my-server
← Wiki

Tert-Butylamine

tert-Butylamine (also erbumine and other names) is an organic chemical compound with the formula (CH<sub>3</sub>)<sub>3</sub>CNH<sub>2</sub>. 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:

<chem>NH3 + CH2=C(CH3)2-> H2NC(CH3)3</chem>

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

<chem>(CH3)2C=CH2 + HCN + H2O -> (CH3)3CNHCHO</chem>
<chem>(CH3)3CNHCHO + H2O -> (CH3)3CNH2 + HCO2H</chem>

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

References