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Hydrolytic cleavage of lignin derived C-O bonds by acid/base catalysis in water

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Abstract

Hydrolytic cleavage of C–O bond was systematically studied in acidic/alkaline aqueous solution. For phenethoxybenzene (PEB) hydrolysis, 2-phenylethanol and phenol were formed as main products in AlCl3 solutions, whereas styrene was preferred with Na2CO3. After a quantitative evaluation of the kinetics of elementary steps, it was concluded that both AlCl3 and Na2CO3 promoted protons assisted C–O bond scission in H2O, whereas alkaline enhanced the dehydration of produced 2-phenylethanol. Kinetic and isotope labeling experiments demonstrated that the hydrolytic rates of PEB were first order with respect to substrate concentrations, hydrolytic cleavage of C–O bond was rate-determining step. The study shed light on the promotional effects and hydrolytic mechanism over acid/base-catalyzed lignin depolymerization in water.

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Acknowledgements

The research is supported financially by NSFC of China (22002113, 21878237, 22072057, 21703179) and the project from Wuhan Institute of Technology (K201913). The authors gratefully acknowledge funding through Science and Technology Department of Hubei Province (2020CFB198) and Wuhan Application Foundation and Frontier Project (2018010401011291).

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Authors and Affiliations

  1. Key Laboratory of Green Chemical Process of Ministry of Education, Hubei Key Laboratory of Novel Chemical Reactor and Green Chemical Technology, School of Chemical Engineering & Pharmacy, Wuhan Institute of Technology, 430073, Wuhan, P. R. China

    Wenjing Song, Mengxue Song & Xingmao Jiang

  2. National Engineering Laboratory for Green Chemical Productions of Alcohols-Ethers-Esters, College of Chemistry and Chemical Engineering, Xiamen University, 361005, Xiamen, P. R. China

    Xiaodong Yi & Weikun Lai

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  1. Wenjing Song
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  2. Mengxue Song
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  5. Weikun Lai
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Correspondence to Weikun Lai.

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Song, W., Song, M., Jiang, X. et al. Hydrolytic cleavage of lignin derived C-O bonds by acid/base catalysis in water. Reac Kinet Mech Cat 133, 371–382 (2021). https://doi.org/10.1007/s11144-021-01990-1

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  • DOI: https://doi.org/10.1007/s11144-021-01990-1

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