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Alkane hydroperoxidation with peroxides catalysed by copper complexes.

Georgiy B Shul'pin1, Julieta Gradinaru, Yuriy N Kozlov

  • 1Semenov Institute of Chemical Physics, Russian Academy of Sciences, ul. Kosygina, dom 4, Moscow 119991, Russia. Shulpin@chph.ras.ru

Organic & Biomolecular Chemistry
|November 6, 2003
PubMed
Summary

Copper catalysts efficiently oxidize saturated hydrocarbons using peroxides, forming hydroperoxides or alcohols. Catalyst activity is sensitive to ligand modifications, impacting reaction rates and product selectivity.

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Area of Science:

  • * Inorganic Chemistry
  • * Organic Chemistry
  • * Catalysis

Background:

  • * Copper(I) and copper(II) derivatives are explored as catalysts.
  • * Oxidation of saturated hydrocarbons is a significant chemical transformation.
  • * Peroxyacetic acid (PAA) and tert-butyl hydroperoxide (TBHP) are common oxidants.

Purpose of the Study:

  • * To investigate the catalytic activity of various copper derivatives in hydrocarbon oxidation.
  • * To understand the influence of N,O-chelating ligands on copper catalyst performance.
  • * To elucidate the mechanism of hydrocarbon oxidation using copper catalysts and peroxides.

Main Methods:

  • * Catalytic oxidation reactions were performed in acetonitrile solution at 60°C.
  • * Various copper(I) and copper(II) complexes, including those with N,O-chelating ligands, were synthesized and tested.

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  • * Reaction products were analyzed to determine selectivity and yield.

    • Main Results:

    • * Copper catalysts demonstrated high efficiency, with turnover numbers up to 2200.
    • * The primary products were alkyl hydroperoxides with PAA and alcohols with TBHP.
    • * Catalyst activity was significantly influenced by minor modifications to N,O-chelating ligands.

    Conclusions:

    • * Copper complexes are effective catalysts for the oxidation of saturated hydrocarbons.
    • * The choice of oxidant (PAA or TBHP) dictates the main product type.
    • * Ligand design is crucial for tuning the activity and selectivity of copper oxidation catalysts.