Carbonylation of ethylene oxide to β-propiolactone: A facile route to poly(3-hydroxypropionate) and acrylic acid

Erin W. Dunn, Jessica R. Lamb, Anne M. Lapointe, Geoffrey W. Coates

Research output: Contribution to journalArticlepeer-review

28 Scopus citations

Abstract

We report an improved synthesis of poly(3-hydroxypropionate) (P3HP) from ethylene oxide (EO) and carbon monoxide (CO) through the intermediate β-propiolactone (PL). The optimized carbonylation of EO resulted in high selectivity for PL using a bimetallic [Lewis acid]+[Co(CO)4]- catalyst. Anionic ring-opening polymerization of PL by organic ionic compounds to afford P3HP was also investigated. A phosphazenium carboxylate initiator displays the highest activity for the polymerization and produces polyesters with molecular weights over 100 kDa and narrow molar mass distributions. Furthermore, the known rearrangement of PL and the thermolysis of P3HP provide efficient EO-based routes to the important commodity chemical acrylic acid.

Original languageEnglish (US)
Pages (from-to)8219-8223
Number of pages5
JournalACS Catalysis
Volume6
Issue number12
DOIs
StatePublished - Dec 2 2016
Externally publishedYes

Bibliographical note

Funding Information:
We thank Drs. Scott Allen and Kevin Noonan for advice regarding research and drafting of this manuscript. We thank the DOE (No. DE-FG02-05ER15687) and Novomer for support of this research, and J.R.L. thanks the NSF (No. DGE-1144153) for a graduate fellowship.

Publisher Copyright:
© 2016 American Chemical Society.

Keywords

  • Acrylic acid
  • Anionic polymerization
  • Biodegradable polymer
  • Epoxide carbonylation
  • Polyester

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