Abstract
The primary objective of this study was to synthesize a novel hyper-crosslinked cellulosic adsorbent (CLC) by a straightforward one-pot esterification reaction using cellulose and sebacoyl chloride as crosslinker agent. Efficient crosslinking of cellulose was confirmed by FTIR, CPMAS 13C NMR, elemental analysis, TGA, SEM and BET surface area analysis. The CLC material with high content of ester groups was employed to remove paracetamol (PCT) and niflumic acid (NFA) from aqueous solutions in batch adsorption experiments. The mesoporous structure of CLC created upon crosslinking was found to be a determinant in the adsorption behavior of the drugs. Indeed, PCT and NFA adsorption isotherms onto CLC were S-shaped and were adjusted by the Gu–Zhu, Frumkin–Fowler–Guggenheim and Hill–de Boer models. From the GZ isotherm model, the results indicate a cooperative adsorption mechanism leading to the formation of aggregates containing 2.53 and 4.25 molecules of PCT and NFA, respectively. Furthermore, FFG and HdB models reflect that the lateral interactions are attractive in nature for both drugs. The experimental kinetic data were fitted to the pseudo-second-order and intraparticle diffusion models, and the obtained parameters were linked to the aggregates arrangement of the drugs.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Alygizakis NA, Gago-Ferrero P, Borova VL, Pavlidou A, Hatzianestis I, Thomaidis NS (2016) Occurrence and spatial distribution of 158 pharmaceuticals, drugs of abuse and related metabolites in offshore seawater. Sci Total Environ 541:1097–1105. https://doi.org/10.1016/j.scitotenv.2015.09.145
Azanova VV, Hradil J (1999) Sorption properties of macroporous and hypercrosslinked copolymers. React Funct Polym 41:163–175. https://doi.org/10.1016/S1381-5148(99)00029-2
Babaei AA, Alavi SN, Akbarifar M, Ahmadi K, Esfahani AR, Kakavandi B (2016) Experimental and modeling study on adsorption of cationic methylene blue dye onto mesoporous biochars prepared from agrowaste. Desalin Water Treat 57:27199–27212. https://doi.org/10.1080/19443994.2016.1163736
Baccar R, Sarrà M, Bouzid J, Feki M, Blánquez P (2012) Removal of pharmaceutical compounds by activated carbon prepared from agricultural by-product. Chem Eng J 211–212:310–317. https://doi.org/10.1016/j.cej.2012.09.099
Bahamon D, Vega LF (2017) Pharmaceutical removal from water effluents by adsorption on activated carbons: a monte carlo simulation study. Langmuir 33:11146–11155. https://doi.org/10.1021/acs.langmuir.7b01967
Bakatula EN, Richard D, Neculita CM, Zagury GJ (2018) Determination of point of zero charge of natural organic materials. Environ Sci Pollut Res 25:7823–7833. https://doi.org/10.1007/s11356-017-1115-7
Bendjelloul M, Elandaloussi EH, de Ménorval LC, Bentouami A (2017) Quaternized triethanolamine-sebacoyl moieties in highly branched polymer architecture as a host for the entrapment of acid dyes in aqueous solutions. J Water Reuse Desalin 7:53–65. https://doi.org/10.2166/wrd.2016.191
Bhatnagar A, Sillanpää M, Witek-Krowiak A (2015) Agricultural waste peels as versatile biomass for water purification—a review. Chem Eng J 270:244–271. https://doi.org/10.1016/j.cej.2015.01.135
Boudrahem N, Delpeux-Ouldriane S, Khenniche L, Boudrahem F, Aissani-Benissad F, Gineys M (2017) Single and mixture adsorption of clofibric acid, tetracycline and paracetamol onto activated carbon developed from cotton cloth residue. Process Saf Environ Prot 111:544–559. https://doi.org/10.1016/j.psep.2017.08.025
Box KJ, Comer JEA (2008) Using measured pKa, LogP and solubility to investigate supersaturation and predict BCS class. Curr Drug Metab 9:869–878. https://doi.org/10.2174/138920008786485155
Box KJ, Völgyi G, Baka E, Stuart M, Takács-Novák K, Comer JEA (2006) Equilibrium versus kinetic measurements of aqueous solubility, and the ability of compounds to supersaturate in solution—a validation study. J Pharm Sci 95:1298–1307. https://doi.org/10.1002/jps.20613
Cheminski T, de Figueiredo NT, Silva PM, Guimarães CH, Prediger P (2019) Insertion of phenyl ethyleneglycol units on graphene oxide as stabilizers and its application for surfactant removal. J Environ Chem Eng 7:102976. https://doi.org/10.1016/j.jece.2019.102976
Ciğeroğlu Z, Küçükyıldız G, Erim B, Alp E (2021) Easy preparation of magnetic nanoparticles-rGO-chitosan composite beads: optimization study on cefixime removal based on RSM and ANN by using Genetic Algorithm Approach. J Mol Struct 1224:129182. https://doi.org/10.1016/j.molstruc.2020.129182
Coelho AD, Sans C, Esplugas S, Dezotti M (2010) Ozonation of NSAID: a biodegradability and toxicity study. Ozone Sci Eng 32:91–98. https://doi.org/10.1080/01919510903508162
El-Aila HJ, Elsousy KM, Hartany KA (2016) Kinetics, equilibrium, and isotherm of the adsorption of cyanide by MDFSD. Arab J Chem 9:S198–S203. https://doi.org/10.1016/j.arabjc.2011.03.002
Escapa C, Coimbra RN, Paniagua S, García AI, Otero M (2017) Paracetamol and salicylic acid removal from contaminated water by microalgae. J Environ Manage 203:799–806. https://doi.org/10.1016/j.jenvman.2016.06.051
Ferreira RC, de Lima HHC, Candido AA, Couto Junior OM, Arroyo PA, de Carvalho KQ, Gauze GF, Barros MASD (2015) Adsorption of paracetamol using activated carbon of dende and babassu coconut mesocarp. Int J Biol Biomol Agric Food Biotechnol Eng 9:575–580
Foston MB, Hubbell CA, Ragauskas AJ (2011) Cellulose isolation methodology for NMR analysis of cellulose ultrastructure. Materials 4:1985–2002. https://doi.org/10.3390/ma4111985
Franca MD, Santos LM, Silva TA, Borges KA, Silva VM, Patrocinio AOT, Trovo AG, Machado AEH (2016) Efficient mineralization of paracetamol using the nanocomposite TiO2/Zn(II) phthalocyanine as photocatalyst. J Braz Chem Soc 27:1094–1102. https://doi.org/10.5935/0103-5053.20160007
Gómez V, Larrechi MS, Callao MP (2007) Kinetic and adsorption study of acid dye removal using activated carbon. Chemosphere 69:1151–1158. https://doi.org/10.1016/j.chemosphere.2007.03.076
Ho YS (2006) Review of second-order models for adsorption systems. J Hazard Mater B136:681–689. https://doi.org/10.1016/j.jhazmat.2005.12.043
Hokkanen S, Bhatnagar A, Sillanpää M (2016) A review on modification methods to cellulose-based adsorbents to improve adsorption capacity. Water Res 91:156–173. https://doi.org/10.1016/j.watres.2016.01.008
Ibanez M, Borova V, Boix C, Aalizadeh R, Bade R, Thomaidis NS, Hernandez F (2016) UHPLC-QTOF MS screening of pharmaceuticals and their metabolites in treated wastewater samples from Athens. J Hazard Mater 323:26–35. https://doi.org/10.1016/j.jhazmat.2016.03.078
Jandura P, Kokta BV, Riedl B (2000) Fibrous long-chain organic acid cellulose esters and their characterization by diffuse reflectance FTIR spectroscopy, solid-state CP/MAS 13C-NMR, and X-ray diffraction. J Appl Polym Sci 78:1354–1365. https://doi.org/10.1002/1097-4628(20001114)78:7%3c1354::AID-APP60%3e3.0.CO;2-V
Ji H, Xiang Z, Qi H, Han T, Pranovich A, Song T (2019) Strategy towards one-step preparation of carboxylic cellulose nanocrystals and nanofibrils with high yield, carboxylation and highly stable dispersibility using innocuous citric acid. Green Chem 21:1956–1964. https://doi.org/10.1039/C8GC03493A
Joss A, Zabczynski S, Göbel A, Hoffmann B, Löffler D, McArdell CS, Ternes TA, Thomsen A, Siegrist H (2006) Biological degradation of pharmaceuticals in municipal wastewater treatment: Proposing a classification scheme. Water Res 40:1686–1696. https://doi.org/10.1016/j.watres.2006.02.014
Larsson PT, Westermark U, Iversen T (1995) Determination of the cellulose Iα allomorph content in a tunicate cellulose by CP/MAS 13C-NMR spectroscopy. Carbohydr Res 278:339–343. https://doi.org/10.1016/0008-6215(95)00248-0
Larsson DGJ, de Pedro C, Paxeus N (2007) Effluent from drug manufactures contains extremely high levels of pharmaceuticals. J Hazard Mater 148:751–755. https://doi.org/10.1016/j.jhazmat.2007.07.008
Li B, Pan Y, Zhang Q, Huang Z, Liu J, Xiao H (2019a) Porous cellulose beads reconstituted from ionic liquid for adsorption of heavy metal ions from aqueous solutions. Cellulose 26:9163–9178. https://doi.org/10.1007/s10570-019-02687-4
Li Y, Xiao H, Pan Y, Zhang M, Jin Y (2019b) Thermal and pH dual-responsive cellulose microfilament spheres for dye removal in single and binary systems. J Hazard Mater 377:88–97. https://doi.org/10.1016/j.jhazmat.2019.05.033
Menk JJ, Nascimento AIS, Leite FG, Oliveira RA, Jozala AF, Oliveira JM Jr, Chaud MV, Grotto D (2019) Biosorption of pharmaceutical products by mushroom stem waste. Chemosphere 237:124515. https://doi.org/10.1016/j.chemosphere.2019.124515
Miege C, Choubert JM, Ribeiro L, Eusebe M, Coquery M (2009) Fate of pharmaceuticals and personal care products in wastewater treatment plants-conception of a database and first results. Envir Pollut 157:1721–1726. https://doi.org/10.1016/j.envpol.2008.11.045
Mila E, Nika MC, Thomaidis NS (2019) Identification of first and second generation ozonation transformation products of niflumic acid by LC-QToF-MS. J Hazard Mater 365:804–812. https://doi.org/10.1016/j.jhazmat.2018.11.046
Moreno-Castilla C (2004) Adsorption of organic molecules from aqueous solutions on carbon materials. Carbon 42:83–94. https://doi.org/10.1016/j.carbon.2003.09.022
Nourmoradi H, Moghadam KF, Jafari A, Kamarehie B (2018) Removal of acetaminophen and ibuprofen from aqueous solutions by activated carbon derived from Quercus Brantii (Oak) acorn as a low-cost biosorbent. J Environ Chem Eng 6:6807–6815. https://doi.org/10.1016/j.jece.2018.10.047
Petrie B, Barden R, Kasprzyk-Hordern B (2015) A review on emerging contaminants in wastewaters and the environment: current knowledge, understudied areas and recommendations for future monitoring. Water Res 72:3–27. https://doi.org/10.1016/j.watres.2014.08.053
Rivera-Utrilla J, Sánchez-Polo M, Ferro-García MÁ, Prados-Joya G, Ocampo-Pérez R (2013) Pharmaceuticals as emerging contaminants and their removal from water. A review. Chemosphere 93:1268–1287. https://doi.org/10.1016/j.chemosphere.2013.07.059
Robberson KA, Waghe AB, Sabatini DA, Butler EC (2006) Adsorption of the quinolone antibiotic nalidixic acid onto anion-exchange and neutral polymers. Chemosphere 63:934–941. https://doi.org/10.1016/j.chemosphere.2005.09.047
Ru-Ling T, Feng-Chin W, Ruey-Shin J (2003) Liquid-phase adsorption of dyes and phenols using pinewood-based activated carbons. Carbon 41:487–495. https://doi.org/10.1016/S0008-6223(02)00367-6
Selkälä T, Suopajärvi T, Sirviö JA, Luukkonen T, Lorite GS, Kalliola S, Sillanpää M, Liimatainen H (2018) Rapid uptake of pharmaceutical salbutamol from aqueous solutions with anionic cellulose nanofibrils: the importance of pH and colloidal stability in the interaction with ionizable pollutants. Chem Eng J 350:378–385. https://doi.org/10.1016/j.cej.2018.05.163
Sim WJ, Lee JW, Lee ES, Shin SK, Hwang SR, Oh JE (2011) Occurrence and distribution of pharmaceuticals in wastewater from households, livestock farms, hospitals and pharmaceutical manufactures. Chemosphere 82:179–186. https://doi.org/10.1016/j.chemosphere.2010.10.026
Streit AFM, Collazzo GC, Druzian SP, Verdi RS, Foletto EL, Oliveira LFS, Dotto GL (2021) Adsorption of ibuprofen, ketoprofen, and paracetamol onto activated carbon prepared from effluent treatment plant sludge of the beverage industry. Chemosphere 262:128322. https://doi.org/10.1016/j.chemosphere.2020.128322
Thakur A, Sharma N, Mann A (2020) Removal of ofloxacin hydrochloride and paracetamol from aqueous solutions: binary mixtures and competitive adsorption. Mater Today Proc 28:1514–1519. https://doi.org/10.1016/j.matpr.2020.04.833
Torrellas SA, Lovera RG, Escalona N, Sepúlveda C, Sotelo JL, García J (2015) Chemical-activated carbons from peach stones for the adsorption of emerging contaminants in aqueous solutions. Chem Eng J 279:788–798. https://doi.org/10.1016/j.cej.2015.05.104
Tsai WT, Lai CW, Su TY (2006) Adsorption of bisphenol-A from aqueous solution onto minerals and carbon adsorbents. J Haz Mat B134:169–175. https://doi.org/10.1016/j.jhazmat.2005.10.055
Valderrama C, Gamisans X, de las Heras FX, Cortina JL, Farrán A (2007) Kinetics of polycyclic aromatic hydrocarbons removal using hyper-cross-linked polymeric sorbents Macronet Hypersol MN200. React Funct Polym 67:1515–1529. https://doi.org/10.1016/j.reactfunctpolym.2007.07.020
Villaescusa I, Fiol N, Poch J, Bianchi A, Bazzicalupi C (2011) Mechanism of paracetamol removal by vegetable wastes: The contribution of π–π interactions, hydrogen bonding and hydrophobic effect. Desalination 270:135–142. https://doi.org/10.1016/j.desal.2010.11.037
Wang D (2019) A critical review of cellulose-based nanomaterials for water purification in industrial processes. Cellulose 26:687–701. https://doi.org/10.1007/s10570-018-2143-2
Xiong P, Hu J (2017) Decomposition of acetaminophen (Ace) using TiO2/UVA/LED system. Catal Today 282:48–56. https://doi.org/10.1016/j.cattod.2016.03.015
Zhou Y, Min Y, Qiao H, Huang Q, Wang E, Ma T (2015) Improved removal of malachite green from aqueous solution using chemically modified cellulose by anhydride. Int J Biol Macromol 74:271–277. https://doi.org/10.1016/j.ijbiomac.2014.12.020
Zhu HY, Jiang R, Xiao L, Zeng GM (2010) Preparation, characterization, adsorption kinetics and thermodynamics of novel magnetic chitosan enwrapping nanosized γ-Fe2O3 and multi-walled carbon nanotubes with enhanced adsorption properties for methyl orange. Bioresour Technol 101:5063–5069. https://doi.org/10.1016/j.biortech.2010.01.107
Author information
Authors and Affiliations
Corresponding author
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Benosmane, S., Bendjelloul, M., Elandaloussi, E.H. et al. Experimental and modeling study on adsorption of emerging contaminants onto hyper-crosslinked cellulose. Chem. Pap. 75, 4021–4034 (2021). https://doi.org/10.1007/s11696-021-01637-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11696-021-01637-4