Article

Unexpected efficiency of cyclic amidine catalysts in depolymerizing poly(ethylene terephthalate)

  1. Kazuki Fukushima1,2,
  2. Daniel J. Coady1,
  3. Gavin O. Jones1,
  4. Hamid A. Almegren3,
  5. Abdullah M. Alabdulrahman3,
  6. Fares D. Alsewailem3,
  7. Hans W. Horn1,
  8. Julia E. Rice1,
  9. James L. Hedrick1,*

Article first published online: 9 JAN 2013

DOI: 10.1002/pola.26530

Issue

Journal of Polymer Science Part A: Polymer Chemistry

Journal of Polymer Science Part A: Polymer Chemistry

Volume 51, Issue 7, pages 1606–1611, 1 April 2013

Additional Information

How to Cite

Fukushima, K., Coady, D. J., Jones, G. O., Almegren, H. A., Alabdulrahman, A. M., Alsewailem, F. D., Horn, H. W., Rice, J. E. and Hedrick, J. L. (2013), Unexpected efficiency of cyclic amidine catalysts in depolymerizing poly(ethylene terephthalate). J. Polym. Sci. A Polym. Chem., 51: 1606–1611. doi: 10.1002/pola.26530

Author Information

  1. 1

    IBM Almaden Research Center, San Jose, California 95120

  2. 2

    Department of Polymer Science and Engineering, Yamagata University, Yonezawa, Yamagata 992-8510, Japan

  3. 3

    Petrochemicals Research Institute, King Abdul Aziz City for Science and Technology, Riyadh 11442, Saudi Arabia

*IBM Almaden Research Center, San Jose, California 95120

Publication History

  1. Issue published online: 26 FEB 2013
  2. Article first published online: 9 JAN 2013
  3. Manuscript Accepted: 1 DEC 2012
  4. Manuscript Received: 25 SEP 2012

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Keywords:

  • degradation;
  • monomer;
  • organocatalysis;
  • polyesters

Abstract

This article describes studies on the catalytic activity of several nitrogen-based organic catalysts for the depolymerization of poly(ethylene terephthalate) (PET), in which a few cyclic amidines work more effectively than a potent, bifunctional guanidine-based catalyst 1,5,7-triazabicyclo-[4,4,0]-dec-5-ene (TBD) in the presence of short chain diols that play a role in activation of carbonyl groups through hydrogen bonding. Further studies prove that the catalytic efficiency at the above specific conditions depends only on the extent of activation of a hydroxyl group rather than simply the pKa of the bases. For glycolysis with excess short-chain alkanediols, 1,8-diazabicyclo[5.4.0]undec-7-ene is the best catalyst. In contrast, TBD shows outstanding catalytic activity in depolymerizations of PET with mono-alcohols and longer-chain diols. © 2013 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013

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