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Related Concept Videos

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

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Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
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Olefin Metathesis Polymerization: Overview01:13

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Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
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Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

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Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

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The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
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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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Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
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Tungsten imido catalysts for selective ethylene dimerisation.

Christopher M R Wright1, Zoë R Turner1, Jean-Charles Buffet1

  • 1Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, Oxfordshire OX1 3TA, UK. dermot.ohare@chem.ox.ac.uk.

Chemical Communications (Cambridge, England)
|January 19, 2016
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Summary

A novel tungsten imido complex selectively dimerizes ethylene into 1-butene. Immobilizing this complex on polymethylaluminoxane creates a highly active solid-state catalyst for ethylene dimerization.

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Polymer Science

Background:

  • Ethylene dimerization is a crucial process in the petrochemical industry.
  • Development of efficient and selective catalysts for ethylene conversion remains a key research area.
  • Tungsten imido complexes have shown promise in catalytic applications.

Purpose of the Study:

  • To investigate the catalytic activity of a tungsten imido complex for ethylene dimerization.
  • To develop immobilized solid-state catalysts for selective ethylene dimerization.
  • To enhance the catalytic performance through immobilization and activation strategies.

Main Methods:

  • Synthesis and characterization of a tungsten imido complex, W(NDipp)Me3Cl.
  • Immobilization of a related tungsten complex, W(NDipp)Cl4(THF), onto various supports: layered double hydroxides, silica, and polymethylaluminoxane (PMAO).
  • Evaluation of the catalytic activity and selectivity of both homogeneous and heterogeneous catalysts for ethylene dimerization under mild conditions.

Main Results:

  • The homogeneous tungsten imido complex W(NDipp)Me3Cl demonstrated selective dimerization of ethylene to 1-butene under mild conditions.
  • Immobilization of W(NDipp)Cl4(THF) on layered double hydroxides, silica, and PMAO yielded active solid-state catalysts.
  • The PMAO-supported catalyst exhibited a significantly higher turnover frequency (4.0 molC2H4 molW(-1) h(-1)), nearly seven times that of the homogeneous catalyst.

Conclusions:

  • Tungsten imido complexes are effective catalysts for the selective dimerization of ethylene.
  • Immobilization onto solid supports, particularly PMAO, dramatically enhances catalytic activity and efficiency.
  • Solid-state catalysts offer a promising alternative to homogeneous systems for industrial ethylene conversion.