Catalytic consequences of hydrogen addition events and solvent-adsorbate interactions during guaiacol-H2 reactions at the H2O-Ru(0 0 0 1) interface

Hensley, Alyssa J. R.; Bray, Jacob; Shangguan, Junnan; Chin, Ya-Huei (Cathy); McEwen, Jean-Sabin

doi:10.1016/j.jcat.2020.09.034

Title: Catalytic consequences of hydrogen addition events and solvent-adsorbate interactions during guaiacol-H₂ reactions at the H₂O-Ru(0 0 0 1) interface

Journal Article · Fri Oct 09 00:00:00 EDT 2020 · Journal of Catalysis

DOI:https://doi.org/10.1016/j.jcat.2020.09.034· OSTI ID:1768743

Hensley, Alyssa J. R. ^[1]; Bray, Jacob ^[2]; Shangguan, Junnan ^[3]; Chin, Ya-Huei (Cathy) ^[3];

^[4]

Univ. of Toronto, ON (Canada); Washington State Univ., Pullman, WA (United States)
Washington State Univ., Pullman, WA (United States)
Univ. of Toronto, ON (Canada)
Washington State Univ., Pullman, WA (United States); Pacific Northwest National Lab. (PNNL), Richland, WA (United States)

Catalytic reactions of biomass-derived phenolics and H₂ occur on transition metal surfaces via competitive C–O cleavage and ring saturation pathways, with both requiring multiple hydrogen addition events before forming their respective rate limiting transition states. These events are markedly affected by solvent chemical identity, with polar protic solvents ionizing hydrogen adatoms (H*) to interfacial protons (H⁺) and opening up new catalytic routes. Here, we establish the reaction coordinate space for guaiacol-H₂ reactions on Ru(0 0 0 1) using density functional theory and describe the atomic-scale effect of a polar protic solvent, H₂O. Coupled H⁺ and H* attack leads to quasi-equilibrated enol and keto intermediates as the precursors for C–O cleavage and ring saturation, respectively. For C–O cleavage, H₂O solvent enables a lower energy pathway via concomitant transfer of the hydroxyl H⁺ to the methoxy oxygen during C–OCH₃ cleavage, forming a charge separated [Ru(s)–(C₆H₅O^–)…(H⁺)…OCH₃] transition state and reducing the barrier by up to 0.8 eV as compared to unassisted C–OCH₃ cleavage. For ring saturation, H* attack onto an unsaturated meta carbon is rate limiting with no direct solvent participation, suggesting that protic polar solvents selectively promote the C–O cleavage pathway. Taken together, we show that activating guaiacol for either C–O bond cleavage or ring saturation product formation depends on the reactive hydrogen identity (H* or H⁺), enol/keto isomerization equilibrium, and accessibility of the proton assisted Car–OCH₃ cleavage transition state. Here, all such factors are tunable via changes to the solvent or metal identity.

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Research Organization:: Washington State Univ., Pullman, WA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Biological and Environmental Research (BER); USDOE Office of Science (SC), Basic Energy Sciences (BES)

Contributing Organization:: University of Toronto

Grant/Contract Number:: SC0014560

OSTI ID:: 1768743

Alternate ID(s):: OSTI ID: 1775868

Journal Information:: Journal of Catalysis, Vol. 395; ISSN 0021-9517

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

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