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Open AccessArticle

A Recyclable, Metal-Free Mechanochemical Approach for the Oxidation of Alcohols to Carboxylic Acids

Department of Chemistry, University of Cincinnati, 301 Clifton court, Cincinnati, OH 45221-0172, USA
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Academic Editors: Vjekoslav Štrukil and Matej Baláž
Molecules 2020, 25(2), 364; https://doi.org/10.3390/molecules25020364
Received: 11 November 2019 / Revised: 23 December 2019 / Accepted: 23 December 2019 / Published: 16 January 2020
(This article belongs to the Special Issue Recent Development of Mechanochemical Synthesis)
The oxidation of primary alcohols under mechanochemical conditions in a Spex8000M Mixer/Mill was investigated. To facilitate ease of separation and recyclability, a polystyrene-bound version of a TEMPO catalyst was employed. When paired with Oxone® in a stainless-steel vial with a stainless-steel ball, several primary alcohols were successfully oxidized to the corresponding carboxylic acids. The product was isolated using gravity filtration, which also allowed for the polystyrene-bound TEMPO catalyst to be recovered and reused in subsequent oxidation reactions. Furthermore, it was demonstrated that the size and steric hindrance of the primary alcohol does not hinder the rate of the reaction. Finally, the aldehyde was selectively obtained from a primary alcohol under ball milling conditions by using a combination of non-supported TEMPO with a copper vial and copper ball. View Full-Text
Keywords: mechanochemistry; polymer supported; tempo; oxidation; recycle mechanochemistry; polymer supported; tempo; oxidation; recycle
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MDPI and ACS Style

Denlinger, K.L.; Carr, P.; Waddell, D.C.; Mack, J. A Recyclable, Metal-Free Mechanochemical Approach for the Oxidation of Alcohols to Carboxylic Acids. Molecules 2020, 25, 364.

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