In multi-step organic syntheses, the protection of functional groups such as amines, alcohols, and carbonyl groups is frequently necessary to avoid undesired side reactions. For example, amines can be protected by benzyl groups, which form toluene after removal by hydrogenation. In the present study, the kinetics of Pd-catalyzed hydrogenation of N-benzyl-4-fluoroaniline, NB4FA, a compound that can undergo both debenzylation and defluorination, were investigated in a semi-batch reactor. The effects of various operating parameters (temperature, H₂ pressure, solvent type, buffer) were examined to identify factors that influence the reaction pathways. Mechanistic Langmuir–Hinshelwood models were evaluated by regressing the experimental data to determine the appropriate reaction expression for NB4FA debenzylation. Separate experiments to determine the hydrogenation kinetics of the main product, 4-fluoroaniline, 4FA, were also conducted. Finally, the complete transient reaction behavior of NB4FA hydrogenation was predicted well by combining the kinetics of NB4FA debenzylation and of 4FA hydrogenation to aniline, which was observed to be the main by-product.

在多步有机合成中，经常需要保护官能团（例如胺，醇和羰基），以避免不希望的副反应。例如，胺可以被苄基保护，该苄基在通过氢化除去后形成甲苯。在本研究中，在半间歇式反应器中研究了Pd催化N-苄基-4-氟苯胺NB4FA氢化的动力学，该化合物可同时经历脱苄基作用和脱氟反应。各种操作参数（温度，H ₂检查压力，溶剂类型，缓冲液）以识别影响反应路径的因素。通过回归实验数据来评估力学Langmuir–Hinshelwood模型，以确定NB4FA脱苄基反应的适当反应表达。还进行了确定主要产物4-氟苯胺4FA氢化动力学的单独实验。最后，结合了NB4FA脱苄基反应和4FA氢化成苯胺的动力学，很好地预测了NB4FA氢化的完全瞬态反应行为。