SYNTHESIS OF POLYPROPYLCALIX[6]ARENE FROM p- t -BUTYLPHENOL AS ADSORBENT FOR Cr(III) METAL ION

Susy Yunita Prabawati; Jumina Jumina; Sri Juari Santosa; Mustofa Mustofa

doi:10.22146/ijc.21417

SYNTHESIS OF POLYPROPYLCALIX[6]ARENE FROM p-t-BUTYLPHENOL AS ADSORBENT FOR Cr(III) METAL ION

https://doi.org/10.22146/ijc.21417

Susy Yunita Prabawati^(1*), Jumina Jumina⁽²⁾, Sri Juari Santosa⁽³⁾, Mustofa Mustofa⁽⁴⁾

(1) Department of Chemistry, Faculty of Science and Technology, Sunan Kalijaga State Islamic University of Yogyakarta
(2) Chemistry Department, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Yogyakarta 55281
(3) Chemistry Department, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Yogyakarta
(4) Department of Pharmacology and Toxicology, Faculty of Medicine, Universitas Gadjah Mada, Yogyakarta
(*) Corresponding Author

Abstract

A study has been conducted to synthesize a novel polypropylcalix[6]arene polymer using p-t-butylphenol as a starting material. It was of interest to investigate the capability of the polymer with a tunnel-like structure, as adsorbent to trap the heavy metal cation such as Cr³⁺. The synthesis was carried out in several steps i.e (1) formation of p-t-butylcalix[6]arene from p-t-butylphenol as a starting material, (2) treatment of p-t-butylcalix[6]arene with 4.95 equivalents of allyl bromide under alkaline conditions to yield p-t-butyl-37,40-diallyloxy-38,39,41,42-tetra-hydroxy-calix[6]arene, and (3) polymerization of p-t-butyl-37,40-diallyloxy-38,39,41,42-tetrahydroxycalix[6]arene by treatment with concentrated sulfuric acid to yield polypropyl-calix[6]arene. The application of polypropylcalix[6]arene for trapping Cr(III) was investigated by stirring the suspension of calixarene under variation of pH, time, and adsorbent mass. IR and ¹H NMR spectra, showed that two allyl groups had been incorporated to the lower rim of the p-t-butylcalix[6]arene and the polymer was obtained as brownish green crystals with the melting point of 108-110 °C. The study also showed that the polypropylcalix[6]arene was able to trap Cr(III) cation. The optimum adsorption conditions were achieved at pH 5, contact time 60 min and concentration 12 mg/l for every 0,008 g of polymer.

Keywords

p-tert-butylphenol; polypropylcalix[6]arene; trapping Cr(III)

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References

[1] Bohmer, V., 1995, Angew. Chem. Int. Ed., 34, 7, 713–745.

[2] Gutsche, C.D., 1998, Calixarenes Revisited, The Royal Society of Chemistry: Cambridge.

[3] Lang, J., Dybal, J., Makrlik, E., Vanura, P., Vasickova, S., and Malon, P., 2007, J. Mol. Struct., 846, 1-3, 157–160.

[4] Stone, M.M., Franz, A.H., and Lebrilla, C.B., 2002, J. Am. Soc. Mass Spectrom., 13, 7, 964–974.

[5] Gac, S.L., Luhmer, M., Reinaud, O., and Jabin, I., 2007, Tetrahedron, 63, 44, 10721–10730.

[6] PengFei, G., WeiPu, Z., and ZhiQuan, S., 2007, Sci. China, Ser. B Chem., 50, 5, 648–653.

[7] Sliwa, W., 2005, J. Inclusion Phenom. Macrocyclic Chem., 52, 13–37.

[8] Rudkevich, D.M., 2005, Kem. Ind., 54, 2, 57–63.

[9] Tabakci, M., and Yilmaz, M., 2008, Bioresour. Technol., 99, 14, 6642–6645.

[10] Maming, Jumina, Siswanta, D., and Sastrohamidjojo, 2007, Indo. J. Chem., 7, 2, 172–179.

[11] Jumina, Utomo, S.B., Wahyuningsih, T.D., Santosa, S.J., Mulyono, P., Siswanta, D., Ohto, K., and Kawakita, H., Synthesis and Use of Polypropylcalix[4]arene for the Adsorbtion of Pb(II) and Cr(III) Cations, Proceeding of the 10^th Pacific Polymer Conferences, Kobe, 4-7 December 2007.

[12] Ho, Z., Ku, M., Shu, C., and Lin, L., 1996, Tetrahedron, 52, 41, 13189–13200.

[13] Shu, C., Yuan, T., Ku, M., Ho, Z., Liu, W., Tang, F., and Lin, L., 1996, Tetrahedron, 52, 29, 9805–9818.

[14] Utomo, S.B., Jumina, and Wahyuningsih, T.D., 2009, Indo. J. Chem., 9, 3, 437–444.

[15] Shu, C., Ku, M., Liu, W., Tang, F., Yeh, M., and Lin, L., 1994, J. Org. Chem., 59, 754.

[16] Brindle, R., Albert, K., Harris, S.J., Tröltzsch, C., Horne, E., and Glennon, J.D., 1996, J. Chromatogr. A, 731, 1-2, 41–46.

[17] Fa Fu Yang., Hong Yu Guo., Jian Rong Lin., and Yuan Yin Chen., 2003, Chin. Chem. Lett., 14, 5, 453-455.

[18] Stumm, W., and Morgan, J.J., 1996, Aquatic Chemistry, 3^th ed., John Wiley and Sons, Inc., New York.

[19] Jumina, Sarjono, R.E., Matsyeh, S., and Kumar, N., 2001, Berkala Ilmiah MIPA, 3, XI, 35–51.

[20] Utomo, S.B., 2007, Synthesis of polypropylcalix[4] arene from p-t-Butylphenol for the Adsorption of Pb(II), Thesis, Universitas Gadjah Mada, Yogyakarta.

DOI: https://doi.org/10.22146/ijc.21417