Fluorous biphase oxidation of ethyl benzene and benzyl alcohol catalyzed by perfluoroalkyl phthalocyanine complexes

  • Tao Qiu
  • , Xiaoyong Xu
  • , Xuhong Qian*
  • *Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

Background: Ketones and aldehydes are important organic chemicals as intermediates for the pharmaceutical and fine-chemical industries. The existing oxidation reactions to obtain ketones and aldehydes are no longer sustainable because of the large amount of waste generated and use of stoichiometric reagents: a cleaner catalytic oxidation system needs to be developed. Results: The experimental results show that cobalt (II) tetra-(perfluorohexyl) phthalocyaninate delivered a high catalytic activity for the oxidation of ethyl benzene (35% conversion and 86% selectivity to acetophenone) at 90°C under ambient pressure of oxygen. The catalyst could be recycled for at least four runs. For the oxidation of benzyl alcohol to benzaldehyde, a conversion of 6% was achieved but with a selectivity of 100% at 90°C under 2 × 105 Pa O2. Conclusion: Perfluoroalkyl metallophthalocyanines can be used for the fluorous biphasic oxidation of ethyl benzene and benzyl alcohol with molecular oxygen. The cobalt (II) tetra-(perfluorohexyl) phthalocyaninate exhibited the highest catalytic activity for the oxidation of ethyl benzene. The catalytic oxidation of benzyl alcohol using our method may be feasible in industrial applications.

Original languageEnglish
Pages (from-to)1051-1055
Number of pages5
JournalJournal of Chemical Technology and Biotechnology
Volume84
Issue number7
DOIs
StatePublished - 2009
Externally publishedYes

Keywords

  • Benzyl alcohol
  • Ethyl benzene
  • Fluorous biphasic catalysis
  • Oxidation
  • Perfluoroalkyl phthalocyanines

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