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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

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Abstract

A metal-free iodine/NaOH-catalyzed oxidation of alcohols and aldehydes has been developed for the practical synthesis of a wide range of carboxylic acids using water as the solvent. This transformation involves dehydrogenation of an alcohol, followed by a fast attack of water on an aldehyde. This method is mostly free from chromatographic purification, which makes it suitable for large-scale synthesis. The iodine species formed during the reaction as the active oxidation catalyst has been deduced as IO2 by control experiments. We also demonstrate a 10 gram scale synthesis of furandicarboxylic acid (FDCA) from HMF in good yield using our method.

Graphical abstract: 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

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Publication details

The article was received on 14 Sep 2017, accepted on 20 Oct 2017 and first published on 20 Oct 2017


Article type: Communication
DOI: 10.1039/C7GC02802D
Citation: Green Chem., 2017, Advance Article
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    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

    S. Hazra, M. Deb and A. J. Elias, Green Chem., 2017, Advance Article , DOI: 10.1039/C7GC02802D

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