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Issue 8, 2015
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Solid base catalysed 5-HMF oxidation to 2,5-FDCA over Au/hydrotalcites: fact or fiction?

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Abstract

Nanoparticulate gold has emerged as a promising catalyst for diverse mild and efficient selective aerobic oxidations. However, the mechanism of such atom-economical transformations, and synergy with functional supports, remains poorly understood. Alkali-free Mg–Al hydrotalcites are excellent solid base catalysts for the aerobic oxidation of 5-hydroxymethylfurfural (HMF) to 2,5-furan dicarboxylic acid (FDCA), but only in concert with high concentrations of metallic gold nanoparticles. In the absence of soluble base, competitive adsorption between strongly-bound HMF and reactively-formed oxidation intermediates site-blocks gold. Aqueous NaOH dramatically promotes solution phase HMF activation, liberating free gold sites able to activate the alcohol function within the metastable 5-hydroxymethyl-2-furancarboxylic acid (HMFCA) reactive intermediate. Synergistic effects between moderate strength base sites within alkali-free hydrotalcites and high gold surface concentrations can afford highly selective and entirely heterogeneous catalysts for aqueous phase aldehyde and alcohol cascade oxidations pertinent to biomass transformation.

Graphical abstract: Solid base catalysed 5-HMF oxidation to 2,5-FDCA over Au/hydrotalcites: fact or fiction?

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Publication details

The article was received on 09 Mar 2015, accepted on 08 Jun 2015 and first published on 08 Jun 2015


Article type: Edge Article
DOI: 10.1039/C5SC00854A
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Citation: Chem. Sci., 2015,6, 4940-4945
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    Solid base catalysed 5-HMF oxidation to 2,5-FDCA over Au/hydrotalcites: fact or fiction?

    L. Ardemani, G. Cibin, A. J. Dent, M. A. Isaacs, G. Kyriakou, A. F. Lee, C. M. A. Parlett, S. A. Parry and K. Wilson, Chem. Sci., 2015, 6, 4940
    DOI: 10.1039/C5SC00854A

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