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Effect of Methoxy Substituents on Wet Peroxide Oxidation of Lignin and Lignin Model Compounds: Understanding the Pathway to C4 Dicarboxylic Acids

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    Kinetics, Catalysis, and Reaction Engineering

    Effect of Methoxy Substituents on Wet Peroxide Oxidation of Lignin and Lignin Model Compounds: Understanding the Pathway to C4 Dicarboxylic Acids
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    • Carlos A. Vega-Aguilar
      Carlos A. Vega-Aguilar
      Laboratory of Separation and Reaction Engineering−Laboratory of Catalysis and Materials (LSRE-LCM), Faculdade de Engenharia, Universidade do Porto, Rua Dr. Roberto Frias s/n, 4200-465 Porto, Portugal
      Centro de Investigação de Montanha−CIMO, Instituto Politécnico de Bragança, Campus de Santa Apolónia, 5300-253 Bragança, Portugal
      More by Carlos A. Vega-Aguilar
      Orcidhttp://orcid.org/0000-0001-8542-8732
    • M. Filomena Barreiro
      M. Filomena Barreiro
      Centro de Investigação de Montanha−CIMO, Instituto Politécnico de Bragança, Campus de Santa Apolónia, 5300-253 Bragança, Portugal
      More by M. Filomena Barreiro
    • Alírio E. Rodrigues*
      Alírio E. Rodrigues
      Laboratory of Separation and Reaction Engineering−Laboratory of Catalysis and Materials (LSRE-LCM), Faculdade de Engenharia, Universidade do Porto, Rua Dr. Roberto Frias s/n, 4200-465 Porto, Portugal
      *Email: [email protected]
      More by Alírio E. Rodrigues
      Orcidhttp://orcid.org/0000-0002-0715-4761
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    Industrial & Engineering Chemistry Research

    Cite this: Ind. Eng. Chem. Res. 2021, 60, 9, 3543–3553
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.iecr.0c05085
    Published January 18, 2021
    Copyright © 2021 American Chemical Society
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    Abstract

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    Lignin depolymerization through peroxide oxidation produces dicarboxylic acids (DCA), especially C4-DCA, like succinic acid. In this work, the effect of methoxy substituents on C4-DCA production using peroxide oxidation of lignin model compounds (p-hydroxybenzoic acid, vanillic acid, and syringic acid) and hardwood and softwood lignin samples was studied. It was concluded that methoxy substituents increased the reactivity toward peroxide oxidation. The succinic acid yield was higher for the model compounds with fewer methoxy groups, achieving 5.8 wt % of succinic acid for p-hydroxybenzoic acid. For Eucalyptus globulus kraft lignin (hardwood lignin with guaiacyl and syringyl units), an increased reactivity was verified, and more succinic acid (3.5 wt %) was produced in a shorter time, comparatively with Indulin AT lignin (softwood lignin, with only guaiacyl units), which produced 2.7 wt %. This evidence suggests that E. globulus kraft lignin might be a better raw material than Indulin AT for succinic acid production by peroxide oxidation.

    Copyright © 2021 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.iecr.0c05085.

    • Additional graphics of the pH behavior during model compound oxidation (Figure S1); chemical structures of the compounds detected by GC-MS analysis for pHBA, VA, and SA oxidation with H2O2 at 140 °C (Figure S2); a table with the compounds identified by GC-MS for pHBA, VA, and SA oxidation at 140 °C (Table S1) (PDF)

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    Cited By

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    This article is cited by 15 publications.

    1. Fika Andriani, Martin Lawoko. Oxidative Carboxylation of Lignin: Exploring Reactivity of Different Lignin Types. Biomacromolecules 2024, 25 (7) , 4246-4254. https://doi.org/10.1021/acs.biomac.4c00326
    2. Yeddula Nikhileshwar Reddy, Seema Kirar, Neeraj Singh Thakur, Mahesh Daga Patil, Jayeeta Bhaumik. Sunlight Assisted Photocatalytic Valorization of Lignin Using Recyclable Light Harvesters. ACS Sustainable Chemistry & Engineering 2023, 11 (12) , 4568-4579. https://doi.org/10.1021/acssuschemeng.2c05917
    3. Carlos A. Vega-Aguilar, Carina Costa, Maria Filomena Barreiro, Alírio E. Rodrigues. Microwave-Assisted Lignin Wet Peroxide Oxidation to C4 Dicarboxylic Acids. Industrial & Engineering Chemistry Research 2022, 61 (10) , 3570-3581. https://doi.org/10.1021/acs.iecr.1c05004
    4. Jiaxiang Li, Donghui Guan, Shengpeng Xia, Yuyang Fan, Kun Zhao, Zengli Zhao, Anqing Zheng. Recent advances, challenges, and opportunities in lignin valorization for value-Added chemicals, biofuels, and polymeric materials. Energy Conversion and Management 2024, 322 , 119123. https://doi.org/10.1016/j.enconman.2024.119123
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    6. Stefano Salvestrini, Angelo Fenti, Lin Qian, Frank-Dieter Kopinke. Oxidation of organic pollutants over MnO2 in cold water assisted by peroxydisulfate. Chemical Engineering Journal 2024, 479 , 147170. https://doi.org/10.1016/j.cej.2023.147170
    7. Hifza Rouf, Anita Ramli, Nur Akila Syakida Idayu Khairul Anuar, Normawati Mohamad Yunus. Ce–Zr-based mixed oxide catalyst for oxidative depolymerization of kenaf stalk (biomass) into vanillin. Bioresources and Bioprocessing 2023, 10 (1) https://doi.org/10.1186/s40643-023-00698-5
    8. Goutham Rangarajan, Jia Min Koh, Ramin Farnood. Touch wood: Conversion of lignin to dicarboxylic acids using biochar-based solid-acid photo-Fenton catalysts. Journal of Cleaner Production 2023, 415 , 137816. https://doi.org/10.1016/j.jclepro.2023.137816
    9. Shirong Sun, Xueqing Qiu, Shuhua Hao, Sabarinathan Ravichandran, Jinliang Song, Wenli Zhang. Electrochemical conversion of lignin to short-chain carboxylic acids. Green Chemistry 2023, 25 (8) , 3127-3136. https://doi.org/10.1039/D3GC00324H
    10. Zheli Ding, Sanjeev Kumar Awasthi, Manish Kumar, Vinay Kumar, Andrei Mikhailovich Dregulo, Vivek Yadav, Raveendran Sindhu, Parameswaran Binod, Surendra Sarsaiya, Ashok Pandey, Mohammad J. Taherzadeh, Rashmi Rathour, Lal Singh, Zengqiang Zhang, Zihao Lian, Mukesh Kumar Awasthi. A thermo-chemical and biotechnological approaches for bamboo waste recycling and conversion to value added product: Towards a zero-waste biorefinery and circular bioeconomy. Fuel 2023, 333 , 126469. https://doi.org/10.1016/j.fuel.2022.126469
    11. Emmanuel B. Castillo-Contreras, Jean Michel Lauzon, Brian R. James. Cleavage of lignin model compounds using ruthenium/KOH or KOH-only systems. Catalysis Today 2023, 407 , 59-67. https://doi.org/10.1016/j.cattod.2022.05.040
    12. Li Zhang, Yi Xiao, Wensheng Mao, Jiyan Huang, Hongmei Huang, Ronghua Yang, Youyu Zhang, Xiaoxiao He, Kemin Wang. A pyrene-pyridyl nanooligomer as a methoxy-triggered reactive probe for highly specific fluorescence assaying of hypochlorite. Chemical Communications 2022, 58 (15) , 2520-2523. https://doi.org/10.1039/D1CC06606D
    13. Carlos A. Vega-Aguilar, M. Filomena Barreiro, Alírio E. Rodrigues. Lignin conversion into C4 dicarboxylic acids by catalytic wet peroxide oxidation using titanium silicalite-1. Industrial Crops and Products 2021, 173 , 114155. https://doi.org/10.1016/j.indcrop.2021.114155
    14. Xiu-Zhi Wei, Jianguo Liu, Longlong Ma. Cleavage via Selective Catalytic Oxidation of Lignin or Lignin Model Compounds into Functional Chemicals. ChemEngineering 2021, 5 (4) , 74. https://doi.org/10.3390/chemengineering5040074
    15. Carina A. Esteves Costa, Carlos A. Vega-Aguilar, Alírio E. Rodrigues. Added-Value Chemicals from Lignin Oxidation. Molecules 2021, 26 (15) , 4602. https://doi.org/10.3390/molecules26154602
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    Industrial & Engineering Chemistry Research

    Cite this: Ind. Eng. Chem. Res. 2021, 60, 9, 3543–3553
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.iecr.0c05085
    Published January 18, 2021
    Copyright © 2021 American Chemical Society
    Request reuse permissions

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