A Three-Step Synthesis of Azo Dye

Organol brown azo dye was synthesized and altered with functional group conversions to see the effect it would have on its color. This allowed for the testing of what reactions can be used to create new variations of azo dyes. Azo dyes are organic compounds that have a R-N=N-R functional group, and are commonly used in dyeing materials like clothing. In total three steps were completed to synthesize and alter organol brown azo dye. In order to create organol brown dye 1-napthol was reacted with analine, sodium nitrate, and silica gel. The second step converted the alcohol functional group of organol brown into a ketoester functional group. The final step of this process converted an alpha hydrogen on the keto-ester to a bromine using a photoreaction. After each step changes in UV max were recorded to see how alterations in the dye affected color. The final step was attempted using ethyl acetate instead of chloroform in order to make this process greener. This change was more cost efficient, equally effective, and less hazardous to humans and the environment. The information collected in this study will be useful for finding new ways to create azo dyes using more green processes.