Ethylamine

From Wikipedia, the free encyclopedia
Ethylamine[1]
IUPAC name

Ethanamine[2]

Other names

  • Aminoethane[citation needed]
  • 1-Aminoethane[citation needed]
  • Ethamine[citation needed]
  • Monoethylamine[citation needed]

Identifiers
CAS number 75-04-7 YesY
PubChem 6341
ChemSpider 6101 YesY
UNII YG6MGA6AT5 YesY
EC number 200-834-7
UN number 1036
KEGG C00797 YesY
MeSH ethylamine
ChEBI CHEBI:15862 YesY
ChEMBL CHEMBL14449 YesY
RTECS number KH2100000
Beilstein Reference 505933
Gmelin Reference 897
3DMet B00176
Jmol-3D images Image 1
Properties
Molecular formula C2H7N
Molar mass 45.08 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
Solubility in water Miscible
log P 0.037
Vapor pressure 116.5 kPa (at 20 °C)
kH 350 μmol Pa−1 kg−1
Thermochemistry
Std enthalpy of
formation ΔfHo298		 −57.7 kJ mol−1
Hazards
GHS pictograms
GHS signal word DANGER
GHS hazard statements H220, H319, H335
GHS precautionary statements P210, P261, P305+351+338, P410+403
EU Index 612-002-00-4
EU classification F+ Xi
R-phrases R12, R36/37
S-phrases (S2), S16, S26
NFPA 704
4
3
0
Flash point −37 °C; −35 °F; 236 K
Autoignition temperature 383 °C; 721 °F; 656 K
Explosive limits 3.5–14%
LD50
  • 265 mg kg−1 (dermal, rabbit)
  • 400 mg kg−1 (oral, rat)
Related compounds
Related alkanamines
Related compounds
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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[3]

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.[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. Ethylene and ammonia combine to give ethylamine in the presence of an sodium amide or related basic catalysts.[5]

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 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.[8] 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[9] and alkynes.

Ethylamine is a precursor to many herbicides including atrazine and simazine. It is found in rubber products as well.

References

  1. ↑ Merck Index, 12th Edition, 3808.
  2. ↑ "ethylamine - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 3 May 2012. 
  3. ↑ 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.
  4. ↑ 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
  5. ↑ Ulrich Steinbrenner, Frank Funke, Ralf Böhling, Method and device for producing ethylamine and butylamine, United States Patent 7161039.
  6. ↑ Nucleophilic substitution, Chloroethane & Ammonia, St Peter's School
  7. ↑ NRAO, "Discoveries Suggest Icy Cosmic Start for Amino Acids and DNA Ingredients", Feb 28 2013
  8. ↑ Ohme, R.; Preuschhof, H.; Heyne, H.-U. Azoethane, Organic Syntheses, Collected Volume 6, p.78 (1988)
  9. ↑ Kaiser, E. M.; Benkeser R. A. Δ9,10-Octalin, Organic Syntheses, Collected Volume 6, p.852 (1988)

External links

This article is issued from Wikipedia. The text is available under the Creative Commons Attribution/Share Alike; additional terms may apply for the media files.