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Continuous Flow Aerobic Alcohol Oxidation Reactions Using a Heterogeneous Ru(OH) /Al2O3 Catalyst
David S Mannel1, Shannon S Stahl1, Thatcher W Root1
1Department of Chemical and Biological Engineering and Department of Chemistry, University of Wisconsin-Madison , Madison, Wisconsin 53706, United States.
Organic Process Research & Development
|January 27, 2015
Summary
This study presents a continuous-flow method for aerobic alcohol oxidation and nitrogen heterocycle dehydrogenation using a Ruthenium on Alumina (Ru(OH)/Al2O3) catalyst. The new method achieves high yields and stable performance over extended periods.
Area of Science:
- Catalysis
- Chemical Engineering
- Organic Chemistry
Background:
- Ruthenium on Alumina (Ru(OH)/Al2O3) is a versatile catalyst for alcohol oxidation and nitrogen heterocycle dehydrogenation.
- Batch reaction methods can be limited in scalability and efficiency for these transformations.
Approach:
- Developed a continuous-flow process for aerobic alcohol oxidation and dehydrogenation reactions.
- Utilized a packed bed reactor operated isothermally in an up-flow configuration for optimal liquid-solid contact.
- Employed a dilute oxygen source (8% O2 in N2) in toluene solvent to ensure a nonflammable reaction mixture.
Key Points:
- Achieved high steady-state conversion and single-pass yields for benzylic alcohol oxidation and indoline dehydrogenation.
- Catalyst deactivation was empirically modeled to optimize extended reaction performance.
- Demonstrated sustained high conversion and yield (99+%) over 72 hours for aerobic oxidation of 2-thiophene methanol.
Conclusions:
- The continuous-flow method offers a scalable and efficient alternative to batch processes for Ru(OH)/Al2O3 catalyzed reactions.
- This approach enhances safety by maintaining a nonflammable reaction environment.
- The developed model for catalyst deactivation enables predictable and high-performance operation.
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