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Related Concept Videos

Catalysis02:50

Catalysis

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The presence of a catalyst affects the rate of a chemical reaction. A catalyst is a substance that can increase the reaction rate without being consumed during the process. A basic comprehension of a catalysts’ role during chemical reactions can be understood from the concept of reaction mechanisms and energy diagrams.
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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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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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Radical Substitution: Halogenation of Alkanes and Alkyl Substituents01:27

Radical Substitution: Halogenation of Alkanes and Alkyl Substituents

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In the presence of heat or light, alkanes react with molecular halogens to form alkyl halides by a substitution reaction called radical halogenation. This reaction has three steps: initiation, propagation, and termination, as seen in the radical chlorination of methane to produce methyl chloride.
In the initiation step of the reaction, the chlorine molecule undergoes homolytic cleavage in the presence of light or heat, forming two highly reactive chlorine radicals. Propagation occurs in two...
8.7K
Radical Substitution: Allylic Chlorination01:31

Radical Substitution: Allylic Chlorination

2.6K
Typically, when alkenes react with halogens at low temperatures, an addition reaction occurs. However, upon increasing the temperature or under reaction conditions that form radicals, providing a low but steady concentration of halogen radicals, allylic substitution reaction is favored. This is because allylic hydrogens are very reactive as the formed intermediate is resonance stabilized. For example, when propene is treated with chlorine in the gas phase at 400 °C, it undergoes allylic...
2.6K
Halogenation of Alkenes02:46

Halogenation of Alkenes

16.5K
Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
16.5K
Radical Halogenation: Thermodynamics01:34

Radical Halogenation: Thermodynamics

4.0K
The thermodynamic favorability of a reaction is determined by the change in Gibbs free energy (ΔG). ΔG has two components- enthalpy (ΔH) and entropy (ΔS). The entropy component is negligible for alkane halogenation because the number of reactants and product molecules are equal. In this case, the ΔG is governed only by the enthalpy component. The most crucial factor that determines ΔH is the strength of the bonds. ΔH can be determined by comparing the energy...
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Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
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Dynamic Active Site Evolution in Lanthanum-Based Catalysts Dictates Ethane Chlorination Pathways.

Graham John Hutchings1,2, Yuting Li3, Haifeng Qi1,2

  • 1State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, China.

Angewandte Chemie (International Ed. in English)
|June 20, 2025
PubMed
Summary

Lanthanum oxychloride (LaOCl) transforms to LaCl3 during ethane chlorination, causing over-chlorination. Stabilizing LaOCl and managing hydroxyl groups are key for selective polyvinyl chloride (PVC) precursor synthesis.

Keywords:
Ethane chlorinationLanthanum oxychlorideNatural gasOver chlorinationPolyvinyl chlorideStructural evolution

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Area of Science:

  • Catalysis
  • Materials Science
  • Chemical Engineering

Background:

  • Radical chlorination of ethane is a low-carbon route to polyvinyl chloride (PVC) precursors.
  • Selectivity issues in ethane chlorination are linked to over-chlorination, with lanthanum oxychloride (LaOCl) as a promising catalyst.
  • The structural behavior of LaOCl under chlorine-rich conditions and its role in selectivity loss are not well understood.

Purpose of the Study:

  • To investigate the structural dynamics of LaOCl during ethane chlorination.
  • To elucidate the mechanism behind selectivity loss in LaOCl-catalyzed chlorination.
  • To understand the role of surface hydroxyl groups and catalyst structure in controlling selectivity.

Main Methods:

  • Integration of advanced spectroscopic techniques.
  • Application of theoretical calculations.
  • Synthesis and characterization of Al2O3-supported LaCl3 model catalysts.

Main Results:

  • A sequential transformation from LaOCl to LaCl3 was observed, correlating with a shift in product distribution towards trichloroethane.
  • Surface hydroxyl groups, formed during chlorination, facilitate 1,2-dichloroethane adsorption and subsequent over-chlorination.
  • Monolayer-dispersed LaCl3 on Al2O3 exhibits size-dependent chlorophilicity, with interfacial oxygen stabilizing Cl radicals for selective ethane to 1,2-dichloroethane conversion.
  • Aggregated LaCl3 nanoparticles showed no activity due to an inability to stabilize Cl radicals.

Conclusions:

  • Catalyst structure significantly influences selectivity in lanthanum-catalyzed chlorination.
  • Stabilizing metastable LaOClx species and controlling surface hydroxyl chemistry are crucial for enhancing selectivity.
  • The findings provide guiding principles for designing improved catalysts for selective ethane chlorination.