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Selective Hydrogenation and Hydrodeoxygenation of Aromatic Ketones to Cyclohexane Derivatives Using a Rh@SILP Catalyst

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Moos,  Gilles
Research Department Leitner, Max Planck Institute for Chemical Energy Conversion, Max Planck Society;

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Bordet,  Alexis
Research Department Leitner, Max Planck Institute for Chemical Energy Conversion, Max Planck Society;

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Leitner,  Walter
Research Department Leitner, Max Planck Institute for Chemical Energy Conversion, Max Planck Society;
Institut für Technische Chemie und Makromolekulare Chemie, Rheinisch‐Westfälische Technische Hochschule Aachen, Worringer Weg 1, 52074 Aachen, Germany;

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Citation

Moos, G., Emondts, M., Bordet, A., & Leitner, W. (2020). Selective Hydrogenation and Hydrodeoxygenation of Aromatic Ketones to Cyclohexane Derivatives Using a Rh@SILP Catalyst. Angewandte Chemie, International Edition in English, 59(29), 11977-11983. doi:10.1002/anie.201916385.


Cite as: http://hdl.handle.net/21.11116/0000-0007-D30C-E
Abstract
Rhodium nanoparticles immobilized on an acid-free triphenylphosphonium-based supported ionic liquid phase (Rh@SILP(Ph-3-P-NTf2)) enabled the selective hydrogenation and hydrodeoxygenation of aromatic ketones. The flexible molecular approach used to assemble the individual catalyst components (SiO2, ionic liquid, nanoparticles) led to outstanding catalytic properties. In particular, intimate contact between the nanoparticles and the phosphonium ionic liquid is required for the deoxygenation reactivity. The Rh@SILP(Ph-3-P-NTf2) catalyst was active for the hydrodeoxygenation of benzylic ketones under mild conditions, and the product distribution for non-benzylic ketones was controlled with high selectivity between the hydrogenated (alcohol) and hydrodeoxygenated (alkane) products by adjusting the reaction temperature. The versatile Rh@SILP(Ph-3-P-NTf2) catalyst opens the way to the production of a wide range of high-value cyclohexane derivatives by the hydrogenation and/or hydrodeoxygenation of Friedel-Crafts acylation products and lignin-derived aromatic ketones.