Chemical Recycling of Pop Bottles: The Synthesis of Dibenzyl Terephthalate from the Plastic Polyethylene Terephthalate

A laboratory procedure involving the chemical recycling of the plastic polyethylene terephthalate (PET or PETE) from 2-L pop bottles is described. A transesterification reaction is employed to depolymerize PET. At atmospheric pressure in refluxing benzyl alcohol in the presence of a catalyst, PET is converted to dibenzyl terephthalate in moderate yields. This procedure models an industrial process that involves the transesterification reaction of PET with methanol at high temperature and pressure, conditions not normally accessible in an undergraduate laboratory, to yield dimethyl terephthalate and ethylene glycol. A second method of preparing dibenzyl terephthalate starting with terephthaloyl chloride is also described. The diester from these two approaches is characterized using melting points, TLC, and IR and NMR spectroscopy. This experiment has been used in a general chemistry sequence that has sections on organic chemistry and polymer chemistry, but is also well suited for an introductory organic chemistry laboratory course or a polymer chemistry laboratory course. This lab experiment is part of a larger effort to develop a general chemistry sequence for engineering students using the theme of chemistry and the automobile. Student results are presented.