Ethylamine
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Names | |||
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Preferred IUPAC name
Ethanamine | |||
Other names
Ethylamine
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Identifiers | |||
3D model (
JSmol ) |
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3DMet | |||
505933 | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard
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100.000.759 | ||
EC Number |
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897 | |||
KEGG | |||
MeSH | ethylamine | ||
PubChem CID
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RTECS number
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UNII | |||
UN number | 1036 | ||
CompTox Dashboard (EPA)
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Properties | |||
C2H7N | |||
Molar mass | 45.085 g·mol−1 | ||
Appearance | Colourless gas | ||
Odor | fishy, ammoniacal | ||
Density | 688 kg m−3 (at 15 °C) | ||
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) | ||
Henry's law
constant (kH) |
350 μmol Pa−1 kg−1 | ||
Acidity (pKa) | 10.8 (for the Conjugate acid )
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Basicity (pKb) | 3.2 | ||
Thermochemistry | |||
Std enthalpy of (ΔfH⦵298)formation |
−57.7 kJ mol−1 | ||
Hazards | |||
GHS labelling: | |||
Danger | |||
H220, H319, H335 | |||
P210, P261, P305+P351+P338, P410+P403 | |||
NFPA 704 (fire diamond) | |||
Flash point | −37 °C (−35 °F; 236 K) | ||
383 °C (721 °F; 656 K) | |||
Explosive limits
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3.5–14% | ||
Lethal dose or concentration (LD, LC): | |||
LD50 (median dose)
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LC50 (median concentration)
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1230 ppm (mammal)[3] | ||
LCLo (lowest published)
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3000 ppm (rat, 4 hr) 4000 ppm (rat, 4 hr)[3] | ||
NIOSH (US health exposure limits): | |||
PEL (Permissible)
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TWA 10 ppm (18 mg/m3)[2] | ||
REL (Recommended)
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TWA 10 ppm (18 mg/m3)[2] | ||
IDLH (Immediate danger) |
600 ppm[2] | ||
Related compounds | |||
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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Ethylamine, also known as ethanamine, is an organic compound with the formula CH3CH2NH2. This colourless gas has a strong ammonia-like odor. It condenses just below room temperature to a liquid miscible with virtually all solvents. It is a nucleophilic base, as is typical for amines. Ethylamine is widely used in chemical industry and organic synthesis.[4]
Synthesis
Ethylamine is produced on a large scale by two processes. Most commonly
- 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.[4] 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.
- 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.[6]
- CH3CH2Cl + NH3 + KOH → CH3CH2NH2 + KCl + H2O
Ethylamine is also produced naturally in the cosmos; it is a component of interstellar gases.[7]
Reactions
Like other simple
Ethylamine undergoes the reactions anticipated for a primary alkyl amine, such as
Ethylamine like some other small primary amines is a good solvent for
Applications
Ethylamine is a precursor to many herbicides including atrazine and simazine. It is found in rubber products as well.[4]
Ethylamine is used as a precursor chemical along with
References
- ^ Merck Index, 12th Edition, 3808.
- ^ a b c NIOSH Pocket Guide to Chemical Hazards. "#0263". National Institute for Occupational Safety and Health (NIOSH).
- ^ a b "Ethylamine". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
- ^
- ^ Ulrich Steinbrenner, Frank Funke, Ralf Böhling, Method and device for producing ethylamine and butylamine Archived 2012-09-12 at archive.today, United States Patent 7161039.
- ^ Nucleophilic substitution, Chloroethane & Ammonia Archived 2008-05-28 at the Wayback Machine, St Peter's School
- ^ NRAO, "Discoveries Suggest Icy Cosmic Start for Amino Acids and DNA Ingredients", Feb 28 2013
- ^ 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 and 10.63.
- .
- .
- ^ Kaiser, E. M.; Benkeser R. A. Δ9,10-Octalin Archived 2007-09-30 at the Wayback Machine, Organic Syntheses, Collected Volume 6, p.852 (1988)
- ^ "World Health Organization Critical Review Report of Ketamine, 34th ECDD 2006/4.3" (PDF).