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

doi:10.1016/j.tet.2015.10.057

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

School of Engineering

Research output: Contribution to journal › Article › peer-review

16 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 language	English
Pages (from-to)	9403-9407
Number of pages	5
Journal	Tetrahedron
Volume	71
Issue number	50
DOIs	https://doi.org/10.1016/j.tet.2015.10.057
Publication status	Published - Dec 16 2015

Keywords

Baeyer-Villiger oxidation
Iron oxide
Oxidation
Silicon
Synergetic effect

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.tet.2015.10.057

Cite this

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

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 M{\"o}ssbauer 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.",

keywords = "Baeyer-Villiger oxidation, Iron oxide, Oxidation, Silicon, Synergetic effect",

author = "Kyoko Mandai and Minae Hanata and Koichi Mitsudo and Hiroki Mandai and Seiji Suga and Hideki Hashimoto and Jun Takada",

note = "Publisher Copyright: {\textcopyright} 2015 Elsevier Ltd.",

year = "2015",

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doi = "10.1016/j.tet.2015.10.057",

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T1 - Bacteriogenic iron oxide as an effective catalyst for Baeyer-Villiger oxidation with molecular oxygen and benzaldehyde

AU - Mandai, Kyoko

AU - Hanata, Minae

AU - Mitsudo, Koichi

AU - Mandai, Hiroki

AU - Suga, Seiji

AU - Hashimoto, Hideki

AU - Takada, Jun

PY - 2015/12/16

Y1 - 2015/12/16

N2 - 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.

AB - 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.

KW - Baeyer-Villiger oxidation

KW - Iron oxide

KW - Oxidation

KW - Silicon

KW - Synergetic effect

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SP - 9403

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JO - Tetrahedron

JF - Tetrahedron

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

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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