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Selective phenol hydrogenation to cyclohexanone over a dual supported Pd-Lewis acid catalyst
Huizhen Liu1, Tao Jiang, Buxing Han
1Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
Efficiently synthesizing cyclohexanone from phenol is now possible. A novel catalyst combination of palladium and a Lewis acid achieves over 99.9% conversion and selectivity, overcoming previous over-reduction issues.
Area of Science:
- Catalysis
- Organic Chemistry
- Materials Science
Background:
- Cyclohexanone is a key intermediate for nylon production.
- Direct phenol hydrogenation to cyclohexanone is challenging due to over-reduction to cyclohexanol.
Purpose of the Study:
- To develop an efficient method for cyclohexanone synthesis via direct phenol hydrogenation.
- To identify catalyst systems that prevent over-reduction to cyclohexanol.
Main Methods:
- Utilized nanoparticulate palladium catalysts (supported on carbon, alumina, or NaY zeolite) in combination with a Lewis acid (e.g., AlCl3).
- Performed hydrogenation of phenol under varying conditions including temperature, hydrogen pressure (1.0 MPa), and solvent (compressed CO2).
Main Results:
- Achieved >99.9% conversion of phenol with >99.9% selectivity to cyclohexanone within 7 hours at 50°C.
- The synergistic effect of palladium and Lewis acid catalysts was demonstrated.
- Reaction rate was accelerated by higher temperatures or the use of compressed CO2 as a solvent.
Conclusions:
- A highly efficient and selective catalytic system for cyclohexanone production from phenol has been established.
- The Lewis acid plays a dual role in enhancing phenol hydrogenation and inhibiting ketone over-reduction.
- This method offers a significant advancement in the industrial synthesis of cyclohexanone.
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