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  Home > JCE Print > Journal of Chemical Education > Issues > 2008  > February  >
In the Laboratory
Green Chemistry
Ring-Opening Polymerization of Lactide To Form a Biodegradable Polymer
Jennifer L. Robert and Katherine B. Aubrecht
Department of Chemistry, College of the Holy Cross, Worcester, MA 01610
Cover
February 2008
Vol. 85 No. 2
p. 258
Abstract
In this laboratory activity for introductory organic chemistry, students carry out the tin(II) bis(2-ethylhexanoate)/benzyl alcohol mediated ring-opening polymerization of lactide to form the biodegradable polymer polylactide (PLA). As the mechanism of the polymerization is analogous to that of a transesterification reaction, the experiment can be used to demonstrate reactions of carboxylic acid derivatives. The polymerization can be successfully carried out using standard teaching laboratory (non-Schlenk) conditions. Analysis of polymer stereochemistry by 1H NMR and a discussion of the effect of monomer stereochemistry on the stereochemistry of the polymer are included in the experiment. The effect of adventitious water on the rate of the polymerization and the number-average molecular weight, Mn of the resulting polymer are discussed in the Supplemental Material.
Supplement
Instructions for the students, including pre- and postlab questions, and notes for the instructor are available.
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 Download
Contents
  JCE2008p0258W.pdf
 
More Information
*
Citation
Robert, Jennifer L.; Aubrecht, Katherine B. J. Chem. Educ. 2008, 85, 258.
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Keywords
Esters; Green Chemistry; Hands-On Learning / Manipulatives; Laboratory Instruction; NMR Spectroscopy; Organic Chemistry; Polymer Chemistry; Polymerization; Second-Year Undergraduate; Stereochemistry; Upper-Division Undergraduate
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History
Created:
Last Updated:
1/4/2008
1/9/2008
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