Ionic TEMPO in Ionic Liquids

Specific Promotion of the Aerobic Oxidation of Alcohols

Journal article (2016)

Authors

Tsunehisa Hirashita Nagoya Institute of Technology
Makoto Nakanishi Nagoya Institute of Technology
Tomoya Uchida Nagoya Institute of Technology
Masakazu Yamamoto Nagoya Institute of Technology
Shuki Araki Nagoya Institute of Technology
I.W.C.E. Arends BT/Biotechnologie
R.A. Sheldon BT/Biocatalysis - AS , University of Witwatersrand
Research Group
BT/Biocatalysis (AS) (TU Delft)
Ionic liquids Oxidation Radicals Oxygen Alcohols
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Published Date

22-08-2016

Language

English

Reuse Rights

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Faculty

Applied Sciences

Department

BT/Biotechnologie

Research Group

BT/Biocatalysis

Abstract

The main objective of this study was to design a recyclable TEMPO (2,2,6,6-tetramethylpiperidinyl-N-oxyl) derivative that could be used as a catalyst in an ionic liquid solvent for the aerobic oxidation of alcohols by using NaNO2 and HCl as co-catalysts. To this end, a TEMPO derivative bearing a quaternary ammonium group, [4-Bu2MeN-TEMPO][PF6] (1), was prepared. It was subsequently shown that this ionic TEMPO derivative is an efficient catalyst for the aerobic oxidation of a variety of primary and secondary alcohols. It exhibits a synergistic effect with ionic liquid solvents and readily outperforms analogous oxidations in methylene chloride. Moreover, the ionic TEMPO could be recycled five times with no loss of activity.