Zhao, Y, King, G, Kwan, MHT et al. (1 more author) (2016) A Mild and Selective Method for the Catalytic Hydrodeoxygenation of Cyanurate Activated Phenols in Multi-Phasic Continuous Flow. Organic Process Research and Development, 20 (11). pp. 2012-2018. ISSN 1083-6160
Abstract
A low energy, high selectivity approach to the catalytic hydrodeoxygenation of phenols is reported using batch or continuous flow methods to react 3 equivalents of phenol with cyanuric chloride then hydrogenolyzing the triarylcyanurate intermediate to give 3 equivalents of de-oxo aromatic. The use of cyanuric chloride compares favorably with existing activation methods, showing improved scalability, atom efficiency and economics. The scope of both the activation and hydrogenolysis stages are explored using lignin-related phenols. Initial development has identified that continuous stir tank reactors (CSTRs) enable a multi-phasic process for converting guaiacol to anisole, and at steady-state overcome the catalyst deactivation issues observed in batch, seemingly caused by the cyanurate by-product. Green chemistry aspects, and the potential for industrial adoption are discussed.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2016 American Chemical Society. This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Process Research and Development, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.oprd.6b00314. Uploaded in accordance with the publisher's self-archiving policy. |
Keywords: | Aromatic phenol deoxygenation; catalytic hydrodeoxygenation; continuous stirred tank reactor; multi-phasic continuous flow; lignin derived phenols; guaiacol |
Dates: |
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Institution: | The University of Leeds |
Academic Units: | The University of Leeds > Faculty of Engineering & Physical Sciences (Leeds) > School of Chemistry (Leeds) > Organic Chemistry (Leeds) |
Depositing User: | Symplectic Publications |
Date Deposited: | 15 Nov 2016 15:53 |
Last Modified: | 04 Nov 2017 02:41 |
Published Version: | https://doi.org/10.1021/acs.oprd.6b00314 |
Status: | Published |
Publisher: | American Chemical Society |
Identification Number: | 10.1021/acs.oprd.6b00314 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:107352 |