Epoxidation of the commercially relevant divinylbenzene with [tetrakis-(pentafluorophenyl)porphyrinato]iron(III) chloride and its derivatives

Kainan Zhang, Ying Yu, SonBinh Nguyen, Joseph T Hupp, Linda J Broadbelt, Omar k Farha*

*Corresponding author for this work

Research output: Contribution to journalArticle

8 Scopus citations

Abstract

Fluorinated Fe-porphyrins, especially [tetrakis(pentafluorophenyl)porphyrinato]iron(III) chloride (tetrakis(pentafluorophenyl)porphyrinato = TPFPP) (TPFPP)FeCl (Fepor-2a), were found to be highly efficient for catalyzing the double epoxidation of divinylbenzene (DVB) to divinylbenzene dioxide (DVBDO), a novel component of epoxy resin formulation. The electronic properties of the catalysts are highly dependent on the substituents on the phenyl groups of these metalloporphyrins. The electron-rich fluorinated Fe-porphyrins are more selective toward epoxidation but are more vulnerable toward decomposition in H2O2. On the other hand, the electron deficient Fe-porphyrins are more stable, yet more Lewis acidic, which facilitates the formation of byproducts such as epoxide ring opening and overoxidation.

Original languageEnglish (US)
Pages (from-to)922-927
Number of pages6
JournalIndustrial and Engineering Chemistry Research
Volume54
Issue number3
DOIs
StatePublished - Jan 1 2015

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Chemistry(all)
  • Industrial and Manufacturing Engineering

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