On the product selectivity in the electrochemical reductive cleavage of 2-phenoxyacetophenone, a lignin model compound

Cruz, Márcia G.A.; Rodrigues, Bruno V. M.; Ristić, Andjelka; Budnyk, Serhiy; Das, Shoubhik; Slabon, Adam

doi:10.1080/17518253.2022.2025462

Cited by 16 publications

(30 citation statements)

References 45 publications

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“…The effect of reactor type (single-cell vs. divided cell) on the electrocatalytic reductive cleavage of β-O-4 lignin model compound, 2-phenoxyacetophenone, was evaluated in the presence of DES (ethylene glycol and choline chloride in a 2:1 ratio with 10% water) at a Cu electrode [ 101 ]. Different monomers and oligomers were obtained depending on the type of reactor used, a higher number of carbonyl compounds was observed in the divided cell while hydroxyl-end products were obtained in a single cell.…”

Section: Electrocatalytic Cleavage Of Model Compoundsmentioning

confidence: 99%

High-Value Chemicals from Electrocatalytic Depolymerization of Lignin: Challenges and Opportunities

Ayub¹,

Raheel

2022

IJMS

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Lignocellulosic biomass is renewable and one of the most abundant sources for the production of high-value chemicals, materials, and fuels. It is of immense importance to develop new efficient technologies for the industrial production of chemicals by utilizing renewable resources. Lignocellulosic biomass can potentially replace fossil-based chemistries. The production of fuel and chemicals from lignin powered by renewable electricity under ambient temperatures and pressures enables a more sustainable way to obtain high-value chemicals. More specifically, in a sustainable biorefinery, it is essential to valorize lignin to enhance biomass transformation technology and increase the overall economy of the process. Strategies regarding electrocatalytic approaches as a way to valorize or depolymerize lignin have attracted significant interest from growing scientific communities over the recent decades. This review presents a comprehensive overview of the electrocatalytic methods for depolymerization of lignocellulosic biomass with an emphasis on untargeted depolymerization as well as the selective and targeted mild synthesis of high-value chemicals. Electrocatalytic cleavage of model compounds and further electrochemical upgrading of bio-oils are discussed. Finally, some insights into current challenges and limitations associated with this approach are also summarized.

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Section: Electrocatalytic Cleavage Of Model Compoundsmentioning

confidence: 99%

High-Value Chemicals from Electrocatalytic Depolymerization of Lignin: Challenges and Opportunities

Ayub¹,

Raheel

2022

IJMS

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“…[8] In this framework, technical lignins find a prominent space as potential resources to produce aromatic chemicals and phenolic-containing macromolecules. [9][10][11][12][13][14] The lignin macromolecule, often referred to as a polymer (or biopolymer), can be successively broken (or "depolymerized") to generate high value-added products. [9,10] This depolymerization process has represented a challenge since the 1930s, when the first findings in the field were published.…”

Section: Introductionmentioning

confidence: 99%

“…[9][10][11][12][13][14] The lignin macromolecule, often referred to as a polymer (or biopolymer), can be successively broken (or "depolymerized") to generate high value-added products. [9,10] This depolymerization process has represented a challenge since the 1930s, when the first findings in the field were published. [9,12] Given its heterogeneous nature, a wide range of phenolic-containing polymers and aromatic compounds can be obtained via lignin depolymerization.…”

Section: Introductionmentioning

confidence: 99%

“…[16] Among different catalytic approaches, electrocatalysis (EC) has found a prominent space due to a better integration with the principles of green chemistry. [10,17,18] Furthermore, while being possible to control cell potential, EC enhances the catalyst selectivity and activity and allows for the use of mild reaction conditions, such as room temperature and green solvents. [9,19,20] Due to the possibility of carbonylation of α-hydroxy groups present in the lignin chain (Figure 1), electrocatalytic oxidation (ECO) is currently the most reported approach for lignin depolymerization.…”

Section: Introductionmentioning

confidence: 99%

“…[24] Conversely, electrocatalytic hydrogenation (ECH) appears as an alternative to the thermal catalytic hydrogenation, while generating final products with reduced oxygen content. [10,25] Ideally, the complete reduction of the oxygenated carbonylic groups would be advantageous towards the production of bio-fuels. However, when reacted in open cell, the ECH is exposed to oxygenated products generated on the anodic surface of the counter electrode.…”

Section: Introductionmentioning

confidence: 99%

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Electrochemical Depolymerization of Lignin in a Biomass‐based Solvent**

et al. 2022

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Breaking down lignin into smaller units is the key to generate high value‐added products. Nevertheless, dissolving this complex plant polyphenol in an environment‐friendly way is often a challenge. Levulinic acid, which is formed during the hydrothermal processing of lignocellulosic biomass, has been shown to efficiently dissolve lignin. Herein, levulinic acid was evaluated as a medium for the reductive electrochemical depolymerization of the lignin macromolecule. Copper was chosen as the electrocatalyst due to the economic feasibility and low activity towards the hydrogen evolution reaction. After depolymerization, high‐resolution mass spectrometry and nuclear magnetic resonance spectroscopy revealed lignin‐derived monomers and dimers. A predominance of aryl ether and phenolic groups was observed. Depolymerized lignin was further evaluated as an anti‐corrosion coating, revealing enhancements on the electrochemical stability of the metal. Via a simple depolymerization process of biomass waste in a biomass‐based solvent, a straightforward approach to produce high value‐added compounds or tailored biobased materials was demonstrated.

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Sustainable Routes for the Depolymerization of Lignocellulosic Biomass

Lindenbeck,

Liu,

Beele

et al. 2023

Encyclopedia of Inorganic and Bioinorganic Chemistry

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Lignocellulosic biomass is the world largest renewable resource used as a raw material to produce high‐value‐added chemicals, such as biofuels and other biomaterials. However, the complex chemical structures of its main constituents, named cellulose, hemicelluloses, and lignin, pose a challenge to the breakdown of these biopolymers into smaller units. In this scenario, sustainable methods for the depolymerization of lignocellulosic biomass aim to chemically break these macromolecules into simple monomers and dimers, while minimizing the use of hazardous chemicals and energy‐intensive processes. Different depolymerization strategies have been proposed, including enzymatic, electrochemical, acid‐catalyzed, and solvent‐based methods. Nevertheless, the development and improvement of sustainable approaches toward depolymerization technologies is still ongoing, and there is still room for further research to optimize the efficiency, cost‐effectiveness, and scalability of the processes. While the successful depolymerization of biomass may significantly contribute to the transition to a more sustainable and environmentally friendly economy, this article outlines the most recent developments focusing on the particularities of these processes, including biological, electrochemical, thermal, and chemical methods.

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On the product selectivity in the electrochemical reductive cleavage of 2-phenoxyacetophenone, a lignin model compound

Cited by 16 publications

References 45 publications

High-Value Chemicals from Electrocatalytic Depolymerization of Lignin: Challenges and Opportunities

High-Value Chemicals from Electrocatalytic Depolymerization of Lignin: Challenges and Opportunities

Electrochemical Depolymerization of Lignin in a Biomass‐based Solvent**

Sustainable Routes for the Depolymerization of Lignocellulosic Biomass

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