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Catalytic Hydrogenolysis of Lignin: The Influence of Minor Units and Saccharides.

ABSTRACT: The precise elucidation of native lignin structures plays a vital role for the development of "lignin first" strategies such as reductive catalytic fractionation. The structure of lignin and composition of the starting material has a major impact on the product yield and distribution. Here, the differences in structure of lignin from birch, pine, reed, and walnut shell were investigated by combining detailed analysis of the whole cell wall material, residual enzyme lignin, and milled wood lignin. The results of the 2D heteronuclear single quantum coherence NMR analysis could be correlated to the product from Ru/C-catalyzed hydrogenolysis if monomeric products from ferulate and p-coumaryl and its analogous units were also appropriately considered. Notably, residual polysaccharide constituents seemed to influence the selectivity towards hydroxy-containing monomers. The results reinforced the importance of adequate structural characterization and compositional analysis of the starting materials as well as distinct (dis)advantages of specific types of structural characterization and isolation methods for guiding valorization potential of different biomass feedstocks.

SUBMITTER: Wang Z

PROVIDER: S-EPMC9293178 | biostudies-literature | 2021 Dec

REPOSITORIES: biostudies-literature

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Catalytic Hydrogenolysis of Lignin: The Influence of Minor Units and Saccharides.

Wang Zhiwen Z Deuss Peter J PJ

ChemSusChem 20210920 23

The precise elucidation of native lignin structures plays a vital role for the development of "lignin first" strategies such as reductive catalytic fractionation. The structure of lignin and composition of the starting material has a major impact on the product yield and distribution. Here, the differences in structure of lignin from birch, pine, reed, and walnut shell were investigated by combining detailed analysis of the whole cell wall material, residual enzyme lignin, and milled wood lignin ...[more]

PMID: 34398518

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Project description:This article explores the important, and yet often overlooked, solid-state structures of selected bioaromatic compounds commonly found in lignin hydrogenolysis oil, a renewable bio-oil that holds great promise to substitute fossil-based aromatic molecules in a wide range of chemical and material industrial applications. At first, single-crystal X-ray diffraction (SCXRD) was applied to the lignin model compounds, dihydroconiferyl alcohol, propyl guaiacol, and eugenol dimers, in order to elucidate the fundamental molecular interactions present in such small lignin-derived polyols. Then, considering the potential use of these lignin-derived molecules as building blocks for polymer applications, structural analysis was also performed for two chemically modified model compounds, i.e., the methylene-bridging propyl-guaiacol dimer and propyl guaiacol and eugenol glycidyl ethers, which can be used as precursors in phenolic and epoxy resins, respectively, thus providing additional information on how the molecular packing is altered following chemical modifications. In addition to the expected H-bonding interactions, other interactions such as π-π stacking and C-H∙∙∙π were observed. This resulted in unexpected trends in the tendencies towards the crystallization of lignin compounds. This was further explored with the aid of DSC analysis and CLP intermolecular energy calculations, where the relationship between the major interactions observed in all the SCXRD solid-state structures and their physico-chemical properties were evaluated alongside other non-crystallizable lignin model compounds. Beyond lignin model compounds, our findings could also provide important insights into the solid-state structure and the molecular organization of more complex lignin fragments, paving the way to the more efficient design of lignin-based materials with improved properties for industrial applications or improving downstream processing of lignin oils in biorefining processes, such as in enhancing the separation and isolation of specific bioaromatic compounds).

Dataset Information

Catalytic Hydrogenolysis of Lignin: The Influence of Minor Units and Saccharides.

Publications

Catalytic Hydrogenolysis of Lignin: The Influence of Minor Units and Saccharides.

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