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Issue 2, 2014
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Aqueous-phase hydrodeoxygenation of highly oxygenated aromatics on platinum

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Abstract

Utilization of renewable sugars from biomass by a hybrid chemical process produces highly oxygenated aromatic compounds, such as phloroglucinol, which require catalytic reduction for desirable aromatic products. Aqueous phase hydrodeoxygenation of phloroglucinol on carbon-supported platinum produces resorcinol, phenol, cyclohexanol, cyclohexanone, and 1,3-cyclohexanediol by combinations of carbon–oxygen bond cleavage and carbon–carbon double bond hydrogenation. Carbon–carbon σ-bond cleavage was not observed. Hydrodeoxygenation was the primary reaction of phloroglucinol, leading to the production of resorcinol in the overall rate-limiting reaction, with an activation energy barrier of Ea = 117 kJ mol−1. Subsequent reactions of resorcinol produced 1,3-cyclohexanediol and phenol with similar energy barriers, Ea = 46 and Ea = 54 kJ mol−1, respectively. Further hydrogenation of phenol (Ea = 42 kJ mol−1) occurs through the intermediate, cyclohexanone, which is further reduced (Ea = 14 kJ mol−1) to the dominant product, cyclohexanol.

Graphical abstract: Aqueous-phase hydrodeoxygenation of highly oxygenated aromatics on platinum

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Publication details

The article was received on 12 Jun 2013, accepted on 13 Aug 2013 and first published on 14 Aug 2013


Article type: Paper
DOI: 10.1039/C3GC41138A
Citation: Green Chem., 2014,16, 675-682
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    Aqueous-phase hydrodeoxygenation of highly oxygenated aromatics on platinum

    J. Yang, C. L. Williams, A. Ramasubramaniam and P. J. Dauenhauer, Green Chem., 2014, 16, 675
    DOI: 10.1039/C3GC41138A

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