Green and continuous aerobic oxidation of ethylbenzene over homogeneous and heterogeneous NHPI in a micro-packed bed reactor

Zhang, Chenghao; Luo, Jin; Xie, Bingqi; Liu, Wei; Zhang, Jisong

doi:10.1016/j.cej.2023.143674

Cited by 11 publications

(3 citation statements)

References 44 publications

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“…[18] Following the initial concept of the ideal catalyst, a simple continuous packed bed reactor were readily assembled (Figure 2f and Figure S6). [49][50][51] By using a syringe pump to control the reactant feeding speed, this continuous reactor successfully achieved stable > 90 % conversion to oxidize the alcohol 1 a to ketone 2 a, while using the same equivalent of NHPI as homogeneous catalyst added into the reactant solution a much lower conversion of ca. 50 % was obtained although it was homogeneous catalysis, demonstrating the superiority of the porous heterogeneous catalyst in the continuous reactions (Figure S7).…”

Section: Recyclability and Flow Reactionmentioning

confidence: 99%

Porous Aromatic Framework Covalently Embedded with N‐Hydroxyphthalimide as Metal‐free Heterogeneous Catalyst for Highly Efficient and Selective Aerobic Oxidation

Fan,

Wang,

Yin

et al. 2023

ChemCatChem

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Ideal catalysts with all‐around advantages including high efficiency and selectivity, environment‐benign and good recyclability, etc. have been long‐sought yet challenging. Herein, the stable porous aromatic framework covalently embedded with N‐Hydroxyphthalimide (NHPI) organocatalytic site was constructed to establish an ideal catalytic system. The synthesized PAF‐NHPI catalyst was demonstrated to be metal‐free, highly efficient, selective, recyclable and heterogeneous for the aerobic oxidation of various alcohols, aldehydes, olefins, and hydrosilanes (totally 66 examples). As a proof‐of‐concept, the continuous PAF‐NHPI packed bed reactor achieved persistent conversion of 1‐phenylethanol to acetophenone up to 95% yield. This work provides the inspiration for developing ideal catalysts in practical production of fine chemicals.

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Section: Recyclability and Flow Reactionmentioning

confidence: 99%

Porous Aromatic Framework Covalently Embedded with N‐Hydroxyphthalimide as Metal‐free Heterogeneous Catalyst for Highly Efficient and Selective Aerobic Oxidation

Fan,

Wang,

Yin

et al. 2023

ChemCatChem

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“…In recent years, direct C–H bond activation of hydrocarbons to carbonyl compounds has been recognized as one of the most straightforward methods and a valuable strategy in organic synthesis and industrial chemistry. − Acetophenone (AP), as a crucial chemical intermediate for the petrochemical industry, has been widely utilized in manufacturing pharmaceuticals, alcohol, esters, perfumes, and other products. − AP has conventionally been prepared by Friedel–Crafts acylation using aluminum trichloride as a catalyst, , which requires a corresponding stoichiometric inorganic oxidant (such as permanganate or dichromate), producing large amounts of corrosive and hazardous waste . Therefore, it is highly essential to develop an efficient and eco-friendly approach to preparing AP for a sustainable society.…”

Section: Introductionmentioning

confidence: 99%

Novel Cobalt(II)-Decorated 1D Covalent Organic Framework for Selective Oxidation of Ethylbenzene

Lin,

Wang,

Qiao

et al. 2024

ACS Sustainable Chem. Eng.

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As one of the most direct methods to construct molecular scaffolds in fine chemicals, C–H bond oxidation is a hot research area in catalysis. One-dimensional covalent organic frameworks (1D-COFs) developed recently have attracted growing attention for catalytic applications owing to their unique edge microstructure. Herein, a novel crystalline 1D-COF (FZU-66) was constructed and further decorated with cobalt(II), which led to excellent heterogeneous catalytic performance in the C–H bond oxidation of ethylbenzene. In an aqueous solution at room temperature within 16 h, the conversion is nearly 100%, while the acetophenone selectivity is around 99%. More impressively, the designed single-dispersed cobalt(II)-coordinated 1D-COF (FZU-66-Co) retained good catalytic activity while maintaining high crystallinity after at least five consecutive recycling experiments. This work will prompt the application of porous polymers in the catalyzed oxidation of C–H bonds and make it an efficient and sustainable platform for activating C–H bonds of aromatic hydrocarbons.

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“…Micropacked bed reactors (μPBRs), characterized by the filling of various material solid particles and structural elements with a particle or pore size of less than 500 μm in small-size tubes, have been widely concerned in recent years. − μPBRs have excellent mass and heat transfer, which have been applied in multiphase reactions such as hydrogenation, , oxidation, , and CO 2 absorption . Especially for high-pressure and -temperature hydrogenation and oxidation, the potential security risks are significantly reduced due to the small volume of μPBRs compared with those of conventional large-scale STRs and TBRs.…”

Section: Introductionmentioning

confidence: 99%

External Mass Transfer Performance Studies in a Micropacked Bed Reactor with Pd/PDA/Nickel Foam

Duan,

Zhang,

Huang

et al. 2024

Ind. Eng. Chem. Res.

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The coating materials of monolithic foam catalysts have a remarkable influence on the mass transfer and reaction process of packed bed reactors. However, the external mass transfer performance of micropacked bed reactors (μPBRs) based on the organic polymer-coated foam catalyst has not been investigated. This study explores the αmethylstyrene hydrogenation reaction and external mass transfer performance of μPBRs with a polydopamine (PDA)-coated foam catalyst. Pd/PDA/nickel foam has excellent αmethylstyrene hydrogenation activity and stability compared to Pd/Al 2 O 3 /nickel foam in μPBRs. The effect of pressure, gas and liquid superficial velocities, and pore size of foam packing on external mass transfer coefficient ((ka) OV ) was investigated. The (ka) OV of the PDA-coated foam packing can reach 0.31−1.03 s −1 , which shows a notable improvement over the Al 2 O 3 coating. Furthermore, an empirical correlation equation for (ka) OV in μPBRs with PDA-coated foam packing is developed to provide a foundation for further design optimization and industrial applications.

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Green and continuous aerobic oxidation of ethylbenzene over homogeneous and heterogeneous NHPI in a micro-packed bed reactor

Cited by 11 publications

References 44 publications

Porous Aromatic Framework Covalently Embedded with N‐Hydroxyphthalimide as Metal‐free Heterogeneous Catalyst for Highly Efficient and Selective Aerobic Oxidation

Porous Aromatic Framework Covalently Embedded with N‐Hydroxyphthalimide as Metal‐free Heterogeneous Catalyst for Highly Efficient and Selective Aerobic Oxidation

Novel Cobalt(II)-Decorated 1D Covalent Organic Framework for Selective Oxidation of Ethylbenzene

External Mass Transfer Performance Studies in a Micropacked Bed Reactor with Pd/PDA/Nickel Foam

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