Selective C–C Coupling Reaction of Dimethylphenol to Tetramethyldiphenoquinone Using Molecular Oxygen Catalyzed by Cu Complexes Immobilized in Nanospaces of Structurally-Ordered Materials

Maeno, Zen; Mitsudome, Takato; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi

doi:10.3390/molecules20023089

Cited by 7 publications

(5 citation statements)

References 50 publications

(65 reference statements)

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“…These compounds could be generated by the coupling reaction (C-C coupling) of 2,6-M-PhOH (CR pathway) (Fig. 3f ) 26 , 27 . The other substances dissolved in toluene were identified as chain-like polyphenyl ethers with a molecular weight of ~6062 Da (Fig.…”

Section: Resultsmentioning

confidence: 99%

Simultaneous nanocatalytic surface activation of pollutants and oxidants for highly efficient water decontamination

et al. 2022

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Removal of organic micropollutants from water through advanced oxidation processes (AOPs) is hampered by the excessive input of energy and/or chemicals as well as the large amounts of residuals resulting from incomplete mineralization. Herein, we report a new water purification paradigm, the direct oxidative transfer process (DOTP), which enables complete, highly efficient decontamination at very low dosage of oxidants. DOTP differs fundamentally from AOPs and adsorption in its pollutant removal behavior and mechanisms. In DOTP, the nanocatalyst can interact with persulfate to activate the pollutants by lowering their reductive potential energy, which triggers a non-decomposing oxidative transfer of pollutants from the bulk solution to the nanocatalyst surface. By leveraging the activation, stabilization, and accumulation functions of the heterogeneous catalyst, the DOTP can occur spontaneously on the nanocatalyst surface to enable complete removal of pollutants. The process is found to occur for diverse pollutants, oxidants, and nanocatalysts, including various low-cost catalysts. Significantly, DOTP requires no external energy input, has low oxidant consumption, produces no residual byproducts, and performs robustly in real environmental matrices. These favorable features render DOTP an extremely promising nanotechnology platform for water purification.

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Section: Resultsmentioning

confidence: 99%

Simultaneous nanocatalytic surface activation of pollutants and oxidants for highly efficient water decontamination

et al. 2022

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“…The acidic properties of the magadiite could be enhanced by the insertion of other cations into the layered silicate, achieved during the synthesis by adding the cations precursors to the mixture of the silica source and NaOH. This adjustment allowed for the diversification of magadiite as a catalyst in special catalytic reactions [ 14 , 15 , 16 ]. However, using long alkyl ammonium cations, the modified cetyltrimethylammonium-magadiite was used as an intermediate precursor to synthesize mesoporous materials with a controlled distribution of pores sizes [ 17 , 18 ].…”

Section: Introductionmentioning

confidence: 99%

Application of Organo-Magadiites for the Removal of Eosin Dye from Aqueous Solutions: Thermal Treatment and Regeneration

et al. 2018

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Na-magadiite exchanged with cetyl-trimethylammonium cations provided organophilic silicate materials that allowed for the effective removal of the acidic dye “eosin”. The organic cations were intercalated into the interlayer spacing of the layered silicate via an exchange reaction between the organic cations from their bromide salt and the solid Na-magadiite at room temperature. Different techniques were used to characterize the effect of the initial concentration of the surfactant on the structure of the organo-magadiites. The C, H, and N analysis indicated that a maximum of organic cations of 0.97 mmol/g was achieved and was accompanied by an expansion of the basal spacing of 3.08 nm, with a tilted angle of 59° to the silicate layers. The conformation of the organic surfactants was probed using solid-state 13C, finding mainly the trans conformation similar to that of the starting cetyl trimethylammonium bromide salt (C16TMABr). Thermal gravimetric analysis was carried out to study the thermal stability of the resulting organo-magadiites. The intercalated surfactants started to decompose at 200 °C, with a mass loss percentage of 8% to 25%, depending on the initial loading of the surfactant, and was accompanied by a decrease of the basal spacing from 3.16 nm to 2.51 nm, as deduced from the in situ X-ray diffraction studies. At temperatures below 220 °C, an expansion of the basal spacing from 3.15 to 3.34 nm occurred. These materials were used as a removal agent for the anionic dye eosin. The maximum amount of the dye removed was related to the organic cation content and to the initial concentration of eosin, with an improvement from 2.5 mg/g to 80.65 mg/g. This value decreased when the organo-magadiite was preheated at temperatures above 200 °C. The regeneration tests indicated that an 85% removal efficiency was maintained after six cycles of use for the organo-magadiite using Ci of 200 mg/L.

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“…The former could be generated by the C–C coupling of 2,6-M-PhOH (i.e., Fig. 2 C ) ( 27 , 28 ), and the latter may be derived from the C–O polymerization of 2,6-M-PhOH ( Fig. 2 F ) ( 29 , 30 ).…”

Section: Resultsmentioning

confidence: 99%

Distinguishing homogeneous advanced oxidation processes in bulk water from heterogeneous surface reactions in organic oxidation

Zhang

Chen

Huang

et al. 2023

Proc. Natl. Acad. Sci. U.S.A.

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Clarifying the reaction pathways at the solid–water interface and in bulk water solution is of great significance for the design of heterogeneous catalysts for selective oxidation of organic pollutants. However, achieving this goal is daunting because of the intricate interfacial reactions at the catalyst surface. Herein, we unravel the origin of the organic oxidation reactions with metal oxide catalysts, revealing that the radical-based advanced oxidation processes (AOPs) prevail in bulk water but not on the solid catalyst surfaces. We show that such differing reaction pathways widely exist in various chemical oxidation (e.g., high-valent Mn 3+ and MnO X ) and Fenton and Fenton-like catalytic oxidation (e.g., Fe 2+ and FeOCl catalyzing H 2 O 2 , Co 2+ and Co 3 O 4 catalyzing persulfate) systems. Compared with the radical-based degradation and polymerization pathways of one-electron indirect AOP in homogeneous reactions, the heterogeneous catalysts provide unique surface properties to trigger surface-dependent coupling and polymerization pathways of a two-electron direct oxidative transfer process. These findings provide a fundamental understanding of catalytic organic oxidation processes at the solid–water interface, which could guide the design of heterogeneous nanocatalysts.

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Selective C–C Coupling Reaction of Dimethylphenol to Tetramethyldiphenoquinone Using Molecular Oxygen Catalyzed by Cu Complexes Immobilized in Nanospaces of Structurally-Ordered Materials

Cited by 7 publications

References 50 publications

Simultaneous nanocatalytic surface activation of pollutants and oxidants for highly efficient water decontamination

Simultaneous nanocatalytic surface activation of pollutants and oxidants for highly efficient water decontamination

Application of Organo-Magadiites for the Removal of Eosin Dye from Aqueous Solutions: Thermal Treatment and Regeneration

Distinguishing homogeneous advanced oxidation processes in bulk water from heterogeneous surface reactions in organic oxidation

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