Gas Phase Hydrotreatment of Chlorophenols over Pd Catalysts as an Alternative Route to Cyclohexanone

Mark A Keane, Santiago Gomez Quero, Fernando Cardenas-Lizana

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Abstract

We have established viability of cyclohexanone (C6ONE) production via coupled gas phase (1 atm, 423 K) continuous hydrodechlorination/hydrogenation of mono- and di-chlorophenols over bulk Pd and Pd/Al2O3. The catalysts have been characterised by temperature programmed reduction, H2 chemisorption, powder XRD and TEM analyses. Hydrodechlorination is not a thermodynamically limiting step where under catalytic control we achieve significantly greater C6ONE yields relative to those from standard phenol hydrogenation. We account for this response in terms of a direct chlorophenol  C6ONE conversion facilitated by electron delocalisation in the intermediate generated via electrophilic hydrogen cleavage of C–Cl bond(s). The C6ONE selectivity/conversion profiles coincided for bulk and supported Pd and we demonstrate structure sensitivity for the production of C6ONE from 2,4-dichlorophenol with higher specific rates over larger Pd particles (2→250 nm).
Original languageEnglish
Pages (from-to)35–48
Number of pages14
JournalReaction Kinetics, Mechanisms and Catalysis
Volume119
Issue number1
Early online date22 Jun 2016
DOIs
Publication statusPublished - Oct 2016

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