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The Efficient Knoevenagel Condensation Promoted by Bifunctional Heterogenized Catalyst Based Chitosan-EDTA at Room Temperature

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Abstract

An efficient heterogeneous catalyst-based low molecular weight chitosan (LWC) modified with EDTA groups were prepared and applied as a bifunctional heterogenized catalyst in the Knoevenagel Condensation reaction, promoting fast reactions between malononitrile and aldehydes or isatins at room temperature. Chitosan-EDTA (LWC-EDTA) catalysts were characterized by Fourier transform infrared spectroscopy (FT-IR), thermogravimetric analysis (TGA/DTA), powder X-ray diffraction (XRD). UV–Vis absorption spectrophotometry showed that the functionalization of chitosan with EDTA for 72 h promotes the most significant modification of the matrix surface compared to the others applied, reflecting shorter reaction times. The reactions using the LWC-EDTA-72 catalyst present excellent isolated yields (78–98%) in short reaction times (0.50–120 min) for differents Knoevenagel compounds. Additionaly, the catalyst was easily recovered and reused up to six times without significant losses of its catalytic activity.

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Acknowledgements

The authors are grateful to the Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq, 304403/2017-2) and the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES, 88882.440011/2019-01) for their financial support. They are also grateful to the Financiadora de Estudos e Projetos (FINEP), and Projeto Produtividade em Pesquisa (PROPESQ/PRPG/UFPB, PVA13317-2020).

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Authors and Affiliations

  1. Departamento de Química, Universidade Federal da Paraíba - UFPB, Jardim Cidade Universitária, João Pessoa, PB, CEP 58051-900, Brazil

    Paloma Gomes de Abrantes, Israel Ferreira Costa, Nathalia Kellyne da Silva Marinho Falcão, João Marcos Gomes de Oliveira Ferreira, Claudio Gabriel Lima Junior, Ercules Epaminondas de Sousa Teotonio & Juliana Alves Vale

  2. Departamento de Química Fundamental, Instituto de Química da Universidade de São Paulo, Av. Prof. Lineu Prestes, 748, São Paulo, SP, CEP 05508-000, Brazil

    Israel Ferreira Costa

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  1. Paloma Gomes de Abrantes
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  2. Israel Ferreira Costa
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Correspondence to Juliana Alves Vale.

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10562_2022_4034_MOESM1_ESM.docx

Supplementary file1 (DOCX 4527 kb) The reagents and instruments, TGA/DTA in synthetic air atmosphere of the studied samples, the quantification of NH2- groups in the functionalized chitosan polymers and precursors and the 1H and 13C NMR spectral data of the products for the selected compounds will be found in the supplementary data.

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de Abrantes, P.G., Costa, I.F., Falcão, N.K.S.M. et al. The Efficient Knoevenagel Condensation Promoted by Bifunctional Heterogenized Catalyst Based Chitosan-EDTA at Room Temperature. Catal Lett 153, 945–955 (2023). https://doi.org/10.1007/s10562-022-04034-y

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