Campus Units

Chemistry, Ames Laboratory

Document Type

Article

Publication Version

Accepted Manuscript

Publication Date

3-20-2020

Journal or Book Title

Applied Catalysis B: Environmental

First Page

118890

DOI

10.1016/j.apcatb.2020.118890

Abstract

The conversion of guaiacol into the nylon precursors, cyclohexanol and cyclohexanone, is catalyzed by palladium supported on high surface area ceria (Pd/HS CeO2) under mild conditions (100 °C, ≤1 bar H2) via sequential hydrodemethoxylation and hydrogenation. In contrast, the 2-methoxycyclohexanol side product is generated by direct guaiacol hydrogenation. Reaction selectivity is determined by competing C-O bond hydrogenolysis versus arene hydrogenation. Hydrogenolysis selectivity increases as H2 pressure decreases, and over 80% H2 is incorporated into the products at 1 bar H2. Higher reactivity of guaiacol than anisole implies that the hydroxyl group is essential in Pd/HS CeO2 catalysis. Participation of water in the conversion is evidenced by deuterium incorporation at non-exchangeable positions when the reaction is performed in D2O. The combination of near quantitative mass balance of H2, high recyclability, and use of water as a solvent offers a simple, green and efficient conversion of lignin-derived aromatics into commercial products.

Comments

This is a manuscript of an article posted as Zhou, Hui, Hsin Wang, Aaron D. Sadow, and Igor I. Slowing. "Toward Hydrogen Economy: Selective Guaiacol Hydrogenolysis under Ambient Hydrogen Pressure." Applied Catalysis B: Environmental (2020): 118890. DOI: 10.1016/j.apcatb.2020.118890. Posted with permission.

Creative Commons License

Creative Commons Attribution-Noncommercial-No Derivative Works 4.0 License
This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 4.0 License.

Copyright Owner

Elsevier B.V.

Language

en

File Format

application/pdf

Available for download on Sunday, March 20, 2022

Published Version

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