Ethylamine

Ethylamine

[eth-uhl-uh-meen, -min, -am-in]
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Ethylamine is a chemical compound with the formula CH3CH2NH2. It has a strong ammonia-like odor. It is miscible with virtually all solvents and is considered to be a weak base, as is typical for amines. Ethylamine is widely used in chemical industry and organic synthesis.

Ethylamine, like some other amines, has the unusual property of dissolving lithium metal to give the ion [Li(amine)4]+ and the solvated electron. Evaporation of these solutions, gives back lithium metal. Such solutions are used for the reduction of unsaturated organic compounds, such as naphthalenes and alkynes.

Synthesis

H2C=CH2 + NH3 → CH3CH2NH2
:

2 CH3CHO + NH4Cl → CH3CH2NH3Cl + CH3CO2H
CH3CH2NH3Cl + NaOH → CH3CH2NH2 + NaCl + H2O

  • Ethylamine can be made directly from Ethanol and Ammonia in the presence of hydrogen using a hydrogenation catalyst such as a 4:1 ratio nickel-copper alloy. This reaction requires elevated temperatures and/or pressure.

:

  • Amines such as ethylamine may also be synthesized by the reduction of amides such as Acetamide, for example using Lithium aluminum hydride (LiAlH4 or LAH), according to the following formula:

2RCONR2 + LiAlH4 → 2RCH2NR2 + LiAlO2

:

C2H5Cl + NH3 → C2H8N+ + Cl-
C2H8N+ + Cl- + KOH → C2H7N + KCl + H2O

:

If instead, a halomethane is used in the above reaction, it will yield methylamine although the other byproducts dimethylamine, trimethylamine and tetramethylammonium are much harder to separate as they have similar boiling points.

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