Ethylamine

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Ethylamine[1]
Skeletal formula of ethylamine Skeletal formula of ethylamine with all explicit hydrogens added
Ball and stick model of ethylamine Spacefill model of ethylamine
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 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
GHS hazard statements H220, H319, H335
GHS precautionary statements P210, P261, P305+351+338, P410+403
EU Index 612-002-00-4
EU classification 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)
Explosive limits 3.5–14%
LD50
  • 265 mg kg−1 (dermal, rabbit)
  • 400 mg kg−1 (oral, rat)
Related compounds
Related alkanamines
Related compounds
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
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[edit]

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[edit]

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.

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. [10]

References[edit]

  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)
  10. ^ "World Health Organization Critical Review Report of Ketamine, 34th ECDD 2006/4.3". 

External links[edit]