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Related Concept Videos

Acid Halides to Esters: Alcoholysis01:12

Acid Halides to Esters: Alcoholysis

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Alcoholysis is a nucleophilic acyl substitution reaction in which an alcohol functions as a nucleophile. Acid halides react with alcohol to produce esters. The mechanism proceeds in three steps:
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Nucleophilic Aromatic Substitution: Elimination–Addition01:11

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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
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E2 Reaction: Kinetics and Mechanism02:45

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SN2 substitutions and E2 eliminations of alkyl halides proceed via a concerted pathway. While the nucleophile attacks the alpha carbon in SN2 reactions, it functions as a strong base and abstracts a beta hydrogen in the E2 mechanism. The rate-limiting transition state in E2 elimination reactions is characterized by partially broken carbon–hydrogen and carbon–halogen bonds and a partially formed pi bond between the alpha and beta carbons. The beta hydrogen and halide are eliminated...
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High-Performance Liquid Chromatography: Elution Process01:05

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In High-Performance Liquid Chromatography (HPLC), the elution process is critical to the separation of analytes and the quality of chromatographic results. Elution describes how compounds move through the column and separate based on their interactions with the mobile and stationary phases. This process determines the resolution, peak shape, and retention times in the chromatogram, which are essential for identifying and quantifying components in complex mixtures. Understanding the elution...
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Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

3.8K
Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...
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A Scalable Balz-Schiemann Reaction Protocol in a Continuous Flow Reactor
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Amination of Aryl Halides and Esters Using Intensified Continuous Flow Processing.

Thomas M Kohl1, Christian H Hornung2, John Tsanaktsidis3

  • 1CSIRO Manufacturing Flagship, Bag 10, Clayton South, Victoria 3169, Australia. Thomas.Kohl@csiro.au.

Molecules (Basel, Switzerland)
|October 2, 2015
PubMed
Summary

Continuous flow processing intensifies amination reactions of aryl halides and esters. This technology enables safe, high-temperature reactions, overcoming previous limitations in both laboratory and preparatory scales.

Keywords:
aminationcontinuous flow processingflow chemistryprocess intensification

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Area of Science:

  • Organic Chemistry
  • Chemical Engineering
  • Process Chemistry

Background:

  • Amination reactions involving aryl halides and esters are crucial in organic synthesis.
  • Traditional batch methods for these reactions can be challenging, especially at elevated temperatures.
  • Process intensification offers potential solutions for improving efficiency and safety.

Purpose of the Study:

  • To demonstrate significant process intensification for amination reactions using continuous flow processing.
  • To enable the safe execution of traditionally difficult amination reactions at elevated temperatures.
  • To evaluate the scalability of continuous flow amination from laboratory to preparatory scales.

Main Methods:

  • Utilized continuous flow reactor technology for amination reactions.
  • Employed laboratory scale coil reactor modules (1 mm internal diameter).
  • Scaled up the process using a preparatory scale tubular reactor (6 mm internal diameter) with static mixers.

Main Results:

  • Achieved significant process intensification for amination of aryl halides and esters.
  • Successfully performed difficult amination reactions safely at elevated temperatures.
  • Demonstrated successful reaction conduct across different scales, from laboratory to preparatory.

Conclusions:

  • Continuous flow processing is a viable and effective technology for process intensification of amination reactions.
  • The methodology allows for safe operation at elevated temperatures, expanding reaction capabilities.
  • The approach is scalable, showing promise for industrial applications.