Role of peracetic acid on the disruption of lignin packing structure and its consequence on lignin depolymerisation

Ruoshui Ma; Udishnu Sanyal; Mariefel V. Olarte; Heather M. Job; Marie S. Swita; Susanne B. Jones; Pimphan A. Meyer; Sarah D. Burton; John R. Cort; Mark E. Bowden; Xiaowen Chen; Michael P. Wolcott; Xiao Zhang

doi:10.1039/D1GC02300D

Role of peracetic acid on the disruption of lignin packing structure and its consequence on lignin depolymerisation†

Ruoshui Ma,‡^a Udishnu Sanyal,‡^bc Mariefel V. Olarte,

*^ad Heather M. Job,^a Marie S. Swita,^a Susanne B. Jones,^a Pimphan A. Meyer,^a Sarah D. Burton,^e John R. Cort,

^ef Mark E. Bowden,

^e Xiaowen Chen,^g Michael P. Wolcott

^h and Xiao Zhang

*^ac

Author affiliations

* Corresponding authors

^a Energy and Environment Directorate, Pacific Northwest National Laboratory, 902 Battelle Boulevard, Richland, WA 99354, USA
E-mail: mariefel.olarte@pnnl.gov, xiao.zhang1@pnnl.gov

^b Physical and Computational Sciences Directorate, Pacific Northwest National Laboratory, 902 Battelle Boulevard, Richland, WA 99354, USA

^c Voiland School of Chemical Engineering & Bioengineering, Washington State University, Richland, WA, 99354, USA
E-mail: x.zhang@wsu.edu

^d Biological Systems Engineering, Washington State University, Pullman, WA 99164, USA

^e Earth and Biological Sciences Directorate, Pacific Northwest National Laboratory, 902 Battelle Boulevard, Richland, WA 99354, USA

^f Institute of Biological Chemistry, Washington State University, Pullman, WA 99164, USA

^g National Bioenergy Centre, National Renewable Energy Lab, Golden, CO 80127, USA

^h Composite Materials Engineering Centre, Washington State University, Pullman, WA 99164, USA

Abstract

Peracetic acid (PAA) is an effective oxidant capable of solubilising lignin and efficiently depolymerising it to selective phenolic compounds; however, the specific role by which PAA initiates the depolymerisation is still elusive. Herein, interaction between PAA and the lignin macromolecule and the consequent structural changes of the latter were studied by characterising the lignin packing structure and its associated changes during the oxidation process. While the lignin packing structure and its changes associated with the PAA-mediated oxidation were probed by X-ray diffraction, the impact of the PAA on different chemical functionalities present in the lignin structure was established by ¹³C and ¹H–¹³C heteronuclear single-quantum coherence nuclear magnetic resonance (NMR) spectroscopy. Combining the NMR spectroscopy results, and the product distribution, we conclude that the predominant reaction pathway for the oxidative depolymerisation of lignin with PAA is the Baeyer–Villiger oxidation of the ketone formed by the oxidation of the benzylic hydroxyl group adjacent to the β-O-4 linkage. The experimental evidence provided herein corroborated that PAA instigates oxygen insertion to the lignin macromolecule resulting in disruption of its packing structures and facilitates depolymerisation. We also investigated various metal oxide and mixed metal oxide catalysts to identify effective catalysts that further enhance the efficiency of PAA-mediated depolymerisation of lignin and produce selective monomeric phenolic compounds. Techno-economic analysis was also conducted to identify the key parameters associated with this oxidative process that need to be considered for possible commercial application.

Green Chemistry

Role of peracetic acid on the disruption of lignin packing structure and its consequence on lignin depolymerisation†

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Role of peracetic acid on the disruption of lignin packing structure and its consequence on lignin depolymerisation

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