Abstract
Heavy metal ions from single and ternary systems of Pb(II), Cu(II), and Ni(II) adsorbed by calix[4]resorcinarenes in water–chloroform extraction were studied. Comparison was made of calix[4]resorcinarenes, 2,8,14,20-tetraundecyl calix[4]resorcinarene-4,6,10,12,16,18,22,24-octol, and diethylaminomethyl-calix[4]resorcinarene, 5,11,17,23-tetra(diethylaminomethyl)-2,8,14,20- tetraundecylcalix[4]resorcinarene-4,6,10,12,16,18,22,24-octol, for predominant extraction of their ions from the ternary mixture of aqueous solution at different pH in a water layer. The hosting of Pb(II) by the diethylaminomethyl-calix[4]resorcinarene occurred efficiently at pH 6–7. The hosting of Pb(II), Cu(II), and Ni(II) ions for the ternary aqueous mixture was applied to the Langmuir isotherm. Adsorption was studied using nuclear magnetic resonance spectroscopy in a water–deuterium chloroform extraction system. Results showed that as the heavy metal ions were included into the host cavity, the observation of shifted peaks of water molecules from downfield to higher field was visible in the nuclear magnetic resonance spectra, meaning that water molecules were included with heavy metal ion into the host cavity. The spectra also showed that the diethylamino group expressed formation of the coordination complex between the diethylaminomethyl-calix[4]resorcinarene and Pb(II) for the purpose of predominant hosting of Pb(II).
Similar content being viewed by others
References
Acemioglu B, Samil A, Alma HM, Gundogan R (2003) Copper(II) removal from aqueous solution by organosolve lignin and its recovery. J Appl Polym Sci 89:1537–1541
Aoyama Y, Tanaka Y, Sugahara S (1989) Molecular recognition of sugars via hydrogen-bonding interaction with synthetic polyhydroxymacrocycle. J Am Che Soc 111:5397–5404
Castillo M, Pina-Luis GM, Diaz-Garcia E, Rivero IA (2005) Solid phase organic synthesis of sensing sorbent materials for copper and lead recovery. J Braz Chem Soc 16:412–417
Faizal CKM, Kikuchi Y, Kobayashi T (2009) Molecular imprinting targeted for alpha-tocopherol by calix[4]resorcinarene derivative in membrane scaffold prepared by phase inversion. J Membrane Sci 334:110–116
Friberg L, Nordberg GF, Vouk B (1979) Introduction-general consideration and international perspectives. In: Nordberg GF, Fowler BA, Nordberg M, Friberg L (eds) Handbook on the toxicology of metals. Elsevier, Amsterdam
Gutsche CD (1989) Filling the baskets: complex formation with calixarenes. In: Gutsche CD (ed) calixarenes. The Royal Society of Chemistry, Cambridge
Izatt RM, Lamb JD, Hawkins RT, Brown PR, Izatt SR, Christensen JJ (1983) Selective M+–H+ coupled transport of cations through a liquid membrane by macrocyclic calixarene ligands. J Am Chem Soc 105:1782–1785
Izatt SR, Hawkins RT, Christensen JJ, Izatt RM (1985) Cation transport from multiple alkali mixture using a liquid membrane system containing a sereis of calixarene carriers. J Am Chem Soc 107:63–66
Jain VK, Kanaiya PH (2011) Chemistry of calix[4]resorcinarenes. Russ Chem R 80(1):75–102
Johnson PD, Watson MA, Brown J, Jefcoat IA (2002) Peanut hull pellets as a single use sorbent for the capture of Cu(II) from wastewater. Waste Manage 22:471–480
Jumina Sarjono RE, Paramitha B, Hendanyani I, Siswanty D, Santosa SJ, Anwar C, Sastrohamidjojo H, Ohto K, Oshima T (2007) Adsorption characteristic of Pb(II) and Cr(III) onto c-4-methoxyphenylcalix[4]resorcinarene in batch and fixed bed column system. J Chin Chem Soc-Taip 54:1167–1178
Karthikeyan T, Rajgopal S, Miranda LR (2005) Chromium (VI) adsorption from aqueous solution by Hevea brasilinesis saw dust activated carbon. J Hazard Mater B124:192–199
Knyazeva IR, Sadykova YM, Burilov AR, Pudovik MA, Konovalov AI (2009) Mannich reaction in the calix[4]resorcinarenes series containing organophosphorus fragments on the lower molecule rim. Zh Obshch Khim 79(11):1930–1931
Ma BQ, Zhang Y, Coppens P (2001) The chair conformation of c-methylcalix[4]resorcinarene in a novel, stepped, supramolecular framework. Cryst Eng Comm 20:1–3
Minhas FT, Memon S, Banger MI (2010) Transport of Hg(II) through bulk liquid membrane containing calix[4]arene thioalkyl derivative as a carrier. Desalination 262:215–220
Ngah WSW, Hanafiah MAKM (2008) Adsorption of copper on rubber (Heavea bransiliensis) leaf powder: kinetic, equilibrium and thermodynamic studies. Biochem Eng J 39:521–530
Osu Charles I, Odoemelam SA (2010) Studies on adsorbent dossage, particle sizes and pH constraints on biosorption of Pb(II) and Cd (II) ions from aqueous solution using modified and unmodified Crasstrotrea gasar (bivalve) biomass. Int Arch Appl Sci Tech 1(1):62–68
Panida S, Pisit C (2010) Equlibrium isotherm, thermodynamic and kinetic studies of lead adsorption onto pineapple and paper waste sludges. Int J Energ Environ 3(4):88–98
Rengaraj S, Yeon KH, Moon SH (2001) Removal of chromium from water and wastewater by ion exchange resins. J Hazard Mater 87:273–287
Turshatov AA, Melnikova YD, Semchikov IS, Ryzhkina TN, Pashirova D, Mobiu S, Zaitsev Y (2004) Interaction of monolayers of calix[4]resorcinarene derivatives with copper ions in the aqueous subphase. Colloid Surface A 240:101–106
Acknowledgments
The authors deeply thank to the support of facilities from Department of Materials Science and Technology, Nagaoka University of Technology, Japan for this research.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Yusof, N.N.M., Kikuchi, Y. & Kobayashi, T. Predominant hosting lead(II) in ternary mixtures of heavy metal ions by a novel of diethylaminomethyl-calix[4]resorcinarene. Int. J. Environ. Sci. Technol. 11, 1063–1072 (2014). https://doi.org/10.1007/s13762-013-0298-9
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s13762-013-0298-9