An Efficient and Green Route to Synthesize Azo Compounds through Methyl Nitrite

Kejie Cai; Hongqiang He; Yuwei Chang; Weiming Xu

doi:10.4236/gsc.2014.43016

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GSC> Vol.4 No.3, August 2014

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An Efficient and Green Route to Synthesize Azo Compounds through Methyl Nitrite

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DOI: 10.4236/gsc.2014.43016 4,759 Downloads 5,893 Views Citations

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Kejie Cai, Hongqiang He, Yuwei Chang, Weiming Xu

Affiliation(s)

College of Material Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, China.

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.

KEYWORDS

Methyl Nitrite, Substituted Benzenamine, Diazotization, Azo Coupling, Dyes, Pigments, Environmentally Benign, Toxicological

Conflicts of Interest

The authors declare no conflicts of interest.

Cite this paper

Cai, K. , He, H. , Chang, Y. and Xu, W. (2014) An Efficient and Green Route to Synthesize Azo Compounds through Methyl Nitrite. Green and Sustainable Chemistry, 4, 111-119. doi: 10.4236/gsc.2014.43016.

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