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Suryadi Budi Utomo
Chemical Education Study Program, PMIPA FKIP, Sebelas Maret University, Surakarta
Chemical Engineering, Chemistry & Bioengineering Chemistry

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SYNTHESIS OF TETRAKIS-N,N,N-TRIMETHYLAMMONIUMMETHYL-C-3,4-DIMETHOXYPHENYLCALIX[4]RESORCINARENE IODIDE BASED VANILLIN AND ITS ANTIDOTE ACTIVITY FOR CHROMIUM(VI) INTOXICATION Suryadi Budi Utomo; Jumina Jumina; Dwi Siswanta; Mustofa Mustofa
Indonesian Journal of Chemistry Vol 13, No 2 (2013)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (247.122 KB) | DOI: 10.22146/ijc.21299

Abstract

A research has been conducted to synthesize tetrakis-N,N,N-trimethylammoniummethyl-C-3,4-dimethoxyphenylcalix[4]resorcinarene iodide from vanillin and investigate its antidote capability for Cr(VI) intoxication. The synthesis was carried out in four steps i.e. (1) O-alkylation of 4-hydroxy-3-methoxybenzaldehyde, (2) HCl-catalyzed condensation of 3,4-dimethoxybenzaldehyde with resorcinol, (3) Mannich reaction of C-3,4-dimethoxyphenylcalix[4]resorcinarene with formaldehyde and dimethylamine in the presence of HCl to yield tetrakis-N,N-dimethylaminomethyl-C-3,4-dimethoxyphenylcalix[4]resorcinarene, and (4) treatment the Mannich base with methyl iodide to produce the quaternary ammonium salt of tetrakis-N,N,N-trimethylammoniummethyl-C-3,4-dimethoxyphenylcalix[4]resorcinarene iodide. According to the analysis of 1H-NMR spectrometer, the targeted compounds tend to exist in the chair (C2h) conformation. The capability of resorcinarene for Cr(VI) antidote was examined by orally injection method on mice groups. Based on LD50 determination, the resorcinarene was classified as non toxic compound according to Loomis criteria. Therapeutic using quaternary ammonium-modified resorcinarene was able to reduce metal concentrations of Cr(VI) in liver, kidney, and serum in the magnitude of 78.30; 85.72, and 88.79%, respectively. The higher dose of drug administered the greater decrease in the level of heavy metal. Judging from the amount of milligrams of reduced chromium per gram of organ, kidney is the organ having highest decreasing metal concentrations.
KINETICS AND EQUILIBRIUM MODEL OF Pb(II) AND Cd(II) ADSORPTION ONTO TETRAKIS-THIOMETHYL-C-4-METHOXYPHENYLCALIX[4]RESORCINARENE Suryadi Budi Utomo; Jumina Jumina; Dwi Siswanta; Mustofa Mustofa
Indonesian Journal of Chemistry Vol 12, No 1 (2012)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (370.022 KB) | DOI: 10.22146/ijc.21371

Abstract

The ability of tetrakis-thiomethyl-C-4-methoxyphenylcalix[4]resorcinarene for trapping Pb(II) and Cd(II) from aqueous solution at different pH, contact times, and initial metal concentration was investigated. Concentration of metal ions before and after interaction was analyzed by Atomic Absorption Spectrophotometer (AAS). The result indicated that tetrakis-thiomethyl-C-4-methoxyphenylcalix[4]resorcinarene is a good host for metal ions, where Cd(II) sorption capacity was higher than that of Pb(II). Effect of pH on batch experiments for the mentioned ions indicated that the optimum pH for metal binding were 5 for both of lead(II) and cadmium(II). In order to investigate the mechanism of adsorption, the 1st-order, pseudo 1st-order, and pseudo 2nd-order kinetic models were used. The adsorption model of metal ions on the resorcinarene followed pseudo second order of Ho & McKay expression. The equilibrium adsorption isotherm has been analyzed by Langmuir and Freundlich equations. Langmuir model had the higher correlation coefficient than that of Freundlich model.
SYNTHESIS OF THIOMETHYLATED CALIX[4]RESORCINARENE BASED ON FENNEL OIL VIA CHLOROMETHYLATION Suryadi Budi Utomo; Jumina Jumina; Dwi Siswanta; Mustofa Mustofa; Naresh Kumar
Indonesian Journal of Chemistry Vol 11, No 1 (2011)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (435.978 KB) | DOI: 10.22146/ijc.21411

Abstract

A research has been conducted to synthesize thiomethylated-C-4-methoxyphenylcalix[4]resorcinarene using fennel oil as a starting material. The synthesis was carried out in four steps i.e. (1) oxidation of anethole to yield p-anisaldehyde, (2) HCl-catalyzed condensation of p-anisaldehyde with resorcinol, (3) chloromethylation of C-4-methoxyphenylcalix[4]resorcinarene with paraformaldehyde and HCl in the presence of ZnCl2 to yield tetrakis-chloromethyl-C-4-methoxyphenylcalix[4]resorcinarene, and (4) reaction of tetrakis-chloromethyl-C-4-methoxyphenylcalix[4]resorcinarene with thiourea followed by hydrolysis with sodium hydroxide solution to yield tetrakis-thiomethyl-C-4-methoxyphenylcalix[4]resorcinarene. The prepared compounds were characterized based on melting point, FT-IR, and NMR spectrometers. According to the analysis of 1H-NMR spectrometer, C-4-methoxyphenylcalix[4]resorcinarene and tetrakis-chloromethyl-C-4-methoxyphenylcalix[4]resorcinarene were observed in the chair or flattened partial cone conformation, while tetrakis-thiomethyl-C-4-methoxyphenylcalix[4]resorcinarene tend to exist in the crown or cone conformation.
Co-Authors Dwi Siswanta Dwi Siswanta Dwi Siswanta Jumina Jumina Jumina Jumina Jumina Jumina Mustofa Mustofa Mustofa Mustofa Naresh Kumar