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

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...

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Autores principales: Denlinger, Kendra Leahy, Carr, Preston, Waddell, Daniel C., Mack, James
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7024246/
https://www.ncbi.nlm.nih.gov/pubmed/31963148
http://dx.doi.org/10.3390/molecules25020364
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author Denlinger, Kendra Leahy
Carr, Preston
Waddell, Daniel C.
Mack, James
author_facet Denlinger, Kendra Leahy
Carr, Preston
Waddell, Daniel C.
Mack, James
author_sort Denlinger, Kendra Leahy
collection PubMed
description 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.
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spelling pubmed-70242462020-03-19 A Recyclable, Metal-Free Mechanochemical Approach for the Oxidation of Alcohols to Carboxylic Acids Denlinger, Kendra Leahy Carr, Preston Waddell, Daniel C. Mack, James Molecules Article 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. MDPI 2020-01-16 /pmc/articles/PMC7024246/ /pubmed/31963148 http://dx.doi.org/10.3390/molecules25020364 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Denlinger, Kendra Leahy
Carr, Preston
Waddell, Daniel C.
Mack, James
A Recyclable, Metal-Free Mechanochemical Approach for the Oxidation of Alcohols to Carboxylic Acids
title A Recyclable, Metal-Free Mechanochemical Approach for the Oxidation of Alcohols to Carboxylic Acids
title_full A Recyclable, Metal-Free Mechanochemical Approach for the Oxidation of Alcohols to Carboxylic Acids
title_fullStr A Recyclable, Metal-Free Mechanochemical Approach for the Oxidation of Alcohols to Carboxylic Acids
title_full_unstemmed A Recyclable, Metal-Free Mechanochemical Approach for the Oxidation of Alcohols to Carboxylic Acids
title_short A Recyclable, Metal-Free Mechanochemical Approach for the Oxidation of Alcohols to Carboxylic Acids
title_sort recyclable, metal-free mechanochemical approach for the oxidation of alcohols to carboxylic acids
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7024246/
https://www.ncbi.nlm.nih.gov/pubmed/31963148
http://dx.doi.org/10.3390/molecules25020364
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