Abstract
Poly(hydroxylmethyl methacrylate-co-glycidyl methacrylate) (p(HEMA-GMA)) macroporous cryogel with high density of epoxy groups was synthesized, and the epoxy groups of the cryogel were modified into phosphonate groups. The effects of dye concentrations, adsorption time, pH, salt concentration, and adsorption temperature on the adsorption of Direct Blue-53 (DB-53) and Reactive Blue-160 (RB-160) dyes were studied. The maximum adsorption capacity was found to be 245.3 and 155.8 mg/g (0.255 or 0.119 mmol/g) for the DB-53 and RB-160 dyes, respectively. The higher adsorption capacity achieved for the DB-53 compared with the RB-160 dye can result from the pendant primary amino groups of the DB-53 dye as well as the smaller size of the dye molecule. The Langmuir isotherm model and the pseudo-second-order kinetic model well described the experimental data. The p(HEMA-GMA)-PO42− adsorbent has many operational advantages for the removal of pollutants. It could be a promising adsorbent to be used in industrial wastewater treatment.
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Abbreviations
- A :
-
differential surface capacity for dye adsorption (mg/g)
- b T :
-
Temkin constant (equilibrium binding constant; mL/g)
- C 0 :
-
initial concentration of dye (mg/L)
- C e :
-
equilibrium dye concentration (mg/L)
- C t :
-
dye concentration after time t (min)
- E a :
-
activation energy (kJ/mol)
- h :
-
initial adsorption rate (mg/g/min)
- k 1 :
-
first-order rate constant (min−1)
- k 2 :
-
second-order rate constant (g/mg/min)
- K a :
-
association constant of the solute/surface interaction
- K F :
-
Freundlich constant for adsorption capacity
- n :
-
Freundlich constant related to adsorption intensity or surface heterogeneity
- q :
-
amount of dye adsorbed at time t (mg/g)
- q exp :
-
experimental adsorption capacity (mg/g)
- q max :
-
maximum adsorption capacity (mg/g)
- q eq :
-
theoretical or calculated adsorption capacity at equilibrium (mg/g)
- q t :
-
adsorbed amount of dye at time t (mg/g)
- R :
-
universal gas constant (kJ/mol K)
- R L :
-
separation factor
- T :
-
absolute temperature (K)
- V :
-
volume of solution (L)
- W :
-
weight of the adsorbent (g)
- ΔG°:
-
Gibbs free energy (kJ/mol)
- ΔH°:
-
enthalpy (kJ/mol) of adsorption
- ΔS°:
-
entropy (J/mol K) of adsorption
- Θ :
-
contact angle (°)
- γ l :
-
surface tension of liquid (mN/m)
- APS:
-
ammonium persulfate
- DB-53:
-
Direct Blue-53
- GMA:
-
glycidyl methacrylate
- HEMA:
-
2-hydroxylmethyl methacrylate
- MBA:
-
N,N′-methylenebisacrylamide
- RB-160:
-
Reactive Blue
- SDS:
-
sodium dodecylsulfate
- TEMED:
-
N,N,N′,N′-tetramethylene diamine
References
Adeyi AA, Jamil SNAM, Abdullah LC, Choong TSY (2019) Adsorption of malachite green dye from liquid phase using hydrophilic thiourea-modified poly(acrylonitrile-co-acrylic acid): kinetic and isotherm studies. J Chemother:4321475. https://doi.org/10.1155/2019/4321475
Ahmed S, Unar IN, Khan HA, Maitlo G, Mahar RB, Jatoi AS, Memon AQ, Shah AK (2020) Experimental study and dynamic simulation of melanoidin adsorption from distillery effluent. Environ Sci Pollut Res 27:9619–9636. https://doi.org/10.1007/s11356-019-07441-8
Alardhi SM, Albayati TM, Alrubaye JM (2020) Adsorption of the methyl green dye pollutant from aqueous solution using mesoporous materials MCM-41 in a fixed-bed column. Heliyon 6:3253. https://doi.org/10.1016/j.heliyon.2019.e02539
Arica TA, Ayas E, Arica MY (2017) Magnetic MCM- 41 silica particles grafted with poly (glycidylmethacrylate) brush: modification and application for removal of direct dyes. Microporous Mesoporous Mater 243:164–175. https://doi.org/10.1016/j.micromeso.2017.02.011
Arica TA, Kuman M, Gercel O, Ayas E (2019) Poly(dopamine) grafted bio-silica composite with tetraethylenepentamine ligands for enhanced adsorption of pollutants. Chem Eng Res Des 141:317–327. https://doi.org/10.1016/j.cherd.2018.11.003
Bai S, Wang L, Ma F, Zhu S, Xiao T, Yu T, Wang Y (2020) Self-assembly biochar colloids mycelial pellet for heavy metal removal from aqueous solution. Chemosphere 242:125182. https://doi.org/10.1016/j.chemosphere.2019.125182
Balea A, Monte MC, Fuente E, Sanchez-Salvador JL, Blanco A, Negro C (2019) Cellulose nanofibers and chitosan to remove flexographic inks from wastewaters. Environ Sci: Water Res Technol 5:1558–1567. https://doi.org/10.1039/c9ew00434c
Bayramoglu G, Arica MY (2005) Surface energy components of a dye-ligand immobilized pHEMA membranes: effects of their molecular attracting forces for non-covalent interactions with IgG and HSA in aqueous media. Int J Biol Macromol 37:249–256. https://doi.org/10.1016/j.ijbiomac.2005.12.005
Bayramoglu G, Arica MY (2013) Preparation and characterization of strong cation exchange terpolymer resin as effective adsorbent for removal of disperse dyes. Color Technol 129:114–124. https://doi.org/10.1002/pen.25272
Bayramoglu G, Arica MY (2017) Polyethylenimine and tris(2-aminoethyl)amine modified p(GA–EGMA) microbeads for sorption of uranium ions: equilibrium, kinetic and thermodynamic studies. J Radioanal Nucl Chem 312:1–11. https://doi.org/10.1007/s10967-017-5216-z
Bayramoglu G, Arica MY (2018) Adsorption of Congo Red dye by native amine and carboxyl modified biomass of Funalia trogii: isotherms, kinetics and thermodynamics mechanisms. Korean J Chem Eng 35:1303–1311. https://doi.org/10.1007/s11814-018-0033-9
Bayramoglu G, Altintas B, Arica MY (2012) Synthesis and characterization of magnetic beads containing aminated fibrous surfaces for removal of Reactive Green 19 dye: kinetics and thermodynamic parameters. J Chem Technol Biotechnol 87:705–713. https://doi.org/10.1002/jctb.3693
Bayramoglu G, Ozalp VC, Arica MY (2017) Removal of Disperse Red 60 dye from aqueous solution using free and composite fungal biomass of Lentinus concinnus. Water Sci Technol 75:366–377. https://doi.org/10.2166/wst.2016.529
Bayramoglu G, Kunduzcu G, Arica MY (2020) Preparation and characterization of strong cation exchange terpolymer resin as effective adsorbent for removal of disperse dyes. Polym Eng Sci 60:192–201. https://doi.org/10.1002/pen.25272
Bhatti HN, Safa Y, Yakout SM, Shair OH, Iqbal M, Nazir A (2020) Efficient removal of dyes using carboxymethyl cellulose/alginate/polyvinyl alcohol/rice husk composite: adsorption/desorption, kinetics and recycling studies. Int J Biol Macromol 150:861–870. https://doi.org/10.1016/j.ijbiomac.2020.02.093
Bouraada M, Bessaha H, de Ménorval LC (2014) Removal of Evans Blue and Yellow Thiazole dyes from aqueous solution by Mg–Al–CO3 layered double hydroxides as anion-exchanger. Mediterr J Chem 3:894–906. https://doi.org/10.13171/mjc.3.3.2014.01.06.18
Campano C, Balea A, Blanco A. Negro C (2020) A reproducible method to characterize the bulk morphology of cellulose nanocrystals and nanofibers by transmission electron microscopy. Cellulose 27:4871–4887. https://doi.org/10.1007/s10570-020-03138-1.
Celekli A, Al-Nuaimi AI, Bozkurt H (2019) Adsorption kinetic and isotherms of Reactive Red 120 on Moringa oleifera seed as an eco-friendly process. J Mol Struct 1195:168–178. https://doi.org/10.1016/j.molstruc.2019.05.106
Chahinez H-O, Abdelkader O, Leila Y, Tran HN (2020) One-stage preparation of palm petiole-derived biochar: characterization and application for adsorption of crystal violet dye in water. Environ Technol Innov 19:100872. https://doi.org/10.1016/j.eti.2020.100872
Ding J, Pan Y, Li L, Liu H, Zhang Q, Gao G, Pan B (2020) Synergetic adsorption and electrochemical classified recycling of Cr(VI) and dyes in synthetic dyeing wastewater. Chem Eng J 384:123232. https://doi.org/10.1016/j.cej.2019.123232
Dobritoiu R, Patachia S (2013) A study of dyes sorption on biobased cryogels. Appl Surf Sci 285:56–64. https://doi.org/10.1016/j.apsusc.2013.07.164
Farias T, Hajizadeh S, Ye L (2020) Cryogels with high cisplatin adsorption capacity: towards removal of cytotoxic drugs from wastewater. Sep Purif Technol 235:116203. https://doi.org/10.1016/j.seppur.2019.116203
Gemeay AH, Keshta BE, El-Sharkawy RG, Zaki AB (2020) Chemical insight into the adsorption of reactive wool dyes onto amine-functionalized magnetite/silica core-shell from industrial wastewaters. Environ Sci Pollut Res. https://doi.org/10.1007/s11356-019-06530-y
He X, Male KB, Nesterenko PN, Brabazon D, Paull B, Luong JHT (2013) Adsorption and desorption of Methylene Blue on porous carbon monoliths and nanocrystalline cellulose. ACS Appl Mater Interfaces 5:8796–8804. https://doi.org/10.1021/am403222u
Huo J, Luo B, Chen Y (2019) Crystalline covalent organic frameworks from triazine nodes as porous adsorbents for dye pollutants. ACS Omega 4:22504. https://doi.org/10.1021/acsomega.9b03176
Karunarathne HDSS, Amarasinghe BMWPK (2013) Fixed bed adsorption column studies for the removal of aqueous phenol from activated carbon prepared from sugarcane bagasse. Energy Procedia 34:83–90. https://doi.org/10.1016/j.egypro.2013.06.736
Khan N, Husain Q (2019) Continuous degradation of Direct Red 23 by calcium pectate-bound Ziziphus mauritiana peroxidase: identification of metabolites and degradation routes. Environ Sci Pollut Res 26:3517–3529. https://doi.org/10.1007/s11356-018-3847-4
Liu D, Yuan J, Li J, Zhang G (2019a) Preparation of chitosan poly(methacrylate) composites for adsorption of Bromocresol Green. ACS Omega 4:12680–12686. https://doi.org/10.1021/acsomega.9b01576
Liu Z, Chen G, Zhou F, Huang J (2019b) Imidazolium salt incorporated poly(N-vinylimidazole-co-ethylene glycol dimethacrylate) for efficient adsorption of Congo Red and Hg2+ from aqueous solution. J Chem Eng Data 64:2627–2633. https://doi.org/10.1021/acs.jced.9b00092
Liu D, Huang Z, Li M, Li X, Sun P, Zhou L (2020) Construction of magnetic bifunctional β-cyclodextrin nanocomposites for adsorption and degradation of persistent organic pollutants. Carbohydr Polym 230:115564. https://doi.org/10.1016/j.carbpol.2019.115564
Manjunatha CR, Nagabhushana BM, Raghu MS, Pratibha S, Dhananjaya N, Narayana A (2019) Perovskite lanthanum aluminate nanoparticles applications in antimicrobial activity, adsorptive removal of Direct Blue 53 dye and fluoride. Mater Sci Eng C 101:674–685. https://doi.org/10.1016/j.msec.2019.04.013
Neolaka YAB, Lawa Y, Naat JN, Riwu AAP, Darmokoesoemo H, Supriyanto G, Holdsworth CI, Amenaghawon AN, Kusuma HS (2020) A Cr(VI)-imprinted-poly(4-VP-co-EGDMA) sorbent prepared using precipitation polymerization and its application for selective adsorptive removal and solid phase extraction of Cr(VI) ions from electroplating industrial wastewater. React Funct Polym 147:104451. https://doi.org/10.1016/j.reactfunctpolym.2019.104451
Otero-Gonzalez L, Mikhalovsky SV, Vaaclavikova M, Trenikhin MV, Cundy AB, Savina IN (2020) Novel nanostructured iron oxide cryogels for arsenic (As(III)) removal. J Hazard Mater 381:120996. https://doi.org/10.1016/j.jhazmat.2019.120996
Pereira D, Rocha LS, Gil MV, Otero M, Silva NJO, Esteves VI, Calisto V (2020) In situ functionalization of a cellulosic-based activated carbon with magnetic iron oxides for the removal of carbamazepine from wastewater. Environ Sci Pollut Res. https://doi.org/10.1007/s11356-020-09314-x
Pratibha S, Dhananjaya N, Manjunatha CR, Narayana A (2019) Fast adsorptive removal of Direct Blue-53 dye on rare-earth doped Lanthanum aluminate nanoparticles: equilibrium and kinetic studies. Mater Res Express 6:1–15. https://doi.org/10.1088/2053-1591/ab6f36
Prola LDT, Machado FM, Bergmann CP, de Souza FE, Gally CR, Lima EC, Adebayo MA, Dias SLP, Calvete T (2013a) Adsorption of Direct Blue 53 dye from aqueous solutions by multi-walled carbon nanotubes and activated carbon. J Environ Manag 130:166–175. https://doi.org/10.1016/j.jenvman.2013.09.003
Prola LD, Acayanka E, Lima EC, Bestetti C, Santos WO, Pavan FA, Dias SL, Tarley CR (2013b) Application of aqai stalks as biosorbent for the removal of Evans Blue and Vilmafix Red RR-2B dyes from aqueous solutions. Desalin Water Treat 51:4582–4592. https://doi.org/10.1080/19443994.2013.770588
Safavi-Mirmahalleh S-A, Mehdi S-K, Roghani-Mamaqani H (2020) Adsorption kinetics of methyl orange from water by pH-sensitive poly(2-(dimethylamino)ethyl methacrylate)/nanocrystalline cellulose hydrogels. Environ Sci Pollut Res 27:28091–28103. https://doi.org/10.1007/s11356-020-09127-y
Semiao MA, Haminiuk CWI, Maciel GM (2020) Residual diatomaceous earth as a potential and cost effective biosorbent of the azo textile dye Reactive Blue 160. J Environ Chem Eng 8:103617. https://doi.org/10.1016/j.jece.2019.103617
Shabnam R, Miah MAJ, Sharafat MK, Alam MA, Islam HMT, Ahmad H (2019) Cumulative effect of hydrophobic PLMA and surface epoxide groups in composite polymer particles on adsorption behavior of Congo Red and Direct Red-75. Arab J Chem 12:4989–4999. https://doi.org/10.1016/j.arabjc.2016.10.016
Sivakumar P, Palanisamy PN (2011) Non-conventional low-cost adsorbent from Euphorbia antiquorum L for the removal of Direct Blue 53 from its aqueous solution. Indian J Chem Technol 18:188–196 http://mctdhblab.com
Ul’yabaeva GR, Podorozhko EA, Kil’deeva NR, Lozinskii VI (2019) Adsorption of an acid textile dye from aqueous solutions by a chitosan-containing polyvinyl alcohol composite cryogel. Fibre Chem 51:199–203. https://doi.org/10.1007/s10692-019-10074-9
Unuabonah EI, Olu-Owolabi BI, Fasuyi EI, Adebowale KO (2010) Modeling of fixed-bed column studies for the adsorption of cadmium onto novel polymer-clay composite adsorbent. J Hazard Mater 179:415–423. https://doi.org/10.1016/j.jhazmat.2010.03.020
Wang J, Yan Y, Tian L, Wang Q, Zhang Y, Cao W, Yang C (2018) Efficient electrochemical oxidation of charged cryogel adsorbed reactive dyes in non-aqueous media. Water Air Soil Pollut 229:180–191. https://doi.org/10.1007/s11270-018-3833-y
Wu Y, Jiang L, Wen YJ, Zhou JX, Feng S (2012) Biosorption of Basic Violet 5BN and Basic Green by waste brewery’s yeast from single and multicomponent systems. Environ Sci Pollut Res 19:510–521. https://doi.org/10.1007/s11356-011-0577-2
Xu J, Du P, Bi W, Yao G, Li S, Liu H (2020) Graphene oxide aerogels co-functionalized with polydopamine and polyethylenimine for the adsorption of anionic dyes and organic solvents. Chem Eng Res Des 154:192–202. https://doi.org/10.1016/j.cherd.2019.12.014
Yuvaraja G, Chen D-Y, Pathak JL, Long J, Subbaiah MV, Wen JC, Pan CL (2020) Preparation of novel aminated chitosan Schiff’s base derivative for the removal of methyl orange dye from aqueous environment and its biological applications. Int J Biol Macromol 146:1100–1110. https://doi.org/10.1016/j.ijbiomac.2019.09.236
Zhang H, Ruan Y, Feng Y, Su M, Diao Z, Chen D, Hou L, Lee PH, Shih K, Kong L (2019) Solvent-free hydrothermal synthesis of gamma-aluminum oxide nanoparticles with selective adsorption of Congo red. J Colloid Interface Sci 536:180–188. https://doi.org/10.1016/j.jcis.2018.10.054
Zhang M, Zhang S, Liu X, Chen H, Ming Y, Xu Q, Wang Z (2020) One-pot synthesis of multi-functional and environmental friendly tannic acid polymer with Fe3+ and formaldehyde as double crosslinking agents for selective removal of cation pollutants. Environ Sci Pollut Res In press. https://doi.org/10.1007/s11356-019-06297-2
Zhou Y, Fu S, Liu H, Yang S, Zhan H (2011) Removal of methylene blue dyes from wastewater using cellulose-based super adsorbent hydrogels. Polym Eng Sci 51:2417–2424. https://doi.org/10.1002/pen.22020
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Bayramoglu, G., Arica, M.Y. Modification of epoxy groups of poly(hydroxylmethyl methacrylate-co-glycidyl methacrylate) cryogel with H3PO4 as adsorbent for removal of hazardous pollutants. Environ Sci Pollut Res 27, 43340–43358 (2020). https://doi.org/10.1007/s11356-020-10170-y
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DOI: https://doi.org/10.1007/s11356-020-10170-y