Ring opening polymerization of β-acetoxy-δ-methylvalerolactone, a triacetic acid lactone derivative

Hussnain Sajjad, Emily A Prebihalo, William B Tolman, Theresa M. Reineke

Research output: Contribution to journalArticlepeer-review

5 Scopus citations


We report here the synthesis and polymerization of a novel disubstituted valerolactone, β-acetoxy-δ-methylvalerolactone, derived from the renewable feedstock triacetic acid lactone (TAL). The bulk polymerization proceeds to 45% equilibrium monomer conversion at room temperature using diphenyl phosphate as the organic catalyst. The resultant amorphous material displays a glass transition temperature of 25 °C. The ring opening polymerization (ROP) behavior of the disubstituted valerolactone was examined, and the enthalpy and entropy ∗ of polymerization were calculated to be -25 ± 2 kJ mol-1 and -81 ± 5 mol-1 K-1, respectively. The polymerization kinetics were also measured and compared to those of other substituted valerolactones reported in the literature. This report is the first to demonstrate the successful ROP of a disubstituted valerolactone as well as the first to establish the ROP of a derivative of TAL.

Original languageEnglish (US)
Pages (from-to)6724-6730
Number of pages7
JournalPolymer Chemistry
Issue number46
StatePublished - Dec 14 2021

Bibliographical note

Funding Information:
This work was supported by the National Science Foundation under the Center for Sustainable Polymers (CHE-1901635). Any opinions, findings, and conclusions or recommendations expressed in this material are those of the author(s) and do not necessarily reflect the views of the National Science Foundation.

Publisher Copyright:
© The Royal Society of Chemistry.


Dive into the research topics of 'Ring opening polymerization of β-acetoxy-δ-methylvalerolactone, a triacetic acid lactone derivative'. Together they form a unique fingerprint.

Cite this