Controlling Reaction Routes in Noble‐Metal‐Catalyzed Conversion of Aryl Ethers

Schmid, Julian; Wang, Meng; Gutiérrez, Oliver Y.; Bullock, R. Morris; Camaioni, Donald M.; Lercher, Johannes A.

doi:10.1002/anie.202203172

Title: Controlling Reaction Routes in Noble‐Metal‐Catalyzed Conversion of Aryl Ethers

Journal Article · 13 June 2022 · Angewandte Chemie (International Edition)

DOI: https://doi.org/10.1002/anie.202203172 · OSTI ID:1872488

Schmid, Julian ^[1]; Wang, Meng ^[1];

^[1]; Bullock, R. Morris ^[1]; Camaioni, Donald M. ^[1];

^[2]

Institute for Integrated Catalysis Pacific Northwest National Laboratory (PNNL) P.O. Box 999 Richland WA 99352 USA
Institute for Integrated Catalysis Pacific Northwest National Laboratory (PNNL) P.O. Box 999 Richland WA 99352 USA, Department of Chemistry and Catalysis Research Institute Technische Universität München Lichtenbergstrasse 4 85748 Garching Germany

Abstract Hydrogenolysis and hydrolysis of aryl ethers in the liquid phase are important reactions for accessing functionalized cyclic compounds from renewable feedstocks. On supported noble metals, hydrogenolysis is initiated by a hydrogen addition to the aromatic ring followed by C−O bond cleavage. In water, hydrolysis and hydrogenolysis proceed by partial hydrogenation of the aromatic ring prior to water or hydrogen insertion. The mechanisms are common for the studied metals, but the selectivity to hydrogenolysis increases in the order Pd2 pressure, thus, the selectivity to hydrogenolysis is maximized by increasing temperature and decreasing H ₂ pressure. Selectivity to C−O bond cleavage reaches >95 % in water and alkaline conditions.

View Journal Article

Cite

Export

Save

Research Organization:: Pacific Northwest National Laboratory (PNNL), Richland, WA (United States)

Sponsoring Organization:: USDOE; USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division

Grant/Contract Number:: AC05-76RL01830

OSTI ID:: 1872488

Report Number(s):: PNNL-SA-172526; e202203172

Journal Information:: Angewandte Chemie (International Edition), Journal Name: Angewandte Chemie (International Edition) Journal Issue: 30 Vol. 61; ISSN 1433-7851

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

References (28)

Catalytic Ethanolysis of Kraft Lignin into High‐Value Small‐Molecular Chemicals over a Nanostructured α‐Molybdenum Carbide Catalyst Ma, Rui; Hao, Wenyue; Ma, Xiaolei Angewandte Chemie, Vol. 126, Issue 28 https://doi.org/10.1002/ange.201402752	journal	June 2014
Palladium-Catalyzed Hydrolytic Cleavage of Aromatic C−O Bonds Wang, Meng; Shi, Hui; Camaioni, Donald M. Angewandte Chemie, Vol. 129, Issue 8 https://doi.org/10.1002/ange.201611076	journal	January 2017
Palladium-Catalyzed Reductive Insertion of Alcohols into Aryl Ether Bonds Wang, Meng; Gutiérrez, Oliver Y.; Camaioni, Donald M. Angewandte Chemie, Vol. 130, Issue 14 https://doi.org/10.1002/ange.201709445	journal	March 2018
The Critical Role of Reductive Steps in the Nickel‐Catalyzed Hydrogenolysis and Hydrolysis of Aryl Ether C−O Bonds Wang, Meng; Zhao, Yuntao; Mei, Donghai Angewandte Chemie, Vol. 132, Issue 4 https://doi.org/10.1002/ange.201909551	journal	December 2019
Catalytic Ethanolysis of Kraft Lignin into High-Value Small-Molecular Chemicals over a Nanostructured α-Molybdenum Carbide Catalyst Ma, Rui; Hao, Wenyue; Ma, Xiaolei Angewandte Chemie International Edition, Vol. 53, Issue 28 https://doi.org/10.1002/anie.201402752	journal	June 2014
Palladium-Catalyzed Hydrolytic Cleavage of Aromatic C−O Bonds Wang, Meng; Shi, Hui; Camaioni, Donald M. Angewandte Chemie International Edition, Vol. 56, Issue 8 https://doi.org/10.1002/anie.201611076	journal	January 2017
Palladium-Catalyzed Reductive Insertion of Alcohols into Aryl Ether Bonds Wang, Meng; Gutiérrez, Oliver Y.; Camaioni, Donald M. Angewandte Chemie International Edition, Vol. 57, Issue 14 https://doi.org/10.1002/anie.201709445	journal	March 2018
The Critical Role of Reductive Steps in the Nickel‐Catalyzed Hydrogenolysis and Hydrolysis of Aryl Ether C−O Bonds Wang, Meng; Zhao, Yuntao; Mei, Donghai Angewandte Chemie International Edition, Vol. 59, Issue 4 https://doi.org/10.1002/anie.201909551	journal	December 2019
Bifunctional Ni catalysts for the one-pot conversion of Organosolv lignin into cycloalkanes Wang, Xingyu; Rinaldi, Roberto Catalysis Today, Vol. 269 https://doi.org/10.1016/j.cattod.2015.11.047	journal	July 2016
From models to lignin: Transition metal catalysis for selective bond cleavage reactions Deuss, Peter J.; Barta, Katalin Coordination Chemistry Reviews, Vol. 306 https://doi.org/10.1016/j.ccr.2015.02.004	journal	January 2016
Mild Continuous Hydrogenolysis of Kraft Lignin over Titanium Nitride–Nickel Catalyst Molinari, Valerio; Clavel, Guylhaine; Graglia, Micaela ACS Catalysis, Vol. 6, Issue 3 https://doi.org/10.1021/acscatal.5b01926	journal	February 2016
Role of Cu–Mg–Al Mixed Oxide Catalysts in Lignin Depolymerization in Supercritical Ethanol Huang, Xiaoming; Atay, Ceylanpinar; Korányi, Tamás I. ACS Catalysis, Vol. 5, Issue 12 https://doi.org/10.1021/acscatal.5b02230	journal	November 2015
β-O-4 Bond Cleavage Mechanism for Lignin Model Compounds over Pd Catalysts Identified by Combination of First-Principles Calculations and Experiments Lu, Jianmin; Wang, Min; Zhang, Xiaochen ACS Catalysis, Vol. 6, Issue 8 https://doi.org/10.1021/acscatal.6b00502	journal	July 2016
Impact of pH on Aqueous-Phase Phenol Hydrogenation Catalyzed by Carbon-Supported Pt and Rh Singh, Nirala; Lee, Mal-Soon; Akhade, Sneha A. ACS Catalysis, Vol. 9, Issue 2 https://doi.org/10.1021/acscatal.8b04039	journal	December 2018
The Catalytic Valorization of Lignin for the Production of Renewable Chemicals Zakzeski, Joseph; Bruijnincx, Pieter C. A.; Jongerius, Anna L. Chemical Reviews, Vol. 110, Issue 6, p. 3552-3599 https://doi.org/10.1021/cr900354u	journal	June 2010
A Series of NiM (M = Ru, Rh, and Pd) Bimetallic Catalysts for Effective Lignin Hydrogenolysis in Water Zhang, Jiaguang; Teo, Jason; Chen, Xi ACS Catalysis, Vol. 4, Issue 5 https://doi.org/10.1021/cs401199f	journal	April 2014
Lignin Depolymerization into Aromatic Monomers over Solid Acid Catalysts Deepa, Ayillath K.; Dhepe, Paresh L. ACS Catalysis, Vol. 5, Issue 1 https://doi.org/10.1021/cs501371q	journal	November 2014
Catalytic Hydrogenolysis of Aryl Ethers: A Key Step in Lignin Valorization to Valuable Chemicals Zaheer, Muhammad; Kempe, Rhett ACS Catalysis, Vol. 5, Issue 3 https://doi.org/10.1021/cs501498f	journal	February 2015
Aqueous organic chemistry. 4. Cleavage of diaryl ethers Siskin, Michael; Katritzky, Alan R.; Balasubramanian, Marudai Energy & Fuels, Vol. 5, Issue 5 https://doi.org/10.1021/ef00029a028	journal	September 1991
Ni-Catalyzed Cleavage of Aryl Ethers in the Aqueous Phase He, Jiayue; Zhao, Chen; Lercher, Johannes A. Journal of the American Chemical Society, Vol. 134, Issue 51, p. 20768-20775 https://doi.org/10.1021/ja309915e	journal	December 2012
Aromatic Monomers by in Situ Conversion of Reactive Intermediates in the Acid-Catalyzed Depolymerization of Lignin Deuss, Peter J.; Scott, Martin; Tran, Fanny Journal of the American Chemical Society, Vol. 137, Issue 23 https://doi.org/10.1021/jacs.5b03693	journal	June 2015
Direct hydrodeoxygenation of raw woody biomass into liquid alkanes Xia, Qineng; Chen, Zongjia; Shao, Yi Nature Communications, Vol. 7, Issue 1 https://doi.org/10.1038/ncomms11162	journal	March 2016
Synthesis of ketones from biomass-derived feedstock Meng, Qinglei; Hou, Minqiang; Liu, Huizhen Nature Communications, Vol. 8, Issue 1 https://doi.org/10.1038/ncomms14190	journal	January 2017
Solvent-mediated charge separation drives alternative hydrogenation path of furanics in liquid water Zhao, Zheng; Bababrik, Reda; Xue, Wenhua Nature Catalysis, Vol. 2, Issue 5 https://doi.org/10.1038/s41929-019-0257-z	journal	April 2019
Critical role of solvent-modulated hydrogen-binding strength in the catalytic hydrogenation of benzaldehyde on palladium Cheng, Guanhua; Jentys, Andreas; Gutiérrez, Oliver Y. Nature Catalysis, Vol. 4, Issue 11 https://doi.org/10.1038/s41929-021-00701-2	journal	November 2021
Insights into the catalytic activity and surface modification of MoO ₃ during the hydrodeoxygenation of lignin-derived model compounds into aromatic hydrocarbons under low hydrogen pressures Prasomsri, Teerawit; Shetty, Manish; Murugappan, Karthick Energy Environ. Sci., Vol. 7, Issue 8 https://doi.org/10.1039/C4EE00890A	journal	January 2014
Hydrogen Effects in Metal Catalysts Paál, Z.; Menon, P. G. Catalysis Reviews, Vol. 25, Issue 2 https://doi.org/10.1080/01614948308079667	journal	June 1983
Heats of Chemisorption of O ₂ , H ₂ , CO, CO ₂ , and N ₂ on Polycrystalline and Single Crystal Transition Metal Surfaces Toyoshima, I.; Somorjai, G. A. Catalysis Reviews, Vol. 19, Issue 1 https://doi.org/10.1080/03602457908065102	journal	January 1979

Similar Records

Controlling Reaction Routes in Noble‐Metal‐Catalyzed Conversion of Aryl Ethers

Journal Article · 2022 · Angewandte Chemie · OSTI ID:1872472

Schmid, Julian; Wang, Meng; Gutiérrez, Oliver Y.; +3 more

The Critical Role of Reductive Steps in the Nickel‐Catalyzed Hydrogenolysis and Hydrolysis of Aryl Ether C−O Bonds

Journal Article · 2019 · Angewandte Chemie · OSTI ID:1579369

Wang, Meng; Zhao, Yuntao; Mei, Donghai; +4 more

The Critical Role of Reductive Steps in the Nickel‐Catalyzed Hydrogenolysis and Hydrolysis of Aryl Ether C−O Bonds

Journal Article · 2019 · Angewandte Chemie (International Edition) · OSTI ID:1605477

Wang, Meng; Zhao, Yuntao; Mei, Donghai; +4 more

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
C-O bond Cleavage
biomass conversion
hydrogen
noble-metal catalysts
solvent effects

Title: Controlling Reaction Routes in Noble‐Metal‐Catalyzed Conversion of Aryl Ethers

Citation Formats

References (28)

Similar Records

Related Subjects