Aerobic Epoxidation of Olefin by Platinum Catalysts Supported on Mesoporous Silica Nanoparticles

Munz, Dominik; Wang, Daoyong; Moyer, Megan M.; Webster-Gardiner, Michael S.; Kunal, Pranaw; Watts, David; Trewyn, Brian G.; Vedernikov, Andrei N.; Gunnoe, T. Brent

doi:10.1021/acscatal.6b01532

Aerobic Epoxidation of Olefin by Platinum Catalysts Supported on Mesoporous Silica Nanoparticles

Journal Article · Wed Jun 15 00:00:00 EDT 2016 · ACS Catalysis

DOI:https://doi.org/10.1021/acscatal.6b01532· OSTI ID:1605983

Munz, Dominik ^[1]; Wang, Daoyong ^[2]; Moyer, Megan M. ^[3]; Webster-Gardiner, Michael S. ^[4]; Kunal, Pranaw ^[3]; Watts, David ^[2]; Trewyn, Brian G. ^[3]; Vedernikov, Andrei N. ^[2]; Gunnoe, T. Brent ^[4]

Univ. of Virginia, Charlottesville, VA (United States); University of Virginia
Univ. of Maryland, College Park, MD (United States)
Colorado School of Mines, Golden, CO (United States)
Univ. of Virginia, Charlottesville, VA (United States)

Here, we report platinum catalysts for the efficient aerobic oxidation of olefins to form epoxides and/or derived glycol monoethers. The catalysts, diaqua and dichloro PtII complexes supported by the ligand di(2-pyridine)methanesulfonate (dpms), are most active when they are covalently tethered to mesoporous silica nanoparticles (MSNs). Supporting the molecular Pt complexes on the MSNs prevents bimolecular catalyst deactivation. Using this strategy, turnovers > 40,000 are achieved for the aerobic oxidation of norbornene in 2,2,2-trifluoroethanol. The position of the tether and the nature of other ligands in the metal co-ordination sphere (aqua, hydroxo or chloro) are illustrated to affect the catalyst activity. The new MSN-supported Pt materials were characterized by NMR spectroscopy, nitrogen physisorption, powder X-ray diffraction (PXRD), scanning electron mi-croscopy (SEM), transmission electron microscopy (TEM) and thermogravimetric analysis (TGA).

View Accepted Manuscript (DOE)

Research Organization:: Univ. of Virginia, Charlottesville, VA (United States); Energy Frontier Research Centers (EFRC) (United States). Center for Catalytic Hydrocarbon Functionalization (CCHF)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22). Chemical Sciences, Geosciences & Biosciences Division

Grant/Contract Number:: SC0001298; SC0000776

OSTI ID:: 1605983

Journal Information:: ACS Catalysis, Journal Name: ACS Catalysis Journal Issue: 7 Vol. 6; ISSN 2155-5435

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Manganese porphyrin immobilized on montmorillonite: a highly efficient and reusable catalyst for the aerobic epoxidation of olefins under ambient conditions Zhou, Xiantai; Ji, Hongbing Journal of Porphyrins and Phthalocyanines, Vol. 16, Issue 09 https://doi.org/10.1142/S1088424612500721	journal	September 2012
Aerobic Epoxidation of Olefinic Compounds Catalyzed by Tris(1,3-diketonato)iron(III) Takai, Toshihiro; Hata, Eiichiro; Yamada, Tohru Bulletin of the Chemical Society of Japan, Vol. 64, Issue 8 https://doi.org/10.1246/bcsj.64.2513	journal	August 1991
Aerobic Epoxidation of Olefins Catalyzed by Cobalt(II) Complex Using Propionaldehyde Diethyl Acetal as a Reductant Mukaiyama, Teruaki; Yorozu, Kiyotaka; Takai, Toshihiro Chemistry Letters, Vol. 22, Issue 3 https://doi.org/10.1246/cl.1993.439	journal	March 1993
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