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

• DOI: 10.1021/acs.oprd.6b00314
• Publication Date: 2016-11-04T12:56:26Z
• Authors: Yuhan Zhao; Georgina King; Maria H.T. Kwan; A. John Blacker
• Keywords: Hydrodeoxygenation; Guaiacol; Anisole; Cyanuric chloride; Hydroxybenzoic acid

A low-energy, high-selectivity approach to the catalytic hydrodeoxygenation of phenols is reported using batch or continuous flow methods react 3 equiv phenol with cyanuric chloride then hydrogenolyzing triarylcyanurate intermediate give deoxo aromatic. The use compares favorably existing activation methods, showing improved scalability, atom efficiency, and economics. scope both hydrogenolysis stages are explored lignin-related phenols. Initial development has identified that stir tank reactors (CSTRs) enable a multiphasic process for converting guaiacol anisole at steady state overcome catalyst deactivation issues observed in batch, seemingly caused by cyanurate byproduct. Green chemistry aspects potential industrial adoption discussed.