Cellulose polymers with β-amino ester pendant group: design, synthesis, molecular docking and application in adsorption of toxic metals from wastewater

Noor Nairat; Othman Hamed; Avni Berisha; Shehdeh Jodeh; Manuel Algarra; Khalil Azzaoui; Omar Dagdag; Subhi Samhan

doi:10.1186/s13065-022-00837-7

Cellulose polymers with β-amino ester pendant group: design, synthesis, molecular docking and application in adsorption of toxic metals from wastewater

BMC Chem. 2022 Jun 10;16(1):43. doi: 10.1186/s13065-022-00837-7.

Authors

Noor Nairat¹, Othman Hamed², Avni Berisha^{3

4}, Shehdeh Jodeh⁵, Manuel Algarra⁶, Khalil Azzaoui⁷, Omar Dagdag⁸, Subhi Samhan⁹

Affiliations

¹ Chemistry Department, Faculty of Science, An-Najah National University, P.O. Box 7, Nablus, Palestine.
² Chemistry Department, Faculty of Science, An-Najah National University, P.O. Box 7, Nablus, Palestine. ohamed@najah.edu.
³ Department of Chemistry, Faculty of Natural and Mathematics Science, University of Prishtina, Prishtina, 10000, Kosovo.
⁴ Materials Science-Nanochemistry Research Group, NanoAlb-Unit of Albanian Nanoscience and Nanotechnology, 1000, Tirana, Albania.
⁵ Chemistry Department, Faculty of Science, An-Najah National University, P.O. Box 7, Nablus, Palestine. sjodeh@najah.edu.
⁶ Department of Science, INAMAT2 Institute for Advanced Materials and Mathematics, Public University of Navarra, Campus of Arrosadia, 31006, Pamplona, Spain.
⁷ Laboratory of Mineral Solid and Analytical Chemistry LMSAC, Department of Chemistry, Faculty of Sciences, Mohamed 1st University, P.O. Box 717, Oujda, Morocco.
⁸ Institute of Nanotechnology and Water Sustainability, College of Science, Engineering and Technology, University of South Africa, Johannesburg, South Africa.
⁹ Palestine Water Authority, Ramallah, 00001, Palestine.

Abstract

Background: Cellulose polymers with multidentate chelating functionalities that have high efficiency for toxic metal ions present in water were designed, synthesized, and analyzed. The synthesis was carried out by reacting microcrystalline cellulose extracted from the solid waste of the olive industry with tert-Butyl acetoacetate (Cell-AA), produced cellulose with β-ketoester functionality was then reacted with aniline and the amino acid glycine to produce Cell-β-AN and Cell-β-GL, respectively.

Results: The adsorption efficiency of the three polymers toward Pb(II) and various toxic metal ions present in sewage was evaluated as a function of adsorbent dose, time, temperature, pH value, and initial ion concentration to determine optimum adsorption conditions. The three polymers showed excellent efficiency toward about 20 metal ions present in a sewage sample collected from the sewer. The adsorption process follows the Langmuir adsorption isotherm model with a second-order of adsorption rate, the calculated qe values (2.675, 15.252, 20.856 mg/g) were close to the experimental qe values (2.133, 13.91, 18.786 mg/g) for the three polymers Cell-AA, Cell-β-AG and Cell-β-AN, respectively. Molecular Dynamic (MD) and Monte Carlo (MC) simulations were performed on the three polymers complexed with Pb(II).

Conclusion: The waste material of the olive industry was used as a precursor for making the target cellulose polymers with β-Amino Ester Pendant Group. The polymer was characterized by SEM, proton NMR, TGA, and FT-IR spectroscopy. The efficacy of adsorption was quantitative for metal ions present in a real sample of wastewater and the efficiency didn't drop even after 7 cycles of use. The results indicate the existence of strong complexation. The thermodynamic study results showed a spontaneous bonding between of Pb(II) and the polymers pendant groups expressed by the negative value of the Gibbs free energy.

Keywords: 2-furan carbonyl chloride; Adsorption; Cellulose; Cellulose nanocrystalline; Difenoconazole; Glycine; Molecular dynamic; Monte Carlo; Persistent pesticides; Wastewater; Water treatment.