Regioselective Baeyer-Villiger oxidation of lignin model compounds with tin beta zeolite catalyst and hydrogen peroxide


Lignin depolymerization represents a promising approach to the sustainable production of aromatic molecules. One potential approach to the stepwise depolymerization of lignin involves oxidation of the benzylic alcohol group in β-O-4 and β-1 linkages, followed by Baeyer-Villiger oxidation (BVO) of the resulting ketones and subsequent ester hydrolysis. Towards this goal, BVO reactions were performed on 2-adamantanone, a series of acetophenone derivatives, and lignin model compounds using a tin beta zeolite/hydrogen peroxide biphasic system. XRD, 119Sn MAS NMR spectroscopy, DRUVS and XPS were used to determine tin speciation in the catalyst, the presence of both framework Sn and extra framework SnO2 being inferred. Conversion of ketones to BVO products was affected by electron donation as well as steric hindrance, 4′-methoxyacetophenone affording the highest yield of ester (81%). As the size and complexity of the ketone increased, excess hydrogen peroxide was typically needed for successful BVO. Yields of ester products derived from β-O-4 and β-1 lignin models were modest due to the formation of polymeric material stemming from direct ring hydroxylation.

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Divisions: Engineering & Applied Sciences
Additional Information: This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence.
Uncontrolled Keywords: Chemistry(all),Chemical Engineering(all)
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Related URLs: http://www.scop ... tnerID=8YFLogxK (Scopus URL)
http://pubs.rsc ... 0e#!divAbstract (Publisher URL)
PURE Output Type: Article
Published Date: 2017-05-16
Published Online Date: 2017-05-16
Accepted Date: 2017-05-08
Authors: Jennings, John A.
Parkin, Sean
Munson, Eric
Delaney, Sean P.
Calahan, Julie L.
Isaacs, Mark
Hong, Kunlun
Crocker, Mark



Version: Published Version

License: Creative Commons Attribution

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