Ethyl nitrate

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Ethyl nitrate
Names
IUPAC name
Ethyl nitrate
Other names
Nitric acid ethyl ester
Nitric ether
Properties
C2H5NO3
Molar mass 91.07 g/mol
Appearance Colorless liquid
Odor Sweet, pleasant
Density 1.1084 g/cm3 (20 °C)
Melting point −102 °C (−152 °F; 171 K)
Boiling point 87.5 °C (189.5 °F; 360.6 K)
Slightly soluble
Solubility Miscible with diethyl ether, ethanol, methanol
Vapor pressure 64.0 mm Hg at 25 °C
Thermochemistry
Hazards
Safety data sheet None
Related compounds
Related compounds
Methyl nitrate
Ethylene glycol dinitrate
Propyl nitrate
Isopropyl nitrate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Ethyl nitrate is an organic chemical compound, the ethyl ester of nitric acid. It has the chemical formula C2H5NO3.

Properties

Chemical

Ethyl nitrate burns in air releasing carbon dioxide, water vapors and nitrogen oxides.

Physical

Ethyl nitrate is a colorless liquid, with an odor and taste described as sweet, typical of organic nitrate esters.

Explosive

Ethyl nitrate, like all low-weight nitrate esters is a sensitive explosive, especially to strong impact or exposure to very high temperatures, though less so than methyl nitrate. It has been claimed to explode during distillation, though the exact reason is not given. Ethyl nitrate has a detonation velocity of 6010 m/s at a density of 1.11.[1] It has an oxygen balance of -61.5%.[2]

Availability

Ethyl nitrate, like most organic nitrate esters is not sold by chemical suppliers, due to its hazards, and has to be prepared in situ.

Preparation

Ethyl nitrate has been prepared in high yield by reacting ethyl halide (like ethyl chloride or ethyl iodide) with silver nitrate in a solvent.

C2H5X + AgNO3 → C2H5NO3 + AgX

Silver chloride/iodide precipitates out of the solution, and the ethyl nitrate solution is filtered and purified. Although it's possible to remove the ethyl nitrate from the resulting solution, concentrating this compounds carries a risk of explosion.

Ethyl nitrate can also be prepared by nitrating ethanol with fuming nitric acid or a mixture of concentrated sulfuric and nitric acids, in the presence of urea.[3] Further purifying by distillation carries a serious risk of explosion, especially if done at atmospheric pressure.

Ethyl nitrate has been prepared by bubbling gaseous nitryl fluoride through ethanol at −10 °C.[4]

Projects

  • Make blasting cap
  • Vasodilator

Handling

Safety

Ethyl nitrate in its pure form is sensible to shock and may explode if struck. This property is greatly increased by its volatility. Contact with skin or inhaled, like in the case of nitroglycerin, will lead to severe headaches.

Storage

Do not store ethyl nitrate! Use it as quickly as possible.

Disposal

Small amounts of ethyl nitrate can be detonated in a safe area, or heavily diluted with a flammable solvent, like an alcohol and burned.

For a chemical, safer method, ethyl 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. https://link.springer.com/article/10.1007/BF02672682
  2. Jiping Liu, 2015, Liquid Explosives
  3. https://www.prepchem.com/synthesis-of-ethyl-nitrate/
  4. https://pubs.rsc.org/en/content/articlelanding/1954/JR/jr9540003512#!divAbstract

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