Oxidation of glycerol using polymer-supported IBX

Abstract

A new polymer-supported IBX was prepared in this research to use as an oxidizing agent in the oxidation reaction of glycerol. The appropriate method for the synthesis of polymer-supported IBX consisted of 8 steps using p-toluic acid as a starting material for IBX and aminomethyl polystyrene as a supporting material. For the synthesis of aminomethyl polymer-supported IBX, a new process for oxidation of C-H bond of 3-iodo-4-methylbenzoic acid was discovered. This oxidation using sodium hypochlorite (NaOCl) as an oxidant gave higher conversion than using sodium periodate (NaIO4) as an oxidant. The new polymer-supported IBX was used to oxidize benzyl alcohol and glycerol and its oxidation was also compared with IBX (1), DMP (2), aminomethyl polymer-supported IBX amide (3), N-phenyl-2-iodoxybenzamide (4), and N-phenyl-3-iodoxybenzoic acid (5). Benzyl alcohol was oxidized with IBX (1), DMP (2), aminomethyl polystyrene-supported IBX amide (3) and aminomethyl polymer-supported IBX amide (6) as oxidizing agents while glycerol was not oxidized by those oxidizing agents.