Continuous-Flow Synthesis of Nitro-o-xylenes: Process Optimization, Impurity Study and Extension to Analogues
Qiao Song, Xiangui Lei, Sheng Yang, Sheng Wang, Jianhui Wang, Jiujun Chen, Yong Xiang, Qingwu Huang, Zhouyu Wang
Abstract
An efficient continuous-flow nitration process of o-xylene at pilot scale was demonstrated. The effects of parameters such as temperature, ratio of H2SO4 to HNO3, H2SO4 concentration, flow rate, and residence time on the reaction were studied. Under the optimal conditions, the yield of products reached 94.1%, with a product throughput of 800 g/h. The main impurities of this continuous-flow nitration process were also studied in detail. Compared with batch process, phenolic impurity decreased from 2% to 0.1%, which enabled the omission of the alkaline solution washing step and thus reduced the wastewater emission. The method was also successfully applied to the nitrification of p-xylene, toluene, and chlorobenzene with good yields.