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Molecules 2014, 19(12), 21335-21349; doi:10.3390/molecules191221335

Lignin Hydrolysis and Phosphorylation Mechanism during Phosphoric Acid–Acetone Pretreatment: A DFT Study

National Engineering Laboratory for Biomass Power Generation Equipment, School of Renewable Energy Engineering, North China Electric Power University, Beijing 102206, China
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Received: 11 October 2014 / Revised: 7 December 2014 / Accepted: 8 December 2014 / Published: 18 December 2014
(This article belongs to the Section Medicinal Chemistry)
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Abstract

The study focused on the structural sensitivity of lignin during the phosphoric acid–acetone pretreatment process and the resulting hydrolysis and phosphorylation reaction mechanisms using density functional theory calculations. The chemical stabilities of the seven most common linkages (β-O-4, β-β, 4-O-5, β-1, 5-5, α-O-4, and β-5) of lignin in H3PO4, CH3COCH3, and H2O solutions were detected, which shows that α-O-4 linkage and β-O-4 linkage tend to break during the phosphoric acid–acetone pretreatment process. Then α-O-4 phosphorylation and β-O-4 phosphorylation follow a two-step reaction mechanism in the acid treatment step, respectively. However, since phosphorylation of α-O-4 is more energetically accessible than phosphorylation of β-O-4 in phosphoric acid, the phosphorylation of α-O-4 could be controllably realized under certain operational conditions, which could tune the electron and hole transfer on the right side of β-O-4 in the H2PO4 functionalized lignin. The results provide a fundamental understanding for process-controlled modification of lignin and the potential novel applications in lignin-based imprinted polymers, sensors, and molecular devices. View Full-Text
Keywords: lignin; lignocellulose; biomass; pretreatment; DFT lignin; lignocellulose; biomass; pretreatment; DFT
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Qin, W.; Wu, L.; Zheng, Z.; Dong, C.; Yang, Y. Lignin Hydrolysis and Phosphorylation Mechanism during Phosphoric Acid–Acetone Pretreatment: A DFT Study. Molecules 2014, 19, 21335-21349.

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