Beta-cyclodextrin adsorbents to remove water pollutants—a commentary

Abstract

Beta-cyclodextrin-based adsorbent is a promising adsorbent because it has unique characteristics and able to form host-guest complexes with various organic compounds. Adsorption using beta-cyclodextrin-based adsorbent has continuously improved by various preparation strategies and crosslinking agents. This commentary aims to highlight the preparation strategies, properties, and adsorption mechanisms of beta-cyclodextrin-based adsorbents. The adsorbents can be generally classified according to the preparation methods and display high adsorption capacity especially for dyes. Particularly, composite/nanocomposite beta-cyclodextrin-based adsorbents exhibit outstanding adsorption capacity even though the surface area is lower than that of porous and magnetic beta-cyclodextrin-based adsorbents. The beta-cyclodextrin/chitosan functionalized graphene oxide hydrogel with specific surface of 17.6 m²·g^–1 yields an extraordinarily maximum adsorption capacity of 1499 mg·g^–1 methylene blue, while beta-cyclodextrin/chitosan modified with iron(II, III) oxide nanoparticles displays a much greater maximum adsorption capacity at 2780 mg·g^–1. The hydrophobic interaction, functional groups, hydrogen bonding, and electrostatic interaction govern the adsorption to a greater capacity. Although this commentary is not exhaustive, the preparation strategies and illustrated mechanisms provide useful insights into the adsorbent–adsorbate interactions, cost-effective analysis, challenges, and future directions of beta-cyclodextrin-based adsorbents in wastewater treatment.

Graphical abstract

Keywords

beta-cyclodextrin adsorbent / adsorption / inclusion complex / mechanism / water pollutant / wastewater treatment

References

[1] NataleF D, ErtoA, MusmarraD. Experimental and modelling analysis of As(V) ions adsorption on granular activated carbon. Water Research, 2008, 42( 8-9): 2007– 2016

[2] WangZ, LiT T, PengH K, RenH T, LouC W, LinJ H. Low-cost hydrogel adsorbent enhanced by trihydroxy melamine and β-cyclodextrin for the removal of Pb(II) and Ni(II) in water. Journal of Hazardous Materials, 2021, 411 : 125029

[3] HuangW, HuY, LiY, ZhouY, NiuD, LeiZ, ZhangZ. Citric acid-crosslinked β-cyclodextrin for simultaneous removal of bisphenol A, methylene blue and copper: the roles of cavity and surface functional groups. Journal of the Taiwan Institute of Chemical Engineers, 2018, 2018( 82): 189– 197

[4] AriffM M, ZainiM A A. Carbon-based beta-cyclodextrin adsorbent for methylene blue and reactive orange 16 removal from water. Acta Chemica Iasi, 2020, 28( 1): 19– 30

[5] SulaimanN S, ZainiM A A, ArsadA. Evaluation of dyes removal by beta-cyclodextrin adsorbent. Materials Today, 2021, 39( 2): 907– 910

[6] BadruddozaA Z M, ShawonZ B Z, DanielT W J, HidajatK, UddinM S. Fe₃O₄/cyclodextrin polymer nanocomposites for selective heavy metals removal from industrial wastewater. Carbohydrate Polymers, 2013, 91( 1): 322– 332

[7] TanP, HuY. Improved synthesis of graphene/β-cyclodextrin composite for highly efficient dye adsorption and removal. Journal of Molecular Liquids, 2017, 242 : 181– 189

[8] MousaviS H, MohammadiA. A cyclodextrin/glycine-functionalized TiO₂ nanoadsorbent: synthesis, characterization and application for the removal of organic pollutants from water and real textile wastewater. Process Safety and Environmental Protection, 2018, 114 : 1– 15

[9] FanL, LuoC, SunM, QiuH. Synthesis of graphene oxide decorated with magnetic cyclodextrin for fast chromium removal. Journal of Materials Chemistry, 2012, 22( 47): 24577– 24583

[10] FanL, LuoC, SunM, QiuH, LiX. Synthesis of magnetic beta-cyclodextrin-chitosan/graphene oxide as nanoadsorbent and its application in dye adsorption and removal. Colloids and Surfaces B: Biointerfaces, 2013, 103 : 601– 607

[11] JiangY, LiuB, XuJ, PanK, HouH, HuJ, YangJ. Crosslinked chitosan/β-cyclodextrin composite for selective removal of methyl orange: adsorption performance and mechanism. Carbohydrate Polymers, 2018, 182 : 106– 114

[12] ZhaoF, RepoE, YinD, MengY, JafariS, SillanpaaM. EDTA-crosslinked β-cyclodextrin: an environmentally friendly bifunctional adsorbent for simultaneous adsorption of metals and cationic dyes. Environmental Science & Technology, 2015, 49( 17): 10570– 10580

[13] LiuN, WuY, ShaH. Characterization of EDTA-crosslinked β-cyclodextrin grafted onto Fe–Al hydroxides as an efficient adsorbent for methylene blue. Journal of Colloid and Interface Science, 2018, 516 : 98– 109

[14] FanL, ZhangY, LuoC, LuF, QiuH, SunM. Synthesis and characterization of magnetic β-cyclodextrin-chitosan nanoparticles as nano-adsorbents for removal of methyl blue. International Journal of Biological Macromolecules, 2012, 50( 2): 444– 450

[15] WangD, LiuL, JiangX, YuJ, ChenX. Adsorption and removal of malachite green from aqueous solution using magnetic β-cyclodextrin-graphene oxide nanocomposites as adsorbents. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2014, 466 : 166– 173

[16] LiuY, HuangS, ZhaoX, ZhangY. Fabrication of three-dimensional porous β-cyclodextrin/chitosan functionalized graphene oxide hydrogel for methylene blue removal from aqueous solution. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2018, 539 : 1– 10

[17] LiuQ, ZhouY, ZhouY. Novel cyclodextrin-based adsorbents for removing pollutants from wastewater: a critical review. Chemosphere, 2019, 241 : 125043

[18] TianB, HuaS, TianY, LiuJ. Cyclodextrin-based adsorbents for the removal of pollutants from wastewater: a review. Environmental Science and Pollution Research International, 2020, 28( 2): 1317– 1340

[19] Alzate-SanchezD M, SmithB J, AlsbaieeA, HinestrozaJ P, DichtelW R. Cotton fabric functionalized with a β-cyclodextrin polymer captures organic pollutants from comtaminated air and water. Chemistry of Materials, 2016, 28( 22): 8340– 8346

[20] YangZ, LiuJ, YaoX, RuiZ, JiH. Efficient removal of BTEX from aqueous solution by β-cyclodextrin modified poly(butymethacrylate) resin. Separation and Purification Technology, 2016, 158 : 417– 421

[21] Morin-CriniN, CriniG. Environmental applications of water-insoluble β-cyclodextrin-epichlorohydrin polymers. Progress in Polymer Science, 2012, 38( 2): 344– 368

[22] SahraouiM, AbderrahmenA, MlikaR, OuadaH B, GharbiA. Dielectric relaxation behaviour of nematic liquid crystal cell using β-cyclodextrin as an alignment layer. Mediterranean Journal of Chemistry, 2016, 5( 1): 347– 355

[23] ZhaoD, ZhaoL, ZhuC, HuangW, HuJ. Water-insoluble β-cyclodextrin polymer crosslinked by citric acid: synthesis and adsorption properties toward phenol and methylene blue. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2009, 63( 3-4): 195– 201

[24] CriniG. Recent developments in polysaccharide-based materials used as adsorbents in wastewater treatment. Progress in Polymer Science, 2005, 30( 1): 38– 70

[25] CriniG, PeindyH N. Adsorption of C. I. Basic Blue 9 on cyclodextrin-based material containing carboxylic groups. Dyes and Pigments, 2006, 70( 3): 204– 211

[26] CriniG. Kinetic and equilibrium studies on the removal of cationic dyes from aqueous solution by adsorption onto a cyclodextrin polymer. Dyes and Pigments, 2008, 77( 2): 415– 426

[27] MakS, ChenD. Fast adsorption of methylene blue on polyacrylic acid-bound iron oxide magnetic nanoparticles. Dyes and Pigments, 2004, 61( 1): 93– 98

[28] GuptaV K, AgarwalS, SadeghH, AliG A M, BhartiA K, HamdyA S. Facile route synthesis of novel graphene oxide-β-cyclodextrin nanocomposite and its application as adsorbent for removal of toxic bisphenol A from the aqueous phase. Journal of Molecular Liquids, 2017, 237 : 466– 472

[29] WangZ, ZhangP, HuF, ZhaoY, ZhuL. A crosslinked β-cyclodextrin polymer used for rapid removal of a broad-spectrum of organic micropollutants from water. Carbohydrate Polymers, 2017, 177 : 224– 231

[30] ZhaoD, ZhaoL, ZhuC, TianZ, ShenX. Synthesis and properties of water-insoluble β-cyclodextrin polymer crosslinked by citric acid with PEG-400 as modifier. Carbohydrate Polymers, 2009, 78( 1): 125– 130

[31] LiX, ZhouM, JiaJ, MaJ, JiaQ. Design of a hyper-crosslinked β-cyclodextrin porous polymer for highly efficient removal toward bisphenol A from water. Separation and Purification Technology, 2018, 195 : 130– 137

[32] ZhouY, HuY, HuangW, ChengG, CuiC, LuJ. A novel amphoteric β-cyclodextrin-based adsorbent for simultaneous removal of cationic/anionic dyes and bisphenol A. Chemical Engineering Journal, 2018, 341 : 47– 57

[33] ZhouY, ZhangR, ChenK, ZhaoX, GuX, LuJ. Enhanced adsorption and photo-degradation of bisphenol A by β-cyclodextrin modified pine sawdust in an aquatic environment. Journal of the Taiwan Institute of Chemical Engineers, 2017, 78 : 510– 616

[34] CriniG, MorcelletM. Synthesis and applications of adsorbents containing cyclodextrins. Journal of Separation Science, 2002, 25( 13): 789– 813

[35] KonoH, NakamuraT. Polymerization of β-cyclodextrin with 1,2,3,4-butanetetracarboxylic dianhydride: synthesis, structural characterization, and bisphenol A adsorption capacity. Reactive & Functional Polymers, 2013, 73( 8): 1096– 1102

[36] PhilipsB, WangC, TuX, ChangC, BanerjeeS, Al-HashimiM, HuW, FangL. Cyclodextrin-derived polymer networks for selective molecular adsorption. Chemical Communications, 2020, 56( 79): 11783– 11786

[37] WangJ, ChengG, LuJ, ChenH, ZhouY. PDA-crosslinked beta-cyclodextrin: a novel adsorbent for the removal of BPA and cationic dyes. Water Science and Technology, 2020, 81( 11): 2337– 2350

[38] ZhouY, ChengG, ChenK, LuJ, LeiJ, PuS. Adsorptive removal of bisphenol A, chloroxylenol, and carbamazepine from water using a novel β-cyclodextrin polymer. Ecotoxicology and Environmental Safety, 2019, 170 : 278– 285

[39] XiaoG, FuL, LiA. Enhanced adsorption of bisphenol A from water by acetylaniline modified hyper-cross-linked polymeric adsorbent: effect of the cross-linked bridge. Chemical Engineering Journal, 2012, 191 : 171– 176

[40] SeoP W, BhadraB N, AhmedI, KhanN A, JhungS H. Adsorptive removal of pharmaceuticals and personal care products from water with functionalized metal-organic frameworks: remarkable adsorbents with hydrogen-bonding abilities. Scientific Reports, 2016, 6( 1): 334462

[41] LiY, YangC, YanX. Controllable preparation of core-shell magnetic covalent-organic framework nanospheres for efficient adsorption and removal of bisphenols in aqueous solution. Chemical Communications, 2017, 53( 16): 2511– 2514

[42] TanL, TanB. Hypercrosslinked porous polymer materials: design, synthesis, and applications. Chemical Society Reviews, 2017, 46( 11): 3322– 3356

[43] AlsbaieeA, SmithB J, XiaoL, LingY, HelblingD E, DichtelW R. Rapid removal of organic micropollutants from water by a porous β-cyclodextrin polymer. Nature, 2016, 529( 7585): 190– 194

[44] ShenH, ZhuG, YuW, WuH, JiH, ShiH, SheY, ZhengY. Fast adsorption of p-nitrophenol from aqueous solution using β-cyclodextrin grafted silica gel. Applied Surface Science, 2015, 356 : 1155– 1167

[45] KamelA H, MohammadS G, AwwadN S, MohammedY Y. Survey on the integration of molecularly imprinted polymers as artificial receptors in potentiometric transducers for pharmaceutical drugs. International Journal of Electrochemical Science, 2019, 14 : 2085– 2124

[46] MammanS, SuahF B M, RaaovM, MehamodF S, AsmanS, ZainN N M. Removal of bisphenol A from aqueous media using a highly selective adsorbent of hybridization cyclodextrin with magnetic molecularly imprinted polymer. Royal Society Open Science, 2021, 8( 3): 201604

[47] LiuJ, LiuG, LiuW. Preparation of water-soluble β-cyclodextrin/poly(acrylic acid)/graphene oxide nanocomposites as new adsorbents to remove cationic dyes from aqueous solutions. Chemical Engineering Journal, 2014, 257 : 299– 308

[48] ChenJ, PuY, WangZ, HanJ, ZhongY, LiuK. Synthesis of a novel nanosilica-supported poly β-cyclodextrin sorbent and its properties for the removal of dyes from aqueous solution. Colloids and Surfaces A: Physicochem, 2018, 538 : 808– 817

[49] ChenH, ZhouY, WangJ, LuJ, ZhouY. Polydopamine modified cyclodextrin polymer as efficient adsorbent for removing cationic dyes and Cu²⁺. Journal of Hazardous Materials, 2020, 389 : 121897

[50] ZhuJ, HeJ, DuX, LuR, HuangL, GeX. A facile and flexible process of β-cyclodextrin grafted on Fe₃O₄ magnetic nanoparticles and host–guest inclusion studies. Applied Surface Science, 2011, 257( 21): 9056– 9062

[51] LiuG, LiL, XuD, HuangX, XuX, ZhengS, ZhangY, LinH. Metal-organic framework preparation using magnetic graphene oxide-β-cyclodextrin for neonicotinoid pesticide adsorption and removal. Carbohydrate Polymers, 2017, 175 : 584– 591

[52] BadruddozaA Z M, TayA S H, TanP Y, HidajatK, UddinM S. Carboxymethyl-β-cyclodextrin conjugated magnetic nanoparticles as nano-adsorbents for removal of copper ions: synthesis and adsorption studies. Journal of Hazardous Materials, 2011, 185( 2-3): 1177– 1186

[53] BadruddozaA Z M, HazelG S S, HidajatK, UddinM S. Synthesis of carboxymethyl-β-cyclodextrin conjugated magnetic nano-adsorbent for removal of methylene blue. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2010, 367( 1-3): 85– 95

[54] CaiD, ZhangT, ZhangF, LuoX. Quaternary ammonium β-cyclodextrin-conjugated magnetic nanoparticles as nano-adsorbents for the treatment of dyeing wastewater: synthesis and adsorption studies. Journal of Environmental Chemical Engineering, 2017, 5( 3): 2869– 2878

[55] CriniG, PeindyH N, GimbertF, RobertC. Removal of C. I. basic green 4 (malachite green) from aqueous solutions by adsorption using cyclodextrin-based adsorbent: kinetic and equilibrium studies. Separation and Purification Technology, 2007, 53( 1): 97– 110

[56] SzejtliJ. Introduction and general overview of cyclodextrin chemistry. Chemical Reviews, 1998, 98( 5): 1743– 1753

[57] AmranF, ZainiM A A. Correlations between pore textures of activated carbons and Langmuir constants—case studies on methylene blue and Congo red adsorption. Toxin Reviews, 2022, 41( 1): 315– 325

[58] Al-GhoutiM A, Al-AbsiR S. Mechanistic understanding of the adsorption and thermodynamic aspects of cationic methylene blue dye onto cellulosic olive stones biomass from wastewater. Scientific Reports, 2020, 10( 1): 15928

[59] KhodaieM, GhasemiN, MoradiB, RahimiM. Removal of methylene blue from wastewater by adsorption onto ZnCl₂ activated corn husk carbon equilibrium studies. Journal of Chemistry, 2013, 2013 : 1– 6

[60] MallI D, SrivastavaV C, AgarwalN K, MishraI M. Adsorptive removal of malachite green dye from aqueous solution by bagasse fly ash and activated carbon-kinetic study and equilibrium isotherm analyses. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2005, 264( 1-3): 17– 28

[61] IllesE, TombaczE. The effect of humic acid adsorption on pH-dependent surface charging and aggregation of magnetite nanoparticles. Journal of Colloid and Interface Science, 2006, 295( 1): 115– 123

[62] HuQ, GaoD, PanH, HaoL, WangP. Equilibrium and kinetics of aniline adsorption onto crosslinked sawdust-cyclodextrin polymers. RSC Advances, 2014, 4( 75): 40071– 40077

[63] KongL, YanL, QuZ, YanN, LiL. β-Cyclodextrin stabilized magnetic Fe₃S₄ nanoparticles for efficient removal of Pb(II). Journal of Materials Chemistry A: Materials for Energy and Sustainability, 2015, 3( 30): 1– 9

[64] BradderP, LingS K, WangS, LiuS. Dye adsorption on layered graphite oxide. Journal of Chemical & Engineering Data, 2011, 56( 1): 138– 141

[65] WangY, ZhouA. Spectroscopic studies on the binding of methylene blue with DNA by means of cyclodextrin supramolecular systems. Journal of Photochemistry and Photobiology A: Chemistry, 2007, 190( 1): 121– 127

[66] GuptaV K, TyagiI, SadeghH, Shahryari-GhoshekandiR, MakhloufA S H, MaazinejadB. Nanoparticles as adsorbent; a positive approach for removal of noxious metal ions: a review. Science, Technology and Development, 2015, 34( 3): 195– 214

[67] GuptaV K, TyagiaI, AgarwalS, MoradiO, SadeghH, Shahryari-ghoshekandiR, MakhloufA S H, GoodarziM, GarshasbiA. Study on the removal of heavy metal ions from industry waste by carbon nanotubes: effect of the surface modification: a review. Critical Reviews in Environmental Science and Technology, 2016, 46( 2): 93– 118

[68] DenisP A, IribarneF. A first-principles study on the interaction between alkyl radicals and graphene. Chemistry—A European Journal, 2012, 18( 24): 7568– 7574

[69] JiL, ChenW, XuZ, ZhengS, ZhuD. Graphene nanosheets and graphite oxide as promising adsorbents for removal of organic contaminants from aqueous solution. Journal of Environmental Quality, 2013, 42( 1): 191– 198

[70] YuJ, ZhaoX, YangH, ChenX, YangQ, YuL, JiangJ, ChenX. Aqueous adsorption and removal of organic contaminants by carbon nanotubes. Science of the Total Environment, 2014, 482-483 : 241– 251

[71] DuanC, MaT, WangJ, ZhouY. Removal of heavy metals from aqueous solution using carbon-based adsorbents: a review. Journal of Water Process Engineering, 2020, 37 : 101339

[72] ZhouY, HeJ, LuJ, LiuY, ZhouY. Enhanced removal of bisphenol A by cyclodextrin in photocatalytic systems: degradation intermediates and toxicity evaluation. Chinese Chemical Letters, 2020, 31( 10): 2623– 2626

[73] ZhouY, LiuQ, LuJ, HeJ, LiuY, ZhouY. Accelerated photoelectron transmission by carboxymethyl β-cyclodextrin for organic contaminants removal: an alternative to noble metal catalyst. Journal of Hazardous Materials, 2020, 393 : 122414

[74] ZhouW, MengX, GaoJ, ZhaoH, ZhaoG, MaJ. Electrochemical regeneration of carbon-based adsorbents: a review of regeneration mechanisms, reactors, and future prospects. Chemical Engineering Journal Advances, 2021, 5 : 100083

[75] DottoG L, MckayG. Current scenario and challenges in adsorption for water treatment. Journal of Environmental Chemical Engineering, 2020, 8( 4): 103988

Acknowledgments

This work was fully supported by the Ministry of Education Malaysia through Fundamental Research Grant Scheme (FRGS No. 4F995).

Electronic Supplementary Material

Supplementary material is available in the online version of this article at https://dx.doi.org/10.1007/s11705-022-2146-2 and is accessible for authorized users.

RIGHTS & PERMISSIONS

2022 Higher Education Press