Cooperative catalysis of cyclic carbonate ring opening: Application towards non-isocyanate polyurethane materials

Vince M. Lombardo, Elizabeth A. Dhulst, Emily K. Leitsch, Nathan Wilmot, William H. Heath, Anthony P. Gies, Matthew D. Miller, John M Torkelson*, Karl A Scheidt

*Corresponding author for this work

Research output: Contribution to journalArticle

37 Scopus citations

Abstract

The reaction between cyclic carbonates and amines to produce hydroxyurethanes is an important alternative to current urethane chemistry. In order to address the issue of slow reaction rates, an efficient ring opening of cyclic carbonates with amines has been achieved utilizing cooperative catalysis. A new Lewis acid/Lewis base combination substantially decreases the reaction times for small molecule systems to reach complete conversion. Although triazabicyclodecene (TBD) has a substantial impact on the reaction rate, the addition of lithium triflate (LiOTf) as a co-catalyst allows for the fastest ring opening reported in the current literature. Cooperative catalysis is also applied to the synthesis of polymers containing hydroxyurethane linkages and is able to achieve rapid conversion of the bis-cyclic carbonate and diamine precursors when compared with the uncatalyzed reaction.

Original languageEnglish (US)
Pages (from-to)2791-2795
Number of pages5
JournalEuropean Journal of Organic Chemistry
Volume2015
Issue number13
DOIs
StatePublished - May 1 2015

Keywords

  • Amines
  • Cooperative catalysis
  • Cyclic carbonates
  • Polymers
  • Polyurethane

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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