Synthesis and characterization of N-hydroxyphthalimide immobilized on SiO2-coated Fe3O4 nanoparticles as magnetic catalyst for oxidation of benzyl alcohols and hydrocarbons

Hosseinzadeh, Rahman; Mavvaji, Mohammad; Tajbakhsh, Mahmood; Lasemi, Zahra

doi:10.1007/s13738-017-1288-5

Cited by 12 publications

(4 citation statements)

References 31 publications

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“…The NHPI moieties are most often grafted onto the surface through amide (C=O)−N−C, [10a] ester (C=O)−O−C [10b] and, sporadically, other bonds. NHPI acid derivatives were deposited on silicas functionalized with propylchlorine [11c] and (3‐aminopropyl)triethoxysilane [15,11d] . Furthermore, NHPI was anchored on cross‐linked polystyrene, [10c] aminoethylstyrene and chloroethylstyrene, [10a,16] poly(glycidyl methacrylate‐ co ‐methylmethacrylate) [17] as well as poly(2‐hydroxyethylacrylate‐ co ‐divinylbenzene) [10b] …”

Section: Introductionmentioning

confidence: 99%

Covalent bonding of N‐hydroxyphthalimide on mesoporous silica for catalytic aerobic oxidation of p‐xylene at atmospheric pressure

Berniak,

Łątka,

Drozdek

et al. 2024

ChemPlusChem

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The surface of SBA‐15 mesoporous silica was modified by N‐hydroxyphthalimide (NHPI) moieties acting as immobilized active species for aerobic oxidation of alkylaromatic hydrocarbons. The incorporation was carried out by four original approaches: the grafting‐from and grafting‐onto techniques, using the presence of surface silanols enabling the formation of particularly stable O‐Si‐C bonds between the silica support and the organic modifier. The strategies involving the Heck coupling led to the formation of NHPI groups separated from the SiO2 surface by a vinyl linker, while one of the developed modification paths based on the grafting of an appropriate organosilane coupling agent resulted in the active phase devoid of this structural element. The successful course of the synthesis was verified by FTIR and 1H NMR measurements. Furthermore, the formed materials were examined in terms of their chemical composition (elemental analysis, thermal analysis), structure of surface groups (13C NMR, XPS), porosity (low‐temperature N2 adsorption), and tested as catalysts in the aerobic oxidation of p‐xylene at atmospheric pressure. The highest conversion and selectivity to p‐toluic acid were achieved using the catalyst with enhanced availability of non‐hydrolyzed NHPI groups in the pore system. The catalytic stability of the material was additionally confirmed in several subsequent reaction cycles.

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Section: Introductionmentioning

confidence: 99%

Covalent bonding of N‐hydroxyphthalimide on mesoporous silica for catalytic aerobic oxidation of p‐xylene at atmospheric pressure

Berniak,

Łątka,

Drozdek

et al. 2024

ChemPlusChem

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“…Among all, the 2 + 3 cycloaddition approach using benzonitrile compounds with an equal amount of azide gained much attention due to its simplicity and good conversion. Hence researchers have wanted to develop simple and effective protocols for this skeleton construction by using various catalysts through the same approach like cyanuric chloride, [14] tetrabutyl ammonium fluoride, [15] FeCl 3 À SiO 2 , [16] ceric ammonium nitrate supported HY-zeolite, [17] POCl 3 , [18] L-proline, [19] DPPA, [20] Montmorillonite KSF, [21] CdCl 2 , [22] and Sc-(OTf) 3 . [23] Despite their potential utility, several of the documented procedures have limitations such as the use of poisonous, corrosive acid or metals as imputes, severe reaction conditions, inadequate yields, expensive and high catalyst loading, longer reaction periods, and so on affecting its largescale production.…”

Section: Introductionmentioning

confidence: 99%

Metal‐free organic transformation: 2,6‐Pyridine dicarboxylic acid catalyzed synthesis of 5‐substituted‐1H‐tetrazoles and β‐aminoketones

Govindhan¹,

Selvam²

2022

ChemistrySelect

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A highly efficient, clean, and easy technique for the one‐pot metal‐free synthesis of 5‐substituted‐1H‐tetrazoles through click chemistry approach and β‐aminoketones via Mannich reaction employing 2,6‐pyridine dicarboxylic acid (PDCA) as an organocatalyst has been established. These conversions occur under gentle reaction conditions to give excellent to superior yields. This methodology offers benefits such as short reaction time, a low impetus stacking %, a multi‐component approach, and metal‐free ecobenign synthesis.

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“…NHPI species were immobilized on various solid supports, including silicas [29][30][31][32], zeolites [33], MOFs [34], diamond particles [35] or carbon nanotubes [36]. An interesting approach to anchoring NHPI groups on the surface of mesoporous silica was described by Li et al [37].…”

Section: Introductionmentioning

confidence: 99%

Selective Aerobic Oxidation of P-Methoxytoluene by Co(II)-Promoted NHPI Incorporated into Cross-Linked Copolymer Structure

et al. 2021

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A wide series of copolymer materials with various contents of 4-vinyl-diisopropyl-phtalate ester (10–90 mol%), divinylbenzene (1–11 mol%) and styrene, as monomers, were obtained by radical copolymerization. In the last steps of the synthesis, diisopropyl ester functionalities were converted into the form of N-hydroxyphthalimide (NHPI) rings. The obtained materials with the NHPI groups immobilized in the copolymer structure were studied by various physicochemical techniques, including FT-IR, UV-Vis-DR, XPS, elemental analysis, and tested as catalysts in aerobic oxidation of p-methoxytoluene in the presence of Co(II) acetate co-catalyst. Conversion of the aromatic substrate was correlated with the NHPI content and cross-linking degree. The best catalytic performance (conversions higher than 23%) was achieved for the copolymer catalysts containing 60% and 30% of 4-vinyl-diisopropyl-phtalate ester. At too high concentrations of NHPI and DVB, some of the NHPI groups were transformed into inactive (C=O)-N=O species or not available due to embedding inside the copolymer structure. The mechanism of the process involving both NHPI centers, forming phthalimide N-oxyl (PINO) radicals, and Co(II) cations was discussed. Stability of the developed catalysts was also tested. The opening of imide rings took place during the catalytic process, resulting in the formation of carboxyl groups and the release of hydroxylamine molecules. The deactivated catalyst could be easily regenerated by repeating two last steps of closing imide ring.

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Synthesis and characterization of N-hydroxyphthalimide immobilized on SiO2-coated Fe3O4 nanoparticles as magnetic catalyst for oxidation of benzyl alcohols and hydrocarbons

Cited by 12 publications

References 31 publications

Covalent bonding of N‐hydroxyphthalimide on mesoporous silica for catalytic aerobic oxidation of p‐xylene at atmospheric pressure

Covalent bonding of N‐hydroxyphthalimide on mesoporous silica for catalytic aerobic oxidation of p‐xylene at atmospheric pressure

Metal‐free organic transformation: 2,6‐Pyridine dicarboxylic acid catalyzed synthesis of 5‐substituted‐1H‐tetrazoles and β‐aminoketones

Selective Aerobic Oxidation of P-Methoxytoluene by Co(II)-Promoted NHPI Incorporated into Cross-Linked Copolymer Structure

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