Synthesis and characterization of β-cyclodextrin functionalized ionic liquid polymer as a macroporous material for the removal of phenols and As(V)

International Journal of Molecular Sciences

Volumn 15, Issue 1, 2014, Pages 100-119

  Raoov, Muggundha ^a,b   Mohamad, Sharifah ^a   Abas, Mhd Radzi ^a  

^a UNIVERSITY OF MALAYA   (Malaysia)

^b ADVANCED MEDICAL AND DENTAL INSTITUTE   (Malaysia)

Author keywords

Adsorption; Cyclodextrin; Ionic liquid; Polymer

Indexed keywords

6 O MONOTOSYL 6 DEOXY BETA CYCLODEXTRIN; BETA CYCLODEXTRIN; MONO 6 DEOXY 6 (3 BENZYLIMIDAZOLIUM) BETA CYCLODEXTRIN; POLYMER; UNCLASSIFIED DRUG; 1-BENZYLIMIDAZOLE; ARSENIC; BETA CYCLODEXTRIN DERIVATIVE; CELLULOSE; CYCLODEXTRIN; CYCLODEXTRIN POLYMER; IMIDAZOLE DERIVATIVE; IONIC LIQUID; PHENOL DERIVATIVE;

ARTICLE; DIFFERENTIAL SCANNING CALORIMETRY; DRUG SYNTHESIS; GRAVIMETRY; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANC; PROTON NUCLEAR MAGNETIC RESONANCE; SCANNING ELECTRON MICROSCOPY; X RAY DIFFRACTION; ADSORPTION; CHEMISTRY; ISOLATION AND PURIFICATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POROSITY; SYNTHESIS; THERMOGRAVIMETRY;

ADSORPTION; ARSENIC; BETA-CYCLODEXTRINS; CALORIMETRY, DIFFERENTIAL SCANNING; CELLULOSE; CYCLODEXTRINS; IMIDAZOLES; IONIC LIQUIDS; MAGNETIC RESONANCE SPECTROSCOPY; PHENOLS; POROSITY; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; THERMOGRAVIMETRY;

EID: 84891090471     PISSN: 16616596     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms15010100     Document Type: Article

References (42)

1. Sun, Z.Y.; Shen, M.X.; Cao, G.P.; Deng, J.; Liu, Y.; Liu, T.; Zhao, L.; Yuan, W.K. Preparation of bimodal porous copolymer containing β-cyclodextrin and its inclusion adsorption behavior. J. App. Polym. Sci. 2010, 118, 2176-2185.
2. Szejtli, J. Past, present, and future of cyclodextrin research. Pure Appl. Chem. 2004, 76, 1825-1845.
3. Pandian, K.; Mohamad, S.; Sarih, N.M.; Ismail, N.A. Synthesis and characterization of the inclusion complex of β-cyclodextrin with azomethine. Int. J. Mol. Sci. 2013, 14, 3671-3682.
4. Mohamad, S.; Surikumaran, H.; Raoov, M.; Marimuthu, T.; Chandrasekaram, K.; Subramaniam, P. Conventional Study on Novel Dicationic Ionic Liquid Inclusion with β-Cyclodextrin. Int. J. Mol. Sci. 2011, 12, 6329-6345.
5. Mohamad, S.; Kamal, S.N.R.M. Study on an inclusion complex of β-cyclodextrin-dithizone-zinc (β-CD-H2Dz-Zn) by spectrophotometry and its analytical application. Asian J. Chem. 2013, 25, 1965-1969.
6. Zhang, J.; Shen, X.; Chen, Q. Separation processes in the presence of cyclodextrins using molecular imprinting technology and ionic liquid cooperating approach. Curr. Org. Chem. 2011, 15, 75-85.
7. Crini, G. Kinetic and equilibrium studies on the removal of cationic dyes from aqueous solution by adsorption onto a cyclodextrin polymer. Dyes Pigments 2008, 77, 415-426.
8. Chin, Y.P.; Mohamad, S.; Abas, M.R. Removal of parabens from aqueous solution using cyclodextrin cross-linked polymer. Int. J. Mol. Sci. 2010, 11, 3459-3471.
9. Mohamad, S.; Yusof, N.H.M.; Asman, S. The effect of bifunctional isocyanate linker on adsorption of chromium(VI)-diphenylcarbazide complex onto β-cyclodextrin polymer. Asian J. Chem. 2013, 25, 2213-2220.
10. Li, N.; Wei, X.; Mei, Z.; Xiong, X.; Chen, S.; Ye, M.; Ding, S. Synthesis and characterization of a novel polyamidoamine-cyclodextrin crosslinked copolymer. Carbohyd. Res. 2011, 346, 1721-1727.
11. López-de-Dicastillo, C.; Gallur, M.; Catalá, R.; Gavara, R.; Hernandez-Muñoz, P. Immobilization of β-cyclodextrin in ethylene-vinyl alcohol copolymer for active food packaging applications. J. Membr. Sci. 2010, 353, 184-191.
12. Qian, L.; Guan, Y.; Xiao, H. Preparation and characterization of inclusion complexes of a cationic β-cyclodextrin polymer with butylparaben or triclosan. Int. J. Pharm. 2008, 357, 244-251.
13. Subramaniam, P.; Mohamad, S.; Alias, Y. Synthesis and characterization of the inclusion complex of dicationic ionic liquid and cyclodextrin. Int. J. Mol. Sci. 2010, 11, 3675-3685.
14. McEwen, A.B.; Ngo, H.L.; LeCompte, K.; Goldman, J.L. Electrochemical properties of imidazolium salt electrolytes for electrochemical capacitor applications. J. Electrochem. Soc. 1999, 146, 1687-1695.
15. Rahim, N.Y.; Mohamad, S.; Alias, Y.; Sarih, N.M. Extraction behavior of cu(ii) ion from chloride medium to the hydrophobic ionic liquids using 1,10-phenanthroline. Separ. Sci. Technol. 2012, 47, 250-255.
16. Mecerreyes, D. Polymeric ionic liquid: Broadening the properties and applications of polyelectrolytes. Prog. Polym. Sci. 2011, 36, 1629-1648.
17. Qiu, H.; Sawada, T.; Jiang, S.; Ihara, H. Synthesis and chacterization of poly(ionic liquid)-grafted silica hybrid materials through surface radical chain-transfer polymerization and aqueous anion-exchange. Mater. Lett. 2010, 64, 1653-1655.
18. Zhou, Z.; Li, X.; Chen, X.; Hao, X. Synthesis of ionic liquids functionalized β-cyclodextrin-bonded chiral stationary phases and their applications in high-performance liquid chromatography. Anal. Chim. Acta 2010, 678, 208-214.
19. Ong, T.T.; Tang, W.; Muderawan, W.; Ng, S.C.; Chan, H.S.O. Synthesis and application of single isomer 6-mono(alkylimidazolium)-β-cyclodextrin as chiral selectors in chiral capillary electrophoresis. Electrophoresis 2005, 26, 3839-3848.
20. Melton, L.D.; Slessor, K.N. Synthesis of monosubstituted cyclohexaamy-loses. Carbohyd. Res. 1971, 18, 29-37.
21. Khan, A.R.; Forgo, P.; Stine, K.J.; D'Souza, V.T. Methods for selective modifications of cyclodextrins. Chem. Rev. 1998, 98, 1977-1996.
22. Zhong, N.; Byun, H.-S.; Bittman, R. An improved synthesis of 6-O-monotosyl-6-deoxy-β-cyclodextrin. Tetrahedron Lett. 1998, 39, 2919-2920.
23. Bhaskar, M.; Aruna, P.; Jeevan, R.G.; Radhakrishnan, G. β-Cyclodextrin-polyurethane polymer as solid-phase extraction material for the analysis of carcinogenic aromatic amines. Anal. Chim. Acta 2004, 509, 39-45.
24. Zha, F.; Li, S.; Chang, Y. Preparation and adsorption property of chitosan beads bearing β-cyclodextrin cross-linked by 1,6-hexamaethylene diisocyanate. Carbohyd. Polym. 2008, 72, 456-461.
25. Sing, K.S.W.; Everett, D.H.; Haul. R.A.W.; Moscou, L.; Pierotti, R.A.; Rouquerol, J.; Siemieniewska, T. Reporting physisorption data for gas/solid systems with special reference to the determination of surface area and porosity. IUPAC 1985, 57, 603-619.
26. Schroden, R.C.; Al-Daous, M.; Sokolov, S.; Melde, B.J.; Lytle, J.C.; Stein, A.; Carbajo, M.C.; Fernandez, J.T.; Rodriquez, E.E. Hybrid macroporous materials for heavy metal ion adsorption. J. Mater. Chem. 2002, 12, 3261-3267.
27. Zhang, X.J.; Ma, T.Y.; Yuan, Z.Y. Titania-phosphonate hybrid porous materials: Preparation, photocatalytic activity and heavy metal ion adsorption. J. Mater. Chem. 2008, 18, 2003-2010.
28. Liu, A.M.; Hidajat, K.; Kawi, S.; Zhao, D.Y. A new class of hybrid mesoporous materials with functionalized organic monolayers for selective adsorption of heavy metal ions. Chem. Commun. 2000, 1145-1146.
29. Gokmen, M.T.; Prez, F.E.D. Porous polymer particles-A comprehensive guide to synthesis, characterization, functionalization and applications. Prog. Polym. Sci. 2012, 37, 365-405.
30. Dua, K.F.; Yan, M.; Wanga, Q.Y.; Songa, H. Preparation and characterization of novel macroporous cellulose beads regenerated from ionic liquid for fast chromatography. J. Chromatogr. A 2010, 1217, 1298-1304.
31. Alahmadi, S.M.; Mohamad, S.; Maah, M.J. Synthesis and characterization of mesoporous silica functionalized with calix[4] arene derivatives. Int. J. Mol. Sci. 2012, 13, 13726-13736.
32. Li, N.; Mei, Z.; Wei, X. Study on sorption of chlorophenols from aqueous solution by an insoluble copolymer containing β-cyclodextrin and polyamidoamine units. Chem. Eng. J. 2012, 192, 138-145.
33. Yoo, K.S.; Lee, S.H. Influence of ionic liquid as a template on preparation of porous n-Al2O3 to DME synthesis from methanol. Bull. Korean Chem. Soc. 2010, 31, 1628-1632.
34. Salipira, K.L.; Krause, R.W.; Mamba, B.B.; Malesfetse, T.J.; Cele, L.M.; Durbach, S.H. Cyclodextrin polyurethanes polymerized with multi-walled carbon nanotubes: Synthesis and chacterization. Mater. Chem. Phys. 2008, 111, 218-224.
35. Abay, I.; Denizli, A.; Biskin, E.; Salih, B. Removal and pre-concentration of phenolic species onto β-cyclodextrin modified poly(hydroxyethylmethacrylate ethyleneglycoldimethacrylate) microbeads. Chemosphere 2005, 61, 1263-1272.
36. Noble, R.D.; Gin, D.L. Perspective on ionic liquids and ionic liquid membranes. J. Membr. Sci. 2011, 369, 1-4.
37. Hanna, K.; de Brauer, C.; Germain, P. Solubilization of the neutral and charged forms of 2,4,6-trichlorophenol by β-cyclodextrin, methyl-β-cyclodextrin and hydroxypropyl-β-cyclodextrin in water. J. Hazard. Mater. 2003, 100, 109-116.
38. Leyva, E.; Moctezuma, E.; Strouse, J.; GarcÍagaribay, M.A. Spectrometric and 2D NMR studies on the complexation of chlorophenols with cyclodextrins. J. Incl. Phenom. Macrocycl. Chem. 2001, 39, 41-46.
39. Chattopadhyay, P.; Sinha, C.; Pal, D.K. Preparation and properties of a new chelating resin containing imidazolyl azo groups. Fresen. J. Anal. Chem. 1997, 357, 368-372.
40. Li, J.; Ni, X.; Zhou, Z.; Leong, K.W. Preparation and characterization of polypseudorotaxanes based on block-selected inclusion complexation between poly(propylene oxide)-poly(ethyleneoxide)-poly(propylene oxide) triblock copolymers and α-cyclodextrin. J. Am. Chem. Soc. 2003, 125, 1788-1795.
41. Gonil, P.; Sajomsanga, W.; Ruktanonchaia, U.R.; Pimphaa, N.; Sramalaa, I.; Nuchuchuaa, O.; Saesooa, S.; Chaleawlert-umpona, S.; Puttipipatkhachornb, S. Novel quaternized chitosan containing β-cyclodextrin moiety: Synthesis, characterization and antimicrobial activity. Carbohyd. Polym. 2011, 83, 905-913.
42. Mahlambi, M.M.; Malefetse, T.J.; Mamba, B.B.; Krause, R.W. β-Cyclodextrin-ionic liquid polyurethanes for the removal of organic pollutants and heavy metals from water: Synthesis and characterization. J. Polym. Res. 2010, 17, 589-600.