Abstract
Microcrystalline cellulose (MCC) was isolated from the almond shell after its pretreatment with an acidic deep eutectic solvent (DES) of choline chloride/oxalic acid under microwave irradiation. The Fourier transform infrared spectroscopy analysis showed that the spectrum of the isolated (MCC) includes an additional peak at 1747.0 cm−1 which refers to the (C=O) esters and carboxylic peak. This indicates that the MCC surface has undergone simultaneous partial esterification during the isolation process. Owing to its favorable structural and morphological properties, the isolated MCC was successfully employed for the adsorption of aqueous Pb2+ ions with (50 mg/g) efficiency using a 3.0 g/L adsorbent dose at pH (6.5) and 20 °C. The adsorption was spontaneous near the ambient temperature, pH dependent, and exothermic. The Coulomb forces are the foremost adsorption driving force. The reusing of the spent DES and adsorbent for four successive rounds, affirmed their applicability on industrial scales.
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The data that support the findings of this study are available from the corresponding author upon reasonable request.
References
Abdelaziz RM, El-Maghraby A, Sadik WA-A, El-Demerdash A-GM, Fadl EA (2022) Biodegradable cellulose nanocrystals hydrogels for removal of acid red 8 dye from aqueous solutions. Sci Rep 12:1–17
Abegunde SM, Idowu KS, Adejuwon OM, Adeyemi-Adejolu T (2020) A review on the influence of chemical modification on the performance of adsorbents. Resour Environ Sustain 1:100001
Abo-Hamad A, Hayyan M, AlSaadi MA, Hashim MA (2015) Potential applications of deep eutectic solvents in nanotechnology. Chem Eng J 273:551–567
Abuhatab S, El-Qanni A, Al-Qalaq H, Hmoudah M, Al-Zerei W (2020) Effective adsorptive removal of Zn2+, Cu2+, and Cr3+ heavy metals from aqueous solutions using silica-based embedded with NiO and MgO nanoparticles. J Environ Manag 268:110713
Arain MB, Yilmaz E, Soylak M (2016) Deep eutectic solvent based ultrasonic assisted liquid phase microextraction for the FAAS determination of cobalt. J Mol Liq 224:538–543
Argun ME, Dursun S (2008) A new approach to modification of natural adsorbent for heavy metal adsorption. Biores Technol 99:2516–2527
Ashour EA, Tony MA (2020) Eco-friendly removal of hexavalent chromium from aqueous solution using natural clay mineral: activation and modification effects. SN Appl Sci 2:1–13
Asrat Y, Adugna AT, Kamaraj M, Beyan SM (2021) Adsorption phenomenon of arundinaria alpina stem-based activated carbon for the removal of lead from aqueous solution. J Chem 2021:1–9
Atefi M, Nayebzadeh K, Mohammadi A, Mortazavian AM (2017) Using ß-cyclodextrin and Arabic gum as wall materials for encapsulation of Saffron essential oil. Iran J Pharm Res IJPR 16:93
Aydin F, Yilmaz E, Soylak M (2017) A simple and novel deep eutectic solvent based ultrasound-assisted emulsification liquid phase microextraction method for malachite green in farmed and ornamental aquarium fish water samples. Microchem J 132:280–285
Balarak D, Azarpira H, Mostafapour FK (2016) Study of the adsorption mechanisms of cephalexin on to Azolla filiculoides. Der Pharm Chem 8:114–121
Balzar D (1993) X-ray diffraction line broadening: Modeling and applications to high-Tc superconductors. J Res Nat Inst Stand Technol 98:321
Baskar AV, Bolan N, Hoang SA, Sooriyakumar P, Kumar M, Singh L, Jasemizad T, Padhye LP et al (2022) Recovery, regeneration and sustainable management of spent adsorbents from wastewater treatment streams: a review. Sci Total Environ 822:153555
Beksissa R, Tekola B, Ayala T, Dame B (2021) Investigation of the adsorption performance of acid treated lignite coal for Cr (VI) removal from aqueous solution. Environ Chall 4:100091
Bişgin AT (2019) Surfactant-assisted emulsification and surfactant-based dispersive liquid–liquid microextraction method for determination of Cu (II) in food and water samples by flame atomic absorption spectrometry. J AOAC Int 102:1516–1522
Bozorgzadeh E, Pasdaran A, Ebrahimi-Najafabadi H (2021) Determination of toxic heavy metals in fish samples using dispersive micro solid phase extraction combined with inductively coupled plasma optical emission spectroscopy. Food Chem 346:128916
Chen Z, Wan C (2018) Ultrafast fractionation of lignocellulosic biomass by microwave-assisted deep eutectic solvent pretreatment. Biores Technol 250:532–537
Chen Y, Zhang L, Yu J, Lu Y, Jiang B, Fan Y, Wang Z (2019) High-purity lignin isolated from poplar wood meal through dissolving treatment with deep eutectic solvents. R Soc Open Sci 6:181757
Colella M, Romanazzi G, Petrelli V, Baldassarre F, Ciccarella G, Catauro M, Mastrorilli P, Dell'Anna MM (2022) Microwave‐assisted treatment of waste wood biomass with deep eutectic solvents. Paper presented at the Macromolecular Symposia
Dada A, Olalekan A, Olatunya A, Dada O (2012) Langmuir, Freundlich, Temkin and Dubinin-Radushkevich isotherms studies of equilibrium sorption of Zn2+ unto phosphoric acid modified rice husk. IOSR J Appl Chem 3:38–45
Dan Y, Xu L, Qiang Z, Dong H, Shi H (2021) Preparation of green biosorbent using rice hull to preconcentrate, remove and recover heavy metal and other metal elements from water. Chemosphere 262:127940
Dutta SD, Patel DK, Ganguly K, Lim K-T (2021) Isolation and characterization of cellulose nanocrystals from coffee grounds for tissue engineering. Mater Lett 287:129311
Elboughdiri N (2020) The use of natural zeolite to remove heavy metals Cu (II), Pb (II) and Cd (II), from industrial wastewater. Cogent Eng 7:1782623
Fakhre NA, Ibrahim BM (2018) The use of new chemically modified cellulose for heavy metal ion adsorption. J Hazard Mater 343:324–331
Fayomi O, Ike D, Iorhemba M, Ameh O, Ihegwuagu N, Kalu R (2021) Investigation on the corrosion inhibiting property of modified cashew nutshell liquid. Int J Corros Scale Inhib 10:1307–1322
Freundlich H (1906) Over the adsorption in solution. J Phys Chem 57:1100–1107
Gil A (2021) Current insights into lignocellulose related waste valorization. Chem Eng J Adv 8:100186
Greda K, Welna M, Szymczycha-Madeja A, Pohl P (2022) Sensitive determination of Ag, Bi, Cd, Hg, Pb, Tl, and Zn by inductively coupled plasma optical emission spectrometry combined with the microplasma-assisted vapor generation. Talanta 249:123694
Henschen J, Li D, Ek M (2019) Preparation of cellulose nanomaterials via cellulose oxalates. Carbohyd Polym 213:208–216
Hosseinzadeh M (2019) Sorption of lead ion from aqueous solution by carboxylic acid groups containing adsorbent polymer. J Chil Chem Soc 64:4466–4470
Hussain A, Iqbal MA, Javid A, Razaq A, Aslam S, Hasan A, Akmal M, Qazi JI (2019) Application of fruit wastes as cost-effective carbon sources for biological sulphate reduction. Iran J Sci Technol Trans A Sci 43:33–41
Ibrahim BM, Fakhre NA, Jalhoom MG, Qader IN, Shareef HY, Jalal AF (2022) Removal of lead ions from aqueous solutions by modified cellulose. Environ Technol 43:1–27
Jalu RG, Chamada TA, Kasirajan R (2021) Calcium oxide nanoparticles synthesis from hen eggshells for removal of lead (Pb (II)) from aqueous solution. Environ Chall 4:100193
Jamshidi P, Shemirani F (2019) Adsorption and desorption of Pb2+ on magnetic Mn2O3 as highly efficient adsorbent: isotherm, kinetic and thermodynamic studies. Colloids SurfA 571:151–159
Ji F, Li C, Tang B, Xu J, Lu G, Liu P (2012) Preparation of cellulose acetate/zeolite composite fiber and its adsorption behavior for heavy metal ions in aqueous solution. Chem Eng J 209:325–333
Karimi F, Ayati A, Tanhaei B, Sanati AL, Afshar S, Kardan A, Dabirifar Z, Karaman C (2022) Removal of metal ions using a new magnetic chitosan nano-bio-adsorbent; a powerful approach in water treatment. Environ Res 203:111753
Kassab Z, Hannache H, El Achaby M (2019) Isolation of cellulose nanocrystals from various lignocellulosic materials: physico-chemical characterization and application in polymer composites development. Mater Today Proc 13:964–973
Kohli K, Katuwal S, Biswas A, Sharma BK (2020) Effective delignification of lignocellulosic biomass by microwave assisted deep eutectic solvents. Biores Technol 303:122897
Kończyk J, Dlugosz J (2020) Selective solvent extraction of some heavy metal ions from aqueous solutions by octafunctionalized resorcin [4] arenes. Physicochemical Probl Mineral Process 56:271–285
Krishnamoorthy R, Govindan B, Banat F, Sagadevan V, Purushothaman M, Show PL (2019) Date pits activated carbon for divalent lead ions removal. J Biosci Bioeng 128:88–97
Kuthi FAA, Norzali NRA, Badri KH (2016) Thermal Characteristics of microcrystalline cellulose from oil palm biomass. Malays J Anal Sci 20:1112–1122
Langmuir I (1916) The constitution and fundamental properties of solids and liquids. Part I. Solids. J Am Chem Soc 38:2221–2295
Lease J, Kawano T, Andou Y (2021) Esterification of cellulose with long fatty acid chain through mechanochemical method. Polymers 13:4397
Li X, Liu Y, Hao J, Wang W (2018) Study of almond shell characteristics. Materials 11:1782
Li C, Ma H, Venkateswaran S, Hsiao BS (2020) Highly efficient and sustainable carboxylated cellulose filters for removal of cationic dyes/heavy metals ions. Chem Eng J 389:123458
Liu P, Hao J-W, Mo L-P, Zhang Z-H (2015) Recent advances in the application of deep eutectic solvents as sustainable media as well as catalysts in organic reactions. RSC Adv 5:48675–48704
Liu Q, He W-Q, Aguedo M, Xia X, Bai W-B, Dong Y-Y, Song J-Q, Richel A et al (2021a) Microwave-assisted alkali hydrolysis for cellulose isolation from wheat straw: Influence of reaction conditions and non-thermal effects of microwave. Carbohyd Polym 253:117170
Liu S, Zhang Q, Gou S, Zhang L, Wang Z (2021b) Esterification of cellulose using carboxylic acid-based deep eutectic solvents to produce high-yield cellulose nanofibers. Carbohyd Polym 251:117018
Lv S-W, Liu J-M, Li C-Y, Zhao N, Wang Z-H, Wang S (2019) A novel and universal metal-organic frameworks sensing platform for selective detection and efficient removal of heavy metal ions. Chem Eng J 375:122111
Maaloul N, Oulego P, Rendueles M, Ghorbal A, Diaz M (2021a) Biopolymer composite from cellulose nanocrystals of almond (Prunus dulcis) shell as effective adsorbents for Cu2+ ions from aqueous solutions. J Environ Chem Eng 9:105139
Maaloul N, Oulego P, Rendueles M, Ghorbal A, Díaz M (2021b) Biopolymer composite from cellulose nanocrystals of almond (Prunus dulcis) shell as effective adsorbents for Cu2+ ions from aqueous solutions. J Environ Chem Eng 9:105139
Mariana M, Mistar EM, Syabriyana M, Zulkipli AS, Aswita D, Alfatah T (2022) Properties and adsorptive performance of candlenut shell and its porous charcoals for aqueous mercury (II) removal. Bioresour Technol Rep 19:101182
Mbiri A, Onditi A, Oyaro N, Murago E (2011) Determination of essential and heavy metals in Kenyan honey by atomic absorption and emission spectroscopy. J Agricult Sci Technol 13:107–115
Meng F, Zhang Y, Cai Y, Yuan G, Han FX (2021) Kinetic and Thermodynamic features of Pb (II) removal from aqueous solution by Leonardite-derived humic acid. Water Air Soil Pollut 232:1–12
Naseem K, Begum R, Wu W, Usman M, Irfan A, Al-Sehemi AG, Farooqi ZH (2019) Adsorptive removal of heavy metal ions using polystyrene-poly (N-isopropylmethacrylamide-acrylic acid) core/shell gel particles: adsorption isotherms and kinetic study. J Mol Liq 277:522–531
Oboh O, Aluyor E (2008) The removal of heavy metal ions from aqueous solutions using sour sop seeds as biosorbent. Afri J Biotechnol 7:4508–4511
Ozalp O, Soylak M (2021) Magnetic dispersive solid phase extraction of Cu (II) as 1-(2-pyridylazo)-2-naphthol Chelates on Fe3O4@ XAD-16. Iran J Sci Technol Trans A Sci 45:1971–1980
Pehlivan E, Altun T, Cetin S, Bhanger MI (2009) Lead sorption by waste biomass of hazelnut and almond shell. J Hazard Mater 167:1203–1208
Pereira PHF, Ornaghi HL Jr, Arantes V, Cioffi MOH (2021) Effect of chemical treatment of pineapple crown fiber in the production, chemical composition, crystalline structure, thermal stability and thermal degradation kinetic properties of cellulosic materials. Carbohyd Res 499:108227
Perelonia KBS, Benitez KCD, Banicod RJS, Tadifa GC, Cambia FD, Montojo UM (2021) Validation of an analytical method for the determination of cadmium, lead and mercury in fish and fishery resources by graphite furnace and cold vapor atomic absorption spectrometry. Food Control 130:108363
Qiu B, Tao X, Wang H, Li W, Ding X, Chu H (2021) Biochar as a low-cost adsorbent for aqueous heavy metal removal: A review. J Anal Appl Pyrol 155:105081
Sekharan TR, Chandira RM, Tamilvanan S, Rajesh S, Venkateswarlu B (2022) Deep eutectic solvents as an alternate to other harmful solvents. Review 12:847–860
Shafaghat J, Ghaemi A (2021) Comparison of Pb (II) Adsorption by ground granulated blast-furnace and phosphorus slags; exploitation of RSM. Iran J Sci Technol Trans A Sci 45:899–911
Shaikh HM, Anis A, Poulose AM, Al-Zahrani SM, Madhar NA, Alhamidi A, Aldeligan SH, Alsubaie FS (2022) Synthesis and characterization of cellulose triacetate obtained from date palm (Phoenix dactylifera L.) trunk mesh-derived cellulose. Molecules 27:1434
Smith EL, Abbott AP, Ryder KS (2014) Deep eutectic solvents (DESs) and their applications. Chem Rev 114:11060–11082
Şölener M, Tunali S, Özcan AS, Özcan A, Gedikbey T (2008) Adsorption characteristics of lead (II) ions onto the clay/poly (methoxyethyl) acrylamide (PMEA) composite from aqueous solutions. Desalination 223:308–322
Tran HN, Lima EC, Juang R-S, Bollinger J-C, Chao H-P (2021) Thermodynamic parameters of liquid–phase adsorption process calculated from different equilibrium constants related to adsorption isotherms: a comparison study. J Environ Chem Eng 9:106674
Wang H, Li J, Zeng X, Tang X, Sun Y, Lei T, Lin L (2020) Extraction of cellulose nanocrystals using a recyclable deep eutectic solvent. Cellulose 27:1301–1314
Wang X, Li X, Peng L, Han S, Hao C, Jiang C, Wang H, Fan X (2021) Effective removal of heavy metals from water using porous lignin-based adsorbents. Chemosphere 279:130504
Watkins D, Nuruddin M, Hosur M, Tcherbi-Narteh A, Jeelani S (2015) Extraction and characterization of lignin from different biomass resources. J Market Res 4:26–32
Wu R (2019) Removal of heavy metal ions from industrial wastewater based on chemical precipitation method. Ekoloji Dergisi 28:2443–2452
Xie Y, Yuan X, Wu Z, Zeng G, Jiang L, Peng X, Li H (2019) Adsorption behavior and mechanism of Mg/Fe layered double hydroxide with Fe3O4-carbon spheres on the removal of Pb (II) and Cu (II). J Colloid Interface Sci 536:440–455
Yogeshwaran V, Priya A (2021) Adsorption of lead ion concentration from the aqueous solution using tobacco leaves. Mater Today Proc 37:489–496
Zhang H, Lang J, Lan P, Yang H, Lu J, Wang Z (2020) Study on the dissolution mechanism of cellulose by ChCl-based deep eutectic solvents. Materials 13:278
Zhang W, Ou J, Wang B, Wang H, He Q, Song J, Zhang H, Tang M et al (2021) Efficient heavy metal removal from water by alginate-based porous nanocomposite hydrogels: the enhanced removal mechanism and influencing factor insight. J Hazard Mater 418:126358
Zhao H, Ouyang X-K, Yang L-Y (2021) Adsorption of lead ions from aqueous solutions by porous cellulose nanofiber–sodium alginate hydrogel beads. J Mol Liq 324:115122
Zhu F, Li X, Feng Q (2021) Thermal decomposed behavior and kinetic study for untreated and flame retardant treated regenerated cellulose fibers using thermogravimetric analysis. J Therm Anal Calorim 145:423–435
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The experimental works, data collection, data analysis, and writing of the first draft of the manuscript were performed by SKO. NAF revised and approved the final manuscript.
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Omer, S.K., Fakhre, N.A. Removal of Aqueous Pb2+ on Partially esterified Cellulose Obtained by Almond Shell Dissolution Using Deep Eutectic Solvent. Iran J Sci 47, 749–764 (2023). https://doi.org/10.1007/s40995-023-01419-5
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DOI: https://doi.org/10.1007/s40995-023-01419-5