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:
- 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.[1]
- (CH3)2C=CH2 + HCN + H2O → (CH3)3CNHCHO
- (CH3)3CNHCHO + H2O → (CH3)3CNH2 + HCO2H
In the laboratory, it can be prepared by the hydrogenolysis of 2,2-dimethylethylenimine, or via tert-butylphthalimide.[2]
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
<templatestyles src="Reflist/styles.css" />
- ↑ Template:Ullmann
- ↑ Script error: No such module "Citation/CS1".
Script error: No such module "Check for unknown parameters".