Heterogeneous-phase reaction of glycidyl methacrylate and chondroitin sulfate: Mechanism of ring-opening-transesterification competition

Qiang Li, Dong An Wang, Jennifer H. Elisseeff

Research output: Contribution to journalArticle

Abstract

Addressing the different solubility/miscibility of the water-soluble CS and the water-insoluble GMA, a slow heterogeneous-phase reaction of CS with GMA was designed and performed in aqueous medium regardless of GMAs potential side-reaction with water. By monitoring the methacrylate-conjunction with NMR, a different reaction mechanism was discovered. Two reactions, including a rapid reversible transesterification and a slow irreversible ring-opening conjugation, took place simultaneously. As the reaction proceeded, there was a decline in the amount of transesterification products, while the concentration of ring-opening products gradually increased with time.

Original languageEnglish (US)
Pages (from-to)2556-2562
Number of pages7
JournalMacromolecules
Volume36
Issue number7
DOIs
StatePublished - Apr 8 2003

ASJC Scopus subject areas

  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry
  • Materials Chemistry

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