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Selectivity and Lifetime Effects in Zeolite‐Catalysed Baeyer–Villiger Oxidation Investigated in Batch and Continuous Flow
Author(s) -
Yakabi Keiko,
Milne Kirstie,
Buchard Antoine,
Hammond Ceri
Publication year - 2016
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201600955
Subject(s) - catalysis , cyclohexanone , selectivity , chemistry , zeolite , hydrolysis , substrate (aquarium) , chemical engineering , organic chemistry , oceanography , engineering , geology
In this manuscript, we investigate the kinetic, mechanistic and lifetime aspects of the Baeyer–Villiger oxidation of cyclohexanone with Sn‐β as catalyst and H 2 O 2 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 for the desired product ( ϵ ‐caprolactone) only below conversions of 60 %. Above this level of conversion, unavoidable hydrolysis of ϵ ‐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 optimised 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.

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