Bacteriogenic iron oxide as an effective catalyst for Baeyer-Villiger oxidation with molecular oxygen and benzaldehyde

Kyoko Mandai, Minae Hanata, Koichi Mitsudo, Hiroki Mandai, Seiji Suga, Hideki Hashimoto, Jun Takada

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Iron oxide produced by iron-oxidizing bacteria, Leptothrix ochracea, (L-BIOX) obtained from a freshwater purification plant, Joyo City in Kyoto, Japan catalyzed Baeyer-Villiger oxidation with molecular oxygen in the presence of benzaldehyde at 25 °C more efficiently than usual iron compounds. L-BIOX can promote the reactions of various substrates to give the desired products in sufficient yields and was found to be reusable. Scanning transmission electron microscopy and 57Fe Mössbauer spectroscopy revealed that no change of the surface structure of L-BIOX was observed even after four times of the recycling test and the oxidation state of iron in L-BIOX is trivalent before and after the oxidation of cyclohexanone. An investigation with analogous amorphous iron oxides which contain silicon revealed that the catalytic activity of L-BIOX might stem from a synergetic effect of iron and silicon in the structure.

Original languageEnglish
Pages (from-to)943-9407
Number of pages8465
JournalTetrahedron
Volume71
Issue number50
DOIs
Publication statusPublished - Dec 16 2015

Fingerprint

Molecular oxygen
Iron
Silicon
Oxygen
Oxidation
Catalysts
Leptothrix
Iron Compounds
Scanning Transmission Electron Microscopy
Recycling
Fresh Water
Surface structure
Purification
Catalyst activity
Spectrum Analysis
Bacteria
Japan
Spectroscopy
Transmission electron microscopy
Scanning electron microscopy

Keywords

  • Baeyer-Villiger oxidation
  • Iron oxide
  • Oxidation
  • Silicon
  • Synergetic effect

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Bacteriogenic iron oxide as an effective catalyst for Baeyer-Villiger oxidation with molecular oxygen and benzaldehyde. / Mandai, Kyoko; Hanata, Minae; Mitsudo, Koichi; Mandai, Hiroki; Suga, Seiji; Hashimoto, Hideki; Takada, Jun.

In: Tetrahedron, Vol. 71, No. 50, 16.12.2015, p. 943-9407.

Research output: Contribution to journalArticle

Mandai, Kyoko ; Hanata, Minae ; Mitsudo, Koichi ; Mandai, Hiroki ; Suga, Seiji ; Hashimoto, Hideki ; Takada, Jun. / Bacteriogenic iron oxide as an effective catalyst for Baeyer-Villiger oxidation with molecular oxygen and benzaldehyde. In: Tetrahedron. 2015 ; Vol. 71, No. 50. pp. 943-9407.
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AU - Suga, Seiji

AU - Hashimoto, Hideki

AU - Takada, Jun

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