Since the amount of e-waste has been rapidly increasing all over the world, there is a desire to develop the effective recycling process. E-waste has various kinds of electronic components with valuable and/or hazardous materials. Recycling of them is an important subject from the viewpoint of both the recovery of valuable materials and waste treatment. In common with all mineral processing, the comminution of e-waste is a key process because the liberation states after comminution determine the overall efficiency of metal recovery. Since some of useful critical metals are concentrated in a specific component, a special and selective grinding is expected to be effective. However, the knowledge about the mechanism and the effectiveness of the selective grinding is still limited and unclear. To better comprehend the mechanism, in this study, the investigation of comminution process using the particle-based simulation was conducted. Especially, this study focused on the comminution performance of printed circuit boards (PCBs), which are major components of e-waste. The behavior of PCBs and airflow in a drum typed agitation mill having flexible chains was simulated by the discrete element method (DEM) coupled with computational fluid dynamics (CFD). To model the shape of PCBs, the particle based rigid body model was introduced into the DEM. Since this model could not directly simulate the breakage phenomena, collision energy was calculated to qualitatively evaluate the comminution performance. In addition, the simulation results were compared with the experimental comminution tests using simulant PCBs where some capacitors were solder-mounted. These results indicated that comminution performance was affected by the rotation speed of the agitator. It was also demonstrated that the comminution performance was qualitatively evaluated using the particle-based simulation and this particle-based simulation made it possible to investigate the mechanism of e-waste comminution.