Tert-Butylamine
chemical compound
tert-Butylamine (also erbumine and other names) is an organic chemical compound with the formula (CH3)3CNH2. It is a colorless liquid with a typical amine-like odor. tert-Butylamine is one of the four isomeric amines of butane, the others being n-butylamine, sec-butylamine and isobutylamine.
Preparation
tert-Butylamine is produced commercially by direct amination of isobutylene using zeolite catalysts:
NH
3
+
CH
2
=
C
(
CH
3
)
2
⟶
H
2
NC
(
CH
3
)
3
{\displaystyle {\ce {NH3 + CH2=C(CH3)2-> H2NC(CH3)3}}}
The Ritter reaction of isobutene with hydrogen cyanide is not useful because it produces too much waste.
(
CH
3
)
2
C
=
CH
2
+
HCN
+
H
2
O
⟶
(
CH
3
)
3
CNHCHO
{\displaystyle {\ce {(CH3)2C=CH2 + HCN + H2O -> (CH3)3CNHCHO}}}
(
CH
3
)
3
CNHCHO
+
H
2
O
⟶
(
CH
3
)
3
CNH
2
+
HCO
2
H
{\displaystyle {\ce {(CH3)3CNHCHO + H2O -> (CH3)3CNH2 + HCO2H}}}
In the laboratory, it can be prepared by the hydrogenolysis of 2,2-dimethylethylenimine, or via tert-butylphthalimide.
Uses
tert-Butylamine is used as an intermediate in the preparation of the sulfenamides such as N-tert-butyl-2-benzothiazylsulfenamide and N-tert-butyl-2-benzothiazylsulfenimide. As rubber accelerators, these compounds modify the rate of vulcanization of rubber. A variety of pesticides are derived from this amine, including terbacil, terbutryn, and terbumeton.
In pharmacology under the name erbumine, tert-butylamine has been used as a counterion in drug substances such as perindopril erbumine.
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