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Ethylammonium nitrate

Ethylammonium nitrate or ethylamine nitrate (EAN) is a salt with formula . It is an odorless and colorless to slightly yellowish liquid with a melting point of 12 °C. This compound was described by Paul Walden in 1914, and is believed to be the earliest reported example of a room-temperature ionic liquid.

Synthesis and properties

Ethylammonium nitrate can be produced by heating ethyl nitrate with an alcoholic solution of ammonia or by reacting ethylamine with concentrated nitric acid.

The ethylammonium ion () has three easily detachable protons which are tetrahedrally arranged around the central nitrogen atom, whereas the configuration of the anion is planar. Despite the structural differences, EAN shares many properties with water, such as micelle formation, aggregation of hydrocarbons, negative enthalpy and entropy of dissolution of gases, etc. Similar to water, EAN can form three-dimensional hydrogen bonding networks.

Applications

Ethylammonium nitrate is used as an electrically conductive solvent in electrochemistry and as a protein crystallization agent. It has a positive effect on the refolding of denaturated lysozyme, with the refolding yield of about 90%. The refolding action was explained as follows: The ethyl group of ethylammonium nitrate interacts with the hydrophobic part of the protein and thereby protects it from intermolecular association, whereas the charged part of EAN stabilizes the electrostatic interactions.

References

References

  1. (June 2024)
  2. "C&L Inventory".
  3. Wagaman, Kerry L [http://www.freepatentsonline.com/6001197.html Liquid monopropellant] United States Patent 6001197, Publication Date 12/14/1999
  4. (2004). "Room temperature ionic liquids and their mixtures—a review". Fluid Phase Equilibria.
  5. P. Walden. Chem. Zentralbl.. (1914)
  6. Mihkel Koel. (2008). "Ionic Liquids in Chemical Analysis". CRC Press.
  7. Rudolph Fittig. (2008). "Wohler's Outlines of Organic Chemistry". Read Books.
  8. "Safety Data Sheet". Carlroth.
  9. (1985). "Thermodynamic properties of the ethylammonium nitrate + water system: [[Partial molar volume]]s, heat capacities, and expansivities". [[Journal of Solution Chemistry]].
  10. (1999). "Ethylammonium nitrate: a protein crystallization reagent". Acta Crystallographica D.
  11. M. Riad Manaa. (2005). "Chemistry at extreme conditions". Elsevier.
  12. Jochen Decker, Udo Reischl. (2004). "Molecular diagnosis of infectious diseases". Humana Press.
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