Sains Malaysiana 47(6)(2018): 1167–1179

http://dx.doi.org/10.17576/jsm-2018-4706-12

Synthesis, Characterization and Adsorption Study of C-4-Phenacyloxy-phenylcalix[4]resorcinarene for Pb(II), Cd(II) and Cr(III) Ions

(Sintesis, Pencirian dan Kajian Jerapan C-4-fenasiloksifenilkaliks[4]resorsinarena terhadap Pb(II), Cd(II) dan Cr(III))

UNDRI RASTUTI^1,2, DWI SISWANTA¹, WISNU PAMBUDI¹, BETA ACHROMI NUROHMAH¹, BOHARI M. YAMIN³ & JUMINA^1*

¹Department of Chemistry, Faculty of Mathematics and Natural Sciences

Universitas Gadjah Mada, Sekip Utara Bulaksumur, Yogyakarta 55281, Indonesia

²Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Jenderal Soedirman, Jl. dr. Soeparno Karangwangkal, Purwokerto 53122, Indonesia

³Faculty of Science and Technology, Universiti Sains Islam Malaysia, 71800 Nilai, Negeri Sembilan, Malaysia

Received: 23 November 2017/Accepted: 6 January 2018

ABSTRACT

C-4-phenacyloxy phenyl calix[4]resorcinarene (CPPCR) was synthesized by acidic condensation of 4-hydroxybenzaldehyde and resorcinol. The adsorption of CPPCR for Pb(II), Cd(II) and Cr(III) has been studied by measuring the metal concentration in aqueous solution using Atomic Absorption Spectrophotometry (AAS). The effects of solution pH, contact time and initial concentration of metal ions on the adsorption capacity of CPPCR were investigated. The adsorption kinetic of all the ions obeyed the Ho and McKay pseudo 2nd order rate law and the adsorption isotherm profile matched very well with Langmuir model. The separation factor (RL) of CPPCR for Pb(II), Cd(II) and Cr(III) were 0.190, 0.017, and 0.065, respectively, indicating the formation of monolayer behaviour. The Gibb free energy (ΔG) of the adsorption for all the metal ions have negative values indicating the adsorption process of Pb(II), Cd(II) and Cr(III) by CPPCR are spontaneous.

Keywords: Calix[4]resorsinarene; ion adsorption; isotherm adsorption; kinetics adsorption; 4-phenacyloxybenzaldehyde

ABSTRAK

C-4-fenasilloksifenilcalix[4]resorsinarena (CPPCR) telah disintesis melalui tindak balas berasid antara 4-hidroksilbenzaldehid dan resorsinol. Penjerapan terhadap Pb(II), Cd(II) dan Cr(III) oleh CPPCR telah dikaji dengan mengukur kepekatan logam dalam larutan akueous menggunakan spektrofotometer serapan atom (AAS). Kesan pH larutan, masa sentuhan dan kepekatan awal ion logam ke atas kapasiti jerapan CPPCR telah dijalankan. Kinetik jerapan bagi semua ion logam tersebut mematuhi hukum pseudo-2 Ho dan McKay serta profil isoterma jerapan pula menyetujui model Langmuir. Faktor pemisahan (RL) bagi Pb(II), Cd(II) dan Cr(III) masing-masing adalah 0.190, 0.017 dan 0.065 yang menunjukkan berlaku tabii monolapisan. Nilai tenaga bebas Gibb bagi penjerapan semua logam bernilai negatif sekaligus menunjukkan proses yang spontan.

Kata kunci: Kaliks[4]resorsinarena; penjerapan ion; penjerapan isoterma; penjerapan kinetik; 4-fenasiloksibenzaldehid

REFERENCES

Abbas, M., Kaddour, S. & Trari, M. 2014. Kinetic and equilibrium studies of cobalt adsorption on apricot stone activated carbon. Journal of Industrial and Engineering Chemistry 20(3): 745-751.

Akkus, G.U., Memon, S., Sezgin, M. & Yilmaz, M. 2009. Synthesis of calix(aza)crown and its oligomeric analogue for the extraction of selected metal cations and dichromate anions. Clean 37(2): 109-114.

Akpomie, K.G. & Dawodu, F.A. 2014. Efficient abstraction of nickel(II) and manganese(II) ions from solution unto an alkaline modified montmorillonite. Journal of Taibah University for Science 8(4): 343-356.

Arshadi, M., Amiri, M.J. & Mousavi, S. 2014. Kinetic, equilibrium and thermodynamic investigation of Ni(II), Cd(II), Cu(II) and Co(II) adsorption on barley straw ash. Water Resources and Industry 6: 1-17.

Babel, S. & Kurniawan, T.A. 2003. Low-cost adsorbents for heavy metals uptake from contaminated water: A review. Journal of Hazardous Materials B97: 219-243.

Barnhart, J. 1997. Occurrences, uses, and properties of chromium. Regulatory Toxicology and Pharmacology 26: S3-S7.

Bell, S.E.J., Browne, J.K., McKee, V., McKervey, M.A., Malone, J.F., O’Leary, M., Walker, A., Arnaud-Neu, F., Boulangeot, O., Mauprivez, O. & Schwing-Weill, M.J. 1998. Cation complexation by chemically modified calixarenes. 11. Complexation and extraction of alkali cations by calix[5]- and -[6]arene ketones. Crystal and molecular structures of calix[5]arene ketones and Na+ and Rb+ complexes. Journal of Organic Chemistry 63: 489-501.

Benavente, M., Moreno, L. & Martinez, J. 2011. Sorption of heavy metals from gold mining wastewater using chitosan. Journal of the Taiwan Institute of Chemical Engineers 42(6): 976-988.

Bhattacharyya, K.G. & Gupta, S.S. 2008. Adsorption of a few heavy metals on natural and modified kaolinite and montmorillonite: A review. Advances in Colloid and Interface Science 140: 114-131.

Das, N. & Jana, R.K. 2006. Adsorption of some bivalent heavy metal ions from aqueous solutions by manganese nodule leached residues. Journal of Colloid and Interface Science 293(2): 253-262.

de Namor, A.F.D., Kowalska, D., Castellano, E.E., Piro, O.E., Velarde, F.J.S. & Salas, J.V. 2001. Lower rim calix(4) arene ketone derivatives and their interaction with alkali metal cations. Structural and thermodynamic (solution and complexation) characterisation of the tetraphenyl ketone derivative and its sodium complex. Physical Chemistry Chemical Physics 3: 4010-4021.

Flora, G., Gupta, D. & Tiwari, A. 2012. Toxicity of lead: A review with recent updates. Interdisciplinary Toxicology 5(2): 47-58.

Gunatilake, S.K. 2015. Methods of removing heavy metals from industrial wastewater. Journal of Multidisciplinary Engineering Science Studies 1(1): 12-18.

Gupta, S.S. & Bhattacharyya, K.G. 2009. Treatment of water contaminated with Pb(II) and Cd(II) by adsorption on kaolinite, montmorillonite and their acid-activated forms. Indian Journal of Chemical Technology 16: 457-470.

Gutsche, C.D. 2008. Calixarenes: An Introduction. 2nd ed. Monographs in Supramolecular Chemistry. The Royal Society of Chemistry. Cambridge-UK.

Jaishankar, M., Tseten, T., Anbalagan, N., Mathew, B.B. & Beeregowda, K.N. 2014. Toxicity, mechanism and health effects of some heavy metals. Interdisciplinary Toxicology 7(2): 60-72.

Joshi, J. & Sahu, O. 2014. Adsorption of heavy metals by biomass. Journal of Applied & Environmental Microbiology 2(1): 23-27.

Jumina, Sarjono, R.E., Siswanta, D., Santosa, S.J. & Ohto, K. 2011. Adsorption characteristics of Pb(II) and Cr(III) onto C-methylcalix[4]resorcinarene. Journal of the Korean Chemical Society 55(3): 454-462.

Jumina, Sarjono, R.E., Paramitha, B., Hendaryani, I. & Siswanta, D. 2007. Adsorption characteristics of Pb(II) and Cr(III) onto C-4-methoxyphenylcalix[4]resorcinarene in batch and fixed bed column system. Journal of the Chinese Chemical Society 54: 1167-1178.

Kim, J.Y., Morisada, S., Kawakita, H., Ohto, K. & Kim, Y. 2015. Relationship between chemical structure and extraction efficiency toward palladium with ketonic derivatives of p-tertoctylcalix[4]arene in nitric acid media. Journal of Inclusion Phenomena and Macrocyclic Chemistry 82(1): 25-32.

Kunsagi-Mate, S., Szabo, K., Lemli, B., Bitter, I., Nagy, G. & Kollar, L. 2005. Host-guest interaction between water-soluble calix[6]arene hexasulfonate and p-nitrophenol. Thermochimica Acta 425(1-2): 121-126.

Li, X., Wang, Z., Li, Q., Ma, J. & Zhu, M. 2015. Preparation, characterization, and application of mesoporous silica-grafted graphene oxide for highly selective lead adsorption. Chemical Engineering Journal 273: 630-637.

Ming, C., Ting, S., Wei, F. & Guowang, D. 2011. Study on adsorption and desorption properties of the starch grafted p-tert-butyl-calix[n] -arene for butyl Rhodamine B solution. Journal of Hazardous Materials 185: 914-921.

Mouni, L., Merabet, D., Bouzaza, A. & Belkhiri, l. 2011. Adsorption of Pb(II) from aqueous solution using activated carbon developed from apricot stone. Desalination 276(1- 3): 148-153.

Mulya, P.W., Jumina, J., Siswanta, D. & Ngurah, B.I.G.M. 2014. Advanced Materials Research 1043: 129-132.

Mututuvari, T.M. 2014. Supramolecular biopolymeric composite materials: Green synthesis, characterization, and applications. Dissertation. Marquette University, Wilwaukee, Wisconsin (Unpublished).

Peng, W., Li, H., Liu, Y. & Song, S. 2017. A review on heavy metal ions adsorption from water by graphene oxide and its composites. Journal of Molecular Liquids 230: 496-504.

Ramos, R.L., Rubio, L.F., Coronado, R.M.G. & Barron, J.M. 1995. Adsorption of trivalent chromium from aqueous solutions onto activated carbon. Journal of Chemical Technology and Biotechnology 62: 64-67.

Rastuti, U., Siswanta, D. & Jumina. 2016. Synthesis and characterization of 4-Phenacyloxy benzaldehyde derivatives. Oriental Journal of Chemistry 32(5): 2451-2458.

Reddy, N.S. & Rao, K.S.V.K. 2016. Polymeric hydrogels: Recent advance in toxic metal ion removal and anticancer drug delivery applications. Indian Journal of Advances in Chemical Science 4(2): 214-234.

Sajab, M.S., Chia, C.H., Zakaria, S. & Sillanpää, M. 2017. Adsorption of heavy metal ions on surface of functionalized oil palm empty fruit bunch fibers: Single and binary system. Sains Malaysiana 46(1): 157-165.

Sajab, M.S., Chia, C.H., Zakaria, S. & Khiew, P.S. 2013. Cationic and anionic modifications of oil palm empty fruit bunch fibers for the removal of dyes from aqueous solutions. Bioresource Technology 128: 571-577.

Satarug, S., Baker, J.R., Urbenjapol, S., Haswell-Elkins, M., Reilly, P.E.B., Williams, D.J. & Moore, M.R. 2003. A global perspective on cadmium pollution and toxicity in non-occupationally exposed population. Toxicology Letters 137: 65-83.

Schneider, I.A.H., Rubio, J. & Smith, R.W. 2001. Biosorption of metal onto plant biomass: Exchange adsorption or surface precipitation. International Journal of Mineral Processing 62(1-4): 111-120.

Sharififard, H., Nabavinia, M. & Soleimani, M. 2016. Evaluation of adsorption efficiency of activated carbon/chitosan composite for removal of Cr(VI) and Cd(II) from single and bi-solute solution. Advances in Environmental Technology 4: 215-227.

Sitko, R., Turek, E., Zawisza, B., Malicka, E., Talik, E., Heimann, J., Gagor, A., Feist, B. & Wrzalik, R. 2013. Adsorption of divalent metal ions from aqueous solution using graphene oxide. Dalton Transactions 42(16): 5682-5689.

Tran, C.D., Prosenc, F., Franko, M. & Benzi, G. 2016. One-pot synthesis of biocompatible silver nanoparticle composites from cellulose and keratin: Characterization and antimicrobial activity. ACS Applied Materials & Interfaces 8(50): 34791- 34801.

Trawneh, S.A. 2015. Studies on adsorption removal of some heavy metals ions by calix[4]resorcine. Jordan Journal of Earth and Environmental Sciences 7(1): 1-9.

Utomo, S.B., Jumina & Wahyuningsih, T.D. 2009. The adsorption of Pb(II) and Cr(III) by polypropylcalix[4]arene polymer. Indonesian Journal of Chemistry 9(3): 437-444.

Zhang, Y., Zheng, R., Zhao, J., Ma, F., Zhang, Y. & Meng, Q. 2014. Characterization of -treated rice husk adsorbent and adsorption of copper (II) from aqueous solution. BioMed Research International 2014: Article ID. 496878.

*Corresponding author; email: jumina@ugm.ac.id