Everything about Ethylamine totally explained
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Ethylamine is a
chemical compound with the formula CH
3CH
2NH
2. 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 and
alkynes.
Synthesis and reactions
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.
» H
2C=CH
2 + NH
3 → CH
3CH
2NH
2
It can also be synthesized from
acetaldehyde and
ammonium chloride.
» 2 CH
3CHO + NH
4Cl → CH
3CH
2NH
3Cl + CH
3CO
2H
CH
3CH
2NH
3Cl + NaOH → CH
3CH
2NH
2 + NaCl + H
2O
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.
» C
2H
5Cl + NH
3 → C
2H
8N
+ + Cl
-
C
2H
8N
+ + Cl
- + KOH → C
2H
7N + KCl + H
2O
If instead, a halomethane is used in the above reaction, it'll yield
methylamine although the other byproducts
dimethylamine,
trimethylamine and
tetramethylammonium are much harder to separate as they've similar boiling points.
Reaction of ethylamine with
sulfuryl chloride followed by oxidaton of the
sulfonamide give diethyldiazene, EtN=NEt.
Further Information
Get more info on 'Ethylamine'.
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