Mechanocatalytic Hydrogenolysis of the Lignin Model Dimer Benzyl Phenyl Ether over Supported Palladium Catalysts

Phillips, Erin V.; Tricker, Andrew W.; Stavitski, Eli; Hatzell, Marta; Sievers, Carsten

doi:10.1021/acssuschemeng.4c03590

Mechanocatalytic Hydrogenolysis of the Lignin Model Dimer Benzyl Phenyl Ether over Supported Palladium Catalysts

Journal Article · Mon Aug 05 00:00:00 EDT 2024 · ACS Sustainable Chemistry & Engineering

DOI:https://doi.org/10.1021/acssuschemeng.4c03590· OSTI ID:2440574

Phillips, Erin V. ^[1]; ^[2]; ^[3]; ^[1]; ^[1]

Georgia Institute of Technology, Atlanta, GA (United States)
Independent Researcher, Washington, DC (United States)
Brookhaven National Laboratory (BNL), Upton, NY (United States). National Synchrotron Light Source II (NSLS-II)

This work demonstrates the mechanocatalytic hydrogenolysis of the ether bond in the lignin model compound benzyl phenyl ether (BPE) and hardwood lignin isolated by hydrolysis with supercritical water. Pd catalysts with 4 wt % loading on Al₂O₃ and SiO₂ supports achieve 100% conversion of BPE with a toluene production rate of (2.6–2.9) × 10^–5 mol·min^–1. The formation of palladium hydrides under H₂ gas flow contributes to an increase in the turnover frequency by a factor of up to 300 compared to Ni on silica–alumina. While a near-quantitative toluene yield is obtained, some of the phenolic products remain adsorbed on the catalyst.

View Accepted Manuscript (DOE)

Research Organization:: Brookhaven National Laboratory (BNL), Upton, NY (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); National Science Foundation (NSF)

Grant/Contract Number:: SC0012704

OSTI ID:: 2440574

Report Number(s):: BNL--226018-2024-JAAM

Journal Information:: ACS Sustainable Chemistry & Engineering, Journal Name: ACS Sustainable Chemistry & Engineering Journal Issue: 33 Vol. 12; ISSN 2168-0485

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

References (55)

An Orders-of-Magnitude Increase in the Rate of the Solid-Catalyzed CO Oxidation by In Situ Ball Milling Immohr, Sarah; Felderhoff, Michael; Weidenthaler, Claudia Angewandte Chemie International Edition, Vol. 52, Issue 48 https://doi.org/10.1002/anie.201305992	journal	September 2013
Paving the Way for Lignin Valorisation: Recent Advances in Bioengineering, Biorefining and Catalysis Rinaldi, Roberto; Jastrzebski, Robin; Clough, Matthew T. Angewandte Chemie International Edition, Vol. 55, Issue 29 https://doi.org/10.1002/anie.201510351	journal	June 2016
Understanding the Mechanocatalytic Conversion of Biomass: A Low‐Energy One‐Step Reaction Mechanism by Applying Mechanical Force Amirjalayer, Saeed; Fuchs, Harald; Marx, Dominik Angewandte Chemie International Edition, Vol. 58, Issue 16 https://doi.org/10.1002/anie.201811091	journal	April 2019
Mechanocatalytic Room‐Temperature Synthesis of Ammonia from Its Elements Down to Atmospheric Pressure Reichle, Steffen; Felderhoff, Michael; Schüth, Ferdi Angewandte Chemie International Edition, Vol. 60, Issue 50 https://doi.org/10.1002/anie.202112095	journal	November 2021
New Role of Pd Hydride as a Sensor of Surface Pd Distributions in Pd−Au Catalysts Guan, Erjia; Foucher, Alexandre C.; Marcella, Nicholas ChemCatChem, Vol. 12, Issue 3 https://doi.org/10.1002/cctc.201901847	journal	December 2019
Mechanocatalytic Deconstruction of Cellulose: An Emerging Entry into Biorefinery Zhang, Qinghua; Jérôme, François ChemSusChem, Vol. 6, Issue 11 https://doi.org/10.1002/cssc.201300765	journal	October 2013
A Dry Platform for Separation of Proteins from Biomass‐Containing Polysaccharides, Lignin, and Polyphenols Barakat, Abdellatif; Jérôme, François; Rouau, Xavier ChemSusChem, Vol. 8, Issue 7 https://doi.org/10.1002/cssc.201403473	journal	March 2015
Mild and Robust Redox-Neutral Pd/C-Catalyzed Lignol β-O-4′ Bond Cleavage Through a Low-Energy-Barrier Pathway Galkin, Maxim V.; Dahlstrand, Christian; Samec, Joseph S. M. ChemSusChem, Vol. 8, Issue 13 https://doi.org/10.1002/cssc.201500117	journal	April 2015
An Introduction to Model Compounds of Lignin Linking Motifs; Synthesis and Selection Considerations for Reactivity Studies Lahive, Ciaran W.; Kamer, Paul C. J.; Lancefield, Christopher S. ChemSusChem, Vol. 13, Issue 17 https://doi.org/10.1002/cssc.202000989	journal	July 2020
Recent Advances in the Catalytic Depolymerization of Lignin towards Phenolic Chemicals: A Review Liu, Xudong; Bouxin, Florent P.; Fan, Jiajun ChemSusChem, Vol. 13, Issue 17 https://doi.org/10.1002/cssc.202001213	journal	August 2020
Similarities in Recalcitrant Structures of Industrial Non‐Kraft and Kraft Lignin Tricker, Andrew W.; Stellato, Michael J.; Kwok, Thomas T. ChemSusChem, Vol. 13, Issue 17 https://doi.org/10.1002/cssc.202001219	journal	July 2020
Advances in Versatile Nanoscale Catalyst for the Reductive Catalytic Fractionation of Lignin Zhang, Haichuan; Fu, Shiyu; Du, Xu ChemSusChem, Vol. 14, Issue 11 https://doi.org/10.1002/cssc.202100067	journal	April 2021
Formation of palladium hydride nanoparticles in Pd/C catalyst as evidenced by in situ XAS data Stakheev, A. Yu.; Mashkovskii, I. C.; Tkachenko, O. P. Russian Chemical Bulletin, Vol. 58, Issue 2 https://doi.org/10.1007/s11172-010-0002-x	journal	February 2009
Lignin Pyrolysis Components and Upgrading—Technology Review Mu, Wei; Ben, Haoxi; Ragauskas, Art BioEnergy Research, Vol. 6, Issue 4, p. 1183-1204 https://doi.org/10.1007/s12155-013-9314-7	journal	February 2013
Mechanochemical Forces as a Synthetic Tool for Zero- and One-Dimensional Titanium Oxide-Based Nano-photocatalysts Giannakoudakis, Dimitrios A.; Chatel, Gregory; Colmenares, Juan Carlos Topics in Current Chemistry, Vol. 378, Issue 1 https://doi.org/10.1007/s41061-019-0262-3	journal	November 2019
Selective cleavage of C O bond in benzyl phenyl ether to aromatics over Pd–Fe bimetallic catalyst supported on ordered mesoporous carbon Kim, Jeong Kwon; Lee, Jong Kwon; Kang, Ki Hyuk Applied Catalysis A: General, Vol. 498 https://doi.org/10.1016/j.apcata.2015.03.034	journal	June 2015
From lignin to valuable products–strategies, challenges, and prospects Wang, Hongliang; Pu, Yunqiao; Ragauskas, Arthur Bioresource Technology, Vol. 271 https://doi.org/10.1016/j.biortech.2018.09.072	journal	January 2019
IR study of the interaction of phenol with oxides and sulfided CoMo catalysts for bio-fuel hydrodeoxygenation Popov, Andrey; Kondratieva, Elena; Gilson, Jean-Pierre Catalysis Today, Vol. 172, Issue 1 https://doi.org/10.1016/j.cattod.2011.02.010	journal	August 2011
Mechanocatalytic depolymerization of cellulose and raw biomass and downstream processing of the products Schüth, F.; Rinaldi, R.; Meine, N. Catalysis Today, Vol. 234 https://doi.org/10.1016/j.cattod.2014.02.019	journal	October 2014
In situ formation of hydrides and carbides in palladium catalyst: When XANES is better than EXAFS and XRD Bugaev, Aram L.; Guda, Alexander A.; Lazzarini, Andrea Catalysis Today, Vol. 283 https://doi.org/10.1016/j.cattod.2016.02.065	journal	April 2017
A review on thermal chemical reactions of lignin model compounds Yang, Le; Seshan, K.; Li, Yongdan Catalysis Today, Vol. 298 https://doi.org/10.1016/j.cattod.2016.11.030	journal	December 2017
Transfer hydrogenolysis of aromatic ethers promoted by the bimetallic Pd/Co catalyst Mauriello, F.; Ariga-Miwa, H.; Paone, E. Catalysis Today, Vol. 357 https://doi.org/10.1016/j.cattod.2019.06.071	journal	November 2020
Hot spot generation, reactivity, and decay in mechanochemical reactors Tricker, Andrew W.; Samaras, George; Hebisch, Karoline L. Chemical Engineering Journal, Vol. 382 https://doi.org/10.1016/j.cej.2019.122954	journal	February 2020
Surface modification of silica powder by mild ball milling Nakashima, Yuki; Fukushima, Manabu; Hyuga, Hideki Colloids and Surfaces A: Physicochemical and Engineering Aspects, Vol. 652 https://doi.org/10.1016/j.colsurfa.2022.129828	journal	November 2022
Lignin utilization: A review of lignin depolymerization from various aspects Chio, Chonlong; Sain, Mohini; Qin, Wensheng Renewable and Sustainable Energy Reviews, Vol. 107 https://doi.org/10.1016/j.rser.2019.03.008	journal	June 2019
Catalytic Transformation of Lignin for the Production of Chemicals and Fuels Li, Changzhi; Zhao, Xiaochen; Wang, Aiqin Chemical Reviews, Vol. 115, Issue 21, p. 11559-11624 https://doi.org/10.1021/acs.chemrev.5b00155	journal	October 2015
Depolymerization of Lignin over a Ni–Pd Bimetallic Catalyst Using Isopropanol as an in Situ Hydrogen Source Jiang, Bingxing; Hu, Jun; Qiao, Yiheng Energy & Fuels, Vol. 33, Issue 9 https://doi.org/10.1021/acs.energyfuels.9b01976	journal	July 2019
Mechanocatalytic Depolymerization of Lignocellulose Performed on Hectogram and Kilogram Scales Kaufman Rechulski, Marcelo D.; Käldström, Mats; Richter, Udo Industrial & Engineering Chemistry Research, Vol. 54, Issue 16 https://doi.org/10.1021/acs.iecr.5b00224	journal	January 2015
Steric Effect and Evolution of Surface Species in the Hydrodeoxygenation of Bio-Oil Model Compounds over Pt/HBEA Foo, Guo Shiou; Rogers, Allyson K.; Yung, Matthew M. ACS Catalysis, Vol. 6, Issue 2 https://doi.org/10.1021/acscatal.5b02684	journal	January 2016
Mechanochemical Oxidation and Cleavage of Lignin β-O-4 Model Compounds and Lignin Dabral, Saumya; Wotruba, Hermann; Hernández, José G. ACS Sustainable Chemistry & Engineering, Vol. 6, Issue 3 https://doi.org/10.1021/acssuschemeng.7b03418	journal	January 2018
Powered by DFT: Screening Methods That Accelerate Materials Development for Hydrogen in Metals Applications Nicholson, Kelly M.; Chandrasekhar, Nita; Sholl, David S. Accounts of Chemical Research, Vol. 47, Issue 11 https://doi.org/10.1021/ar500018b	journal	June 2014
Mechanocatalytic Depolymerization of Dry (Ligno)cellulose As an Entry Process for High-Yield Production of Furfurals Carrasquillo-Flores, Ronald; Käldström, Mats; Schüth, Ferdi ACS Catalysis, Vol. 3, Issue 5 https://doi.org/10.1021/cs4001333	journal	April 2013
Titanium-Based Hydrides as Heterogeneous Catalysts for Ammonia Synthesis Kobayashi, Yoji; Tang, Ya; Kageyama, Toki Journal of the American Chemical Society, Vol. 139, Issue 50 https://doi.org/10.1021/jacs.7b08891	journal	December 2017
Theoretical Study of the Reactions of 2-Chlorophenol over the Dehydrated and Hydroxylated Silica Clusters Pan, Wenxiao; Zhong, Wenhui; Zhang, Dongju The Journal of Physical Chemistry A, Vol. 116, Issue 1 https://doi.org/10.1021/jp208571d	journal	December 2011
Mechanocatalytic depolymerization of cellulose combined with hydrogenolysis as a highly efficient pathway to sugar alcohols Hilgert, Jakob; Meine, Niklas; Rinaldi, Roberto Energy Environ. Sci., Vol. 6, Issue 1 https://doi.org/10.1039/C2EE23057G	journal	January 2013
Mechanochemical degradation of lignin and wood by solvent-free grinding in a reactive medium Kleine, Tillmann; Buendia, Julien; Bolm, Carsten Green Chem., Vol. 15, Issue 1 https://doi.org/10.1039/C2GC36456E	journal	January 2013
Deciphering ‘water-soluble lignocellulose’ obtained by mechanocatalysis: new insights into the chemical processes leading to deep depolymerization Käldström, Mats; Meine, Niklas; Farès, Christophe Green Chem., Vol. 16, Issue 7 https://doi.org/10.1039/C4GC00004H	journal	January 2014
Warming up for mechanosynthesis – temperature development in ball mills during synthesis Kulla, Hannes; Wilke, Manuel; Fischer, Franziska Chemical Communications, Vol. 53, Issue 10 https://doi.org/10.1039/C6CC08950J	journal	January 2017
Quantitative determination of activation energies in mechanochemical reactions Fischer, Franziska; Wenzel, Klaus-Jürgen; Rademann, Klaus Physical Chemistry Chemical Physics, Vol. 18, Issue 33 https://doi.org/10.1039/C6CP04280E	journal	January 2016
Biphasic extraction of mechanocatalytically-depolymerized lignin from water-soluble wood and its catalytic downstream processing Calvaruso, Gaetano; Clough, Matthew T.; Rinaldi, Roberto Green Chemistry, Vol. 19, Issue 12 https://doi.org/10.1039/C6GC03191A	journal	January 2017
Chemicals from lignin: an interplay of lignocellulose fractionation, depolymerisation, and upgrading Schutyser, W.; Renders, T.; Van den Bosch, S. Chemical Society Reviews, Vol. 47, Issue 3 https://doi.org/10.1039/C7CS00566K	journal	January 2018
Mechanochemistry as an emerging tool for molecular synthesis: what can it offer? Howard, Joseph L.; Cao, Qun; Browne, Duncan L. Chemical Science, Vol. 9, Issue 12 https://doi.org/10.1039/C7SC05371A	journal	January 2018
An in situ XAS study of the activation of precursor-dependent Pd nanoparticles Lopes, Christian W.; Cerrillo, Jose L.; Palomares, Antonio E. Physical Chemistry Chemical Physics, Vol. 20, Issue 18 https://doi.org/10.1039/C8CP00517F	journal	January 2018
Reductive catalytic fractionation of lignocellulose: when should the catalyst meet depolymerized lignin fragments? Qiu, Shi; Wang, Meng; Fang, Yunming Sustainable Energy & Fuels, Vol. 4, Issue 11 https://doi.org/10.1039/D0SE01118E	journal	January 2020
Mechanocatalytic hydrogenolysis of benzyl phenyl ether over supported nickel catalysts Tricker, Andrew W.; Najmi, Sean; Phillips, Erin V. RSC Sustainability, Vol. 1, Issue 2 https://doi.org/10.1039/D2SU00089J	journal	January 2023
The irreversible formation of palladium carbide during hydrogenation of 1-pentyne over silica-supported palladium nanoparticles: in situ Pd K and L3 edge XAS Tew, Min Wei; Nachtegaal, Maarten; Janousch, Markus Physical Chemistry Chemical Physics, Vol. 14, Issue 16 https://doi.org/10.1039/c2cp24068h	journal	January 2012
The historical development of mechanochemistry Takacs, Laszlo Chemical Society Reviews, Vol. 42, Issue 18 https://doi.org/10.1039/c2cs35442j	journal	January 2013
Synthesis and properties of platinum hydride Scheler, Thomas; Degtyareva, Olga; Marqués, Miriam Physical Review B, Vol. 83, Issue 21 https://doi.org/10.1103/PhysRevB.83.214106	journal	June 2011
The Inner Shell Spectroscopy beamline at NSLS-II: a facility for in situ and operando X-ray absorption spectroscopy for materials research Leshchev, Denis; Rakitin, Maksim; Luvizotto, Bruno Journal of Synchrotron Radiation, Vol. 29, Issue 4 https://doi.org/10.1107/S160057752200460X	journal	May 2022
Prediction of Hydrogen Flux Through Sulfur-Tolerant Binary Alloy Membranes Kamakoti, P. Science, Vol. 307, Issue 5709 https://doi.org/10.1126/science.1107041	journal	January 2005
Catalytic hydrogenolysis of ethanol organosolv lignin Nagy, Máté; David, Kasi; Britovsek, George J. P. Holzforschung, Vol. 63, Issue 5 https://doi.org/10.1515/HF.2009.097	journal	September 2009
Mechanocatalytic Depolymerization of Cellulose With Perfluorinated Sulfonic Acid Ionomers Karam, Ayman; Amaniampong, Prince N.; García Fernández, José M. Frontiers in Chemistry, Vol. 6 https://doi.org/10.3389/fchem.2018.00074	journal	March 2018
Pore Blocking by Phenolates as Deactivation Path during the Cracking of 4-Propylphenol over ZSM-5 Stellato, Michael J.; Innocenti, Giada; Bommarius, Andreas S. Catalysts, Vol. 11, Issue 6 https://doi.org/10.3390/catal11060721	journal	June 2021
Catalytic Oxidation of Lignin in Solvent Systems for Production of Renewable Chemicals: A Review Cheng, Chongbo; Wang, Jinzhi; Shen, Dekui Polymers, Vol. 9, Issue 12 https://doi.org/10.3390/polym9060240	journal	June 2017
Selective enzymatic esterification of lignin model compounds in the ball mill Weißbach, Ulla; Dabral, Saumya; Konnert, Laure Beilstein Journal of Organic Chemistry, Vol. 13 https://doi.org/10.3762/bjoc.13.173	journal	August 2017

Similar Records

Influence of supercritical fluid solvent density on benzyl phenyl ether pyrolysis: Indications of diffusional limitations

Journal Article · · Energy and Fuels; (United States) · OSTI ID:5089455

Mechanisms of catalytic cleavage of benzyl phenyl ether in aqueous and apolar phases

Journal Article · Fri Feb 28 23:00:00 EST 2014 · Journal of Catalysis · OSTI ID:1118103

Pyrolysis of silica-immobilized benzyl phenyl ether: Competing radical rearrangement pathways under restricted diffusion

Journal Article · Thu Dec 24 23:00:00 EST 1998 · Journal of Organic Chemistry · OSTI ID:318836

Related Subjects

36 MATERIALS SCIENCE
ball mill
biomass conversion
depolymerization
heterogeneous catalysis
lignin model compounds
mechanochemistry

Mechanocatalytic Hydrogenolysis of the Lignin Model Dimer Benzyl Phenyl Ether over Supported Palladium Catalysts

Citation Formats

References (55)

Similar Records

Related Subjects