Aqueous-phase hydrodeoxygenation of highly oxygenated aromatics on platinum

Jin Yang, C. Luke Williams, Ashwin Ramasubramaniam, Paul J. Dauenhauer

Research output: Contribution to journalArticle

20 Citations (Scopus)

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.

Original languageEnglish (US)
Pages (from-to)675-682
Number of pages8
JournalGreen Chemistry
Volume16
Issue number2
DOIs
StatePublished - Feb 1 2014

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Platinum
platinum
Carbon
Phloroglucinol
carbon
Phenol
Cyclohexanols
Phenols
phenol
Energy barriers
cleavage
Hydrogenation
Aromatic compounds
chemical process
Sugars
activation energy
sugar
Biomass
Activation energy
Oxygen

Cite this

Aqueous-phase hydrodeoxygenation of highly oxygenated aromatics on platinum. / Yang, Jin; Williams, C. Luke; Ramasubramaniam, Ashwin; Dauenhauer, Paul J.

In: Green Chemistry, Vol. 16, No. 2, 01.02.2014, p. 675-682.

Research output: Contribution to journalArticle

Yang, Jin ; Williams, C. Luke ; Ramasubramaniam, Ashwin ; Dauenhauer, Paul J. / Aqueous-phase hydrodeoxygenation of highly oxygenated aromatics on platinum. In: Green Chemistry. 2014 ; Vol. 16, No. 2. pp. 675-682.
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