Ethylamine
From Wikipedia, the free encyclopedia
| Ethylamine[1] | |
|---|---|
 |
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| IUPAC name | Ethanamine |
| Other names | Ethylamine, Monoethylamine, Aminoethane, 1-Aminoethane |
| Identifiers | |
| CAS number | [75-04-7] |
| PubChem | |
| EINECS number | |
| RTECS number | KH2100000 |
| SMILES | CCN |
| InChI | 1/C2H7N/c1-2-3/h2-3H2,1H3 |
| Properties | |
| Molecular formula | C2H7N |
| Molar mass | 45.08 g/mol |
| Appearance | Light yellow liquid |
| Density | 0.689 g/cm3 |
| Melting point |
-81 °C |
| Boiling point |
16.6 °C |
| Solubility in water | Miscible |
| Vapor pressure | 121 kPa (20 °C) |
| Hazards | |
| Main hazards | Harmful, corrosive, highly flammable |
| NFPA 704 |
 4
3
0
ALK
|
| R-phrases | R12, R20, R22, R34, R36, R37, R38 |
| S-phrases | S16, S26, S29 |
| Flash point | -17 °C |
| Autoignition temperature |
385 °C |
| Explosive limits | 3.5-14 %V |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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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[2] and alkynes.
[edit] Synthesis and reactions
Ethylamine can be prepared in a laboratory by reaction of ethylene with ammonia in the presence of an alkali metal amide catalyst such as sodium amide.[3]
- 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
Ethylamine may be synthesized via nucleophilic substitution of a haloethane (such as chloroethane or bromoethane) with ammonia as a reagent, utilizing a strong base such as potassium hydroxide. This forms the ethylammonium cation. Significant amounts of byproducts are formed, including diethylamine and triethylamine, as well as tetraethylammonium cation, from which the ethylamine can be separated via simple distillation as all of these by-products have significantly higher boiling points.[4][5]
- 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.
Reaction of ethylamine with sulfuryl chloride followed by oxidaton of the sulfonamide give diethyldiazene, EtN=NEt.[6]
[edit] References
- ^ Merck Index, 12th Edition, 3808.
- ^ Kaiser, E. M.; Benkeser R. A. Δ9,10-Octalin, Organic Syntheses, Collected Volume 6, p.852 (1988)
- ^ Ulrich Steinbrenner, Frank Funke, Ralf Böhling, Method and device for producing ethylamine and butylamine, United States Patent 7161039.
- ^ Chemistry in Context, John Holman, Graham Hill, Page 461
- ^ Nucleophilic substitution, Chloroethane & Ammonia, St Peter's School
- ^ Ohme, R.; Preuschhof, H.; Heyne, H.-U. Azoethane, Organic Syntheses, Collected Volume 6, p.78 (1988)
