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Ring-Opening Polymerization of Lactide To Form a Biodegradable Polymer

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Jennifer L. Robert and Katherine B. Aubrecht

Department of Chemistry, College of the Holy Cross, Worcester, MA 01610

J. Chem. Educ., 2008, 85 (2), p 258

DOI: 10.1021/ed085p258

Publication Date (Web): February 1, 2008

Section:

History, Education, and Documentation

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, M_n of the resulting polymer are discussed in the Supplemental Material.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Feature):

Green Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Esters

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This article has been cited by 1 ACS Journal articles (1 most recent appear below).

From Lactic Acid to Poly(lactic acid) (PLA): Characterization and Analysis of PLA and Its Precursors
Saara Inkinen, Minna Hakkarainen, Ann-Christine Albertsson, and Anders Södergård
Biomacromolecules2011 12 (3), 523-532
- From Lactic Acid to Poly(lactic acid) (PLA): Characterization and Analysis of PLA and Its Precursors
  Saara Inkinen, Minna Hakkarainen, Ann-Christine Albertsson, and Anders Södergård
  Biomacromolecules2011 12 (3), 523-532
  The quality of the monomers lactic acid and lactide as well as the chemical changes induced during polymerization and processing are crucial parameters for controlling the properties of the resulting poly(lactic acid) (PLA) products. This review presents ...
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