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  Home > JCE Print > Journal of Chemical Education > Issues > 2003  > January  >
In the Laboratory
Chemical Recycling of Pop Bottles: The Synthesis of Dibenzyl Terephthalate from the Plastic Polyethylene Terephthalate
Craig J. Donahue, Jennifer A. Exline, and Cynthia Warner
Department of Natural Sciences, University of Michigan-Dearborn, Dearborn, MI 48128-1491
Cover
January 2003
Vol. 80 No. 1
p. 79
Abstract
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.

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*  Citation
 Donahue, Craig J.; Exline, Jennifer A.; Warner, Cynthia. J. Chem. Educ. 2003 80 79.
*  Keywords
 Environmental Chemistry; General Chemistry; Industrial Chemistry; Organic Synthesis; Plastics; Polymer Chemistry; Laboratory Instruction; Organic Chemistry
*  History
 Created:
Last Updated:		 December 5, 2002
February 28, 2005
Link to Featured Molecules added (April 2004).
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