Ammoximation of Cyclohexanone with O2, NH3 and an anthrahydroquinone salt, and electrolyte-recycle process of the anthrahydroquinone salt

• Ammoximation of cyclohexanone was performed using an anthrahydroquinone salt and O 2 as oxidant. • The anthrahydroquinone salt was recycled via an electrolytic reduction process. • Electrolytic reduction of anthraquinone salt was coupled with electrolytic Cl 2 production . Cyclohexanone oxime, which was an intermediate of nylon-6, was selectively prepared by ammoximation of cyclohexanone with O 2 , NH 3 , and 9,10-anthrahydroquinone-2,7-disulfonic disodium salt (AHQDSNa 2 ) in contacting with TS-1 catalyst. H 2 O 2 oxidant was produced by AHQDSNa 2 and O 2 in situ. The catalytic ammoximation reactions with AHQDSNa 2 /O 2 oxidant showed better ketone conversion and oxime selectivity than these with H 2 O 2 which was due to lower alkalinity caused by the reaction between AHQDSNa 2 and NH 4 OH. AHQDSNa 2 was recycled by an electrolytic reduction process paired with the electrolytic oxidation of HCl, similar to the reported aqueous organic redox flow batteries. The electrolytic cell was performed at 40-150 mAcm -2 and the coulombic efficiency on cathode was >99%. On anode, HCl was oxidized to Cl 2 , which could be applied to many chemical process for HCl recycling. This new approach could be applied for coupling green energy storage with some traditional chemical processes.