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Preparation of Nitriles01:12

Preparation of Nitriles

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One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
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Nitriles to Ketones: Grignard Reaction00:57

Nitriles to Ketones: Grignard Reaction

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Organomagnesium halides, commonly known as Grignard reagents, convert nitriles to ketones and proceed through a nucleophilic acyl substitution. Nitriles react with a Grignard reagent, followed by an aqueous acid, to yield ketones. The reaction introduces a new carbon–carbon bond. The alkyl–magnesium bond in the Grignard reagent is highly polar, so the alkyl carbon develops a carbanionic character and acts as a nucleophile.
The mechanism begins with a nucleophilic attack by the Grignard...
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Interfacial Electrochemical Methods: Overview01:06

Interfacial Electrochemical Methods: Overview

720
Interfacial electrochemical methods focus on the phenomena occurring at the boundary between an electrode and a solution, as opposed to bulk methods that concentrate on the solution's overall properties. These interfacial methods are classified as either static or dynamic based on the presence of a nonzero current in the electrochemical cell and the consistency of analyte concentrations. Static methods, such as potentiometry, measure the cell's potential without any significant current...
720
Nitriles to Carboxylic Acids: Hydrolysis01:08

Nitriles to Carboxylic Acids: Hydrolysis

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Nitriles undergo acid-catalyzed hydrolysis or base-catalyzed hydrolysis to form a carboxylic acid. These reactions proceed via an amide intermediate.
4.8K
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

4.4K
Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
4.4K
Controlled-Potential Coulometry: Electrolytic Methods01:17

Controlled-Potential Coulometry: Electrolytic Methods

555
Controlled-potential coulometry, also known as potentiostatic coulometry, employs a three-electrode system in which the working electrode's potential is precisely regulated using a potentiostat. Platinum working electrodes are utilized for positive potentials, while mercury pool electrodes are favored for extremely negative potentials. The platinum counter electrode is separated from the analyte using a membrane or salt bridge to avoid interference in the analysis.
The chosen potential...
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Toward adequate control of internal interfaces utilizing nitrile-based electrolytes.

C H Krause1, P Röring2, S Röser1

  • 1MEET Battery Research Center, University of Münster, Corrensstrasse 46, 48149 Münster, Germany.

The Journal of Chemical Physics
|May 10, 2020
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Summary

New nitrile-based electrolytes effectively protect lithium-ion battery interfaces by suppressing aluminum dissolution. These formulations offer enhanced stability and performance in full cells compared to traditional electrolytes.

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Area of Science:

  • Electrochemistry
  • Materials Science
  • Energy Storage

Background:

  • Controlling internal interfaces in lithium-ion batteries is crucial for performance and longevity.
  • Current methods for interface control, such as coating deposition, are often complex and difficult to implement.
  • Parasitic reactions at the current collector interface pose a significant challenge for battery stability.

Purpose of the Study:

  • To introduce novel electrolyte formulations for effective control of internal interfaces in lithium-ion batteries.
  • To suppress aluminum dissolution and protect current collector interfaces under application-relevant conditions.
  • To evaluate the performance and stability of these new electrolytes.

Main Methods:

  • Development of electrolyte formulations based on aliphatic cyclic nitriles: cyclopentane-1-carbonitrile and cyclohexane-1-carbonitrile.
  • Testing of these nitrile-based electrolytes in lithium nickel-manganese-cobalt oxide (LiNi3/5Mn1/5Co1/5O2, NMC622)||graphite full cells.
  • Comparison of performance metrics, including capacity retention, oxidative stability, and thermal stability, against state-of-the-art organic carbonate-based electrolytes.

Main Results:

  • Nitrile-based electrolytes successfully suppressed aluminum dissolution and controlled internal interfaces.
  • These electrolytes exhibited higher intrinsic oxidative and thermal stabilities.
  • Similar capacity retentions were observed in NMC622||graphite full cells compared to conventional electrolytes, even with lithium bis(trifluoro-methane)sulfonimide salt.
  • The study highlighted the role of relative permittivity, ion dissociation, and viscosity in protecting current collector interfaces.

Conclusions:

  • Aliphatic cyclic nitrile-based electrolytes offer a promising alternative for enhancing lithium-ion battery stability.
  • These electrolytes provide effective protection against aluminum dissolution and parasitic reactions at current collector interfaces.
  • Electrolyte properties like permittivity, ion dissociation, and viscosity are critical factors for interface management in batteries.