Ethylamine

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.

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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^[2] and alkynes.

Synthesis and reactions

Ethylamine can be prepared in a laboratory by reaction of ethylene with ammonia in the presence of a catalyst.

H₂C=CH₂ + NH₃ → CH₃CH₂NH₂

It can also be synthesized from acetaldehyde and ammonium chloride.^{[citation needed]}

2 CH₃CHO + NH₄Cl → CH₃CH₂NH₃Cl + CH₃CO₂H

CH₃CH₂NH₃Cl + NaOH → CH₃CH₂NH₂ + NaCl + H₂O

Reaction of ethylamine with sulfuryl chloride followed by oxidaton of the sulfonamide give diethyldiazene, EtN=NEt.^[3]

It is a basic compound.

References

1. ^ Merck Index, 12th Edition, 3808.
2. ^ Kaiser, E. M.; Benkeser R. A. "Δ9,10-Octalin" Organic Syntheses, Collected Volume 6, p.852 (1988). http://www.orgsyn.org/orgsyn/pdfs/CV6P0852.pdf
3. ^ Ohme, R.; Preuschhof, H.; Heyne, H.-U. "Azoethane" Organic Syntheses, Collected Volume 6, p.78 (1988). http://www.orgsyn.org/orgsyn/pdfs/CV6P0078.pdf