Anchored macromolecular copper catalysts for oxidative coupling

Verlaan, J.P.J.; Bootsma, J.P.C.; Koning, Cor E.; Challa, G.

doi:10.1016/0304-5102(83)80115-1

Cited by 24 publications

(4 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…41 In the present work we combine both approaches and prepare a silica supported polymer that contains pyridyl groups [SiO 2 ∼PvPy] to immobilize Wilkinson's catalyst on such a solid support material that has previously been utilized by Tamami and co-workers to heterogenize palladium and nickel nanoparticles catalysts 42,43 or by Challa and co-workers who used such carrier material to immobilize copper complexes. 44 Wilkinson's catalyst is then immobilized [SiO 2 ∼PvPy-Wilk] via the pyridyl groups on the carrier material. The success of the synthesis is monitored by elemental analysis and multinuclear ( 13 C and 31 P) solid state NMR spectroscopy (SSNMR) including 2D NMR techniques.…”

Section: ■ Introductionmentioning

confidence: 99%

A Novel Wilkinson’s Type Silica Supported Polymer Catalyst: Insights from Solid-State NMR and Hyperpolarization Techniques

et al. 2021

View full text Add to dashboard Cite

The synthesis of a novel immobilized Wilkinson’s catalyst [SiO2∼PvPy-Wilk] is presented. The support material of this catalyst consists of silica particles that are modified with polymer brushes carrying pyridyl moieties that enable the coordination of Wilkinson’s catalyst. The synthesis of this catalyst is monitored by 1D and 2D multinuclear solid-state NMR techniques to confirm the success of the immobilization. The [SiO2∼PvPy-Wilk] catalyst is then tested in the hydrogenation of styrene, and its reusability is inspected showing that significant structural changes after several reaction cycles yield an activation of the catalyst. Finally, the catalyst is tested in PHIP experiments giving rise to about 200-fold enhancement of the signals of the hydrogenation product ethylbenzene.

show abstract

Section: ■ Introductionmentioning

confidence: 99%

A Novel Wilkinson’s Type Silica Supported Polymer Catalyst: Insights from Solid-State NMR and Hyperpolarization Techniques

et al. 2021

View full text Add to dashboard Cite

show abstract

“…Immobilization of soluble catalysts on an inert support and collection through filtration after reaction is a common technique to recycle catalysts. For example, Challa and Verlaan et al immobilized pyridine and imidazole derivatives on silica or polystyrene to coordinate with Cu(II) and employed these immobilized complexes to catalyze the oxidative polymerization of phenols in organic solutions 5–8. This method combined the advantages of both homogeneous and heterogeneous catalysts.…”

Section: Introductionmentioning

confidence: 99%

Immobilization of copper(II)‐poly(N‐vinylimidazole) complex on magnetic nanoparticles and its catalysis of oxidative polymerization of 2,6‐dimethylphenol in water

Wang¹,

Zhang²,

Shentu³

et al. 2012

J of Applied Polymer Sci

View full text Add to dashboard Cite

Poly(N‐vinylimidazole) (PVI) was grafted onto magnetic Fe3O4 nanoparticles through siloxane bonds to produce PVI‐grafted Fe3O4 nanoparticles (shortened as Fe3O4‐g‐PVI). The amount of imidazolyl groups in Fe3O4‐g‐PVI was estimated to be 1.16 mmol/g by elemental analysis and thermal gravimetric analysis. The Fe3O4‐g‐PVI coordinated with Cu(II) to form the immobilized Cu(II)‐PVI complex. The stoichiometric ratio between imidazolyl groups in Fe3O4‐g‐PVI and Cu(II) was found to be 4 and the complex formation constant (K) was calculated to be 5.6 × 1014 mol−4 L4. The immobilized Cu(II)‐PVI complex was employed to catalyze the oxidative polymerization of 2,6‐dimethylphenol (DMP) in water and showed excellent CO/CC selectivity to form PPO. After polymerization, the immobilized Cu(II)‐PVI complex catalyst was collected by an external magnetic field and reused in the next run with additional immobilized catalyst and copper ions. After three runs of oxidative polymerization of DMP, the recovery rate of the immobilized Cu(II)‐PVI catalyst was above 95% and the yield of PPO maintained as high as 79.2% with the addition of supplementary catalysts. © 2012 Wiley Periodicals, Inc. J Appl Polym Sci, 2012

show abstract

“…Copolymers of styrene and pyridine or imidazole derivatives were used as macromolecular ligands for copper ions in the oxidative polymerization of phenols in organic solvents by Challa and coworkers 5–9. They found that copper–macromolecular ligand complexes were more active in oxidative coupling reactions than the corresponding low‐molecular‐weight analogue.…”

Section: Introductionmentioning

confidence: 99%

“…Third, PVI coordinated with a number of different metal ions, such as Ag(I), Cu(II), Zn(II) and Co(II),14–17 to form metal–PVI complexes, which have been widely applied in industrial effluent detoxification, the recovery of heavy metal ions, and catalytic reactions 18, 19. Although the catalytic properties of Cu(II)–polymeric imidazole complexes in organic solvents have been described extensively in the past 3 decades, few studies have been made dealing with the catalytic properties of these complexes in aqueous medium 5–9…”

Section: Introductionmentioning

confidence: 99%

Aerobic oxidative polymerization of 2,6‐dimethylphenol in water with a highly efficient copper(II)– poly(N‐vinylimidazole) complex catalyst

Zhang

Wang

Shentu

et al. 2010

J of Applied Polymer Sci

View full text Add to dashboard Cite

A Cu(II)-poly(N-vinylimidazole) (PVI) complex was prepared and used to catalyze the oxidative polymerization of 2,6-dimethylphenol (DMP) to form poly(2,6-dimethyl-1,4-phenylene oxide) (PPO) in water. The stoichiometric ratio between imidazole groups in PVI and copper ions was found to be 4 when continuous variation analysis was applied. Compared with a conventional Cu(II)-low-molecular-weight ligand complex, a high catalytic efficiency was observed in the polymerization of DMP catalyzed by the Cu(II)-PVI complex. The influence of the Cu(II)-PVI complex concentration and imidazole/Cu(II) molar ratio on the oxidative polymerization of DMP was studied. Both the yield and molecular weight of PPO increased significantly with the catalyst concentration and decreased with the imidazole/Cu(II) molar ratio. The molecular weight of PVI also played an important role in the improvement of the catalytic efficiency. The high catalytic efficiency of the Cu(II)-PVI complex may have been due to the concentration effect of the catalyst and substrate.

show abstract

Anchored macromolecular copper catalysts for oxidative coupling

Cited by 24 publications

References 12 publications

A Novel Wilkinson’s Type Silica Supported Polymer Catalyst: Insights from Solid-State NMR and Hyperpolarization Techniques

A Novel Wilkinson’s Type Silica Supported Polymer Catalyst: Insights from Solid-State NMR and Hyperpolarization Techniques

Immobilization of copper(II)‐poly(N‐vinylimidazole) complex on magnetic nanoparticles and its catalysis of oxidative polymerization of 2,6‐dimethylphenol in water

Aerobic oxidative polymerization of 2,6‐dimethylphenol in water with a highly efficient copper(II)– poly(N‐vinylimidazole) complex catalyst

Contact Info

Product

Resources

About