Enzymatic hydrolysis lignin dissolution and low-temperature solvolysis in ethylene glycol

Yushuai Sang; Yuhan Ma; Gen Li; Kai Cui; Mingze Yang; Hong Chen; Yongdan Li

doi:10.1016/j.cej.2023.142256

Enzymatic hydrolysis lignin dissolution and low-temperature solvolysis in ethylene glycol

Yushuai Sang, Yuhan Ma, Gen Li, Kai Cui, Mingze Yang, Hong Chen, Yongdan Li^*

^*Corresponding author for this work

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Abstract

The dissolution and solvolysis processes of enzymatic hydrolysis lignin (EHL) in ethylene glycol are investigated. Ethylene glycol exhibits high EHL solubility and achieves complete EHL dissolution at room temperature. Gaussian simulation reveals that van de Waals interactions between ethylene glycol and EHL, including C-H⋯O and lone pair⋯π interactions, break the π-π stacking in EHL, achieving complete EHL dissolution. EHL is partly depolymerized in ethylene glycol at 200 °C even without a catalyst due to the strong van de Waals interactions. When NaOH and Ni are used as co-catalysts, EHL is efficiently depolymerized at 200 °C, and the overall monomer yield reaches 18.8 wt%. Fourier transform infrared spectroscopy (FT-IR) and molecular dynamics simulation results indicate that the adsorption of ethylene glycol over Ni surface hinders the adsorption of lignin fragments and monomers. Hence, EHL catalytic solvolysis in ethylene glycol occurs in the liquid phase, where OH⁻ of NaOH promotes the EHL linkage breakage and active hydrogen atoms formed on Ni surface stabilize the active monomers.

Original language	English
Article number	142256
Number of pages	11
Journal	Chemical Engineering Journal
Volume	463
Early online date	16 Mar 2023
DOIs	https://doi.org/10.1016/j.cej.2023.142256
Publication status	Published - 1 May 2023
MoE publication type	A1 Journal article-refereed

Keywords

Catalysis
Dissolution
Ethylene glycol
Lignin
Solvolysis

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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title = "Enzymatic hydrolysis lignin dissolution and low-temperature solvolysis in ethylene glycol",

abstract = "The dissolution and solvolysis processes of enzymatic hydrolysis lignin (EHL) in ethylene glycol are investigated. Ethylene glycol exhibits high EHL solubility and achieves complete EHL dissolution at room temperature. Gaussian simulation reveals that van de Waals interactions between ethylene glycol and EHL, including C-H⋯O and lone pair⋯π interactions, break the π-π stacking in EHL, achieving complete EHL dissolution. EHL is partly depolymerized in ethylene glycol at 200 °C even without a catalyst due to the strong van de Waals interactions. When NaOH and Ni are used as co-catalysts, EHL is efficiently depolymerized at 200 °C, and the overall monomer yield reaches 18.8 wt%. Fourier transform infrared spectroscopy (FT-IR) and molecular dynamics simulation results indicate that the adsorption of ethylene glycol over Ni surface hinders the adsorption of lignin fragments and monomers. Hence, EHL catalytic solvolysis in ethylene glycol occurs in the liquid phase, where OH− of NaOH promotes the EHL linkage breakage and active hydrogen atoms formed on Ni surface stabilize the active monomers.",

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author = "Yushuai Sang and Yuhan Ma and Gen Li and Kai Cui and Mingze Yang and Hong Chen and Yongdan Li",

note = "| openaire: EC/H2020/101006744/EU//EHLCATHOL Funding Information: This work has received funding from the European Union{\textquoteright}s Horizon 2020 research and innovation program , (BUILDING A LOW-CARBON, CLIMATE RESILIENT FUTURE: SECURE, CLEAN AND EFFICIENT EN-ERGY) under Grant Agreement No 101006744. The content presented in this document represents the views of the authors, and the European Commission has no liability in respect of the content. Y.S. Sang and G. Li would like to express their gratitude to both the China Scholarship Council ( 202006250156 , 202208320030 ) and the EU-101006744 project. Publisher Copyright: {\textcopyright} 2023 The Author(s)",

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AU - Cui, Kai

AU - Yang, Mingze

AU - Chen, Hong

AU - Li, Yongdan

N1 - | openaire: EC/H2020/101006744/EU//EHLCATHOL Funding Information: This work has received funding from the European Union’s Horizon 2020 research and innovation program , (BUILDING A LOW-CARBON, CLIMATE RESILIENT FUTURE: SECURE, CLEAN AND EFFICIENT EN-ERGY) under Grant Agreement No 101006744. The content presented in this document represents the views of the authors, and the European Commission has no liability in respect of the content. Y.S. Sang and G. Li would like to express their gratitude to both the China Scholarship Council ( 202006250156 , 202208320030 ) and the EU-101006744 project. Publisher Copyright: © 2023 The Author(s)

PY - 2023/5/1

Y1 - 2023/5/1

N2 - The dissolution and solvolysis processes of enzymatic hydrolysis lignin (EHL) in ethylene glycol are investigated. Ethylene glycol exhibits high EHL solubility and achieves complete EHL dissolution at room temperature. Gaussian simulation reveals that van de Waals interactions between ethylene glycol and EHL, including C-H⋯O and lone pair⋯π interactions, break the π-π stacking in EHL, achieving complete EHL dissolution. EHL is partly depolymerized in ethylene glycol at 200 °C even without a catalyst due to the strong van de Waals interactions. When NaOH and Ni are used as co-catalysts, EHL is efficiently depolymerized at 200 °C, and the overall monomer yield reaches 18.8 wt%. Fourier transform infrared spectroscopy (FT-IR) and molecular dynamics simulation results indicate that the adsorption of ethylene glycol over Ni surface hinders the adsorption of lignin fragments and monomers. Hence, EHL catalytic solvolysis in ethylene glycol occurs in the liquid phase, where OH− of NaOH promotes the EHL linkage breakage and active hydrogen atoms formed on Ni surface stabilize the active monomers.

AB - The dissolution and solvolysis processes of enzymatic hydrolysis lignin (EHL) in ethylene glycol are investigated. Ethylene glycol exhibits high EHL solubility and achieves complete EHL dissolution at room temperature. Gaussian simulation reveals that van de Waals interactions between ethylene glycol and EHL, including C-H⋯O and lone pair⋯π interactions, break the π-π stacking in EHL, achieving complete EHL dissolution. EHL is partly depolymerized in ethylene glycol at 200 °C even without a catalyst due to the strong van de Waals interactions. When NaOH and Ni are used as co-catalysts, EHL is efficiently depolymerized at 200 °C, and the overall monomer yield reaches 18.8 wt%. Fourier transform infrared spectroscopy (FT-IR) and molecular dynamics simulation results indicate that the adsorption of ethylene glycol over Ni surface hinders the adsorption of lignin fragments and monomers. Hence, EHL catalytic solvolysis in ethylene glycol occurs in the liquid phase, where OH− of NaOH promotes the EHL linkage breakage and active hydrogen atoms formed on Ni surface stabilize the active monomers.

KW - Catalysis

KW - Dissolution

KW - Ethylene glycol

KW - Lignin

KW - Solvolysis

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VL - 463

JO - Chemical Engineering Journal

JF - Chemical Engineering Journal

M1 - 142256

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Enzymatic hydrolysis lignin dissolution and low-temperature solvolysis in ethylene glycol

Abstract

Keywords

UN SDGs

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EHLCATHOL: Chemical transformation of enzymatic hydrolysis lignin (EHL) with catalytic solvolysis to fuel commodities under mild conditions

New Findings from Aalto University in the Area of Chemicals and Chemistry Described (Enzymatic Hydrolysis Lignin Dissolution and Low-temperature Solvolysis In Ethylene Glycol)

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Enzymatic hydrolysis lignin dissolution and low-temperature solvolysis in ethylene glycol

Abstract

Keywords

UN SDGs

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EHLCATHOL: Chemical transformation of enzymatic hydrolysis lignin (EHL) with catalytic solvolysis to fuel commodities under mild conditions

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New Findings from Aalto University in the Area of Chemicals and Chemistry Described (Enzymatic Hydrolysis Lignin Dissolution and Low-temperature Solvolysis In Ethylene Glycol)

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