The identification of byproducts from the catalytic reduction reaction of 4-nitrophenol to 4-aminophenol: A systematic spectroscopic study

Abstract

Acetaminophenol, commonly recognized as paracetamol (considered safer than aspirin) is formed by nitration of phenol (4-nitrophenol (4-NP)) for its conversion to 4-aminophenol (4-AP), followed by the acetylation for the final product. As 4-NP is an intermediate product in acetaminophenol (paracetamol) production from phenol the dynamic analysis of acetylation of amine group is important. This study focuses on the feasibility of spectroscopic studies to monitor the removal of 4-NP using sodium borohydride (NaBH4) probe reaction in the presence of silver, gold, and bimetallic Ag/Au nanoparticles. UV–visible absorbance and fluorescence spectroscopy measurements reveal the formation of 1,4-benzoquinone (BQ), hydroquinone (HQ), and phenol (Ph) as the final products, in addition to the formation of typically reported 4-AP. The intermediates of NaBH4 seem to play a significant role in the formation of BQ, which converts to HQ in the basic medium followed by the formation of phenol in an acidic medium. Complete kinetic analysis with respect to spectroscopic studies of the standard compounds is presented. Similar results were obtained with 4-NP spiked river and seawater samples. The present findings may lead to catalytic benchmarking that can differ from most of the current practices and highlight the importance of adopting a holistic approach towards the fundamental understanding of 4-NP catalytic reduction that must take into account the concentration of NaBH4 and pH interdependencies.