Kinetics and mechanism of p-isopropenylphenol synthesis via hydrothermal cleavage of bisphenol A

Shawn E. Hunter, Phillip E. Savage

Research output: Contribution to journalArticle

35 Scopus citations

Abstract

Although bishydroxyarylalkanes are known to be reactive in high-temperature (T > 200 °C) liquid water (HTW), no mechanistic insight has been given to explain the reactivity of methylene bridge-containing diaryls under hydrothermal conditions. We examined the kinetics and mechanism of p-isopropenylphenol (IPP) synthesis via bisphenol A (BPA) cleavage in HTW. The cleavage reaction is first order in BPA. Cleavage of BPA in HTW occurs by specific acid catalysis, by specific base catalysis, and by general water catalysis. Under neutral conditions, the dominant mechanism is general base catalysis with water serving as the proton acceptor. We generated a detailed chemical kinetics model for the decomposition reaction based on a base-catalyzed mechanism in the literature. This three-parameter model fit the experimental data for BPA disappearance and formation of IPP and phenol and accurately predicted the yield of the IPP hydrolysis product acetone. Using acid- and base-catalyzed mechanisms, we explain the reactivity in HTW reported for other diaryl groups linked by methylene bridges and propose criteria for assessing the reactivity of methylene bridges under hydrothermal conditions.

Original languageEnglish (US)
Pages (from-to)4724-4731
Number of pages8
JournalJournal of Organic Chemistry
Volume69
Issue number14
DOIs
StatePublished - Jul 9 2004

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Kinetics and mechanism of p-isopropenylphenol synthesis via hydrothermal cleavage of bisphenol A'. Together they form a unique fingerprint.

  • Cite this