Influence of Brønsted acid sites on chemoselective synthesis of pyrrolidones over H-ZSM-5 supported copper catalyst

Boosa, Venu; Varimalla, Shirisha; Dumpalapally, Mahesh; Gutta, Naresh; Velisoju, Vijay Kumar; Narender, Nama; Venugopal, A.

doi:10.1016/j.apcatb.2021.120177

Cited by 40 publications

(22 citation statements)

References 64 publications

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“…Apparently, the position of the first reduction temperature of Cu/C-600 was the lowest (218 °C). Cu/C-400 and Cu/C-500 had large peak areas, possibly because some precursor structures were still retained, also confirmed by Figures and . , …”

Section: Results and Discussionsupporting

confidence: 67%

“…Figure clearly presents that all the materials in the figure were hydrophobic. When the catalyst had good lipophilicity, it was favorable for forming a stable oil/water emulsion and accelerating the interface reaction. , Figure a–d depicts contact angle images of samples prepared at different calcination temperatures. It can be found that the contact angle on Cu/C-600 was 146 ± 1° (the maximum), with the best catalytic effect.…”

Section: Results and Discussionmentioning

confidence: 99%

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Copper-Organic Framework-Derived Porous Nanorods for Chemoselective Hydrogenation of Quinoline Compounds at an Aqueous/Oil Interface

Wang

Pan

et al. 2021

ACS Appl. Nano Mater.

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In this work, a Cu-BTC material was first synthesized by a hydrothermal rota-crystallization method using cupric nitrate and benzene-1,3,5-tricarboxylate (BTC) as raw materials. Compared with a conventional hydrothermal method, this route greatly shortened the synthesis time of Cu-BTC to only 2 h. Cu-BTC was then treated under a N 2 atmosphere at different times and temperatures to obtain the derivative Cu/C-x-t with exceptional hydrophobicity (WCA of 146°), where x represents the pyrolysis temperature and t was the pyrolysis time. The size effect of Cu NPs on carbon played a critical role in promoting the reaction efficiency. The thus-synthesized Cu/C-x-t material acted as an excellent catalyst for the quinoline hydrogenation in an aqueous medium. It was found that the catalytic reactivity of Cu/C attained the highest value at 600 °C for 2 h; the conversion of quinoline reached 95.2 mol % and the selectivity of 1,2,3,4-tetrahydroquinoline (THQ) was >99% under mild aqueous reaction conditions. This could be attributed to the hydrophobic surface structure of Cu/C-600 and the interaction between Cu nanoparticles and the surface C matrix, to form a special aqueous/oil microenvironment on the surface of the catalyst and to accelerate the interfacial reactions.

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Section: Results and Discussionsupporting

confidence: 67%

Section: Results and Discussionmentioning

confidence: 99%

Copper-Organic Framework-Derived Porous Nanorods for Chemoselective Hydrogenation of Quinoline Compounds at an Aqueous/Oil Interface

Wang

Pan

et al. 2021

ACS Appl. Nano Mater.

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“…Combined with the catalytic performance of catalysts with different boron loading, the selectivity of 1 increased initially and then deceased, and it reached maximum at boron content of 3 wt.%. The results indicated that suitable acidic sites on the catalysts were benefit to the adsorption of amine compounds, which facilitated the hydrogenation of unsaturated imine intermediates such as 2 on the active sites of the catalysts [9b,34] . The acidity of catalysts and dispersion of Cu species continuous increased with further increasing boron loading (≥5 wt.%).…”

Section: Resultsmentioning

confidence: 98%

Boron Modified Cu/Al₂O₃ Catalysts for the Selective Reductive Amination of Levulinic Acid to N‐Substituted Pyrrolidinones

et al. 2022

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The reductive amination of biomass-derived levulinic acid (LA) to value-added N-substituted pyrrolidinones with amine and molecular hydrogen over heterogeneous catalyst represents an atom-economical and scalable route. In this paper, a series of boron doped Cu/Al 2 O 3 catalysts via kneading and impregnation method are developed for the continuous reductive amination of LA. Compared with Cu/Al 2 O 3 , Cu 10 /AlB 3 O catalyst exhibits greatly improved catalytic performance for this reaction at low operation temperature. Structure-property correlation investiga-tions were performed with diverse characterization methods, and the results revealed that the excellent catalytic performance of boron doped Cu/Al 2 O 3 catalysts was mainly attributed to the synergistic effect of its well-dispersed Cu nanoparticles, appropriate surface Cu electronic state and surface acidic sites nearby. Besides, Cu 10 /AlB 3 O shows great stability during the reaction over 200 h. This work provides a low-cost, efficient and environmentally friendly heterogeneous catalytic system for the continuous production of N-substituted pyrrolidinones.

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“…Reductive amination of LA or levulinates with primary amines over heterogeneous metal catalysts using molecular hydrogen as a reducing agent is a promising method for the synthesis of N-substituted-5-methyl-2-pyrrolidones [9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24], which are an alternative to the carcinogenic solvent N-methyl-2-pyrrolidone (NMP) used in large volumes in industry [3]. Due to the high cost and limited availability of precious metals, the use of non-noble metal catalysts is of particular interest [1,[20][21][22][23][24][25].…”

Section: Introductionmentioning

confidence: 99%

“…A positive role of acid sites on the surface of the support material in achieving a high pyrrolidone yield was observed, which is associated with the acceleration of EL amination and cyclization steps [9][10][11][12][13][14]21,25]. Nickel phosphides are attracting increased attention as bifunctional catalysts due to the presence of both metal and acid sites [26][27][28].…”

Section: Introductionmentioning

confidence: 99%

Effect of Phosphorus Precursor, Reduction Temperature, and Support on the Catalytic Properties of Nickel Phosphide Catalysts in Continuous-Flow Reductive Amination of Ethyl Levulinate

Wang

Nuzhdin

Shamanaev

et al. 2022

IJMS

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Levulinic acid and its esters (e.g., ethyl levulinate, EL) are platform chemicals derived from biomass feedstocks that can be converted to a variety of valuable compounds. Reductive amination of levulinates with primary amines and H2 over heterogeneous catalysts is an attractive method for the synthesis of N-alkyl-5-methyl-2-pyrrolidones, which are an environmentally friendly alternative to the common solvent N-methyl-2-pyrrolidone (NMP). In the present work, the catalytic properties of the different nickel phosphide catalysts supported on SiO2 and Al2O3 were studied in a reductive amination of EL with n-hexylamine to N-hexyl-5-methyl-2-pyrrolidone (HMP) in a flow reactor. The influence of the phosphorus precursor, reduction temperature, reactant ratio, and addition of acidic diluters on the catalyst performance was investigated. The Ni2P/SiO2 catalyst prepared using (NH4)2HPO4 and reduced at 600 °C provides the highest HMP yield, which reaches 98%. Although the presence of acid sites and a sufficient hydrogenating ability are important factors determining the pyrrolidone yield, the selectivity also depends on the specific features of EL adsorption on active catalytic sites.

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Influence of Brønsted acid sites on chemoselective synthesis of pyrrolidones over H-ZSM-5 supported copper catalyst

Cited by 40 publications

References 64 publications

Copper-Organic Framework-Derived Porous Nanorods for Chemoselective Hydrogenation of Quinoline Compounds at an Aqueous/Oil Interface

Copper-Organic Framework-Derived Porous Nanorods for Chemoselective Hydrogenation of Quinoline Compounds at an Aqueous/Oil Interface

Boron Modified Cu/Al₂O₃ Catalysts for the Selective Reductive Amination of Levulinic Acid to N‐Substituted Pyrrolidinones

Effect of Phosphorus Precursor, Reduction Temperature, and Support on the Catalytic Properties of Nickel Phosphide Catalysts in Continuous-Flow Reductive Amination of Ethyl Levulinate

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Influence of Brønsted acid sites on chemoselective synthesis of pyrrolidones over H-ZSM-5 supported copper catalyst

Cited by 40 publications

References 64 publications

Copper-Organic Framework-Derived Porous Nanorods for Chemoselective Hydrogenation of Quinoline Compounds at an Aqueous/Oil Interface

Copper-Organic Framework-Derived Porous Nanorods for Chemoselective Hydrogenation of Quinoline Compounds at an Aqueous/Oil Interface

Boron Modified Cu/Al2O3 Catalysts for the Selective Reductive Amination of Levulinic Acid to N‐Substituted Pyrrolidinones

Effect of Phosphorus Precursor, Reduction Temperature, and Support on the Catalytic Properties of Nickel Phosphide Catalysts in Continuous-Flow Reductive Amination of Ethyl Levulinate

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Boron Modified Cu/Al₂O₃ Catalysts for the Selective Reductive Amination of Levulinic Acid to N‐Substituted Pyrrolidinones