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A Scalable Balz-Schiemann Reaction Protocol in a Continuous Flow Reactor
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The Chapman rearrangement in a continuous-flow microreactor.

Jingjie Fang1, Miaolin Ke2,3, Guanxin Huang2,3

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Summary

A new microreactor method enables safer, continuous-flow Chapman rearrangement reactions. This approach overcomes batch synthesis limitations, achieving high conversions and simplifying scale-up for pharmaceutical and fine chemical applications.

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Area of Science:

  • Chemical Engineering
  • Organic Synthesis

Background:

  • The Chapman rearrangement is crucial in pharmaceutical and fine chemical synthesis but presents challenges in conventional batch processes due to high temperatures and exothermic reactions.
  • Batch synthesis suffers from operational complexities, difficult temperature control, and significant scale-up hurdles.

Purpose of the Study:

  • To develop a microreactor-based continuous-flow approach for the Chapman rearrangement.
  • To enhance safety, control, and efficiency compared to traditional batch methods.
  • To investigate and model the reaction kinetics and explore scale-up strategies.

Main Methods:

  • Utilized a microreactor system for continuous-flow synthesis of the Chapman rearrangement.
  • Explored reaction kinetics using specific benzimidate reactants at varying temperatures.
  • Developed and validated a Computational Fluid Dynamics (CFD) model coupled with experimental data.
  • Performed scale-up studies by increasing microreactor diameter and comparing with batch process scale-up.

Main Results:

  • Achieved high conversions within short residence times (≤20 minutes) in the continuous-flow system.
  • Demonstrated successful 16-fold scale-up of the microreactor system with minimal loss in conversion.
  • Observed a significant decrease in conversion when scaling up the batch reaction.

Conclusions:

  • The microreactor-based continuous-flow approach offers a highly controlled and safer method for the Chapman rearrangement.
  • Continuous-flow systems provide a simpler and more effective scale-up strategy compared to batch processes for high-temperature reactions.
  • The developed CFD model serves as a valuable tool for process design and optimization in continuous-flow chemistry.