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.

Additional recommended knowledge

Daily Sensitivity Test

Daily Visual Balance Check

Essential Laboratory Skills Guide

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