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The hydrogenation of 4-nitrophenol (4-NP) has attracted much attention, since it is typically used as a model reaction for evaluating newly developed catalysts, but its mechanism is still debated. Herein, Co(OH)2-modified CuO catalyst (Co(OH)2/CuO) was used for the reduction of 4-NP to 4-aminophenol (4-AP) in an aqueous sodium borohydride (NaBH4) solution. The reaction mechanism was investigated by UV-Vis spectroscopy (UV-Vis), high-performance liquid chromatography (HPLC), HPLC-Q-orbitrap high-resolution mass spectrometry (LC-MS/MS), and 1HNMR spectroscopy (1HNMR) as an integrated technology at different concentrations of NaBH4. Samples were taken at specified time intervals and monitored using UV-Vis, HPLC, LC-MS/MS, and 1HNMR. With the help of comprehensive analysis, eight intermediates, including azo and azoxy compounds, were effectively captured, and the variation tendency of each intermediate was determined, revealing that the hydrogenation of 4-NP proceeds via a coexistence of the direct and condensation routes. The integrated analysis methods were powerful technical supports for the study of the catalysis mechanism.

Establishment of Integrated Analysis Method for Probing and Reconstructing Hydrogenation Mechanism of a Model Reaction