Selective oxidation of cyclooctene over copper-containing metal-organic frameworks

Junghans, Ulrike; Suttkus, Christian; Lincke, Jörg; Lässig, Daniel; Krautscheid, Harald; Gläser, Roger

doi:10.1016/j.micromeso.2015.01.050

Cited by 42 publications

(17 citation statements)

References 57 publications

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“…Based on previous results on catalytic oxidation of olefins by Cu(II) compounds, a plausible mechanism has been proposed to explain the formation of the products. It is well understood that tBuOO • and tBuO • radicals could be formed from the reaction between TBHP and Cu(II) with the subsequent reduction of the metal center to Cu(I) . Oxidation of styrene under similar conditions has been reported to follow radical mechanism .…”

Section: Catalytic Studiessupporting

confidence: 85%

Cu- and Ni-Grafted Functionalized Mesoporous Silica as Active Catalyst for Olefin Oxidation

et al. 2017

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Mesoporous silica has been functionalized with 3‐aminopropyl triethoxy silane (3‐APTES), followed by Schiff‐base condensation with 2‐hydroxy‐1‐naphthaldehyde. Incorporation of copper and nickel by covalent grafting onto the Schiff‐base loaded materials gives two heterogenized catalysts namely, Cu–Cat and Ni‐Cat, respectively. The materials have been characterized by PXRD analyses, nitrogen sorption studies, TEM, TGA, FT‐IR, UV‐visible and solid state MAS‐NMR spectroscopy. The metal‐contents in the samples are estimated using ICP‐AES studies. Cu–Cat and Ni‐Cat have been used as active catalyst in the oxidation of various olefins e. g. styrene, α‐methyl styrene, cyclohexene, trans stilbene and cyclooctene in the presence of tert‐butyl hydroperoxide as the oxidant in acetonitrile under mild conditions. Different products have been analyzed by gas chromatography and gas chromatography‐mass spectrometry. The results show high conversion of the substrates, moderate to good product selectivity and high TOFs of the reactions. The catalysts are recycled without deteriorating their activities and heterogeneous nature.

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Section: Catalytic Studiessupporting

confidence: 85%

Cu- and Ni-Grafted Functionalized Mesoporous Silica as Active Catalyst for Olefin Oxidation

et al. 2017

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“…It is found that the addition of diphenylamine inhibits the styrene oxidation and the reaction proceeds via a radical mechanism . So, it seems that decomposition of TBHP to tert ‐butoxyl and tert ‐butylperoxyl radicals is catalysed by Cu 2+ in one‐electron transfer processes . According to the radical mechanism operation, the behaviour of the alkenes used is depicted in Scheme .…”

Section: Resultsmentioning

confidence: 99%

Copper(II) Schiff Base Complex Immobilized on Superparamagnetic Fe₃O₄@SiO₂ as a Magnetically Separable Nanocatalyst for Oxidation of Alkenes and Alcohols

Sarkheil

Lashanizadegan

2017

Applied Organom Chemis

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A new heterogeneous catalyst containing a copper(II) Schiff base complex covalently immobilized on the surface of silica-coated Fe 3 O 4 nanoparticles (Fe 3 O 4 @SiO 2 -Schiff base-Cu(II)) was synthesized. Characterization of this catalyst was performed using various techniques. The catalytic potential of the catalyst was investigated for the oxidation of various alkenes (styrene, α-methylstyrene, cyclooctene, cyclohexene and norbornene) and alcohols (benzyl alcohol, 3-methoxybenzyl alcohol, 3-chlorobenzyl alcohol, benzhydrol and n-butanol) using tertbutyl hydroperoxide as oxidant. The catalytic investigations revealed that Fe 3 O 4 @SiO 2 -Schiff base-Cu(II) was especially efficient for the oxidation of norbornene and benzyl alcohol. The results showed that norbornene epoxide and benzoic acid were obtained with 100 and 87% selectivity, respectively. Moreover, simple magnetic recovery from the reaction mixture and reuse for several times with no significant loss in catalytic activity were other advantages of this catalyst

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“…Upon coordination of the oxidizing agent to Cu(II) (Figure 4), peroxyl radicals are formed which then react with olefin to form the oxidized products [34,35]. By using Cu4O(OH)2(Me2trz-pba)4 (Me2trz-pba = 4-(3,5-dimethyl-4-H-1,2,4-triazol-4yl)benzoate) and Cu(Me-4py-trz-ia) (Me-4py-trz-ia = 5-(3methyl-5-(pyridine-4-yl)4H-1,2,4-triazol-4-yl)isophthalate) a significantly higher catalytic activity in the epoxidation of cyclooctane with respect to Cu3(BTC)2 (HKUST-1) has been found, due to the different coordination environment at the catalytically active Cu sites [36]. The catalytic performances of Cu-MOF nanosheets for cyclooctene and 1-hexene epoxidation were nearly twice higher than that of bulk Cu3(BDC)2 crystals.…”

Section: Metal Nodes/clusters As Catalytically Active Sitesmentioning

confidence: 99%

Metal Organic Frameworks as Heterogeneous Catalysts in Olefin Epoxidation and Carbon Dioxide Cycloaddition

Tombesi

Pettinari

2021

Inorganics

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Metal–organic frameworks (MOFs) are a family of porous crystalline materials that serve in some cases as versatile platforms for catalysis. In this review, we overview the recent developments about the use of these species as heterogeneous catalysts in olefin epoxidation and carbon dioxide cycloaddition. We report the most important results obtained in this field relating them to the presence of specific organic linkers, metal nodes or clusters and mixed-metal species. Recent advances obtained with MOF nanocomposites were also described. Finally we compare the results and summarize the major insights in specific Tables, outlining the major challenges for this emerging field. This work could promote new research aimed at producing coordination polymers and MOFs able to catalyse a broader range of CO2 consuming reactions.

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Selective oxidation of cyclooctene over copper-containing metal-organic frameworks

Cited by 42 publications

References 57 publications

Cu- and Ni-Grafted Functionalized Mesoporous Silica as Active Catalyst for Olefin Oxidation

Cu- and Ni-Grafted Functionalized Mesoporous Silica as Active Catalyst for Olefin Oxidation

Copper(II) Schiff Base Complex Immobilized on Superparamagnetic Fe₃O₄@SiO₂ as a Magnetically Separable Nanocatalyst for Oxidation of Alkenes and Alcohols

Metal Organic Frameworks as Heterogeneous Catalysts in Olefin Epoxidation and Carbon Dioxide Cycloaddition

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Selective oxidation of cyclooctene over copper-containing metal-organic frameworks

Cited by 42 publications

References 57 publications

Cu- and Ni-Grafted Functionalized Mesoporous Silica as Active Catalyst for Olefin Oxidation

Cu- and Ni-Grafted Functionalized Mesoporous Silica as Active Catalyst for Olefin Oxidation

Copper(II) Schiff Base Complex Immobilized on Superparamagnetic Fe3O4@SiO2 as a Magnetically Separable Nanocatalyst for Oxidation of Alkenes and Alcohols

Metal Organic Frameworks as Heterogeneous Catalysts in Olefin Epoxidation and Carbon Dioxide Cycloaddition

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Copper(II) Schiff Base Complex Immobilized on Superparamagnetic Fe₃O₄@SiO₂ as a Magnetically Separable Nanocatalyst for Oxidation of Alkenes and Alcohols