Stable diazonium salts of weakly basic amines—Convenient reagents for synthesis of disperse azo dyes

Abstract

A new synthetic strategy for industrially important deep-shade disperse azo dyes was presented in this study. The key procedure is to prepare stable solid diazonium salts of weakly basic amines in the absence of concentrated sulfuric acid. Diazotization by tert-butyl nitrite in ethyl acetate was allowed to proceed in the presence of equivalent 1,5-naphthalenedisulfonic acid as stabilizer of diazonium salts and donor of hydrogen ion for the reaction. The separated solid diazonium salts exhibited good thermal stability. The corresponding disperse azo dyes were subsequently synthesized through the azo-coupling of the prepared solid diazonium salts with a range of aromatic tertiary amines. The azo dyes were produced in short reaction time, excellent yields, mild reaction conditions, simple experimental procedure and low energy consumption.