Ethylamine

{{Chembox | Watchedfields = changed | verifiedrevid = 443744511 | Reference = <ref>''Merck Index'', 12th Edition, '''3808'''.</ref> | ImageFile1 = EtNH2.svg | ImageClass1 = skin-invert-image | ImageNameL1 = Skeletal formula of ethylamine | ImageFileL2 = Ethylamine-3D-balls.png | ImageClassL2 = bg-transparent | ImageFileL2_Ref = {{chemboximage|correct|??}} | ImageNameL2 = Ball and stick model of ethylamine | ImageFileR2 = Ethylamine-3D-vdW.png | ImageClassR2 = bg-transparent | ImageFileR2_Ref = {{chemboximage|correct|??}} | ImageNameR2 = Spacefill model of ethylamine | PIN = Ethanamine | OtherNames = Ethylamine |Section1={{Chembox Identifiers | CASNo = 75-04-7 | CASNo_Ref = {{cascite|correct|CAS}} | PubChem = 6341 | ChemSpiderID = 6101 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | UNII = YG6MGA6AT5 | UNII_Ref = {{fdacite|correct|FDA}} | EINECS = 200-834-7 | UNNumber = 1036 | KEGG = C00797 | KEGG_Ref = {{keggcite|correct|kegg}} | MeSHName = ethylamine | ChEBI = 15862 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEMBL = 14449 | ChEMBL_Ref = {{ebicite|correct|EBI}} | RTECS = KH2100000 | Beilstein = 505933 | Gmelin = 897 | 3DMet = B00176 | SMILES = CCN | StdInChI = 1S/C2H7N/c1-2-3/h2-3H2,1H3 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = QUSNBJAOOMFDIB-UHFFFAOYSA-N | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} }} |Section2={{Chembox Properties | C=2 | H=7 | N=1 | Appearance = Colourless gas | Odor = fishy, ammoniacal | Density = 688 kg m−3 (at 15 °C) | MeltingPtK = 188 to 194 | BoilingPtK = 289 to 293 | Solubility = Miscible | LogP = 0.037 | VaporPressure = 116.5 kPa (at 20 °C) | HenryConstant = 350 μmol Pa−1 kg−1 | pKa = 10.8 (for the Conjugate acid) | pKb = 3.2 }} |Section3={{Chembox Thermochemistry | DeltaHf = −57.7 kJ mol−1 }} |Section4={{Chembox Hazards | GHSPictograms = {{GHS flame}} {{GHS exclamation mark}} | GHSSignalWord = '''DANGER''' | HPhrases = {{H-phrases|220|319|335}} | PPhrases = {{P-phrases|210|261|305+351+338|410+403}} | NFPA-H = 3 | NFPA-F = 4 | NFPA-R = 0 | FlashPtC = −37 | AutoignitionPtC = 383 | ExploLimits = 3.5–14% | LD50 = {{Unbulleted list|265 mg kg−1 (dermal, rabbit)|400 mg kg−1 (oral, rat)}} | PEL = TWA 10 ppm (18 mg/m3)<ref name=NIOSH>{{PGCH|0263}}</ref> | REL = TWA 10 ppm (18 mg/m3)<ref name=NIOSH/> | IDLH = 600 ppm<ref name=NIOSH/> | LC50 = 1230 ppm (mammal)<ref name=IDLH>{{IDLH|75047|Ethylamine}}</ref> | LCLo = 3000 ppm (rat, 4 hr) 4000 ppm (rat, 4 hr)<ref name=IDLH/> }} |Section5={{Chembox Related | OtherFunction_label = alkanamines | OtherFunction = {{Unbulleted list|Methylamine|Ethylenediamine|Propylamine|Isopropylamine|1,2-Diaminopropane|1,3-Diaminopropane|Isobutylamine|''tert''-Butylamine}} | OtherCompounds = {{Unbulleted list|Monomethylhydrazine|2-Methyl-2-nitrosopropane}} }} }} '''Ethylamine''', also known as '''ethanamine''', is an organic compound with the formula {{chem2|C2H7N|auto=1}} or {{chem2|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.<ref name=Ullmann/> It is a DEA list I chemical by 21 CFR § 1310.02.

==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: :<chem>CH3CH2OH + NH3 -> CH3CH2NH2 + H2O</chem> In this reaction, ethylamine is coproduced together with diethylamine and triethylamine. In aggregate, approximately 80M kilograms/year of these three amines are produced industrially.<ref name=Ullmann>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}}</ref> It is also produced by reductive amination of acetaldehyde. :<chem>CH3CH2OH + NH3 + H2 -> CH3CH2NH2 + H2O</chem>

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.<ref>Ulrich Steinbrenner, Frank Funke, Ralf Böhling, [http://www.patentstorm.us/patents/7161039-claims.html Method and device for producing ethylamine and butylamine] {{webarchive|url=https://archive.today/20120912102105/http://www.patentstorm.us/patents/7161039-claims.html |date=2012-09-12 }}, United States Patent 7161039.</ref> :<chem>H2C=CH2 + NH3 -> CH3CH2NH2</chem> 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.<ref>[http://intranet.st-peters.york.sch.uk/fileadmin/user_upload/chemistry/AS_Organic_Mechs/NS-Haloalkane-NH3.ppt Nucleophilic substitution, Chloroethane & Ammonia] {{webarchive|url=https://web.archive.org/web/20080528051626/http://intranet.st-peters.york.sch.uk/fileadmin/user_upload/chemistry/AS_Organic_Mechs/NS-Haloalkane-NH3.ppt |date=2008-05-28 }}, St Peter's School</ref> :<chem>CH3CH2Cl + NH3 + KOH -> CH3CH2NH2 + KCl + H2O</chem>

Ethylamine is also produced naturally in the cosmos; it is a component of interstellar gases.<ref>NRAO, "Discoveries Suggest Icy Cosmic Start for Amino Acids and DNA Ingredients", Feb 28 2013</ref>

==Reactions== Like other simple aliphatic amines, ethylamine is a weak base: the pKa of [CH3CH2NH3]+ has been determined to be 10.8<ref>''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.</ref><ref>{{cite journal|author=H. K. Hall, Jr.|year=1957|journal=J. Am. Chem. Soc.|volume=79|pages=5441–5444|title=Correlation of the Base Strengths of Amines|issue=20|doi=10.1021/ja01577a030}}</ref>

Ethylamine undergoes the reactions anticipated for a primary alkyl amine, such as acylation and protonation. Reaction with sulfuryl chloride followed by oxidation of the sulfonamide give diethyldiazene, EtN=NEt.<ref>{{Cite journal |date=1972 |title=AZOETHANE |url=http://orgsyn.org/demo.aspx?prep=CV6P0078 |journal=Organic Syntheses |volume=52 |pages=11 |doi=10.15227/orgsyn.052.0011|url-access=subscription }}</ref> 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. Such solutions are used for the reduction of unsaturated organic compounds, such as naphthalenes<ref>Kaiser, E. M.; Benkeser R. A. [http://www.orgsyn.org/orgsyn/pdfs/CV6P0852.pdf Δ9,10-Octalin] {{webarchive|url=https://web.archive.org/web/20070930224411/http://www.orgsyn.org/orgsyn/pdfs/CV6P0852.pdf |date=2007-09-30 }}, ''Organic Syntheses'', Collected Volume 6, p.852 (1988)</ref> and alkynes.

==Applications== Ethylamine is a precursor to many herbicides including atrazine and simazine. It is found in rubber products as well.<ref name=Ullmann/>

Ethylamine is used as a precursor chemical along with benzonitrile (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 parasympathomimetic effects.<ref>{{Cite web|title= World Health Organization Critical Review Report of Ketamine, 34th ECDD 2006/4.3|url=https://www.who.int/medicines/areas/quality_safety/4.3KetamineCritReview.pdf}}</ref>

==References== {{Reflist}}

==External links== * [http://www.inchem.org/documents/icsc/icsc/eics0153.htm Safety data at www.inchem.org] * [https://www.cdc.gov/niosh/npg/npgd0263.html CDC - NIOSH Pocket Guide to Chemical Hazards]

Category:Alkylamines Category:Organic compounds with 2 carbon atoms Category:Foul-smelling chemicals