TITLE:
An Efficient and Green Route to Synthesize Azo Compounds through Methyl Nitrite
AUTHORS:
Kejie Cai, Hongqiang He, Yuwei Chang, Weiming Xu
KEYWORDS:
Methyl Nitrite, Substituted Benzenamine, Diazotization, Azo Coupling, Dyes, Pigments, Environmentally Benign, Toxicological
JOURNAL NAME:
Green and Sustainable Chemistry,
Vol.4 No.3,
August
5,
2014
ABSTRACT: A clean preparation of aryl diazonium ions using methyl nitrite is
described. Further reaction of the aryl diazonium ions with substituted
benzenamine, substituted phenol and nathphol in deferent kinds of diazotization
has been developed. In order to improve the water-solubility of the products,
azo coupling reactions of sodium sulfanilate hydrochloride diazonium ions were
also performed. The procedures are easy operations, environmentally benign
conditions and high yields of the products with potential use as azo-dyes and
pigments. Furthermore, no nitrous acid is produced during the diazotization
which avoided the formation of dark decomposition products of the corresponding
aromatic amine. Proposed mechanism is presented according to our procedure.