A Mild and Selective Method for the Catalytic Hydrodeoxygenation of Cyanurate Activated Phenols in Multiphasic Continuous Flow

A low-energy, high-selectivity approach to the catalytic hydrodeoxygenation of phenols is reported using batch or continuous flow methods to react 3 equiv of phenol with cyanuric chloride then hydrogenolyzing the triarylcyanurate intermediate to give 3 equiv of deoxo aromatic. The use of cyanuric ch...

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Bibliographic Details
Published inOrganic process research & development Vol. 20; no. 11; pp. 2012 - 2018
Main Authors Zhao, Yuhan, King, Georgina, Kwan, Maria H.T, Blacker, A. John
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.11.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Applied
Chemistry, Organic
Physical Sciences
Science & Technology
HYDROXYL-GROUPS
HYDROGENOLYSIS
CONVERSION
BIO-OIL
GUAIACOL
DEOXYGENATION
REACTION NETWORK
LIGNIN MODEL COMPOUNDS
ARYL ETHERS
METAL-ASSISTED REACTIONS
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Summary:A low-energy, high-selectivity approach to the catalytic hydrodeoxygenation of phenols is reported using batch or continuous flow methods to react 3 equiv of phenol with cyanuric chloride then hydrogenolyzing the triarylcyanurate intermediate to give 3 equiv of deoxo 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 multiphasic process for converting guaiacol to anisole and at steady state overcome the catalyst deactivation issues observed in batch, seemingly caused by the cyanurate byproduct. Green chemistry aspects and the potential for industrial adoption are discussed.
Bibliography:researchfish
ISSN:1083-6160
1520-586X
DOI:10.1021/acs.oprd.6b00314