A solid acid-catalyzed depolymerization of pine lignin to obtain guaiacol using a hydrogen-free strategy

Li, Zhuang; Bai, Xiang; Wei, Xian‐Yong; Dilixiati, Yierxiati; Fan, Zi-Chun; Kong, Qianqian; Li, Li; Li, Jiahao; Lu, Kun-Lang; Zhao, Ji; Zhang, Xiaoqi; Zong, Zhi‐Min; Bai, Hongcun

doi:10.1016/j.fuproc.2023.107843

Cited by 9 publications

(2 citation statements)

References 52 publications

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“…35,36 Our group found that C ar −C α bond cleavage can be effectively promoted by changing the binding environment around the C α site. 37 Takashi et al 38 found that various acyl aromatics could be selectively deacetylated to aromatics with catalytic amounts of trifluoromethanesulfonic acid (TFMSA) under heated reflux in 1,2-dichloroethane (DCE) containing a small amount of water. However, the difficulty of recycling and environmental pollution constrain the utilization of homogeneous catalysts.…”

Section: Introductionmentioning

confidence: 99%

“…It has been demonstrated that the electronic structure of Ni-based catalysts can be modulated by doping with a second reactive metal or carbon modification to regulate reactivity. , Wang et al showed that the carbon-modified Ni/MgAlO-C catalyst exhibits high selectivity in C–O bond hydrogenolysis of oxidized lignin and aromatic compounds containing ketone groups. Depolymerization of lignin by this strategy usually yields phenolic monomers containing acyl groups. , Our group found that C ar –C α bond cleavage can be effectively promoted by changing the binding environment around the C α site . Takashi et al found that various acyl aromatics could be selectively deacetylated to aromatics with catalytic amounts of trifluoromethanesulfonic acid (TFMSA) under heated reflux in 1,2-dichloroethane (DCE) containing a small amount of water.…”

Section: Introductionmentioning

confidence: 99%

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A Strategy to Obtain Lignin-Based Alkyl-Free Phenols under Mild Conditions: Condensation Inhibition and C_ar–C_α Bond Cleavage

Li,

Fan,

Bai

et al. 2024

ACS Sustainable Chem. Eng.

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The production of alkyl-free phenols (AFPs) from lignin can reduce dependence on fossil sources. Depolymerization (C alk −O bond cleavage) and dealkylation (C ar −C α bond cleavage) are two important steps from lignin to AFPs. Condensation of lignin fragments during depolymerization and harsh reaction conditions during dealkylation have been challenging. Here, we report a selective oxidation−hydrogenolysis−deacylation strategy. The C α H−OH in the β-O-4 structure is oxidized to C α �O by a preoxidation step, and then the phenolic monomers with acyl groups are obtained by hydrogenolysis over Ni-based catalysts and finally by acid-catalyzed deacylation to give AFPs. This strategy achieves effective cleavage of the C ar −C α bond under mild conditions while avoiding condensation. The AFP yield from β-O-4-hydroxy polymers exceeds 87%. Compared to oxidized lignin, the AFP yield reaches 8.8 wt % under optimized conditions. The C ar −C α bond cleavage and condensation reaction pathways were proposed by a combination of controlled experiments and density functional theory studies. This work provides a new route and theoretical support for the conversion of lignin to AFPs.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

A Strategy to Obtain Lignin-Based Alkyl-Free Phenols under Mild Conditions: Condensation Inhibition and C_ar–C_α Bond Cleavage

Li,

Fan,

Bai

et al. 2024

ACS Sustainable Chem. Eng.

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Synthesis of Vanillin and Guaiacol through [Hmim]Tf2N Ionic Liquid Catalyzed Lignin‐Directed Pyrolysis at Low Temperature and Voltage

Qu,

Zhang,

et al. 2024

ChemistrySelect

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Significant attention has been devoted to using biomass as a renewable resource to address the energy crisis and mitigate environmental pollution. Biomass, a potential substitute for fossil fuels, contains a substantial amount of lignin, ranging from 10 % to 25 %. Hence, it is crucial to research lignin depolymerization. In this study, the use of electrochemically catalyzed ionic liquids enabled the cracking of lignin at low temperatures. Specifically, by applying a low voltage at 230 °C, the controlled generation of vanillin and guaiacol was achieved. The concentration of vanillin in the depolymerized lignin reached 88.54 % under 3 V conditions. Similarly, it is presumed that the yield of guaiacol at 4 V is 48.24 %. These findings have significant implications for the targeted management of lignin depolymerization byproducts. Ultimately, this project establishes a framework for the high‐value utilization of biomass and provides new perspectives on addressing the energy problem and environmental degradation.

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Cascade of Acid Sites and Oxygen Vacancy in Mo/Ga@ZSM-11 for Efficient Cracking of Lignin to Produce Alkylphenol

Shi,

Lu,

Xia

et al. 2025

Applied Catalysis B: Environment and Energy

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A solid acid-catalyzed depolymerization of pine lignin to obtain guaiacol using a hydrogen-free strategy

Cited by 9 publications

References 52 publications

A Strategy to Obtain Lignin-Based Alkyl-Free Phenols under Mild Conditions: Condensation Inhibition and C_ar–C_α Bond Cleavage

A Strategy to Obtain Lignin-Based Alkyl-Free Phenols under Mild Conditions: Condensation Inhibition and C_ar–C_α Bond Cleavage

Synthesis of Vanillin and Guaiacol through [Hmim]Tf2N Ionic Liquid Catalyzed Lignin‐Directed Pyrolysis at Low Temperature and Voltage

Cascade of Acid Sites and Oxygen Vacancy in Mo/Ga@ZSM-11 for Efficient Cracking of Lignin to Produce Alkylphenol

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A solid acid-catalyzed depolymerization of pine lignin to obtain guaiacol using a hydrogen-free strategy

Cited by 9 publications

References 52 publications

A Strategy to Obtain Lignin-Based Alkyl-Free Phenols under Mild Conditions: Condensation Inhibition and Car–Cα Bond Cleavage

A Strategy to Obtain Lignin-Based Alkyl-Free Phenols under Mild Conditions: Condensation Inhibition and Car–Cα Bond Cleavage

Synthesis of Vanillin and Guaiacol through [Hmim]Tf2N Ionic Liquid Catalyzed Lignin‐Directed Pyrolysis at Low Temperature and Voltage

Cascade of Acid Sites and Oxygen Vacancy in Mo/Ga@ZSM-11 for Efficient Cracking of Lignin to Produce Alkylphenol

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A Strategy to Obtain Lignin-Based Alkyl-Free Phenols under Mild Conditions: Condensation Inhibition and C_ar–C_α Bond Cleavage

A Strategy to Obtain Lignin-Based Alkyl-Free Phenols under Mild Conditions: Condensation Inhibition and C_ar–C_α Bond Cleavage