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Selectivity and lifetime effects in zeolite-catalyzed Baeyer-Villiger oxidation investigated in batch and continuous flow

Yakabi, Keiko, Milne, Kirstie, Buchard, Antoine and Hammond, Ceri 2016. Selectivity and lifetime effects in zeolite-catalyzed Baeyer-Villiger oxidation investigated in batch and continuous flow. ChemCatChem 8 (22) , pp. 3490-3498. 10.1002/cctc.201600955

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Abstract

In this manuscript, we investigate the kinetic, mechanistic and lifetime aspects of the Baeyer-Villiger oxidation of cyclohexanone with Sn- as catalyst and H2O2 as oxidant, with the aim of 1) elucidating the overall reaction network, 2) closing the carbon balance, particularly at high levels of conversion, and 3) examining the intensification of this process in the continuous regime. The results presented herein conclusively demonstrate that this reaction is highly selective to the desired product (-caprolactone) only below conversions of 60 %. Above this level of conversion, unavoidable hydrolysis of -caprolactone to 6-hydroxyhexanoic acid is observed, which consumes the desired product and leads to a reduction in catalytic activity through poisoning. By elucidating the reaction network and working under optimized conditions, we show the potential viability of this methodology to operate continuously over a 180 h period, both at high levels of productivity (324 g (cyclohexanone converted) cm-3 (reactor volume) kg-1 (catalyst) h-1) and selectivity (± 70 % at 60 % conversion). Over 5000 substrate turnovers were observed during this period, an order of magnitude higher than previously noted for this particular catalyst system.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Cardiff Catalysis Institute (CCI)
Chemistry
Subjects: Q Science > QD Chemistry
Publisher: Wiley
ISSN: 1867-3880
Funders: The Royal Society
Date of First Compliant Deposit: 12 September 2016
Date of Acceptance: 26 August 2016
Last Modified: 26 Oct 2021 03:38
URI: https://orca.cardiff.ac.uk/id/eprint/94442

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