Epoxidation of α-pinene catalyzed by methyltrioxorhenium(VII): Influence of additives, oxidants and solvents

Typhne Michel; Daniel Betz; Mirza Cokoja; Volker Sieber; Fritz E. Kühn

doi:10.1016/j.molcata.2011.03.017

Epoxidation of α-pinene catalyzed by methyltrioxorhenium(VII): Influence of additives, oxidants and solvents

Typhne Michel, Daniel Betz, Mirza Cokoja, Volker Sieber, Fritz E. Kühn

Technical University of Munich

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

35 Scopus citations

Abstract

The epoxidation of α-pinene employing methyltrioxorhenium as catalyst is examined. The influence of mono- and bidentate Lewis basic additives (e.g. ^tbutylpyridine, 4,4′-dimethyl-2,2′-bipyridine, and Schiff-bases) is investigated. Additionally the impact of the oxidant (H ₂O₂ in water or urea-hydrogen peroxide (UHP)) on the catalytic performance is studied. The effect of the solvent is also examined in order to determine the optimal conditions for the epoxidation of α-pinene. The best and straightforwardly applicable result is obtained when a ratio α-pinene:MTO:^tbutylpyridine:UHP of 200:1:40:600 is applied at 0 °C in nitromethane. In this case, α-pinene oxide is formed with 95% yield after 3 h with a turnover frequency (TOF) of 610 h^-1.

Original language	English
Pages (from-to)	9-14
Number of pages	6
Journal	Journal of Molecular Catalysis A: Chemical
Volume	340
Issue number	1-2
DOIs	https://doi.org/10.1016/j.molcata.2011.03.017
State	Published - 23 Apr 2011

Keywords

Epoxidation
Homogeneous catalysis
Methyltrioxorhenium
Pinene oxide
Terpenes

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10.1016/j.molcata.2011.03.017

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title = "Epoxidation of α-pinene catalyzed by methyltrioxorhenium(VII): Influence of additives, oxidants and solvents",

abstract = "The epoxidation of α-pinene employing methyltrioxorhenium as catalyst is examined. The influence of mono- and bidentate Lewis basic additives (e.g. tbutylpyridine, 4,4′-dimethyl-2,2′-bipyridine, and Schiff-bases) is investigated. Additionally the impact of the oxidant (H 2O2 in water or urea-hydrogen peroxide (UHP)) on the catalytic performance is studied. The effect of the solvent is also examined in order to determine the optimal conditions for the epoxidation of α-pinene. The best and straightforwardly applicable result is obtained when a ratio α-pinene:MTO:tbutylpyridine:UHP of 200:1:40:600 is applied at 0 °C in nitromethane. In this case, α-pinene oxide is formed with 95% yield after 3 h with a turnover frequency (TOF) of 610 h-1.",

keywords = "Epoxidation, Homogeneous catalysis, Methyltrioxorhenium, Pinene oxide, Terpenes",

author = "Typhne Michel and Daniel Betz and Mirza Cokoja and Volker Sieber and K{\"u}hn, {Fritz E.}",

note = "Funding Information: S. Hauser, P. Altmann and T. Schr{\"o}ferl are acknowledged for helpful discussions. The authors gratefully acknowledge the support of the Graduate School of Chemistry of the Technische Universit{\"a}t M{\"u}nchen . D. Betz is thankful to the Bayerische Forschungstiftung for a PhD grant and T. Michel is acknowledged to the Fraunhofer society for the financing of her PhD position.",

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journal = "Journal of Molecular Catalysis A: Chemical",

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T1 - Epoxidation of α-pinene catalyzed by methyltrioxorhenium(VII)

T2 - Influence of additives, oxidants and solvents

AU - Michel, Typhne

AU - Betz, Daniel

AU - Cokoja, Mirza

AU - Sieber, Volker

AU - Kühn, Fritz E.

N1 - Funding Information: S. Hauser, P. Altmann and T. Schröferl are acknowledged for helpful discussions. The authors gratefully acknowledge the support of the Graduate School of Chemistry of the Technische Universität München . D. Betz is thankful to the Bayerische Forschungstiftung for a PhD grant and T. Michel is acknowledged to the Fraunhofer society for the financing of her PhD position.

PY - 2011/4/23

Y1 - 2011/4/23

N2 - The epoxidation of α-pinene employing methyltrioxorhenium as catalyst is examined. The influence of mono- and bidentate Lewis basic additives (e.g. tbutylpyridine, 4,4′-dimethyl-2,2′-bipyridine, and Schiff-bases) is investigated. Additionally the impact of the oxidant (H 2O2 in water or urea-hydrogen peroxide (UHP)) on the catalytic performance is studied. The effect of the solvent is also examined in order to determine the optimal conditions for the epoxidation of α-pinene. The best and straightforwardly applicable result is obtained when a ratio α-pinene:MTO:tbutylpyridine:UHP of 200:1:40:600 is applied at 0 °C in nitromethane. In this case, α-pinene oxide is formed with 95% yield after 3 h with a turnover frequency (TOF) of 610 h-1.

AB - The epoxidation of α-pinene employing methyltrioxorhenium as catalyst is examined. The influence of mono- and bidentate Lewis basic additives (e.g. tbutylpyridine, 4,4′-dimethyl-2,2′-bipyridine, and Schiff-bases) is investigated. Additionally the impact of the oxidant (H 2O2 in water or urea-hydrogen peroxide (UHP)) on the catalytic performance is studied. The effect of the solvent is also examined in order to determine the optimal conditions for the epoxidation of α-pinene. The best and straightforwardly applicable result is obtained when a ratio α-pinene:MTO:tbutylpyridine:UHP of 200:1:40:600 is applied at 0 °C in nitromethane. In this case, α-pinene oxide is formed with 95% yield after 3 h with a turnover frequency (TOF) of 610 h-1.

KW - Epoxidation

KW - Homogeneous catalysis

KW - Methyltrioxorhenium

KW - Pinene oxide

KW - Terpenes

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Epoxidation of α-pinene catalyzed by methyltrioxorhenium(VII): Influence of additives, oxidants and solvents

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