Novel pyridine isonicotinoyl hydrazone derivative: synthesis, complexation and investigation for decontamination of DR-81 from wastewater

Abstract

Herein, novel aroylhydrazone (E/Z)-N′-((3-methylpyridin-2-yl)methylene)isonicotinohydrazide ligand (MPIH) 3 and its Zn(II)-MPIH complex 4 were synthesized and investigated to adsorb direct red 81 dye (DR-81) from aqueous media. MPIH was synthesized by the condensation reaction of isonicotinohydrazide with 3-methylpicolinaldehyde 2, then performed in a basic medium with zinc chloride to form Zn(II)-MPIH complex. The synthesized MPIH ligand 3 and Zn(II)-MPIH complex 4 were further characterized via proton nuclear magnetic resonance (¹H NMR), ¹³C nuclear magnetic resonance, Fourier transform infrared spectroscopy (FT-IR), UV-visible, mass spectra analysis (EI MS), and elemental analysis. The synthesized MPIH ligand 3 and Zn(II)-MPIH complex 4 were evaluated for their ability to decontaminate DR-81 from wastewater. The performance of MPIH ligand 3 to adsorb DR-81 from wastewater was lower than Zn(II)-MPIH complex 4 over contact times of 180 minutes. The optimal dosage of the Zn(II)-MPIH complex 4 was determined to be 1.0 g L⁻¹ at pH 7, achieving 88.3% adsorption of 10 ppm DR-81 within 45 minutes. Thermodynamic analysis showed that the decontamination process was spontaneous and exothermic when using the fabricated Zn(II)-MPIH complex 4. The kinetic parameters aligned well with the pseudo-second-order kinetics model, and the adsorption process was accurately described by the Freundlich isotherm. The adsorption data confirmed that the Zn(II)-MPIH complex 4 is an effective adsorbent for DR-81 in aqueous solutions, demonstrating high stability, the ability to be recycled for up to seven cycles, and ease of regeneration.