Catalytic Hydrogenation of Alkylphenols for Renewable Caprolactone

Soeherman, Jimmy K.; Kim, Jaeheon; Onn, Tzia Ming; Reineke, Theresa; Dauenhauer, Paul J.

doi:10.1021/acssuschemeng.4c04610

Catalytic Hydrogenation of Alkylphenols for Renewable Caprolactone

Journal Article · Sat Aug 24 00:00:00 EDT 2024 · ACS Sustainable Chemistry & Engineering

DOI:https://doi.org/10.1021/acssuschemeng.4c04610· OSTI ID:2569386

^[1]; Kim, Jaeheon ^[1]; ^[2]; ^[1]; ^[1]

University of Minnesota, Minneapolis, MN (United States)
University of Cambridge (United Kingdom)

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. Furthermore, 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.

View Accepted Manuscript (DOE)

Research Organization:: University of Minnesota, Minneapolis, MN (United States)

Sponsoring Organization:: USDOE

Grant/Contract Number:: EE0009304

OSTI ID:: 2569386

Journal Information:: ACS Sustainable Chemistry & Engineering, Journal Name: ACS Sustainable Chemistry & Engineering Journal Issue: 36 Vol. 12; ISSN 2168-0485

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Related Subjects

36 MATERIALS SCIENCE
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Alkylphenol
Caprolactone
Catalyst
Cresol
Hydrogen
Hydrogenation
Lignin
Liquids
Palladium
Polymer
Selectivity

Catalytic Hydrogenation of Alkylphenols for Renewable Caprolactone

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