Ethylamine
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| Names | |||
|---|---|---|---|
| IUPAC name
Ethanamine[3]
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Other names
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| Identifiers | |||
75-04-7  |
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| 3DMet | B00176 | ||
| 505933 | |||
| ChEBI | CHEBI:15862 |
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| ChEMBL | ChEMBL14449 |
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| ChemSpider | 6101 |
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| EC Number | 200-834-7 | ||
| 897 | |||
| Jmol 3D model | Interactive image | ||
| KEGG | C00797 |
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| MeSH | ethylamine | ||
| PubChem | 6341 | ||
| RTECS number | KH2100000 | ||
| UNII | YG6MGA6AT5 |
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| UN number | 1036 | ||
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| Properties | |||
| C2H7N | |||
| Molar mass | 45.09 g·mol−1 | ||
| Appearance | Colourless gas | ||
| Odor | fishy, ammoniacal | ||
| Melting point | −85 to −79 °C; −121 to −110 °F; 188 to 194 K | ||
| Boiling point | 16 to 20 °C; 61 to 68 °F; 289 to 293 K | ||
| Miscible | |||
| log P | 0.037 | ||
| Vapor pressure | 116.5 kPa (at 20 °C) | ||
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Henry's law
constant (kH) |
350 μmol Pa−1 kg−1 | ||
| Thermochemistry | |||
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Std enthalpy of
formation (ΔfH |
−57.7 kJ mol−1 | ||
| Vapor pressure | {{{value}}} | ||
| Related compounds | |||
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Related alkanamines
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Related compounds
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |||
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[4]
Synthesis
Ethylamine is produced on a large scale by two processes. Most commonly ethanol and ammonia are combined in the presence of an oxide catalyst:
- 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.[5] It is also produced by reductive amination of acetaldehyde.
- CH3CHO + NH3 + H2 → CH3CH2NH2 + H2O
Ethylamine can be prepared by several other routes, but these are not economical. Ethylene and ammonia combine to give ethylamine in the presence of an sodium amide or related basic catalysts.[6]
- 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.[7]
- CH3CH2Cl + NH3 + KOH → CH3CH2NH2 + KCl + H2O
Ethylamine is also produced naturally in the cosmos; it is a component of interstellar gases.[8]
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.[9] 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[10] and alkynes.
Ethylamine is a precursor to many herbicides including atrazine and simazine. It is found in rubber products as well.
Ethylamine is used as a precursor chemical along with benzilnitrate (as opposed to o-chlorobenzonitrile and methylamine in ketamine synthesis) in the clandestine synthesis of cyclidine dissociative anesthetic agents (the analogue of ketamine which is missing the 2-chloro group on the phenyl ring, and its N-ethyl analog) which are closely related to the well known anesthetic agent ketamine and the recreational drug phencyclidine and have been detected on the black market, being marketed for use as a recreational hallucinogen and tranquilizer. This produces a cyclidine with the same mechanism of action as ketamine (NMDA receptor antagonism) but with a much greater potency at the PCP binding site, a longer half-life, and significantly more prominent sympathomimetic effects. [11]
References
- ↑ Merck Index, 12th Edition, 3808.
- ↑ 2.0 2.1 Cite error: Invalid
<ref>tag; no text was provided for refs namedNIOSH - ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ 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)
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
External links
- Safety data at www.inchem.org
- Safety MSDS data
- Atrazine News - an Atrazine specific news site
- CDC - NIOSH Pocket Guide to Chemical Hazards
