Uncovering Factors That Affect the Efficiency of Azo Dye Synthesis in Organic Chemistry Laboratory

Abstract

The synthesis of azo dyes is an intriguing experiment that can attract students’ attention due to the vivid color of the obtained product. Nevertheless, some students did not obtain the desired product without obvious reasons. In this work, we conducted a series of experiments to probe the effects of various factors that may contribute to the success of the reaction using Sudan I as a model. In contrast to the expectation based on the limited thermal stability of diazonium salts, it was found that low temperature (i.e., <10 °C) is not a critical factor for the success of the reaction. In fact, no statistically significant decrease in yield was found even when the reaction was performed at 20–30 °C. Instead, the key to success lies in the rate of reagent addition, where the coupling step must be performed slowly. Also, the cause of different color hues of the product was investigated. Both the presence of impurities (which were clearly identified in this study) and crystal polymorphisms contribute to the different colors among products from different batches that appeared to be the same Sudan I. Overall, these findings provide important information in designing azo dye synthesis experiments, which have diverse variations and modifications.