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

GSC > Vol.4 No.3, August 2014

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

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DOI: 10.4236/gsc.2014.43016 7,149 Downloads 10,594 Views Citations

Author(s)

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

Share and Cite:

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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