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BioLogicTool: A Simple Visual Tool for Assisting in the Logical Selection of Pathways from Biomass to Products

  • Yann Lie
    Yann Lie
    Green Chemistry Centre of Excellence, Department of Chemistry, University of York, Heslington, York YO10 5DD, United Kingdom
    More by Yann Lie
  • Pablo Ortiz
    Pablo Ortiz
    Separation & Conversion Technology, Flemish Institute for Technological Research (VITO), Boeretang 200, Mol 2400, Belgium
    More by Pablo Ortiz
  • Richard Vendamme
    Richard Vendamme
    Separation & Conversion Technology, Flemish Institute for Technological Research (VITO), Boeretang 200, Mol 2400, Belgium
  • Karolien Vanbroekhoven
    Karolien Vanbroekhoven
    Separation & Conversion Technology, Flemish Institute for Technological Research (VITO), Boeretang 200, Mol 2400, Belgium
  • , and 
  • Thomas J Farmer*
    Thomas J Farmer
    Green Chemistry Centre of Excellence, Department of Chemistry, University of York, Heslington, York YO10 5DD, United Kingdom
    *Email: [email protected]
Cite this: Ind. Eng. Chem. Res. 2019, 58, 35, 15945–15957
Publication Date (Web):April 12, 2019
https://doi.org/10.1021/acs.iecr.9b00575
Copyright © 2019 American Chemical Society

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    Abstract

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    The current chemical industry has been heavily optimized for the use of petroleum-derived base chemicals as its primary source of building blocks. However, incorporation of heteroatoms, absent in the base chemicals, is necessary to meet the different property requirements in the plethora of products the industry makes such as plastics, cosmetics, and pharmaceuticals. As global oil reserves deplete, a shift toward renewable bioderived building blocks, so-called platform molecules, will become a necessity. Bioderived platform molecules are typically rich in heteroatoms as a result of their biomass feedstock also being heteroatom rich, and it would therefore seem logical to carry these heteroatoms through to the aforementioned products. A tool was herein developed to assess the rationality of a synthetic route from feedstock to product, designed specifically to give a visual representation of the pathways and options available. BioLogicTool plots (%heteroatom by mass vs M) are an alternative to the conventional van Krevelen diagram, and are designed to better consider the diversity in heteroatom content encountered in biobased chemicals. The tool can rapidly help its user to design more logical multistep synthetic routes and enhance the mass efficiency of pathways. Several examples were selected to demonstrate the power and limitations of the BioLogicTool, but it was clear from these examples that removing heteroatoms from platform molecules to reincorporate them later in the final product is, in most cases, not logical in a mass efficiency sense.

    Supporting Information

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.iecr.9b00575.

    • Full tables of the base chemicals and platform molecules with all the values (M, O:C and H:C, %oxygen, %heteroatom) used to prepare the BioLogicTool plots; a larger version of Figure 3D with assignment of the all data points; the structures of the platform molecules with an M > 220 g/mol; BioLogicTool plots extended to contain the platform molecules with M > 220 g/mol; discussion on potential benefits of the synthesis of l-dopa from lignin as highlighted by the BioLogicTool; an example of a color-coded plot based on user defined yields for each step (PDF)

    • A spreadsheet form of the tool is available as part of the Supporting Information and accessible through via DOI 10.15124/64d80432-9929-4b74-bcb7-8e3226ec03ce (ZIP)

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    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    This article is cited by 12 publications.

    1. Martin G. Banwell, Xin Liu, Luke A. Connal, Michael G. Gardiner. Synthesis of Functionally and Stereochemically Diverse Polymers via Ring-Opening Metathesis Polymerization of Derivatives of the Biomass-Derived Platform Molecule Levoglucosenone Produced at Industrial Scale. Macromolecules 2020, 53 (13) , 5308-5314. https://doi.org/10.1021/acs.macromol.0c01305
    2. Maryam Nikahd, Jiri Mikusek, Li-Juan Yu, Michelle L. Coote, Martin G. Banwell, Chenxi Ma, Michael G. Gardiner. Exploiting Chitin as a Source of Biologically Fixed Nitrogen: Formation and Full Characterization of Small-Molecule Hetero- and Carbocyclic Pyrolysis Products. The Journal of Organic Chemistry 2020, 85 (7) , 4583-4593. https://doi.org/10.1021/acs.joc.9b03438
    3. J. Gracia-Vitoria, S. Corderí Gándara, E. Feghali, P. Ortiz, W. Eevers, K.S. Triantafyllidis, K. Vanbroekhoven. The chemical and physical properties of lignin bio-oils, facts and needs. Current Opinion in Green and Sustainable Chemistry 2023, 40 , 100781. https://doi.org/10.1016/j.cogsc.2023.100781
    4. Daniel M. Day, Thomas J. Farmer, Joe Granelli, Janice H. Lofthouse, Julie Lynch, Con R. McElroy, James Sherwood, Seishi Shimizu, James H. Clark. Reaction Optimization for Greener Chemistry with a Comprehensive Spreadsheet Tool. Molecules 2022, 27 (23) , 8427. https://doi.org/10.3390/molecules27238427
    5. Tom A. Ewing, Niels Nouse, Matthijs van Lint, Jacco van Haveren, Jeroen Hugenholtz, Daan S. van Es. Fermentation for the production of biobased chemicals in a circular economy: a perspective for the period 2022–2050. Green Chemistry 2022, 24 (17) , 6373-6405. https://doi.org/10.1039/D1GC04758B
    6. Jose Osorio-Tejada, Francesco Ferlin, Luigi Vaccaro, Volker Hessel. Life cycle assessment of multistep benzoxazole synthesis: from batch to waste-minimised continuous flow systems. Green Chemistry 2022, 24 (1) , 325-337. https://doi.org/10.1039/D1GC03202J
    7. Yingxin Liu, Kaiyue Zhang, Liang Zhang, Yun Wang, Zuojun Wei. One-pot synthesis of pyrrolidone derivatives via reductive amination of levulinic acid/ester with nitriles over Pd/C catalyst. Reaction Kinetics, Mechanisms and Catalysis 2021, 134 (2) , 777-792. https://doi.org/10.1007/s11144-021-02073-x
    8. Fergal P. Byrne, James H. Clark, Carlo Angelici, Ed de Jong, Thomas J. Farmer. Greenness Assessment and Synthesis for the Bio-Based Production of the Solvent 2,2,5,5-Tetramethyloxolane (TMO). Sustainable Chemistry 2021, 2 (3) , 392-406. https://doi.org/10.3390/suschem2030023
    9. Martin G. Banwell, Brett Pollard, Xin Liu, Luke A. Connal. Exploiting Nature's Most Abundant Polymers: Developing New Pathways for the Conversion of Cellulose, Hemicellulose, Lignin and Chitin into Platform Molecules (and Beyond). Chemistry – An Asian Journal 2021, 16 (6) , 604-620. https://doi.org/10.1002/asia.202001451
    10. Yehezkiel Steven Kurniawan, Krisfian Tata Aneka Priyangga, Philip Anggo Krisbiantoro, Arif Cahyo Imawan. Green Chemistry Influences in Organic Synthesis : a Review. Journal of Multidisciplinary Applied Natural Science 2021, 1 (1) , 1-12. https://doi.org/10.47352/jmans.v1i1.2
    11. Ydna M. Questell-Santiago, Maxim V. Galkin, Katalin Barta, Jeremy S. Luterbacher. Stabilization strategies in biomass depolymerization using chemical functionalization. Nature Reviews Chemistry 2020, 4 (6) , 311-330. https://doi.org/10.1038/s41570-020-0187-y
    12. Pablo Ortiz, Richard Vendamme, Walter Eevers. Fully Biobased Epoxy Resins from Fatty Acids and Lignin. Molecules 2020, 25 (5) , 1158. https://doi.org/10.3390/molecules25051158

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