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Related Concept Videos

Hydrogen Bonds00:26

Hydrogen Bonds

131.9K
Hydrogen bonds are weak attractions between atoms that have formed other chemical bonds. One of these atoms is electronegative, like oxygen, and has a partial negative charge. The other is a hydrogen atom that has bonded with another electronegative atom and has a partial positive charge.
Hydrogen Bonds Control the World!
Because hydrogen has very weak electronegativity when it binds with a strongly electronegative atom, such as oxygen or nitrogen, electrons in the bond are unequally shared....
131.9K
Hydrogen Bonds01:04

Hydrogen Bonds

13.6K
A hydrogen bond is formed when a weakly positive hydrogen atom already bonded to one electronegative atom (for example, the oxygen in the water molecule) is attracted to another electronegative atom from another polar molecule, such as water (H2O), hydrogen fluoride (HF), or ammonia (NH3). The huge electronegativity difference between the H atom (2.1) and the atom to which it is bonded (4.0 for an F atom, 3.5 for an O atom, or 3.0 for an N atom), combined with the very small size of an H atom...
13.6K
Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

14.0K
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...
14.0K
Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

5.8K
Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
5.8K
IR Spectrum Peak Broadening: Hydrogen Bonding01:23

IR Spectrum Peak Broadening: Hydrogen Bonding

1.8K
The vibrational frequency of a bond is directly proportional to its bond strength. As a result, stronger bonds vibrate at higher frequencies, while weaker bonds vibrate at lower frequencies. The stretching vibration of the strong O–H bond in alcohols and phenols (very dilute solution or gas phase) appears as a sharp peak at 3600–3650 cm−1.
However, the extent of hydrogen bonding influences the observed stretching frequency and band broadening. Intermolecular or intramolecular...
1.8K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.8K
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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Hydrogen Production and Utilization in a Membrane Reactor
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Hydrogen Production and Utilization in a Membrane Reactor

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Efficient Electrocatalytic Hydrogenation with a Palladium Membrane Reactor.

Rebecca S Sherbo1, Aiko Kurimoto1, Christopher M Brown1

  • 1Department of Chemistry , The University of British Columbia , 2036 Main Mall , Vancouver , British Columbia V6T 1Z1 , Canada.

Journal of the American Chemical Society
|April 19, 2019
PubMed
Summary

This study introduces an electrochemical palladium membrane reactor for hydrogenation, improving reaction rates and voltage efficiency. This method enables hydrogenation in organic solvents without gaseous hydrogen or electrolyte contamination.

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Area of Science:

  • Electrochemistry
  • Organic Chemistry
  • Chemical Engineering

Background:

  • Traditional hydrogenation often requires gaseous hydrogen (H2), posing safety and handling challenges.
  • Electrochemical methods for hydrogenation typically involve direct reaction at an electrode, limiting solvent compatibility and efficiency.

Purpose of the Study:

  • To demonstrate the benefits of a palladium membrane reactor for electrochemical hydrogenation.
  • To show improved reaction rates and voltage efficiency compared to traditional methods.
  • To enable hydrogenation in diverse organic solvents without electrolyte contamination.

Main Methods:

  • Utilizing a palladium membrane to physically separate electrochemical and hydrogenation compartments.
  • Performing electrocatalytic hydrogenation using protons in various organic solvents.
  • Comparing reaction rates and voltage efficiency with conventional electrode-based hydrogenation.

Main Results:

  • The palladium membrane reactor significantly enhances hydrogenation reaction rates.
  • Higher voltage efficiency is achieved compared to hydrogenation directly at an electrode.
  • Hydrogenation can be successfully performed in organic solvents, free from electrolyte interference.

Conclusions:

  • The palladium membrane reactor offers a safer and more efficient alternative for electrochemical hydrogenation.
  • This technology broadens the scope of electrolytically-driven organic reactions.
  • Simplified reagent handling and purification are key advantages of this approach.