Ethyl nitrate

Last updated
Ethyl nitrate
Ethyl Nitrate Structural Formulae V.1.svg
Ethyl nitrate 3D ball.png
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 210-903-3
PubChem CID
UNII
UN number 1993
  • InChI=1S/C2H5NO3/c1-2-6-3(4)5/h2H2,1H3 X mark.svgN
    Key: IDNUEBSJWINEMI-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C2H5NO3/c1-2-6-3(4)5/h2H2,1H3
    Key: IDNUEBSJWINEMI-UHFFFAOYAM
  • CCO[N+](=O)[O-]
Properties
C2H5NO3
Molar mass 91.066 g·mol−1
Appearancecolorless 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
GHS labelling:
GHS-pictogram-explos.svg
Danger
H200
P201, P202, P281, P372, P373, P380, P401, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 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. gasolineInstability 4: Readily capable of detonation or explosive decomposition at normal temperatures and pressures. E.g. nitroglycerinSpecial hazards (white): no code
2
3
4
Flash point −37 °C; −34 °F; 236 K
Explosive limits 4.1–50%
Related compounds
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).
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Ethyl nitrate is the ethyl ester of nitric acid and has the chemical formula C 2 H 5 N O 3. 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 vasodilator.

Contents

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]

History and synthesis

Reaction of ethanol with nitric acid was investigated since the Middle Ages, but the fact that it produces mostly ethyl nitrite was not discovered until the 19th century. Eugène Millon was the first to synthesize ethyl nitrate in 1843 by adding urea to the mixture in order to remove any nitrous acid. [3] [4]

Ethyl nitrate can be prepared by nitrosylating ethanol with fuming nitric acid or a mixture of concentrated sulfuric and nitric acids. Besides decomposing nitrous acid, the aforementioned necessary addition of urea prevents explosion. [5] Further purifying by distillation carries a risk of explosion. [6]

Ethyl nitrate has also been prepared by bubbling gaseous nitryl fluoride through ethanol at −10 °C. [7] The reaction was subsequently studied in detail. [8] [9]

A nucleophilic substitution reaction of ethyl halides and silver nitrate can also yield ethyl nitrate. Again, purification poses explosion risks.

Chemical reactions

Ethyl nitrate can be reduced with stannous chloride to form hydroxylammonium chloride, though product separation is somewhat difficult. [10]

Explosive properties

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, [11] and is therefore a high explosive.

References

  1. ↑ Schofield, Kenneth (1980). Aromatic nitration. Cambridge: Cambridge University Press. p. 94. ISBN   9780521233620. OCLC   6357479.
  2. ↑ S. Perkins (August 12, 2002). "Ocean yields gases that had seemed humanmade". Science News (only available to subscribers).
  3. ↑ Roscoe, Henry Enfield; Schorlemmer, Carl (1881). A Treatise on Chemistry: The chemistry of the hydrocarbons and their derivatives, or, Organic chemistry. Macmillan.
  4. ↑ Annales de chimie et de physique (in French). Masson. 1843.
  5. ↑ William M. Cumming, I. Vance Hopper (1937). Systematic Organic Chemistry 3ed.
  6. ↑ Cohen, Julius B. (Julius Berend) (1920). Theoretical organic chemistry. University of California Libraries. London, Macmillan. p.  189.
  7. ↑ G. Hetherington and R. L. Robinson (1954). "Nitryl fluoride as a nitrating agent". J. Chem. Soc. : 3512. doi:10.1039/JR9540003512.
  8. ↑ 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.
  9. ↑ Explosives, 6th Edition, R. Meyer, J. Kohler, A. Homburg; page 125
  10. ↑ 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.
  11. ↑ 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. Bibcode:1998CESW...34..581K. doi:10.1007/BF02672682. ISSN   0010-5082.
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