Role of peracetic acid on the disruption of lignin packing structure and its consequence on lignin depolymerisation

Ma, Ruoshui; Sanyal, Udishnu; Olarte, Mariefel V.; Job, Heather M.; Swita, Marie S.; Jones, Susanne B.; Meyer, Pimphan A.; Burton, Sarah D.; Cort, John R.; Bowden, Mark E.; Chen, Xiaowen; Wolcott, Michael P.; Zhang, Xiao

doi:10.1039/d1gc02300d

Title: Role of peracetic acid on the disruption of lignin packing structure and its consequence on lignin depolymerisation

Journal Article · 02 September 2021 · Green Chemistry

DOI: https://doi.org/10.1039/d1gc02300d · OSTI ID:1909372

Ma, Ruoshui ^[1]; Sanyal, Udishnu ^[2];

^[3]; Job, Heather M. ^[1]; Swita, Marie S. ^[1]; Jones, Susanne B. ^[1];

^[1]; Burton, Sarah D. ^[1];

^[3];

^[1]; Chen, Xiaowen ^[4];

^[5];

^[2]

Pacific Northwest National Lab. (PNNL), Richland, WA (United States)
Pacific Northwest National Lab. (PNNL), Richland, WA (United States); Washington State Univ., Richland, WA (United States)
Pacific Northwest National Lab. (PNNL), Richland, WA (United States); Washington State Univ., Pullman, WA (United States)
National Renewable Energy Lab. (NREL), Golden, CO (United States)
Washington State Univ., Pullman, WA (United States)

Peracetic acid (PAA) is an effective oxidant capable of solubilising lignin and efficiently depolymerising it to selective phenolic compounds; however, the specific role by which PAA initiates the depolymerisation is still elusive. Herein, interaction between PAA and the lignin macromolecule and the consequent structural changes of the latter were studied by characterising the lignin packing structure and its associated changes during the oxidation process. While the lignin packing structure and its changes associated with the PAA-mediated oxidation were probed by X-ray diffraction, the impact of the PAA on different chemical functionalities present in the lignin structure was established by ¹³C and ¹H–¹³C heteronuclear single-quantum coherence nuclear magnetic resonance (NMR) spectroscopy. Further, combining the NMR spectroscopy results, and the product distribution, we conclude that the predominant reaction pathway for the oxidative depolymerisation of lignin with PAA is the Baeyer–Villiger oxidation of the ketone formed by the oxidation of the benzylic hydroxyl group adjacent to the β-O-4 linkage. The experimental evidence provided herein corroborated that PAA instigates oxygen insertion to the lignin macromolecule resulting in disruption of its packing structures and facilitates depolymerisation. We also investigated various metal oxide and mixed metal oxide catalysts to identify effective catalysts that further enhance the efficiency of PAA-mediated depolymerisation of lignin and produce selective monomeric phenolic compounds. Techno-economic analysis was also conducted to identify the key parameters associated with this oxidative process that need to be considered for possible commercial application.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Pacific Northwest National Laboratory (PNNL), Richland, WA (United States). Environmental Molecular Sciences Laboratory (EMSL)

Sponsoring Organization:: National Science Foundation (NSF); US Federal Aviation Administration (FAA), Office of Environment and Energy; USDOE; USDOE Office of Science (SC), Biological and Environmental Research (BER)

Grant/Contract Number:: AC05-76RL01830; AC06-76RL01830

OSTI ID:: 1909372

Report Number(s):: PNNL-SA-159270

Journal Information:: Green Chemistry, Journal Name: Green Chemistry Journal Issue: 21 Vol. 23; ISSN 1463-9262

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

References (54)

Non-Oxidative Vanadium-Catalyzed C-O Bond Cleavage: Application to Degradation of Lignin Model Compounds Son, Sunghee; Toste, F. Dean Angewandte Chemie International Edition, Vol. 49, Issue 22, p. 3791-3794 https://doi.org/10.1002/anie.201001293	journal	April 2010
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
Oxidized Lignin Depolymerization using Formate Ionic Liquid as Catalyst and Solvent Dai, Jinhuo; Patti, Antonio F.; Longé, Lionel ChemCatChem, Vol. 9, Issue 14 https://doi.org/10.1002/cctc.201700632	journal	July 2017
Peracetic Acid Depolymerization of Biorefinery Lignin for Production of Selective Monomeric Phenolic Compounds Ma, Ruoshui; Guo, Mond; Lin, Kuan-ting Chemistry - A European Journal, Vol. 22, Issue 31 https://doi.org/10.1002/chem.201600546	journal	July 2016
Activation of Molecular Oxygen Using Durable Cobalt Encapsulated with Nitrogen‐Doped Graphitic Carbon Shells for Aerobic Oxidation of Lignin‐Derived Alcohols Sun, Yuxia; Ma, Hong; Luo, Yang Chemistry – A European Journal, Vol. 24, Issue 18 https://doi.org/10.1002/chem.201705824	journal	February 2018
Selective Conversion of Biorefinery Lignin into Dicarboxylic Acids Ma, Ruoshui; Guo, Mond; Zhang, Xiao ChemSusChem, Vol. 7, Issue 2 https://doi.org/10.1002/cssc.201300964	journal	January 2014
Catalytic Oxidation of Biorefinery Lignin to Value-added Chemicals to Support Sustainable Biofuel Production Ma, Ruoshui; Xu, Yan; Zhang, Xiao ChemSusChem, Vol. 8, Issue 1 https://doi.org/10.1002/cssc.201402503	journal	October 2014
Organocatalytic Chemoselective Primary Alcohol Oxidation and Subsequent Cleavage of Lignin Model Compounds and Lignin Dabral, Saumya; Hernández, José G.; Kamer, Paul C. J. ChemSusChem, Vol. 10, Issue 13 https://doi.org/10.1002/cssc.201700703	journal	June 2017
New Insights Toward Quantitative Relationships between Lignin Reactivity to Monomers and Their Structural Characteristics Ma, Ruoshui; Zhang, Xiumei; Wang, Yi ChemSusChem, Vol. 11, Issue 13 https://doi.org/10.1002/cssc.201800550	journal	June 2018
Determination of Carbonyl Groups Chen, C. -L. Methods in Lignin Chemistry https://doi.org/10.1007/978-3-642-74065-7_30	book	January 1992
Chemistry of delignification: Part 2: Reactions of lignins during bleaching Gierer, J. Wood Science and Technology, Vol. 20, Issue 1 https://doi.org/10.1007/BF00350692	journal	January 1986
Lignin chemistry?past, present and future Adler, Erich Wood Science and Technology, Vol. 11, Issue 3 https://doi.org/10.1007/BF00365615	journal	January 1977
Chemical aspects of kraft pulping Gierer, J. Wood Science and Technology, Vol. 14, Issue 4 https://doi.org/10.1007/BF00383453	journal	January 1980
Erythro/threo ratio ofβ-O-4 structures as an important structural characteristic of lignin. I: Improvement of ozonation method for the quantitative analysis of lignin side-chain structure Akiyama, Takuya; Sugimoto, Tomoko; Matsumoto, Yuji Journal of Wood Science, Vol. 48, Issue 3 https://doi.org/10.1007/BF00771369	journal	June 2002
Review on Catalytic Cleavage of C–C Inter-unit Linkages in Lignin Model Compounds: Towards Lignin Depolymerisation Guadix-Montero, Susana; Sankar, Meenakshisundaram Topics in Catalysis, Vol. 61, Issue 3-4 https://doi.org/10.1007/s11244-018-0909-2	journal	March 2018
Routes to Potential Bioproducts from Lignocellulosic Biomass Lignin and Hemicelluloses Zhang, Xiao; Tu, Maobing; Paice, Michael G. BioEnergy Research, Vol. 4, Issue 4 https://doi.org/10.1007/s12155-011-9147-1	journal	August 2011
Perspective on Lignin Oxidation: Advances, Challenges, and Future Directions Vangeel, Thijs; Schutyser, Wouter; Renders, Tom Topics in Current Chemistry, Vol. 376, Issue 4 https://doi.org/10.1007/s41061-018-0207-2	journal	July 2018
Oxidation of veratryl alcohol by molecular oxygen in aqueous solution catalyzed by cobalt salen-type complexes: the effect of reaction conditions Kervinen, Kaisa; Korpi, Heikki; Leskelä, Markku Journal of Molecular Catalysis A: Chemical, Vol. 203, Issue 1-2 https://doi.org/10.1016/S1381-1169(03)00156-0	journal	September 2003
Rapid Folin–Ciocalteu method using microtiter 96-well plate cartridges for solid phase extraction to assess urinary total phenolic compounds, as a biomarker of total polyphenols intake Medina-Remón, Alexander; Barrionuevo-González, Ana; Zamora-Ros, Raúl Analytica Chimica Acta, Vol. 634, Issue 1 https://doi.org/10.1016/j.aca.2008.12.012	journal	February 2009
Catalytic oxidation of aromatic oxygenates by the heterogeneous catalyst Co-ZIF-9 Zakzeski, Joseph; Dębczak, Agnieszka; Bruijnincx, Pieter C. A. Applied Catalysis A: General, Vol. 394, Issue 1-2 https://doi.org/10.1016/j.apcata.2010.12.026	journal	February 2011
Recent advances in oxidative valorization of lignin Ma, Ruoshui; Guo, Mond; Zhang, Xiao Catalysis Today, Vol. 302 https://doi.org/10.1016/j.cattod.2017.05.101	journal	March 2018
Catalytic oxidation of lignin to valuable biomass-based platform chemicals: A review Liu, Chao; Wu, Shiliang; Zhang, Huiyan Fuel Processing Technology, Vol. 191 https://doi.org/10.1016/j.fuproc.2019.04.007	journal	August 2019
Characterization of milled wood lignin and ethanol organosolv lignin from miscanthus El Hage, Roland; Brosse, Nicolas; Chrusciel, Laurent Polymer Degradation and Stability, Vol. 94, Issue 10 https://doi.org/10.1016/j.polymdegradstab.2009.07.007	journal	October 2009
Thermodynamic properties of an emerging chemical disinfectant, peracetic acid Zhang, Chiqian; Brown, Pamela J. B.; Hu, Zhiqiang Science of The Total Environment, Vol. 621 https://doi.org/10.1016/j.scitotenv.2017.10.195	journal	April 2018
Rapid Disinfection by Peracetic Acid Combined with UV Irradiation Sun, Peizhe; Zhang, Tianqi; Mejia-Tickner, Benjamin Environmental Science & Technology Letters, Vol. 5, Issue 6 https://doi.org/10.1021/acs.estlett.8b00249	journal	May 2018
Electrochemical Oxidation of Lignin and Waste Plastic Weber, Robert S.; Ramasamy, Karthikeyan K. ACS Omega, Vol. 5, Issue 43 https://doi.org/10.1021/acsomega.0c03989	journal	October 2020
Reductive Catalytic Fractionation of Corn Stover Lignin Anderson, Eric M.; Katahira, Rui; Reed, Michelle ACS Sustainable Chemistry & Engineering, Vol. 4, Issue 12 https://doi.org/10.1021/acssuschemeng.6b01858	journal	October 2016
Lignin Depolymerization to Dicarboxylic Acids with Sodium Percarbonate Cronin, Dylan J.; Zhang, Xiao; Bartley, John ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 7 https://doi.org/10.1021/acssuschemeng.7b01208	journal	June 2017
Relating Dicarboxylic Acid Yield to Residual Lignin Structural Features Cronin, Dylan J.; Dunn, Kameron; Zhang, Xiao ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 12 https://doi.org/10.1021/acssuschemeng.7b03164	journal	November 2017
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
Chemoselective Metal-Free Aerobic Alcohol Oxidation in Lignin Rahimi, Alireza; Azarpira, Ali; Kim, Hoon Journal of the American Chemical Society, Vol. 135, Issue 17, p. 6415-6418 https://doi.org/10.1021/ja401793n	journal	April 2013
Reactivity of Ferulic Acid and Its Derivatives toward Hydrogen Peroxide and Peracetic Acid Pan, George X.; Spencer, Liam; Leary, Gordon J. Journal of Agricultural and Food Chemistry, Vol. 47, Issue 8 https://doi.org/10.1021/jf9902494	journal	August 1999
Peroxyacetic acid oxidation of 4-methylphenols and their methyl ethers Johnson, Donald C.; Farrand, James C. The Journal of Organic Chemistry, Vol. 36, Issue 23 https://doi.org/10.1021/jo00822a032	journal	November 1971
Miscible Blends of Kraft Lignin Derivatives with Low- T _g Polymers Li, Yan; Sarkanen, Simo Macromolecules, Vol. 38, Issue 6 https://doi.org/10.1021/ma047546g	journal	March 2005
Macromolecular lignin replication: A mechanistic working hypothesis Chen, Yi-ru; Sarkanen, Simo Phytochemistry Reviews, Vol. 2, Issue 3 https://doi.org/10.1023/B:PHYT.0000046173.38194.ba	journal	October 2003
Formic-acid-induced depolymerization of oxidized lignin to aromatics Rahimi, Alireza; Ulbrich, Arne; Coon, Joshua J. Nature, Vol. 515, Issue 7526, p. 249-252 https://doi.org/10.1038/nature13867	journal	November 2014
Whole plant cell wall characterization using solution-state 2D NMR Mansfield, Shawn D.; Kim, Hoon; Lu, Fachuang Nature Protocols, Vol. 7, Issue 9 https://doi.org/10.1038/nprot.2012.064	journal	August 2012
Lignin depolymerisation strategies: towards valuable chemicals and fuels Xu, Chunping; Arancon, Rick Arneil D.; Labidi, Jalel Chemical Society Reviews, Vol. 43, Issue 22, p. 7485-7500 https://doi.org/10.1039/C4CS00235K	journal	January 2014
Selective cleavage of the C _α –C _β linkage in lignin model compounds via Baeyer–Villiger oxidation Patil, Nikhil D.; Yao, Soledad G.; Meier, Mark S. Organic & Biomolecular Chemistry, Vol. 13, Issue 11 https://doi.org/10.1039/C4OB01771D	journal	January 2015
Path to plastics composed of ligninsulphonates (lignosulfonates) Wang, Yun-Yan; Chen, Yi-ru; Sarkanen, Simo Green Chemistry, Vol. 17, Issue 11 https://doi.org/10.1039/C5GC01865J	journal	January 2015
An integrated electrochemical process to convert lignin to value-added products under mild conditions Stiefel, Serafin; Schmitz, Annika; Peters, Jens Green Chemistry, Vol. 18, Issue 18 https://doi.org/10.1039/C6GC00878J	journal	January 2016
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
Lignin-first biomass fractionation: the advent of active stabilisation strategies Renders, T.; Van den Bosch, S.; Koelewijn, S. -F. Energy & Environmental Science, Vol. 10, Issue 7 https://doi.org/10.1039/C7EE01298E	journal	January 2017
Highly effective C–C bond cleavage of lignin model compounds Wang, Yinling; Wang, Qianyi; He, Jianghua Green Chemistry, Vol. 19, Issue 13 https://doi.org/10.1039/C7GC00844A	journal	January 2017
Emulsion electro-oxidation of kraft lignin Di Marino, Davide; Aniko, Vadim; Stocco, Antonio Green Chemistry, Vol. 19, Issue 20 https://doi.org/10.1039/C7GC02115A	journal	January 2017
Regioselective Baeyer–Villiger oxidation of lignin model compounds with tin beta zeolite catalyst and hydrogen peroxide Jennings, John A.; Parkin, Sean; Munson, Eric RSC Advances, Vol. 7, Issue 42 https://doi.org/10.1039/C7RA03830E	journal	January 2017
Revisiting alkaline aerobic lignin oxidation Schutyser, Wouter; Kruger, Jacob S.; Robinson, Allison M. Green Chemistry, Vol. 20, Issue 16 https://doi.org/10.1039/C8GC00502H	journal	January 2018
Improving fast pyrolysis of lignin using three additives with different modes of action Ghysels, Stef; Dubuisson, Ben; Pala, Mehmet Green Chemistry, Vol. 22, Issue 19 https://doi.org/10.1039/D0GC02417A	journal	January 2020
Electro-catalytic oxidative cleavage of lignin in a protic ionic liquid Reichert, Elena; Wintringer, Reiner; Volmer, Dietrich A. Physical Chemistry Chemical Physics, Vol. 14, Issue 15 https://doi.org/10.1039/c2cp23596j	journal	January 2012
Degradation of Lignin with Ozone: Reactivity of Lignin Model Compounds Toward Ozone Kaneko, Hidenobu; Hosoya, Shuji; Iiyama, Kenji Journal of Wood Chemistry and Technology, Vol. 3, Issue 4 https://doi.org/10.1080/02773818308085171	journal	January 1983
Lignin Valorization: Improving Lignin Processing in the Biorefinery Ragauskas, A. J.; Beckham, G. T.; Biddy, M. J. Science, Vol. 344, Issue 6185, p. 1246843-1246843 https://doi.org/10.1126/science.1246843	journal	May 2014
Formaldehyde stabilization facilitates lignin monomer production during biomass depolymerization Shuai, Li; Amiri, Masoud Talebi; Questell-Santiago, Ydna M. Science, Vol. 354, Issue 6310 https://doi.org/10.1126/science.aaf7810	journal	October 2016
Lignin Biosynthesis Boerjan, Wout; Ralph, John; Baucher, Marie Annual Review of Plant Biology, Vol. 54, Issue 1, p. 519-546 https://doi.org/10.1146/annurev.arplant.54.031902.134938	journal	June 2003
A highly efficient dilute alkali deacetylation and mechanical (disc) refining process for the conversion of renewable biomass to lower cost sugars Chen, Xiaowen; Shekiro, Joseph; Pschorn, Thomas Biotechnology for Biofuels, Vol. 7, Issue 1 https://doi.org/10.1186/1754-6834-7-98	journal	January 2014

Similar Records

Role of Peracetic Acid on the Disruption of Lignin Packing Structure and its Consequence on Lignin Depolymerisation

Journal Article · 2021 · Green Chemistry · OSTI ID:1866775

Ma, Ruoshui; Sanyal, Udishnu; Olarte, Mariefel V.; +10 more

Peracetic Acid Depolymerization of Biorefinery Lignin for Production of Selective Monomeric Phenolic Compounds

Journal Article · 2016 · Chemistry - A European Journal · OSTI ID:1290390

Ma, Ruoshui; Guo, Mond; Lin, Kuan-ting; +7 more

Peracetic Acid Depolymerization of Biorefinery Lignin for Production of Selective Monomeric Phenolic Compounds

Journal Article · 2016 · Chemistry - A European Journal · OSTI ID:1273066

Ma, Ruoshui; Guo, Mond; Lin, Kuan-ting; +7 more

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
lignin deconstruction
monophenolic compounds
oxidation
peracetic acid

Title: Role of peracetic acid on the disruption of lignin packing structure and its consequence on lignin depolymerisation

Citation Formats

References (54)

Similar Records

Related Subjects