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Ethylamine

Ethylamine
Skeletal formula of ethylamine
Skeletal formula of ethylamine with all explicit hydrogens added
Ball and stick model of ethylamine
Spacefill model of ethylamine
Names
Preferred IUPAC name
Ethanamine
Other names
Ethylamine
Identifiers
3D model (Jmol)
3DMet B00176
505933
ChEBI
ChemSpider
ECHA InfoCard 100.000.759
EC Number 200-834-7
897
KEGG
MeSH ethylamine
PubChem CID
RTECS number KH2100000
UNII
UN number 1036
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)
350 μmol Pa−1 kg−1
Acidity (pKa) 10.7
Thermochemistry
−57.7 kJ mol−1
Hazards
GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H220, H319, H335
P210, P261, P305+351+338, P410+403
Extremely Flammable F+ Irritant Xi
R-phrases R12, R36/37
S-phrases (S2), S16, S26
NFPA 704
Flammability code 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g., propane Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point −37 °C (−35 °F; 236 K)
383 °C (721 °F; 656 K)
Explosive limits 3.5–14%
Lethal dose or concentration (LD, LC):
LD50 (median dose)
  • 265 mg kg−1(dermal, rabbit)
  • 400 mg kg−1(oral, rat)
1230 ppm (mammal)
3000 ppm (rat, 4 hr)
4000 ppm (rat, 4 hr)
US health exposure limits (NIOSH):
PEL (Permissible)
 TWA 10 ppm (18 mg/m3)
REL (Recommended)
 TWA 10 ppm (18 mg/m3)
IDLH (Immediate danger)
 600 ppm
Related compounds
Related alkanamines
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
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 nucleophilic base, as is typical for amines. Ethylamine is widely used in chemical industry and organic synthesis.

pKa (of protonated form) = 10.7

Ethylamine is produced on a large scale by two processes. Most commonly ethanol and ammonia are combined in the presence of an oxide catalyst:

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.

Ethylamine can be prepared by several other routes, but these are not economical. Ethylene and ammonia combine to give ethylamine in the presence of a sodium amide or related basic catalysts.

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.


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Wikipedia

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