tert-Butylamine

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:

$\mathrm{N}\mathrm{H}{\phantom{A}}_3+\mathrm{C}\mathrm{H}{\phantom{A}}_2=\mathrm{C}(\mathrm{C}\mathrm{H}{\phantom{A}}_3){\phantom{A}}_2⟶\mathrm{H}{\phantom{A}}_2\mathrm{N}\mathrm{C}(\mathrm{C}\mathrm{H}{\phantom{A}}_3){\phantom{A}}_3$

The Ritter reaction of isobutene with hydrogen cyanide is not useful because it produces too much waste.

$(\mathrm{C}\mathrm{H}{\phantom{A}}_3){\phantom{A}}_2\mathrm{C}=\mathrm{C}\mathrm{H}{\phantom{A}}_2+\mathrm{H}\mathrm{C}\mathrm{N}+\mathrm{H}{\phantom{A}}_2\mathrm{O}⟶(\mathrm{C}\mathrm{H}{\phantom{A}}_3){\phantom{A}}_3\mathrm{C}\mathrm{N}\mathrm{H}\mathrm{C}\mathrm{H}\mathrm{O}$

$(\mathrm{C}\mathrm{H}{\phantom{A}}_3){\phantom{A}}_3\mathrm{C}\mathrm{N}\mathrm{H}\mathrm{C}\mathrm{H}\mathrm{O}+\mathrm{H}{\phantom{A}}_2\mathrm{O}⟶(\mathrm{C}\mathrm{H}{\phantom{A}}_3){\phantom{A}}_3\mathrm{C}\mathrm{N}\mathrm{H}{\phantom{A}}_2+\mathrm{H}\mathrm{C}\mathrm{O}{\phantom{A}}_2\mathrm{H}$

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.

See also

• Borane tert-butylamine complex