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Isolation of Functionalized Phenolic Monomers through Selective Oxidation and CO Bond Cleavage of the β‐O‐4 Linkages in Lignin
Abstract
Functionalized phenolic monomers have been generated and isolated from an organosolv lignin through a two‐step depolymerization process. Chemoselective catalytic oxidation of β‐O‐4 linkages promoted by the DDQ/t BuONO/O 2 system was achieved in model compounds, including polymeric models and in real lignin. The oxidized β‐O‐4 linkages were then cleaved on reaction with zinc. Compared to many existing methods, this protocol, which can be achieved in one pot, is highly selective, giving rise to a simple mixture of products that can be readily purified to give pure compounds. The functionality present in these products makes them potentially valuable building blocks.
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Cites
The Catalytic Valorization of Lignin for the Production of Renewable Chemicals
Zakzeski, J., Bruijnincx, P. C. A., Jongerius, A. L., & Weckhuysen, B. M. (2010) · Chemical Reviews · doi:10.1021/cr900354u · Cited by 4,468
FitzPatrick, M., Champagne, P., Cunningham, M. F., & Whitney, R. A. (2010) · Bioresource Technology · doi:10.1016/j.biortech.2010.06.125 · Cited by 810
Cited by
Catalytic Transformation of Lignin for the Production of Chemicals and Fuels
Li, C., Zhao, X., Wang, A., Huber, G. W., & Zhang, T. (2015) · Chemical Reviews · doi:10.1021/acs.chemrev.5b00155 · Cited by 2,951
Catalytic conversion of lignocellulosic biomass into chemicals and fuels
Deng, W., Feng, Y., Fu, J., Guo, H., Guo, Y., Han, B., Jiang, Z., Kong, L., Li, C., Liu, H., et al. (2023) · Green Energy & Environment · doi:10.1016/j.gee.2022.07.003 · Cited by 854
Wu, X., Fan, X., Xie, S., Lin, J., Cheng, J., Zhang, Q., Chen, L., & Wang, Y. (2018) · Nature Catalysis · doi:10.1038/s41929-018-0148-8 · Cited by 649
Selective production of arenes via direct lignin upgrading over a niobium-based catalyst
Shao, Y., Xia, Q., Dong, L., Liu, X., Han, X., Parker, S. F., Cheng, Y., Daemen, L. L., Ramirez-Cuesta, A. J., Yang, S., et al. (2017) · Nature Communications · doi:10.1038/ncomms16104 · Cited by 506
Redox Catalysis Facilitates Lignin Depolymerization
Bosque, I., Magallanes, G., Rigoulet, M., Kärkäs, M. D., & Stephenson, C. R. J. (2017) · ACS Central Science · doi:10.1021/acscentsci.7b00140 · Cited by 293
Metadata
- Authors
- Lancefield, C. S., Ojo, O. S., Tran, F., & Westwood, N. J.
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2014-11-05
- Volume
- 54
- Issue
- 1
- Pages
- 258-262
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- OpenAlex
- W2116189397
- Cited by
- 474
- References
- 2
- FWCI
- 18.04
- Type
- journal article
- Language
- en
- Open access
- closed
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- Lancefield, C. S., Ojo, O. S., Tran, F., & Westwood, N. J. (2015). Isolation of Functionalized Phenolic Monomers through Selective Oxidation and CO Bond Cleavage of the β‐O‐4 Linkages in Lignin. Angewandte Chemie International Edition. https://doi.org/10.1002/anie.201409408
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