Efficient Electrooxidation of Alcohols Using TEMPO-Modified Polyaniline Electrode Prepared by Electrochemical Polymerization

Tang, Danyang; Yang, Xianjing; Chen, Qiguo; Shen, Zhenlu; Li, Meichao

doi:10.1149/2.1051605jes

Cited by 12 publications

(7 citation statements)

References 55 publications

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“…The ideology that water being utilized as a solvent during metalfree reaction conditions will be of significant interest to product decontamination giving improvement to the probabilities of inspecting the TEMPO-modified electrodes in an aqueous system, maintaining high electrocatalytic activity for oxidation of alcohol in water. [51] An environmentally benign and simple technique for benzyl alcohol oxidation in an acidic aqueous medium employing an anionic micellar system utilizing β-cyclodextrin-polypyrrole-modified carbon fiber paper (β-CD-PPy/CFP) electrode has been developed and studied. The cyclic voltammetric studies established that the β-CD-PPy modified CFP electrode displayed a strong electrocatalytic activity towards the oxida- tion of benzyl alcohol mediated via TEMPO, and this method could generate excellent yields of benzaldehyde.…”

Section: Tempo Mediated Electrochemical Oxidations Of Alcoholsmentioning

confidence: 99%

2,2,6,6‐Tetramethylpiperidinyloxyl (TEMPO) Radical Mediated Electro‐Oxidation Reactions: A Review

et al. 2021

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Over the last few decades, the interest in green and sustainable chemistry has led to the development of different synthetic methodologies which utilize clean reagents. In that direction, the electro-oxidation reactions are considered as one of the most interesting and promising methods. This is predominantly due to their environmentally benign nature, as oxidation can be achieved without the need for commonly used oxidizing agents. 2,2,6,6-Tetramethylpiperidinyloxyl radical commonly known as TEMPO is a stable aminoxyl radical utilized for the oxidation of various classes of alcohols to carbonyl compounds by using cyclic voltammetry. The present review focuses on the various electrochemical reactions utilizing TEMPO as a mediator such as the oxidative conversion of alcohols, carbohydrates, amines, sulphur-containing compounds, and alkenes in both laboratory as well as industrial scales and covers literature from 1950 till present date. The properties, reactivity, and yield percentages of these reactions would provide a basis for better electrocatalyst design in future studies involving TEMPO and its derivatives as mediators.

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Section: Tempo Mediated Electrochemical Oxidations Of Alcoholsmentioning

confidence: 99%

2,2,6,6‐Tetramethylpiperidinyloxyl (TEMPO) Radical Mediated Electro‐Oxidation Reactions: A Review

et al. 2021

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“…High selectivity and rate conversion achieved utilizing alkaline media allowed the conversion of alcohols to their specific aldehydes. 79 One of the major advantages of this study was that water as a solvent during metal-free reaction conditions will be of great benefit to product purification. This method thus gave rise to the possibilities of exploring TEMPO-modified electrodes in an aqueous system, retaining high electrocatalytic activity for alcohol oxidation in water.…”

Section: Tempo Mediated Electrocatalytic Oxidation Of Alcoholsmentioning

confidence: 99%

“…148 Different modified electrodes employed for the electrocatalytic oxidation of various alcohols shown in Table I clearly highlight that TEMPO supported catalyst system has been able to showcase ameliorated efficiency. 74,78,79,115 However, TEMPO as a homogenous system has been underutilized due to its high cost. The incorporation of various types of conducting polymers such as PPY, 74,81 PANI, 82,97,115,116,118 and PEDOT 119,126 along with nanoparticles for electrodeposition in most of the works shows their utmost importance as a type of modification which has also proved to be highly economic.…”

Section: Reduced Graphene Oxide-based Modification Of Electrodes For ...mentioning

confidence: 99%

“…Few researchers also had tried to highlight the usage of water as a solvent which was found to be more efficient, produced fewer toxic by-products, and was in-expensive. 79 The modified electrodes involved in oxidising the various types of alcohols to aldehydes with their potential scope of application is shown in Fig. 11.…”

Section: Reduced Graphene Oxide-based Modification Of Electrodes For ...mentioning

confidence: 99%

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Review—Electrocatalytic Oxidation of Alcohols Using Chemically Modified Electrodes: A Review

Rajeev

Sharma

Mathew

et al. 2020

J. Electrochem. Soc.

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Electrocatalytic oxidation of alcohols utilizing chemically modified electrodes is considered as a green and facile method. This method is also considered as a feasible solution for a "clean" and efficient energy production, is more economic and produces less toxic and minimal waste. Electrocatalytic oxidation of alcohols is of great interest as many of its products find applications in chemical, pharmaceutical, and food industries. The major classifications of chemical modification to the electrodes for electrocatalytic oxidation of alcohols discussed in this review include conducting polymers, noble metal nanoparticles, metal oxides, or metal-oxides as nanoparticles and reduced graphene oxide-based modifications. Despite its wide range of applications and environmentally benign nature, electrocatalytic oxidation of alcohols using chemically modified electrodes is underutilized, less appreciated, and still in its infancy stages. This review aims to provide the readers with an overview in the field of electrocatalytic oxidation of alcohols by incorporating two significant applications-Electroorganic conversion of alcohols to aldehydes and their applications in alcohol-based fuel cells. Further, this also presents an outlook for gaining deeper insights for making this methodology more economic, and applicable in various synthetic organic chemistry fields.

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“…However, the primary alcohols substituted with strong electron-withdrawing group, such as -nitro and some of secondary alcohols gave low product yields. Lately, we prepared a series of TEMPO-modified polymer electrodes, which could be used successfully for the selective oxidation of alcohols to aldehydes [48,49,50]. It is well known that the detailed information of the electrochemical behaviour of organic compounds is crucial for electrochemical synthesis.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical Performance of ABNO for Oxidation of Secondary Alcohols in Acetonitrile Solution

et al. 2018

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The ketones was successfully prepared from secondary alcohols using 9-azabicyclo[3.3.1]nonane-N-oxyl (ABNO) as the catalyst and 2,6-lutidine as the base in acetonitrile solution. The electrochemical activity of ABNO for oxidation of 1-phenylethanol was investigated by cyclic voltammetry, in situ Fourier transform infrared spectroscopy (FTIR) and constant current electrolysis experiments. The resulting cyclic voltammetry indicated that ABNO exhibited much higher electrochemical activity when compared with 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) under the similar conditions. A reasonable reaction mechanism of the electrocatalytic oxidation of 1-phenylethanol to acetophenone was proposed. In addition, a series of secondary alcohols could be converted to the corresponding ketones at room temperature in 80–95% isolated yields.

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Efficient Electrooxidation of Alcohols Using TEMPO-Modified Polyaniline Electrode Prepared by Electrochemical Polymerization

Cited by 12 publications

References 55 publications

2,2,6,6‐Tetramethylpiperidinyloxyl (TEMPO) Radical Mediated Electro‐Oxidation Reactions: A Review

2,2,6,6‐Tetramethylpiperidinyloxyl (TEMPO) Radical Mediated Electro‐Oxidation Reactions: A Review

Review—Electrocatalytic Oxidation of Alcohols Using Chemically Modified Electrodes: A Review

Electrochemical Performance of ABNO for Oxidation of Secondary Alcohols in Acetonitrile Solution

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