Schofield, Kenneth (1980). Aromatic nitration. Cambridge: Cambridge University Press. p. 94. ISBN 9780521233620. OCLC 6357479.
- ^ S. Perkins (August 12, 2002). "Ocean yields gases that had seemed humanmade". Science News (only available to subscribers).
- ^ G. Hetherington and R. L. Robinson (1954). "Nitryl fluoride as a nitrating agent". J. Chem. Soc.: 3512. doi:10.1039/JR9540003512.
- ^ 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.
- ^ Explosives, 6th Edition, R. Meyer, J. Kohler, A. Homburg; page 125
- ^ William M. Cumming, I. Vance Hopper (1937). Systematic Organic Chemistry 3ed.
- ^ Cohen, Julius B. (Julius Berend) (1920). Theoretical organic chemistry. University of California Libraries. London, Macmillan. p. 189.
- ^ Dumreicher, Oscar Freih v. (December 1880). "Untersuchungen über die Einwirkung von Zinnchlorür auf die Stickstoffsauerstoffverbindungen". Monatshefte für Chemie (in German). 1 (1): 724–754. doi:10.1007/BF01517102. ISSN 0026-9247.
- ^ Kozak, G. D. (September 1998). "Measurement and calculation of the ideal detonation velocity for liquid nitrocompounds". Combustion, Explosion, and Shock Waves. 34 (5): 581–586. doi:10.1007/BF02672682. ISSN 0010-5082.