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P(HEMA)-SO3H catalyst: preparation, characterization and its catalytic activity in Ritter reaction

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Abstract

In this study, poly(hydroxyethyl methacrylate) [P(HEMA)] microsphere-supported sulfuric acid [P(HEMA)-SO3H] was prepared as a novel heterogenous solid acid catalyst and its catalytic activity was investigated in the synthesis of amides via Ritter reaction. The P(HEMA) microspheres were synthesized via suspension polymerization and characterized by Fourier transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM), Brunauer, Emmett and Teller surface area and energy dispersive X-ray (EDX) analyses. The specific surface area and the pore volume of the microspheres were determined as 33.80 m2/g and 1.490 cm3/g, respectively. The pore size was in the range of 9.18–122.59 A°. The specific surface area of P(HEMA)-SO3H catalyst was 26.24 m2/g decreasing after modification with sulfo groups. FTIR, SEM and EDX analyses demonstrated that P(HEMA) microspheres were successfully modified with sulfo groups. The acidity of P(HEMA)-SO3H catalyst was determined as to 7.48 ± 0.16 mmol H+/g P(HEMA)-SO3H catalyst by titration with standardized NaOH solution. The catalyst was then successfully applied in the Ritter reaction to prepare a series of different amides in high to excellent yields. The P(HEMA)-SO3H catalyst was recovered and reused four times without a significant decrease in the catalytic activity. The other advantages of this novel catalyst include excellent yield, short reaction time and solvent-free conditions.

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The supplementary material file includes FTIR spectra of P(HEMA) microspheres and P(HEMA)-SO3H catalyst, and the analytical and spectral data, FTIR, 1H, 13C NMR spectra of all synthesized compounds.

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Funding

This work was supported by the Research Foundation of Bursa Uludag University [Project No. FHIZ-2022-1014].

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BO synthesized P(HEMA) microspheres. P(HEMA)-SO3H catalyst was preparation by NAÖ. BO did the characterization of the catalyst. NAÖ studied the catalytic activity of the catalyst. NAÖ synthesized and characterized all compounds via Ritter reaction. Both authors reviewed the article.

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Correspondence to Nevin Arıkan Ölmez.

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Arıkan Ölmez, N., Osman, B. P(HEMA)-SO3H catalyst: preparation, characterization and its catalytic activity in Ritter reaction. Res Chem Intermed 48, 4987–5001 (2022). https://doi.org/10.1007/s11164-022-04844-0

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