Methyltrioxorhenium-catalyzed oxidation of pseudocumene for vitamin e synthesis: A study of solvent and ligand effects

Mónica Carril; Philipp Altmann; Markus Drees; Werner Bonrath; Thomas Netscher; Jan Schütz; Fritz E. Kühn

doi:10.1016/j.jcat.2011.07.003

Methyltrioxorhenium-catalyzed oxidation of pseudocumene for vitamin e synthesis: A study of solvent and ligand effects

Mónica Carril, Philipp Altmann, Markus Drees, Werner Bonrath, Thomas Netscher, Jan Schütz, Fritz E. Kühn

Associate Professorship of Molecular Catalysis

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

32 Scopus citations

Abstract

Vitamin E is an essential food component of major economical relevance with important antioxidant properties and biological activity. The oxidation of pseudocumene to trimethyl-1,4-benzoquinone would be a key transformation in an alternative industrial production of α-tocopherol that is important for the antioxidant activity of vitamin E. The methyltrioxorhenium (MTO)-catalyzed oxidation of pseudocumene has been revisited to offer a more environmentally friendly, economically beneficial and milder approach to this important industrial product. It has been observed that by choosing the solvent and Lewis base additives (as ligands of MTO), both yield and chemoselectivity are considerably improved, allowing milder reaction conditions compared to previously reported protocols.

Original language	English
Pages (from-to)	55-67
Number of pages	13
Journal	Journal of Catalysis
Volume	283
Issue number	1
DOIs	https://doi.org/10.1016/j.jcat.2011.07.003
State	Published - 6 Oct 2011

Keywords

Arenes
DFT
Hydrogen peroxide
Lewis base
Mechanism
MTO
Oxidation
Schiff base
Vitamin E

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10.1016/j.jcat.2011.07.003

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abstract = "Vitamin E is an essential food component of major economical relevance with important antioxidant properties and biological activity. The oxidation of pseudocumene to trimethyl-1,4-benzoquinone would be a key transformation in an alternative industrial production of α-tocopherol that is important for the antioxidant activity of vitamin E. The methyltrioxorhenium (MTO)-catalyzed oxidation of pseudocumene has been revisited to offer a more environmentally friendly, economically beneficial and milder approach to this important industrial product. It has been observed that by choosing the solvent and Lewis base additives (as ligands of MTO), both yield and chemoselectivity are considerably improved, allowing milder reaction conditions compared to previously reported protocols.",

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AU - Drees, Markus

AU - Bonrath, Werner

AU - Netscher, Thomas

AU - Schütz, Jan

AU - Kühn, Fritz E.

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KW - Hydrogen peroxide

KW - Lewis base

KW - Mechanism

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KW - Oxidation

KW - Schiff base

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Methyltrioxorhenium-catalyzed oxidation of pseudocumene for vitamin e synthesis: A study of solvent and ligand effects

Abstract

Keywords

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