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

Molecules ◽  
2020 ◽  
Vol 25 (2) ◽  
pp. 364 ◽  
Author(s):  
Kendra Leahy Denlinger ◽  
Preston Carr ◽  
Daniel C. Waddell ◽  
James Mack
Keyword(s):  
Stainless Steel ◽  
Ball Milling ◽  
Carboxylic Acids ◽  
Steric Hindrance ◽  
Primary Alcohol ◽  
Oxidation Reactions ◽  
Primary Alcohols ◽  
Metal Free ◽  
Oxidation Of Alcohols ◽  
Stainless Steel Ball

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.

Direct Oxidation of Primary Alcohols to Carboxylic Acids

Synthesis ◽  
2020 ◽  
Author(s):  
Travis J. Williams ◽  
Valeriy Cherepakhin
Keyword(s):  
Carboxylic Acids ◽  
Direct Synthesis ◽  
Primary Alcohol ◽  
Alcohol Oxidation ◽  
Atom Economy ◽  
Primary Alcohols ◽  
Direct Oxidation ◽  
Metal Compounds ◽  
New Methods ◽  
Active Research

AbstractOxidation of primary alcohols to carboxylic acids is a fundamental transformation in organic chemistry, yet despite its simplicity, extensive use, and relationship to pH, it remains a subject of active research for synthetic organic chemists. Since 2013, a great number of new methods have emerged that utilize transition-metal compounds as catalysts for acceptorless dehydrogenation of alcohols to carboxylates. The interest in this reaction is explained by its atom economy, which is in accord with the principles of sustainability and green chemistry. Therefore, the methods for the direct synthesis of carboxylic acids from alcohols is ripe for a modern survey, which we provide in this review.1 Introduction2 Thermodynamics of Primary Alcohol Oxidation3 Oxometalate Oxidation4 Transfer Dehydrogenation5 Acceptorless Dehydrogenation6 Electrochemical Methods7 Outlook

Table salt as a catalyst for the oxidation of aromatic alcohols and amines to acids and imines in aqueous medium: effectively carrying out oxidation reactions in sea water

2019 ◽  
Vol 21 (8) ◽  
pp. 1929-1934 ◽  
Author(s):  
Susanta Hazra ◽  
Ajay Kishor Kushawaha ◽  
Deepak Yadav ◽  
Pritam Dolui ◽  
Mayukh Deb ◽  
...  
Keyword(s):  
Aqueous Medium ◽  
Carboxylic Acids ◽  
Sea Water ◽  
Oxidation Reactions ◽  
Table Salt ◽  
Economical Method ◽  
Oxidation Of Alcohols ◽  
Aromatic Alcohols

A simple, efficient, sustainable and economical method for the oxidation of alcohols and amines has been developed using chloride, a sea abundant anionic catalyst for the synthesis of a range of carboxylic acids, ketones and imines.

Iodine catalyzed oxidation of alcohols and aldehydes to carboxylic acids in water: a metal-free route to the synthesis of furandicarboxylic acid and terephthalic acid

2017 ◽  
Vol 19 (23) ◽  
pp. 5548-5552 ◽  
Author(s):  
Susanta Hazra ◽  
Mayukh Deb ◽  
Anil J. Elias
Keyword(s):  
Carboxylic Acids ◽  
Terephthalic Acid ◽  
Metal Free ◽  
Oxidation Of Alcohols ◽  
Furandicarboxylic Acid ◽  
Catalyzed Oxidation

Iodine(iii) catalyzed metal free method for oxidation of alcohols and aldehydes in water.

Transition-metal-free aerobic oxidation of primary alcohols to carboxylic acids

2013 ◽  
Vol 37 (6) ◽  
pp. 1700 ◽  
Author(s):  
Jing Wang ◽  
Chao Liu ◽  
Jiwen Yuan ◽  
Aiwen Lei
Keyword(s):  
Transition Metal ◽  
Carboxylic Acids ◽  
Aerobic Oxidation ◽  
Primary Alcohols ◽  
Metal Free

A sodium trifluoromethanesulfinate-mediated photocatalytic strategy for aerobic oxidation of alcohols

2020 ◽  
Vol 56 (82) ◽  
pp. 12443-12446
Author(s):  
Xianjin Zhu ◽  
Can Liu ◽  
Yong Liu ◽  
Haijun Yang ◽  
Hua Fu
Keyword(s):  
Carboxylic Acids ◽  
Aerobic Oxidation ◽  
Primary Alcohols ◽  
Oxidation Of Alcohols ◽  
First Time

A sodium trifluoromethanesulfinate-mediated photocatalytic strategy for the aerobic oxidation of secondary and primary alcohols to ketones and carboxylic acids has been developed for the first time.

scholarly journals A green and sustainable phosphine-free NHC-ruthenium catalyst for selective oxidation of alcohols to carboxylic acids in water

2015 ◽  
Vol 44 (39) ◽  
pp. 17409-17414 ◽  
Author(s):  
Jagadeesh Malineni ◽  
Helmut Keul ◽  
Martin Möller
Keyword(s):  
Oxygen Atom ◽  
Carboxylic Acids ◽  
Selective Oxidation ◽  
Direct Synthesis ◽  
Ruthenium Catalyst ◽  
Catalytic Dehydrogenation ◽  
Oxidizing Agent ◽  
Primary Alcohols ◽  
Oxidation Of Alcohols ◽  
Atom Source

An efficient novel protocol is applied for direct synthesis of carboxylic acids from primary alcohols through catalytic dehydrogenation. This reaction occurs in water as the solvent and as the oxygen-atom source and no toxic oxidizing agent is involved.

Stainless-Steel Ball-Milling Method for Hydro-/Deutero-genation using H2O/D2O as a Hydrogen/Deuterium Source

ChemSusChem ◽  
2015 ◽  
Vol 8 (22) ◽  
pp. 3773-3776 ◽  
Author(s):  
Yoshinari Sawama ◽  
Takahiro Kawajiri ◽  
Miki Niikawa ◽  
Ryota Goto ◽  
Yuki Yabe ◽  
...  
Keyword(s):  
Stainless Steel ◽  
Ball Milling ◽  
Steel Ball ◽  
Stainless Steel Ball ◽  
Milling Method ◽  
Hydrogen Deuterium

ChemInform Abstract: Transition-Metal-Free Aerobic Oxidation of Primary Alcohols to Carboxylic Acids.

ChemInform ◽  
2013 ◽  
Vol 44 (45) ◽  
pp. no-no
Author(s):  
Jing Wang ◽  
Chao Liu ◽  
Jiwen Yuan ◽  
Aiwen Lei
Keyword(s):  
Transition Metal ◽  
Carboxylic Acids ◽  
Aerobic Oxidation ◽  
Primary Alcohols ◽  
Metal Free
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