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Preparation of Diols and Pinacol Rearrangement01:57

Preparation of Diols and Pinacol Rearrangement

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Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Alcohols from Carbonyl Compounds: Reduction02:23

Alcohols from Carbonyl Compounds: Reduction

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Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...
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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

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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.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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Reduction of Alkenes: Catalytic Hydrogenation02:13

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Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...
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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
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Reduction behavior of PdO-NiO/SiO2: how Pd location affects cinnamaldehyde hydrogenation.

Rim C J van de Poll1, Heiner Friedrich2, Emiel J M Hensen1

  • 1Laboratory of Inorganic Materials and Catalysis, Department of Chemical Engineering and Chemistry, Eindhoven University of Technology Eindhoven The Netherlands e.j.m.hensen@tue.nl.

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Palladium oxide (PdO) on nickel oxide (NiO) catalysts show enhanced activity in cinnamaldehyde hydrogenation due to improved palladium dispersion at lower reduction temperatures compared to PdO on silica (SiO2).

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Area of Science:

  • Catalysis
  • Materials Science
  • Surface Chemistry

Background:

  • Investigating the reducibility and catalytic performance of palladium-based catalysts is crucial for various chemical transformations.
  • Nickel oxide (NiO) and silica (SiO2) are common supports for metal catalysts, influencing their properties and reactivity.
  • Strong electrostatic adsorption and incipient wetness impregnation are methods used to prepare supported metal catalysts.

Purpose of the Study:

  • To compare the reducibility and catalytic activity of palladium oxide (PdO) precursors supported on NiO versus SiO2.
  • To understand the effect of support material (NiO vs. SiO2) and reduction temperature on palladium dispersion and hydrogenation performance.
  • To evaluate the catalysts in the hydrogenation of cinnamaldehyde.

Main Methods:

  • Preparation of NiO/SiO2 catalysts using incipient wetness impregnation.
  • Strong electrostatic adsorption of PdO precursor onto NiO and SiO2 supports.
  • Characterization using High-Angle Annular Dark-Field Scanning Transmission Electron Microscopy (HAADF-STEM), quasi-in situ X-ray Photoelectron Spectroscopy (XPS), CO Infrared (IR) spectroscopy, and H2 chemisorption.
  • Evaluation of catalytic performance in cinnamaldehyde hydrogenation at varying reduction temperatures.

Main Results:

  • PdO supported on SiO2 required higher reduction temperatures to achieve significant cinnamaldehyde hydrogenation rates.
  • PdO supported on NiO particles dispersed on SiO2 could be reduced at room temperature.
  • The NiO-supported palladium catalyst exhibited higher activity in cinnamaldehyde hydrogenation, attributed to better palladium dispersion at lower reduction temperatures.

Conclusions:

  • The presence of NiO as a support enhances the reducibility of PdO precursors at lower temperatures.
  • Lower reduction temperatures lead to higher palladium dispersion on NiO/SiO2 catalysts, boosting catalytic activity.
  • This study highlights the importance of support-metal interactions in designing efficient hydrogenation catalysts.