In order to develop an efficient and greener method for organic chemical hydride production in the energy carrier system, the electrocatalytic hydrogenation of toluene to methylcyclohexane was carried out using a proton exchange membrane (PEM) reactor, which generally applied a polymer electrolyte fuel cell and industrial electrolysis technologies. The electrochemical conversion proceeded in high current efficiencies (>90%) under sufficiently mild conditions with various metal-supported catalysts such as Pt/C, Rh/C, Ru/C, and PtRu/C. For example, methylcyclohexane was obtained in 94% current efficiency by the electrochemical hydrogenation of toluene with PtRu/C. Although the current efficiency of the hydrogenation with Pt/C, Rh/C, and Ru/C apparently decreased under high current density conditions due to the side reaction (hydrogen evolution), the hydrogenation with PtRu/C catalysts proceeded in excellent efficiencies even under high current density conditions.

We have successfully demonstrated an efficient anodic aromatic C,C cross-coupling reaction using parallel laminar flow mode in a two-inlet flow microreactor. The model reaction proceeded effectively even in single flow-through operations and the desired cross-coupling product was obtained in much higher current yields compared to the reaction in a conventional batch type cell.

We have successfully demonstrated that a microflow reactor is extremely useful in controlling reactions involving an unstable o-benzoquinone. The key features of the method are an effective o-benzoquinone generation and its rapid use for the following reaction without decomposition in a microflow system.

We have successfully demonstrated effective generation of an electrogenerated base (EGB) such as the 2-pyrrolidone anion and its rapid use for the following alkylation reaction in a flow microreactor system without the need for severe reaction conditions.

A paired electrosynthetic conversion of a phenol to a diaryl ether derivative by using an electrochemical microreactor has been demonstrated. Sequential anodic C–O coupling reaction of phenol 1 to dienone aryl ether 2 and following reduction of 2 took place to give diaryl ether derivative 3 selectively by simply passing an electrolytic solution through the electrochemical microreactor.