Catalytic Hydrogenation of Alkylphenols for Renewable Caprolactone
Selective hydrogenation of lignin-derived alkyl-phenol to alkyl-cyclohexanone is a key step in the synthesis of renewable caprolactone from lignin-derived monomers. Selective hydrogenation of p-cresol, a model compound for lignin-derived monomers, to 4-methyl-cyclohexanone was conducted using Pd/γ-A...
Gespeichert in:
Veröffentlicht in: | ACS sustainable chemistry & engineering 2024-09, Vol.12 (36), p.13598-13608 |
---|---|
Hauptverfasser: | , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
Zusammenfassung: | Selective hydrogenation of lignin-derived alkyl-phenol to alkyl-cyclohexanone is a key step in the synthesis of renewable caprolactone from lignin-derived monomers. Selective hydrogenation of p-cresol, a model compound for lignin-derived monomers, to 4-methyl-cyclohexanone was conducted using Pd/γ-Al2O3 in a continuous three-phase flow reactor with side products of 4-methyl cyclohexanol. High conversion (85%) and selectivity (>93%) were demonstrated at ambient reaction pressure. Evaluation of the hydrogenation at different reaction parameters showed that the reaction selectivity was determined by the surface coverage of p-cresol and 4-methyl cyclohexanone. High selectivity to 4-methyl cyclohexanone was also attributed to the lower apparent activation barrier of p-cresol hydrogenation (67 ± 2 kJ mol–1) compared to that of hydrogenation 4-methyl cyclohexanone (92 ± 11 kJ mol–1), with a faster rate of initial hydrogenation of p-cresol relative to carbonyl hydrogenation of 4-methyl-cyclohexanone. |
---|---|
ISSN: | 2168-0485 2168-0485 |
DOI: | 10.1021/acssuschemeng.4c04610 |