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Utilization of Stop-flow Micro-tubing Reactors for the Development of Organic Transformations
Published on: January 4, 2018
Understanding solid/solid organic reactions.
G Rothenberg1, A P Downie, C L Raston
1York Green Chemistry Group, Chemistry Department, University of York, Heslington, York YO10 5DD, UK.
Journal of the American Chemical Society
|September 6, 2001
Summary
Most solid-phase organic reactions involve a liquid phase formed by grinding solid reactants. This eutectic mixture formation explains reaction kinetics and challenges the notion of true solid-phase reactions.
Area of Science:
- Organic Chemistry
- Materials Science
- Physical Chemistry
Background:
- Investigating organic reactions between solid particles is crucial for developing new synthetic methodologies.
- Many reactions are reported to occur in the solid phase, but their mechanisms require clarification.
Purpose of the Study:
- To investigate the concept of solid-phase organic reactions.
- To determine the role of phase changes in reactions between solid reactants.
Main Methods:
- Analysis of 19 reported "solid-phase" organic reactions.
- Mechanical mixing (grinding) of solid reactants.
- Observation of phase changes (liquefaction) and reaction kinetics.
Main Results:
- Grinding solid reactants typically forms a liquid phase, often a eutectic mixture with a melting point below ambient temperature.
- This liquefaction occurs in both catalytic and noncatalytic reactions, including aldol condensations, Baeyer-Villiger oxidations, and aromatic brominations.
- Observed reaction kinetics are explained by the transition from solid to liquid phase.
Conclusions:
- True solid-phase reactions between macroscopic particles are rare; liquefaction is a common phenomenon.
- Eutectic or peritectic formation is key to understanding reactions involving mechanical mixing of solid reagents.
- A general model for reactive systems involving solid reagents should account for potential liquid phase formation.
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