Kinetic study of the phase transfer catalytic epoxidation of dicyclopentadiene in a two-phase medium

Maw Ling Wang, Tsuan Hsuan Huang, Wen Teng Wu

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

Abstract

The epoxidation of dicyclopentadiene catalyzed by quaternary ammonium salt in the presence of hydrogen peroxide, sodium tungstate, and phosphoric acid was successfully carried out in an acidic aqueous solution/organic solvent two-phase medium. The epoxidation of dicyclopentadiene is dramatically enhanced in the presence of quaternary ammonium salt, hydrogen peroxide, sodium tungstate, and phosphoric acid of appropriate quantities. Based on the experimental results, a rational reaction mechanism was proposed and a pseudo steady-state hypothesis was applied to describe the kinetic data. The organic-phase reactions were found to be the rate-determining step of the entire phase transfer catalysis. Four reactions, which include the epoxidation of two single-site double bonds and one two-site double bond of dicyclopentadiene molecule, were obtained, i.e., two primary and two secondary sequential reactions in the organic phase. The purpose of this work is to investigate the effects of the reaction conditions such as agitation speed, quaternary ammonium salt, amount of Aliquat 336 catalyst, sodium tungstate, phosphoric acid, active catalyst, hydrogen peroxide, pH value, organic solvents, volume of chloroform, and temperature on the conversion of dicyclopentadiene. The apparent rate constants of the two primary reactions in the organic phase were determined.

Original languageEnglish
Pages (from-to)27-46
Number of pages20
JournalChemical Engineering Communications
Volume191
Issue number1
DOIs
Publication statusPublished - 2004 Jan

All Science Journal Classification (ASJC) codes

  • General Chemistry
  • General Chemical Engineering

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