Aerobic oxidation of α-pinene catalyzed by homogeneous and MOF-based Mn catalysts

Raupp, Yasmin S.; Yildiz, Ceylan; Kleist, Wolfgang; Meier, Michael A. R.

doi:10.1016/j.apcata.2017.07.047

Cited by 34 publications

(16 citation statements)

References 48 publications

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“…Pinene is a major constituent of the turpentine oil produced from the wood extractives waste, which constitute a platform building block molecule for the synthesis of fine aroma chemicals. The direct catalytic upgrading of turpentine still remains a challenge because of the high variety of its constituent’s reactivity, therefore various pre-treatment steps are required to separate individual components [6,7,8,9,10]. On the other hand, the oxidation and epoxidation of terpenes C–C (alkane) and C=C (olefin) bonds has become an efficient chemical transformation for upgrading their inert hydrocarbon C–H bond into valuable oxygenated chemical derivatives [11,12,13].…”

Section: Introductionmentioning

confidence: 99%

Fabrication of Bimetal CuFe2O4 Oxide Redox-Active Nanocatalyst for Oxidation of Pinene to Renewable Aroma Oxygenates

2019

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This study report on the synthesis of spinel CuFe2O4 nanostructures by surfactant-assisted method. The catalysts were characterized by X-ray diffraction (XRD), laser Raman, transition electron microscope (TEM), scanning electron microscope (SEM), energy dispersive X-ray (EDX), hydrogen temperature programmed reduction (H2-TPR), and Brunauer-Teller-Emmett-Teller (BET) surface area techniques. CuFe2O4 was active for pinene oxidation using tertiary butyl hydroperoxide (TBHP) to pinene oxide, verbenol, and verbenone aroma oxygenates. Under optimized reaction conditions, the spinel CuFe2O4 catalyst could afford 80% pinene conversion at a combined verbenol/verbenone selectivity of 76% within the reaction time of 20 h. The changes in catalyst synthesis solvent composition ratios induced significantly varying redox, phases, and textural structure features, which resulted in various catalytic enhancement effect. Characterization results showed the spinel CuFe2O4 catalyst possessing less than 5 wt% impurity phases, Cu(OH)2, and CuO to afford the best catalytic performance. The CuFe2O4 catalyst was recyclable to up to five reaction cycles without loss of its activity. The recyclability of the bimetal CuFe2O4 oxide catalyst was simply rendered by use of an external magnet to separate it from the liquid solution.

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Section: Introductionmentioning

confidence: 99%

Fabrication of Bimetal CuFe2O4 Oxide Redox-Active Nanocatalyst for Oxidation of Pinene to Renewable Aroma Oxygenates

2019

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“…The lowest TON was achieved by using 0.05 mol % of DUT‐5‐BPyDC(10)‐Mn 2+ (TON ≈ 500). Nevertheless, these values are significantly higher than for other MOF‐based catalysts previously used for epoxidation reactions …”

Section: Resultsmentioning

confidence: 69%

“…Nevertheless, these values are significantly higher than for other MOF-based catalysts previously used for epoxidation reactions. [14,27] The influence of the substrate concentration was also tested. The molar amount of trans-stilbene was increased from 1 to 10 mmol, whereas the amounts of the catalyst and solvent were not varied.…”

Section: Resultsmentioning

confidence: 99%

“…In previous works, our group presented a mixed‐linker MIL‐53(Al)‐NH 2 , which was post‐synthetically modified with maleic anhydride. The resulting materials were transformed into single‐site catalysts via the immobilization of Pd 2+ and Mn 3+ and used in C−C coupling reactions or the selective oxidation of α‐pinene, respectively. Apart from post‐synthetic modifications with anhydrides, reactions of primary amines and aldehydes resulting in Schiff‐bases are well‐suited for the incorporation of well‐defined and highly active metal complexes into the MOF structure .…”

Section: Introductionmentioning

confidence: 99%

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Post‐synthetic Modification of DUT‐5‐based Metal Organic Frameworks for the Generation of Single‐site Catalysts and their Application in Selective Epoxidation Reactions

et al. 2020

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New single‐site catalysts based on mixed‐linker metal‐organic frameworks with DUT‐5 structure, which contain immobilized Co2+, Mn2+ and Mn3+ complexes, have successfully been synthesized via post‐synthetic modification. 2,2’‐Bipyridine‐5,5’‐dicarboxylate linkers were directly metalated, while 2‐amino‐4,4’‐biphenyldicarboxylate linkers were post‐synthetically modified by their conversion to Schiff‐base ligands and a subsequent immobilization of the metal complexes. The resulting materials were used as catalysts in the selective epoxidation of trans‐stilbene and the activities and selectivities of the different catalysts were compared. The influence of various reaction parameters on conversion, yield and selectivity were investigated. Very low catalyst amounts of 0.02 mol % were sufficient to obtain a high conversion of trans‐stilbene using molecular oxygen from air as the oxidant. For cobalt‐containing MOF catalysts, conversions up to 90 % were observed and, thus, they were more active than their manganese‐containing counterparts. Recycling experiments and hot filtration tests proved that the reactions were mainly catalyzed via heterogeneous pathways.

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“…The chemistry between the structure and the special properties of metal–organic frameworks (MOFs) has been widely studied . In this regard, one of the interesting fields in MOFs chemistry is designing of mixed‐metal (MM)‐MOFs and exploring the properties that can differ from the single‐metal MOFs .…”

Section: Introductionmentioning

confidence: 99%

Tandem magnetization and post‐synthetic metal ion exchange of metal–organic framework: Synthesis, characterization and catalytic study

Yadollahi

Hamadi

Nobakht

2019

Applied Organom Chemis

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For the first time, metal‐exchange in a magnetic metal–organic framework (MOF) via tandem magnetization and post‐synthetic modification has been developed. The new magnetic mixed‐metal metal–organic framework nanocomposite, CoFe2O4/[Cu0.63/Zn0.37‐TMU‐17‐NH2] (CoFe2O4/[Cu/Zn‐MOF]) has been synthesized by immersing the CoFe2O4/Zn‐TMU‐17‐NH2 (CoFe2O4/Zn‐MOF) as a template in DMF solution of Cu (II) salts. CoFe2O4/[Cu/Zn‐MOF] showed to be a highly reactive and easily recoverable magnetic catalyst for the preparation of tetrazole derivatives via one‐pot three‐component reactions of different aldehydes with hydroxyl amine hydrochloride and sodium azide. Our results (Fourier transform‐infrared, inductively coupled plasma‐optical emission spectroscopy, powder X‐ray diffraction, field emission‐scanning electron microscopy, energy‐dispersive X‐ray spectroscopy‐mapping and vibrating‐sample magnetometer) show successful partial metal‐exchange in which the framework integrity remained intact during the metal‐exchange process.

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Aerobic oxidation of α-pinene catalyzed by homogeneous and MOF-based Mn catalysts

Cited by 34 publications

References 48 publications

Fabrication of Bimetal CuFe2O4 Oxide Redox-Active Nanocatalyst for Oxidation of Pinene to Renewable Aroma Oxygenates

Fabrication of Bimetal CuFe2O4 Oxide Redox-Active Nanocatalyst for Oxidation of Pinene to Renewable Aroma Oxygenates

Post‐synthetic Modification of DUT‐5‐based Metal Organic Frameworks for the Generation of Single‐site Catalysts and their Application in Selective Epoxidation Reactions

Tandem magnetization and post‐synthetic metal ion exchange of metal–organic framework: Synthesis, characterization and catalytic study

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