Ethylamine

Ethylamine[1]
IUPAC name Ethanamine
Other names Monoethylamine, Aminoethane, 1-Aminoethane, Ethamine
Identifiers
CAS number	75-04-7 Y
PubChem	6341
ChemSpider	6101 Y
UNII	YG6MGA6AT5 Y
EC number	200-834-7
KEGG	C00797 Y
ChEBI	CHEBI:15862 Y
ChEMBL	CHEMBL14449 Y
RTECS number	KH2100000
Jmol-3D images	Image 1
SMILES NCC
InChI InChI=1S/C2H7N/c1-2-3/h2-3H2,1H3 Y Key: QUSNBJAOOMFDIB-UHFFFAOYSA-N Y InChI=1/C2H7N/c1-2-3/h2-3H2,1H3 Key: QUSNBJAOOMFDIB-UHFFFAOYAL
Properties
Molecular formula	C2H7N
Molar mass	45.08 g/mol
Appearance	Light yellow liquid
Density	0.689 g/cm3
Melting point	-81 °C, 192 K, -114 °F
Boiling point	16.6 °C, 290 K, 62 °F
Solubility in water	Miscible
Vapor pressure	121 kPa (20 °C)
Hazards
R-phrases	R12, R20, R22, R34, R36, R37, R38
S-phrases	S16, S26, S29
Main hazards	Harmful, corrosive, highly flammable
NFPA 704	4 3 0 ALK
Flash point	-17 °C
Autoignition temperature	385 °C
Explosive limits	3.5-14%V
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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 considered to be a weak base, as is typical for amines. Ethylamine is widely used in chemical industry and organic synthesis.

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.^[2] 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.^[3]

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.^[4]

CH₃CH₂Cl + NH₃ + KOH → CH₃CH₂NH₂ + KCl + H₂O

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.^[5] 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^[6] 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. ^ 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
3. ^ Ulrich Steinbrenner, Frank Funke, Ralf Böhling, Method and device for producing ethylamine and butylamine, United States Patent 7161039.
4. ^ Nucleophilic substitution, Chloroethane & Ammonia, St Peter's School
5. ^ Ohme, R.; Preuschhof, H.; Heyne, H.-U. Azoethane, Organic Syntheses, Collected Volume 6, p.78 (1988)
6. ^ Kaiser, E. M.; Benkeser R. A. Δ9,10-Octalin, Organic Syntheses, Collected Volume 6, p.852 (1988)

External links

• Safety data at www.inchem.org
• Safety MSDS data
• Atrazine News - an Atrazine specific news site