|Jmol-3D images||Image 1|
|Molar mass||45.08 g mol−1|
-85--79 °C, 188-194 K, -121--110 °F
16-20 °C, 289-293 K, 61-68 °F
|Solubility in water||Miscible|
|Vapor pressure||116.5 kPa (at 20 °C)|
|kH||350 μmol Pa−1 kg−1|
|Std enthalpy of
|−57.7 kJ mol−1|
|GHS signal word||DANGER|
|GHS hazard statements||H220, H319, H335|
|GHS precautionary statements||P210, P261, P305+351+338, P410+403|
|EU classification||F+ Xi|
|S-phrases||(S2), S16, S26|
|Flash point||−37 °C|
| (what is: / ?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Ethylamine is an organic compound with the formula CH3CH2NH2. This colourless gas has a strong ammonia-like odor. It is miscible with virtually all solvents and is a weak base, as is typical for amines. Ethylamine is widely used in chemical industry and organic synthesis.
pKa (of protonated form) = 10.7
- CH3CH2OH + NH3 → CH3CH2NH2 + H2O
In this reaction, ethylamine is coproduced together with diethylamine and triethylamine. In aggregate, approximately 80M kilograms/year of these three amines are produced industrially. It is also produced by reductive amination of acetaldehyde.
- CH3CHO + NH3 + H2 → CH3CH2NH2 + H2O
- H2C=CH2 + NH3 → CH3CH2NH2
Hydrogenation of acetonitrile, acetamide, and nitroethane affords ethylamine. These reactions can be effected stoichiometrically using lithium aluminium hydride. In another route, ethylamine can be synthesized via nucleophilic substitution of a haloethane (such as chloroethane or bromoethane) with ammonia, utilizing a strong base such as potassium hydroxide. This method affords significant amounts of byproducts, including diethylamine and triethylamine.
- CH3CH2Cl + NH3 + KOH → CH3CH2NH2 + KCl + H2O
Ethylamine is also produced naturally in the cosmos; it is a component of interstellar gases.
Reactions and applications
Ethylamine undergoes the reactions anticipated for a primary alkyl amine, such as acylation and protonation. Reaction with sulfuryl chloride followed by oxidaton of the sulfonamide give diethyldiazene, EtN=NEt. Ethylamine may be oxidized using a strong oxidizer such as potassium permanganate to form acetaldehyde.
Ethylamine like some other small primary amines is a good solvent for lithium metal, giving 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.
- Merck Index, 12th Edition, 3808.
- "ethylamine - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 3 May 2012.
- Wilson and Gisvold's Textbook of Organic Medicinal and Pharmaceutical Chemistry, 9th Ed. (1991), (J. N. Delgado and W. A. Remers, Eds.) p.878, Philadelphia: Lippincott.
- Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke, “Amines, Aliphatic” Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.doi:10.1002/14356007.a02_001
- Ulrich Steinbrenner, Frank Funke, Ralf Böhling, Method and device for producing ethylamine and butylamine, United States Patent 7161039.
- Nucleophilic substitution, Chloroethane & Ammonia, St Peter's School
- NRAO, "Discoveries Suggest Icy Cosmic Start for Amino Acids and DNA Ingredients", Feb 28 2013
- Ohme, R.; Preuschhof, H.; Heyne, H.-U. Azoethane, Organic Syntheses, Collected Volume 6, p.78 (1988)
- Kaiser, E. M.; Benkeser R. A. Δ9,10-Octalin, Organic Syntheses, Collected Volume 6, p.852 (1988)