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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
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Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
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The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
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Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
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Hexacoordinate Ti-Anchored Single-Atom Pd Catalyst for High-Efficiency Cyclohexanone Ammoximation with H2 and O2.

Chengwei Zhai1, Zhuoya Dong2, Yue Ma1

  • 1State Key Laboratory of Petroleum Molecular & Process Engineering, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China.

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A novel Pd@Ti-MWW-PI catalyst efficiently produces cyclohexanone oxime using hydrogen and oxygen. This green chemistry approach offers a sustainable alternative for industrial ammoximation reactions.

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Area of Science:

  • Catalysis
  • Materials Science
  • Green Chemistry

Background:

  • Cyclohexanone oxime is typically produced using hydrogen peroxide.
  • Existing catalysts suffer from inefficient precious metal utilization and suboptimal titanium activity.
  • Developing sustainable alternatives for cyclohexanone oxime synthesis is crucial.

Purpose of the Study:

  • To develop a novel bifunctional catalyst for cyclohexanone oxime production via ammoximation.
  • To enhance precious metal utilization and titanium activity in composite catalysts.
  • To establish a green and sustainable method for cyclohexanone oxime synthesis.

Main Methods:

  • One-step synthesis of a Pd@Ti-MWW-PI catalyst using Ti-MWW zeolite support.
  • Anchoring piperidine-modified palladium single atoms on hexacoordinated framework-titanium via Pd-O-Ti bonds.
  • Utilizing hydrogen and oxygen for the ammoximation of cyclohexanone in water.

Main Results:

  • Achieved a record cyclohexanone oxime formation rate of 13000 mol molPd−1 h−1 with ultralow Pd loading (0.02 wt %).
  • Demonstrated exceptional catalyst stability, maintaining >99% selectivity for over 2500 hours in continuous operation.
  • Successfully employed water as a solvent, highlighting environmental sustainability.

Conclusions:

  • The Pd@Ti-MWW-PI catalyst represents a significant advancement in H2/O2-mediated ammoximation.
  • This work offers a practical and environmentally friendly route for cyclohexanone oxime production.
  • The developed catalyst design strategy can be applied to other catalytic systems.