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Catalysts 2019, 9(4), 324; https://doi.org/10.3390/catal9040324

Cyclohexene Oxidation with H2O2 over Metal-Organic Framework MIL-125(Ti): The Effect of Protons on Reactivity

1
Boreskov Institute of Catalysis, Lavrentieva Ave. 5, Novosibirsk 630090, Russia
2
Department of Natural Sciences, Novosibirsk State University, Pirogova Str. 2, Novosibirsk 630090, Russia
3
Research group for nanocatalyst, Korea Research Institute of Chemical Technology, Daejeon 34114, Korea
4
Department of Chemistry, Sungkyunkwan University, Suwon 16419, Korea
*
Author to whom correspondence should be addressed.
Received: 22 February 2019 / Revised: 21 March 2019 / Accepted: 22 March 2019 / Published: 2 April 2019
(This article belongs to the Special Issue Epoxidation Catalysis)
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Abstract

The catalytic performance of the titanium-based metal–organic framework MIL-125 was evaluated in the selective oxidation of cyclohexene (CyH) with environmentally friendly oxidants, H2O2 and tBuOOH. The catalytic activity of MIL-125 as well as the oxidant utilization efficiency and selectivity toward epoxide and epoxide-derived products can be greatly improved by acid additives (HClO4 or CF3SO3H). In the presence of 1 molar equivalent (relative to Ti) of a proton source, the total selectivity toward CyH epoxide and trans-cyclohexane-1,2-diol reached 75–80% at 38–43% alkene conversion after 45 min of reaction with 1 equivalent of 30% H2O2 at 50 °C. With 50% H2O2 as the oxidant, the total selectivity toward heterolytic oxidation products increased up to 92% at the same level of alkene conversion. N2 adsorption, powder X-ray diffraction (PXRD), and infrared (IR) spectroscopy studies before and after the catalytic oxidations confirmed the absence of structural changes in the Metal–organic framework (MOF) structure. MIL-125 was stable toward titanium leaching, behaved as a truly heterogeneous catalyst, and could easily be recovered and reused several times without any loss of the catalytic properties. View Full-Text
Keywords: alkene; epoxidation; heterogeneous catalysis; hydrogen peroxide; metal-organic framework; MIL-125; titanium alkene; epoxidation; heterogeneous catalysis; hydrogen peroxide; metal-organic framework; MIL-125; titanium
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).
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Maksimchuk, N.; Lee, J.S.; Ayupov, A.; Chang, J.-S.; Kholdeeva, O. Cyclohexene Oxidation with H2O2 over Metal-Organic Framework MIL-125(Ti): The Effect of Protons on Reactivity. Catalysts 2019, 9, 324.

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