Mechanistic implications of zinc(II) ions on the degradation of phenol by the fenton reaction

Friedrich, Leidi Cecília; Mendes, Maria Anita; Silva, Volnir O.; Zanta, Carmem Lúcia de Paiva e Silva; Machulek, Amílcar; Quina, Frank H.

doi:10.1590/s0103-50532012000700022

Cited by 33 publications

(12 citation statements)

References 17 publications

(16 reference statements)

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“…It is also known that while quinones are reduced may cause oxidation of other molecules involved in the redox cycle like other 1,2-DHB (107,108) . The quinones can also be oxidized to CO 2 while reducing Fe 3+ (109) (110,111) .…”

Section: Dhb Driven Fenton Reactionmentioning

confidence: 99%

Fenton Reaction Driven by Iron Ligands

Salgado

Melín

Contreras

et al. 2013

J. Chil. Chem. Soc.

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One of the most important sources of reactive oxygen species (ROS) in biological systems is the Fenton reaction. In this, the Fe 2+ or Fe 3+ reacts with H 2 O 2 to produce ROS as the hydroxyl radical (•OH), superoxide radical (O 2 •-) and singlet oxygen ( 1 O 2 ). The main ROS, responsible for the high oxidizing power of the Fenton reaction, is not clear. Some authors claim that the principal reactive species is •OH, while others propose a ferryl specie (Fe 4+ or [FeO] 2+ ) (1,2) . Recently, have been proposed that the kind of reaction species produced depends mainly of pH and the iron composition of the coordination sphere. This is highlighted for Fe 3+ , because in mono and (some) bis-complexes Fe 3+ is reduced to Fe 2+ and there are some positions occupied by water or hydroxide ligands, readily to be exchanged by H 2 O 2 . On the other hand, in tris-complexes there are not any positions occupied by water or hydroxide, avoiding the formation of peroxo-complexes, necessary for Fenton or Fenton like reaction.The 1,2-dihydroxybenzenes (DHBs) have been described as modulators of Fenton reaction. The DHBs driven Fenton reaction have been used for environmental applications as an advanced oxidation process. Furthermore, these systems participate in different biological process, as the wood biodegradation by fungi and oxidative stress in neurodegenerative diseases.In this review, the effect of 1,2-dihydroxybenzenes on the activated species production by the Fenton and Fenton like reaction will be discussed and its participation in different systems.

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Section: Dhb Driven Fenton Reactionmentioning

confidence: 99%

Fenton Reaction Driven by Iron Ligands

Salgado

Melín

Contreras

et al. 2013

J. Chil. Chem. Soc.

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“…Additionally, oxygen produced at the anode via water electrolysis can further react at the cathode and be reduced to hydrogen peroxide that decomposes into a series of reactive oxygen species . Electrochemical cleavage of aromatic monomers and dimers has been widely investigated and many chemical oxidation paths have been suggested, showing the production of dicarboxylic acids such as maleic,, fumaric, oxalic acid and ultimately carbon dioxide …”

Section: Introductionmentioning

confidence: 99%

Carboxylic Acids Production via Electrochemical Depolymerization of Lignin

Marino¹,

Jestel²,

Marks³

et al. 2019

ChemElectroChem

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Facing the challenge of lignin valorization is one of the unsolved key steps for a sustainable and economically feasible biorefinery. Several processes were developed with the aim of producing value-added compounds from lignin. Thermal, enzymatic, and catalytic processes represent common techniques for lignin valorization. However, expensive catalysts or enzymes and harsh conditions hampered the implementation of these methodologies on an industrial scale. Here, we propose the utilization of a simple "swiss-roll" electrochemical reactor for the production of valuable carboxylic acids. We showcase that production of phenolic compounds, such as vanillin, is hindered by the electrochemical mechanism. Additionally, electrochemical stability experiments of possible products showed high reactivity of vanillin against the low reactivity of mono-and dicarboxylic acids. Simultaneously, the electrochemical process leads to stable carboxylic acids with high yields of 6.4, 26.8, and 4.2 % for oxalic, formic, and acetic acids, respectively, thus representing a competitive alternative to the catalytic and hydrothermal degradation process for the production of carboxylic acids.

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“…This reaction may occur in a biological environment where accumulation of hydrogen peroxide is important, for example, in dopaminergic neurons of nerve tissue, where normal catabolism of dopamine produces some levels of hydrogen peroxide . An investigation of the role played by Zn 2+ ions on the phenol degradation by Fenton reaction (Fe 2+ /Fe 3+ + H 2 O 2 ) was reported by Friedrich et al The catechol‐intermediated cycle, one of the first intermediates formed in the reaction, is the principal path of thermal degradation of phenol and its oxidation products. The importance of addition of Zn 2+ ions is to enhance the persistence time of catechol, through stabilization of corresponding semiquinone radical via complexation.…”

Section: Introductionmentioning

confidence: 99%

A DFT study of molecular structure and ¹H NMR, IR, and UV‐Vis spectrum of Zn(II)‐kaempferol complexes: A metal‐flavonoid complex showing enhanced anticancer activity

Souza

Soeiro

2018

Int J of Quantum Chemistry

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The polyphenol compound Kaempferol, a relevant member of the class of flavonoids, is a good example where coordination to Zn(II) ion was found to improve the anticancer effects compared to the free ligand. Determination of the metal‐complex molecular structure (and binding sites on Kaempferol) in the liquid phase is fundamental for an understanding of biological activities. Experimental UV‐Vis and EPR data only provide indirect evidence or limited structural information. Therefore, theoretical study of structural and spectroscopic properties of the metal‐polyphenol complex, using computational quantum chemistry methods, is certainly relevant as starting point for the investigation of mechanism of action at a molecular level. In this article, we used the density functional theory (DFT) methodology to predict the molecular structure of [Zn(Kaempferol)(H2O)n]+ and [Zn(Kaempferol)2(H2O)n] complexes (n = 0, 2, or 4) and B‐ring nonplanar conformation of flavonoid using as strategy the best match between theoretical and experimental 1H NMR, IR, and UV‐Vis spectroscopic data in solution. These are valuable information for further studies involving structure‐activity relationship.

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Mechanistic implications of zinc(II) ions on the degradation of phenol by the fenton reaction

Cited by 33 publications

References 17 publications

Fenton Reaction Driven by Iron Ligands

Fenton Reaction Driven by Iron Ligands

Carboxylic Acids Production via Electrochemical Depolymerization of Lignin

A DFT study of molecular structure and ¹H NMR, IR, and UV‐Vis spectrum of Zn(II)‐kaempferol complexes: A metal‐flavonoid complex showing enhanced anticancer activity

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Mechanistic implications of zinc(II) ions on the degradation of phenol by the fenton reaction

Cited by 33 publications

References 17 publications

Fenton Reaction Driven by Iron Ligands

Fenton Reaction Driven by Iron Ligands

Carboxylic Acids Production via Electrochemical Depolymerization of Lignin

A DFT study of molecular structure and 1H NMR, IR, and UV‐Vis spectrum of Zn(II)‐kaempferol complexes: A metal‐flavonoid complex showing enhanced anticancer activity

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Product

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A DFT study of molecular structure and ¹H NMR, IR, and UV‐Vis spectrum of Zn(II)‐kaempferol complexes: A metal‐flavonoid complex showing enhanced anticancer activity