Ethylamine[1]
IUPAC name	Ethanamine
Other names	Ethylamine, Monoethylamine, Aminoethane, 1-Aminoethane
Identifiers
CAS number	[75-04-7]
PubChem	6341
EINECS number	200-834-7
RTECS number	KH2100000
SMILES	CCN
InChI	1/C2H7N/c1-2-3/h2-3H2,1H3
Properties
Molecular formula	C2H7N
Molar mass	45.08 g/mol
Appearance	Light yellow liquid
Density	0.689 g/cm3
Melting point	-81 °C
Boiling point	16.6 °C
Solubility in water	Miscible
Vapor pressure	121 kPa (20 °C)
Hazards
Main hazards	Harmful, corrosive, highly flammable
NFPA 704	4 3 0 ALK
R-phrases	R12, R20, R22, R34, R36, R37, R38
S-phrases	S16, S26, S29
Flash point	-17 °C
Autoignition temperature	385 °C
Explosive limits	3.5-14 %V
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Ethylamine is a chemical compound with the formula CH₃CH₂NH₂. It 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.

Ethylamine, like some other amines, has the unusual property of dissolving lithium metal to give 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^[2] and alkynes.

Synthesis

• Ethylamine can be prepared in a laboratory by reaction of ethylene with ammonia in the presence of an alkali metal amide catalyst such as sodium amide.^[3]

H₂C=CH₂ + NH₃ → CH₃CH₂NH₂

• It can also be synthesized from acetaldehyde and ammonium chloride.^{[citation needed]}

2 CH₃CHO + NH₄Cl → CH₃CH₂NH₃Cl + CH₃CO₂H

CH₃CH₂NH₃Cl + NaOH → CH₃CH₂NH₂ + NaCl + H₂O

• Ethylamine can be made directly from Ethanol and Ammonia in the presence of hydrogen using a hydrogenation catalyst such as a 4:1 ratio nickel-copper alloy. This reaction requires elevated temperatures and/or pressure.^[4]

• Amines such as ethylamine may also be synthesized by the reduction of amides such as Acetamide, for example using Lithium aluminum hydride (LiAlH4 or LAH), according to the following formula:

2RCONR₂ + LiAlH₄ → 2RCH₂NR₂ + LiAlO₂^[5]

• Ethylamine may be synthesized via nucleophilic substitution of a haloethane (such as chloroethane or bromoethane) with ammonia as a reagent, utilizing a strong base such as potassium hydroxide. This forms the ethylammonium cation. Significant amounts of byproducts are formed, including diethylamine and triethylamine, as well as tetraethylammonium cation, from which the ethylamine can be separated via simple distillation as all of these by-products have significantly higher boiling points.^[6][7]

C₂H₅Cl + NH₃ → C₂H₈N⁺ + Cl^-

C₂H₈N⁺ + Cl^- + KOH → C₂H₇N + KCl + H₂O

If instead, a halomethane is used in the above reaction, it will yield methylamine although the other byproducts dimethylamine, trimethylamine and tetramethylammonium are much harder to separate as they have similar boiling points.

Reactions

• Reaction of ethylamine 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 Nitroethane.

References

1. Merck Index, 12th Edition, 3808.
2. Kaiser, E. M.; Benkeser R. A. Δ9,10-Octalin, Organic Syntheses, Collected Volume 6, p.852 (1988)
3. Ulrich Steinbrenner, Frank Funke, Ralf Böhling, Method and device for producing ethylamine and butylamine, United States Patent 7161039.
4. http://www.freepatentsonline.com/4014933.html,"Production of amines from alcohols"
5. http://pubs.acs.org/cgi-bin/abstract.cgi/joceah/1953/18/i09/f-pdf/f_jo50015a017.pdf?sessid=6006l3,"The reduction of acid amides with lithium aluminum hydride."
6. Chemistry in Context, John Holman, Graham Hill, Page 461
7. Nucleophilic substitution, Chloroethane & Ammonia, St Peter's School
8. Ohme, R.; Preuschhof, H.; Heyne, H.-U. Azoethane, Organic Syntheses, Collected Volume 6, p.78 (1988)

External links

• Safety data at www.inchem.org
• Safety MSDS data

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Source: adapted by the editor from Wikipedia, the free encyclopedia; from the article "Ethylamine". Image Credit.

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