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Molecules 2017, 22(12), 2099; doi:10.3390/molecules22122099

Heterogenization of Ketone Catalyst for Epoxidation by Low Pressure Plasma Fluorination of Silica Gel Supports

1
Department of Chemistry, University of Bari “Aldo Moro”, Via Orabona 4, 70126 Bari, Italy
2
ICCOM-CNR, SS Bari, Via Orabona 4, 70126 Bari, Italy
3
NANOTEC-CNR, c/o Department of Chemistry, University of Bari “Aldo Moro”, Via Orabona 4, 70126 Bari, Italy
*
Authors to whom correspondence should be addressed.
Received: 1 November 2017 / Revised: 22 November 2017 / Accepted: 27 November 2017 / Published: 30 November 2017
(This article belongs to the Special Issue Chemical Transformation of Renewable Material for Green Chemistry)
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Abstract

Low pressure plasma was used for preparing heterogeneous organocatalysts 2-(A)-(C) suitable for dioxirane-mediated epoxidations. Heterogenization was accomplished by adsorption of the methyl perfluoroheptyl ketone (2) on fluorinated supports (A)-(C) deriving from the treatment of commercial C8-silica gel in low pressure plasma fed with fluorocarbons. Catalyst 2-(C) proved to be the most efficient one, promoting epoxidation of an array of alkenes, including unsaturated fatty esters like methyl oleate (10) and the triglyceride soybean oil (11), with the cheap potassium peroxymonosulfate KHSO5 (caroate) as a green oxidant. Notably, the perfluorinated matrix gives rise to the activation of caroate, generating singlet oxygen. Materials were characterized by infrared Attenuated Total Reflectance spectroscopy (ATR-FTIR), X-ray Photoelectron Spectroscopy (XPS ) and Emission Scanning Electron Microscope (FESEM). View Full-Text
Keywords: dioxiranes; PE-CVD; epoxidation; fluorous chemistry dioxiranes; PE-CVD; epoxidation; fluorous chemistry
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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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MDPI and ACS Style

D’Accolti, L.; De Vietro, N.; Fanelli, F.; Fusco, C.; Nacci, A.; Fracassi, F. Heterogenization of Ketone Catalyst for Epoxidation by Low Pressure Plasma Fluorination of Silica Gel Supports. Molecules 2017, 22, 2099.

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