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Cited by 270

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Breaking the Limit of Lignin Monomer Production via Cleavage of Interunit Carbon–Carbon Linkages

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Dong, Lin, Lin, Longfei, Han, Xue, Si, Xiaoqin, Liu, Xiaohui, Guo, Yong, Lu, Fang, Rudić, Svemir, Parker, Stewart F., Yang, Sihai, Wang, Yanqin·2019·Chem
DOI 10.1016/j.chempr.2019.03.007
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Abstract

Summary Conversion of lignin into monocyclic hydrocarbons as commodity chemicals and drop-in fuels is a highly desirable target for biorefineries. However, this is severely hindered by the presence of stable interunit carbon–carbon linkages in native lignin and those formed during lignin extraction. Herein, we report a new multifunctional catalyst, Ru/NbOPO4, that achieves the first example of catalytic cleavage of both interunit C–C and C–O bonds in one-pot lignin conversions to yield 124%–153% of monocyclic hydrocarbons, which is 1.2–1.5 times the yields obtained from the established nitrobenzene oxidation method. This catalyst also exhibits high stability and selectivity (up to 68%) to monocyclic arenes over repeated cycles. The mechanism of the activation and cleavage of 5–5 C–C bonds in biphenyl, as a lignin model adopting the most robust C–C linkages, has been revealed via in situ inelastic neutron scattering coupled with modeling. This study breaks the conventional theoretical limit on lignin monomer production.

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Research works printed but not linked: 41

  1. Ragauskas, 2014, Lignin valorization: improving lignin processing in the biorefinery, Science, 344, 1246843, 10.1126/science.1246843 · DOI · Paper page
  2. Schutyser, 2018, Chemicals from lignin: an interplay of lignocellulose fractionation, depolymerisation, and upgrading, Chem. Soc. Rev., 47, 852, 10.1039/C7CS00566K · DOI · Paper page
  3. Rinaldi, 2016, Paving the way for lignin valorisation: recent advances in bioengineering, biorefining and catalysis, Angew. Chem. Int. Ed., 55, 8164, 10.1002/anie.201510351 · DOI · Paper page
  4. Yan, 2008, Selective degradation of wood lignin over noble-metal catalysts in a two-step process, ChemSusChem, 1, 626, 10.1002/cssc.200800080 · DOI · Paper page
  5. Rahimi, 2014, Formic-acid-induced depolymerization of oxidized lignin to aromatics, Nature, 515, 249, 10.1038/nature13867 · DOI · Paper page
  6. Wu, 2018, Solar energy-driven lignin-first approach to full utilization of lignocellulosic biomass under mild conditions, Nat. Catal., 1, 772, 10.1038/s41929-018-0148-8 · DOI · Paper page
  7. Sun, 2018, Complete lignocellulose conversion with integrated catalyst recycling yielding valuable aromatics and fuels, Nat. Catal., 1, 82, 10.1038/s41929-017-0007-z · DOI · Paper page
  8. Deuss, 2015, Aromatic monocyclics by in situ conversion of reactive intermediates in the acid-catalyzed depolymerization of lignin, J. Am. Chem. Soc., 137, 7456, 10.1021/jacs.5b03693 · DOI · Paper page
  9. Lahive, 2016, Advanced model compounds for understanding acid-catalyzed lignin depolymerization: identification of renewable aromatics and a lignin-derived solvent, J. Am. Chem. Soc., 138, 8900, 10.1021/jacs.6b04144 · DOI · Paper page
  10. Stärk, 2010, Oxidative depolymerization of lignin in ionic liquids, ChemSusChem, 3, 719, 10.1002/cssc.200900242 · DOI · Paper page
  11. Li, 2018, An “ideal lignin” facilitates full biomass utilization, Sci. Adv., 4, eaau2968, 10.1126/sciadv.aau2968 · DOI · Paper page
  12. Rahimi, 2013, Chemoselective metal-free aerobic alcohol oxidation in lignin, J. Am. Chem. Soc., 135, 6415, 10.1021/ja401793n · DOI · Paper page
  13. Parsell, 2015, A synergistic biorefinery based on catalytic conversion of lignin prior to cellulose starting from lignocellulosic biomass, Green Chem., 17, 1492, 10.1039/C4GC01911C · DOI · Paper page
  14. Klein, 2015, Lignin depolymerization over Ni/C catalyst in methanol, a continuation: effect of substrate and catalyst loading, Catal. Sci. Technol., 5, 3242, 10.1039/C5CY00490J · DOI
  15. Matson, 2011, One-pot catalytic conversion of cellulose and of woody biomass solids to liquid fuels, J. Am. Chem. Soc., 133, 14090, 10.1021/ja205436c · DOI · Paper page
  16. Song, 2013, Lignin depolymerization (LDP) in alcohol over nickel-based catalysts via a fragmentation–hydrogenolysis process, Energy Environ. Sci., 6, 994, 10.1039/c2ee23741e · DOI · Paper page
  17. Wang, 2013, A route for lignin and bio-oil conversion: dehydroxylation of phenols into arenes by catalytic tandem reactions, Angew. Chem. Int. Ed., 52, 11499, 10.1002/anie.201304776 · DOI · Paper page
  18. Van den Bosch, 2015, Reductive lignocellulose fractionation into soluble lignin-derived phenolic monomers and dimers and processable carbohydrate pulps, Energy Environ. Sci., 8, 1748, 10.1039/C5EE00204D · DOI · Paper page
  19. Van den Bosch, 2017, Integrating lignin valorization and bio-ethanol production: on the role of Ni-Al2O3 catalyst pellets during lignin-first fractionation, Green Chem., 19, 3313, 10.1039/C7GC01324H · DOI · Paper page
  20. Shuai, 2016, Formaldehyde stabilization facilitates lignin monomer production during biomass depolymerization, Science, 354, 329, 10.1126/science.aaf7810 · DOI · Paper page
  21. Lan, 2018, Protection group effects during α, γ-diol lignin stabilization promote high-selectivity monomer production, Angew. Chem. Int. Ed., 57, 1356, 10.1002/anie.201710838 · DOI · Paper page
  22. Shuai, 2018, Selective C-C bond cleavage of methylene-linked lignin models and Kraft lignin, ACS Catal., 8, 6507, 10.1021/acscatal.8b00200 · DOI
  23. Jan, 2015, Hydropyrolysis of lignin using Pd/HZSM-5, Energy Fuels, 29, 1793, 10.1021/ef502779s · DOI
  24. Mu, 2013, Lignin pyrolysis components and upgrading—technology review, Bioenergy Res., 6, 1183, 10.1007/s12155-013-9314-7 · DOI · Paper page
  25. Li, 2012, Catalytic fast pyrolysis of Kraft lignin with HZSM-5 zeolite for producing aromatic hydrocarbons, Front. Environ. Sci. Eng., 6, 295, 10.1007/s11783-012-0410-2 · DOI · Paper page
  26. Zhao, 2010, Aromatics production via catalytic pyrolysis of pyrolytic lignins from bio-oil, Energy Fuels, 24, 5735, 10.1021/ef100896q · DOI
  27. Vermeiren, 2009, Impact of zeolites on the petroleum and petrochemical industry, Top. Catal., 52, 1131, 10.1007/s11244-009-9271-8 · DOI · Paper page
  28. Zhu, 2013, Mesoporous zeolites as efficient catalysts for oil refining and natural gas conversion, Front. Chem. Sci. Eng., 7, 233, 10.1007/s11705-013-1329-2 · DOI
  29. Michaud, 1998, Hydrodesulfurization of dibenzothiophene and 4,6-dimethyldibenzothiophene: effect of an acid component on the activity of a sulfided NiMo on alumina catalyst, Appl. Catal. A Gen., 169, 343, 10.1016/S0926-860X(98)00021-0 · doi:10.1016/s0926-860x(98)00021-0
  30. Zhang, 2010, Synthesis, characterization, and catalytic performance of NiMo catalysts supported on hierarchically porous beta-KIT-6 material in the hydrodesulfurization of dibenzothiophene, J. Catal., 274, 273, 10.1016/j.jcat.2010.07.012 · DOI
  31. Xia, 2016, Direct hydrodeoxygenation of raw woody biomass into liquid alkanes, Nat. Commun., 7, 11162, 10.1038/ncomms11162 · DOI · Paper page
  32. Li, 2016, NMR assignment for diaryl ether structures (4-O-5 structures) in pine wood lignin, Biomacromolecules, 17, 1921, 10.1021/acs.biomac.6b00257 · DOI
  33. Ma, 2018, New insights toward quantitative relationships between lignin reactivity to monomers and their structural characteristics, ChemSusChem, 11, 2146, 10.1002/cssc.201800550 · doi:10.1002/cssc.201800550
  34. Yamamura, 2010, Microscale alkaline nitrobenzene oxidation method for high-throughput determination of lignin aromatic components, Plant Biotechnol., 27, 305, 10.5511/plantbiotechnology.27.305 · DOI
  35. Chui, 2017, Probing the lignin disassembly pathways with modified catalysts based on Cu-doped porous metal oxides, ACS Sustain. Chem. Eng., 5, 3158, 10.1021/acssuschemeng.6b02954 · DOI
  36. Miyazawa, 2006, Glycerol conversion in the aqueous solution under hydrogen over Ru/C + an ion-exchange resin and its reaction mechanism, J. Catal., 240, 213, 10.1016/j.jcat.2006.03.023 · DOI · Paper page
  37. Fihri, 2012, Fibrous nano-silica supported ruthenium (KCC-1/Ru): a sustainable catalyst for the hydrogenolysis of alkanes with good catalytic activity and lifetime, ACS Catal., 2, 1425, 10.1021/cs300179q · DOI · Paper page
  38. Palkovits, 2010, Hydrogenolysis of cellulose combining mineral acids and hydrogenation catalysts, Green Chem., 12, 972, 10.1039/c000075b · DOI · Paper page
  39. Rahimi, 2011, Catalytic cracking of hydrocarbons over modified ZSM-5 zeolites to produce light olefins: a review, Appl. Catal. A Gen., 398, 1, 10.1016/j.apcata.2011.03.009 · DOI · Paper page
  40. Solcà, 2002, Protonated benzene: IR spectrum and structure of C6H7+, Angew. Chem. Int. Ed., 41, 3628, 10.1002/1521-3773(20021004)41:19<3628::AID-ANIE3628>3.0.CO;2-1 · doi:10.1002/1521-3773(20021004)41:19<3628::aid-anie3628>3.0.co;2-1
  41. Parker, 2014, Recent and future developments on Tosca at ISIS, J. Phys. Conf. Ser., 554, 012003, 10.1088/1742-6596/554/1/012003 · doi:10.1088/1742-6596/554/1/012003

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Metadata

Authors
Dong, L., Lin, L., Han, X., Si, X., Liu, X., Guo, Y., Lu, F., Rudić, S., Parker, S. F., Yang, S., & Wang, Y.
Venue
Chem
Publisher
Elsevier BV
Published
2019-06
Volume
5
Issue
6
Pages
1521-1536
ISSN
2451-9294 (ISSN-L)
DOI
10.1016/j.chempr.2019.03.007
OpenAlex
W2936709985
Cited by
270
References
5
FWCI
10.28
Type
journal article
Language
en
Open access
bronze
Licence
Funders
  • National Natural Science Foundation of China (91545103, 21808063, 21872050, 21832002)
  • Fundamental Research Funds for the Central Universities (222201718003)
  • Project 211 (B16017)
  • Engineering and Physical Sciences Research Council (EP/P011632/1)
  • Royal Society
  • University of Manchester
  • Science and Technology Commission of Shanghai Municipality (2018SHZDZX03)

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CoChat. (2026). Citation check: Breaking the Limit of Lignin Monomer Production via Cleavage of Interunit Carbon–Carbon Linkages. https://app.cochat.ai/papers/10.1016/j.chempr.2019.03.007
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Dong, L., Lin, L., Han, X., Si, X., Liu, X., Guo, Y., Lu, F., Rudić, S., Parker, S. F., Yang, S., & Wang, Y. (2019). Breaking the Limit of Lignin Monomer Production via Cleavage of Interunit Carbon–Carbon Linkages. Chem. https://doi.org/10.1016/j.chempr.2019.03.007

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