JSCS Vol 78, No 2

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J. Serb. Chem. Soc. 78 (2) 155–164 (2013)

UDC 678.746+547.821+549.456.4:542.913+547.532+547.78; JSCS–4404; doi: 10.2298/JSC120401089P Original scientific paper

 

Polystyrene-supported pyridinium chloroaluminate ionic liquid as a new heterogeneous Lewis acid catalyst for selective synthesis of benzimidazoles

KAVEH PARVANAK BOROUJENI, ASHKAN ZHIANINASAB and MINA JAFARINASAB

Department of Chemistry, Shahrekord University, Shahrekord 115, Iran

 

(Received 1 April, revised 27 August 2012)

Polystyrene-supported pyridinium chloroaluminate ionic liquid was prepared from the reaction of a Merrifield resin with pyridine followed by reaction with aluminium chloride. This catalyst was used as a new chemoselective Lewis acid catalyst for the exclusive synthesis of 2-substituted benzimidazoles from the reaction of aldehydes with o-phenylenediAMines. The catalyst was stable (as a benchtop catalyst) and could easily be recovered and reused without appreciable change in its efficiency.

 

Keywords: ionic liquids; chloroaluminate salts; heterogeneous catalysis; polymer-supported ionic liquids; benzimidazoles.

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J. Serb. Chem. Soc. 78 (2) 165–172 (2013)

UDC 547.532+547.78+547.853+547.235:616.89–008.441; JSCS–4405; doi: 10.2298/JSC120409082S Original scientific paper

 

Synthesis of some novel 7-(1H-benzimidazol-2-ylazo)-1,3-dimethyl-6,8-disubstituted-1H-pyrimido[4,5-b][1,4]diazepine-2,4-diones as potential anti-anxiety agents

KANTI SHARMA AND RENUKA JAIN

Department of Chemistry, university of Rajasthan, Jaipur 302 004, India

 

(Received 9 April, revised 29 July 2012)

An efficient and mild method for the synthesis of some novel 7-(1H-benzimidazol-2-ylazo)-1,3-dimethyl-6,8-disubstituted-1H-pyrimido[4,5-b][1,4]diazepine-2,4-diones in water has been developed. This method is a good option to obtain the title compounds in quantitative yields in a simple and inexpensive manner. Further, the NH of the title compounds was replaced by various substituents in an ionic liquid, [bmim]PF6, a recyclable and environmentally benign solvent. The synthesized compounds were characterized by analytical and spectral (IR, 1H-NMR, 13C-NMR and FAB mass) data and have been screened for their anti-anxiety activity in mice.

 

Keywords: 2-AMinobenzimidazole, diketones, benzimidazolyl-pyrimido-diazepines, aqueous/ionic liquid mediated synthesis; anti-anxiety activity.

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J. Serb. Chem. Soc. 78 (2) 173–178 (2013)

UDC 546.215+546.153.3–32+544.47:544.344:547.367; JSCS–4406; doi: 10.2298/JSC120223054G Short Communication

 

SHORT COMMUNICATION

In situ generated hypoiodous acid in an efficient and heterogeneous catalytic system for the homo-oxidative
coupling of thiols

ARASH GHORBANI-CHOGHAMARANI, MOHSEN NIKOORAZM and GOUHAR AZADI

Department of Chemistry, Faculty of Science, IlAM University, P. O. Box 69315516, IlAM, Iran

 

(Received 23 February, revised 17 May 2012)

Supported hydrogen peroxide on polyvinylpolypyrrolidone (PVPP–H2O2), silica sulfuric acid (SiO2–OSO3H) and catalytic AMounts of potassium iodide (KI) was developed as a heterogeneous medium for the rapid oxidative coupling of thiols into symmetrical homodisulfides. This oxidizing system proceeds under extremely mild conditions and gives no other oxidized side products.

 

Keywords: supported hydrogen peroxide on polyvinylpolypyrrolidone; potassium iodide; silica sulfuric acid.

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J. Serb. Chem. Soc. 78 (2) 179–195 (2013)

*paracetAMol+547.262:612.354; JSCS–4407; doi: 10.2298/JSC120724127M Short Communication

 

The effects of ethanol on paracetAMol-induced oxidative stress in mice liver

DUŠAN MLADENOVIĆ, MILICA NINKOVIĆ*, DANIJELA VUČEVIĆ, MIODRAG ČOLIĆ*, MARJAN MICEV**, VERA TODOROVIĆ***, MILENA N. STANKOVIĆ and TATJANA RADOSAVLJEVIĆ

Department of Pathophysiology, Faculty of Medicine, University of Belgrade, Serbia

*Institute for Medical Research, Military Medical Academy, Belgrade, Serbia

**Institute for Digestive Diseases, Clinical Centre of Serbia, Belgrade, Serbia

***Faculty of Stomatology Pančevo, University of Business Academy, Novi Sad, Serbia

 

(Received 24 July, revised 21 November 2012)

The aim of this study was to investigate the effects of binge drinking on paracetAMol-induced oxidative stress in mice liver. Male Swiss mice were divided into groups: control; ethanol-treated group (E) in five sequential doses of 2 g kg-1, administered through an orogastric tube; paracetAMol-treated group (P) in a dose of 300 mg kg-1, intraperitoneally and a group that received paracetAMol 12 h after the last dose of ethanol (PE). Blood and liver sAMples were collected for the determination of oxidative stress parAMeters 6, 24 and 48 h after treatment. Prior binge drinking potentiated the paracetAMol-induced increase in the liver malondialdehyde level 48 h after treatment in comparison with the P and E groups (17.14±1.98 vs. 13.14±0.82 and 12.99±1.18 μmol L-1, respectively, p < 0.01). Ethanol and paracetAMol in combination induced a more pronounced decrease in the liver GSH level than either of the individual substances alone at all time intervals (p < 0.01). Total liver superoxide dismutase (SOD) activity was significantly lower in PE 48 h after treatment in comparison with the P and E groups (251.73±80.63 vs. 707.62±179.92 and 1179.62±147.94 U mg-1 protein, respectively, p < 0.01). The lowest MnSOD activity in the PE group was detected 48 h after treatment (86.52±28.31; 41.13±11.07 and 23.16±5.18 U mg-1 protein in the P, E and PE groups, respectively, p < 0.05). Prior binge ethanol drinking potentiates paracetAMol-induced reduction of antioxidative capacity of hepatocytes due to GSH depletion and SOD activity reduction, simultaneously increasing lipid peroxidation caused by paracetAMol.

 

Keywords: ethanol; paracetAMol; oxidative stress; liver; mice.

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J. Serb. Chem. Soc. 78 (2) 197–207 (2013)

UDC 546.48+546.815+66.094.3–92:541.459:547.915:547.466.22; JSCS–4395; doi: 10.2298/JSC120214053J; Original scientific paper

 

Glutathione protects liver and kidney tissue from cadmium-and lead-provoked lipid peroxidation

JASMINA M. JOVANOVIĆ, RUŽICA S. NIKOLIĆ, GORDANA M. KOCIĆ*, NENAD S. KRSTIĆ AND MILENA M. KRSMANOVIĆ1Department of Chemistry, Faculty of Science and Mathematics, University of Niš, Višegradska Street 33, P. O. Box 224, 18000 Niš, Serbia *Faculty of Medicine, University of Niš, Bulevar dr Zorana Đinđića 81, 18000 Niš, Serbia

 

(Received 14 February, revised 17 April 2012)

Cd and Pb represent a serious ecological problem due to their soluble nature, their mobility and ability to accumulate in the soil. The exposure to these heavy metals can originate from different sources (drinking water, food and air), and they can enter into the human body through the respiratory and digestive systems. The effects of glutathione on Cd and Pb accumulation and lipid peroxidation effects in the liver and kidneys of heavy metal intoxicated rats were investigated. The content of the marker of lipid peroxidation, malondialdehyde, was increased several fold in the tissues of the exposed animals, the effects being more pronounced in the liver. The treatment of intoxicated animals with glutathione drastically suppressed lipid peroxidation. The obtained results imply that the application of glutathione may have a protective role in heavy metal intoxication by inhibiting lipid peroxidation. However, precaution should be exercised when Cd is considered, since it seems that glutathione promotes Cd accumulation in the liver.

 

Keywords: cadmium; lead; glutathione; lipid peroxidation; malondialdehyde.

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J. Serb. Chem. Soc. 78 (2) 209–216 (2013)

UDC 582.998.1+665.52/.54:632.951–188:543.51/.544.3; JSCS–4409; doi: 10.2298/JSC120130043C; Original scientific paper

 

Chemical composition and insecticidal activities of the essential oil of the flowering aerial parts of Aster ageratoides

SHA SHA CHU, SHAO LIANG LIU*, QI ZHI LIU, GUO HUA JIANG** and ZHI LONG LIU

Department of Entomology, China Agricultural University, Haidian District, Beijing 100193, China

*Department of Biology, Faculty of Preclinical Medicine, Guang Xi Traditional Chinese Medical University, Nanning 530001, China

**Analytic and Testing Center, Beijing Normal University, Haidian District, Beijing 100875, China

 

(Received 30 January, revised 12 April 2012)

Water-distilled essential oil from the flowering aerial parts of Aster ageratoides Turcz. (Compositae) was analyzed by gas chromatography-mass spectrometry (GC–MS) for the first time. Forty-three compounds, accounting for 96.4 % of the oil, were identified. The main compounds found were α-terpineol (10.8 %), β-caryophyllene (10.3 %), linalool (7.2 %), D-limonene (6.9 %), spathulenol (6.5 %), bornyl acetate (5.8 %) and bicyclosesquiphellandrene (5.6 %). The essential oil of A. ageratoides flowering aerial parts possessed contact toxicity against two grain storage insects Sitophilus zeAMais and Tribolium castaneum adults with LD50 values of 27.16 and 8.09 μg per adult, respectively. The essential oil also exhibited fumigant toxicity against S. zeAMais and T. castaneum adults with LC50 values of 13.73 and 12.14 mg L-1, respectively. The essential oil showed potential for development as a possible natural fumigant/insecticide for control of insects in stored products.

 

Keywords: Aster ageratoides; Sitophilus zeAMais; Tribolium castaneum; essential oil.

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J. Serb. Chem. Soc. 78 (2) 217–227 (2013)

UDC 546.982+547.857.6+547.496.3+542.913:576+615.9; JSCS–4410; doi: 10.2298/JSC120725154S; Original scientific paper

 

Synthesis, characterization and cytotoxicity of a palladium(II) complex of 3-[(2-hydroxybenzylidene)AMino]-2-thioxo-midazolidin-4-one

BILJANA ŠMIT, RADOSLAV Z. PAVLOVIĆ, ANA RADOSAVLJEVIĆ-MIHAILOVIĆ*, ANJA DOŠEN*, MILENA G. ĆURČIĆ, DRAGANA S. ŠEKLIĆ and MARKO N. ŽIVANOVIĆ

Faculty of Science, University of Kragujevac, Radoja Domanovića 12, P. O. Box 60, 34000 Kragujevac, Serbia

*Vinča Institute of Nuclear Sciences, P. O. Box 522, 11001 Belgrade, Serbia

 

(Received 25 May, revised 21 December 2012)

The polydentate ligand 3-[(2-hydroxybenzylidene)AMino]-2-thioxo-imidazolidin-4-one was synthesized in the intermolecular cyclocondensation reaction of 2-hydroxybenzaldehyde thiosemicarbazone and ethyl chloroacetate. A novel palladium(II) complex was obtained from cis-[Pd(DMSO)2Cl2] by nucleophilic substitution of both DMSO ligands with the iminic nitrogen and the thiolactAMic sulfur from the ligand. The structures of the compounds were characterized based on their spectral data. The cytotoxic activities of the ligand and the palladium(II) complex were studied on the tumor cell lines: human colon carcinoma HCT-116 and SW-480 cells using the MTT viability test. The results showed that the investigated palladium(II) complex had a significantly greater cytotoxic effect compared to that of the ligand.

 

Keywords: thiohydantoins; palladium(II) complexes; cytotoxic activity.

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J. Serb. Chem. Soc. 77 (2) 229–240 (2012)

UDC 547.496/.497+546.302+542.913:615.27:543.4; JSCS–4411; doi: 10.2298/JSC120325099K Original scientific paper

 

Synthesis, characterization of thiosemicarabzone metal complexes and their antioxidant activity in different in vitro model systems

DESIREDDY HARIKISHORE KUMAR REDDY, SEUNG-MOK LEE, KALLURU SESHAIAH* and K. RAMESH BABU**

1Department of Environmental Engineering, Kwandong University, Gangneung, Republic of Korea,

*Inorganic and Analytical Chemistry Division, Department of Chemistry, Sri Venkateswara University, Tirupati – 517 502, India

**Department of Biochemistry, Sri Venkateswara University, Tirupati – 517 502, India

 

(Received 25 March, revised 12 September 2012)

The synthesis of bimetallic Cu(II), Co(II), Ni(II), Zn(II) and U(VI) complexes with general stoichiometry [H2L M(X2)(H2O)2] (where H2L is the di-deprotanated ligand and X is chloride/sulphate) were obtained with the ligand terephthaladehyde bis(thiosemicarbazone) (H2L) and are discussed. The ligand and its binuclear complexes were characterized by micro analysis (CHNS), 1H-NMR, FT-IR, UV-vis, TG-DTA and conductance measurements. The thermal behaviour of these complexes showed that the hydrated complexes loose water molecules of hydration in the first step, followed immediately by decomposition of the anions and ligand molecules in the subsequent steps. The molar conductance measurements of the complexes in DMF correspond to the non-electrolytic nature of the complexes. Furthermore, the antioxidant activity of the ligand and its complexes were determined in vitro by the hydroxyl radical scavenging, DPPH, NO and reducing power methods. The obtained IC50 value of the DPPH activity for complex 2 (IC50 = 0.254 M) was shown to be the best.

 

Keywords: thiosemicarbazone; transition metal complexes; spectral analysis; bimetallic complexes; antioxidant activity

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J. Serb. Chem. Soc. 78 (2) 241–253 (2013)

UDC 547.221/.224:536.77:536.7.004.12; JSCS–4412; doi: 10.2298/JSC120113049N; Original scientific paper

 

Correlation between standard enthalpy of formation, structural parAMeters and ionicity for alkali halides

ABU NASAR

Department of Applied Chemistry, Faculty of Engineering &AMp; Technology, Aligarh Muslim University, Aligarh – 202002, India

 

(Received 13 January, revised 18 April 2012)

The standard enthalpy of formation (∆HsTANDARD STATE) is considered to be an interesting and useful parAMeter for the correlation of various properties of alkali halides. The interrelation between ∆HsTANDARD STATE and structural parAMeters for the halides of Li, Na, K and Rb has been thoroughly analyzed. When the cationic component element is kept constant in a homologous series of alkali halides, the negative value of ∆HsTANDARD STATE was observed to decrease linearly with increasing interionic distance (d). Accordingly, the following empirical equation ∆HsTANDARD STATE = α + + βd (where α and β are empirical constants) was established. However, for common anionic series of alkali halides, an opposing non-linear trend was observed, with the exception of common fluorides. The correlation study on the standard enthalpy of formation was extended in term of the radius ratio and also discussed in the light of ionization energy of the metal, electron affinity of the halogen, size of the ions, ionic character of the bond and the lattice energy of the compound.

 

Keywords: thermodynAMic properties; exothermicity; interionic distance; radius ratio; interrelation.

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J. Serb. Chem. Soc. 78 (2) 255–263 (2013)

UDC 547.565.2+547.815+547.538+547.496.2:536.6; JSCS–4413; doi: 10.2298/JSC101005103R; Original scientific paper

 

A calorimetric investigation for the bindings of mushroom tyrosinase to p-phenylene-bis(dithiocarbAMate) and to alkyl xanthates

GHOLAM REZA REZAEI BEHBEHANI, MELISA MEHRESHTIAGH, LYLA BARZEGAR* and ALI AKBAR SABOURY**1Department of Chemistry, ImAM Khomeini International University, Qazvin, Iran

*Department of Chemistry, IslAMk Azad University, Takestan Branch, Takestan, Iran

**Institute of Biochemistry and Biophysics, University of Tehran, Tehran, Iran

 

(Received 5 October 2010, revised 12 September 2012)

A comprehensive, simple and rapid thermodynAMic study on the interaction of mushroom tyrosinase, MT, with three isoalkyldithiocarbonates (xanthates) as sodium salts, C3H7OCS2Na (I), C4H9OCS2Na (II), and C5H11OCS2Na (III), with p-phenylene-bis(dithiocarbAMate) (IV), was performed using isothermal titration calorimetry to clarify the thermodynAMics of these bindings as well as structural changes of the enzyme due to its interaction with inhibitors at 300 K in phosphate buffer (10 m mol L-1; pH 6.8). The extended solvation theory was used to elucidate the effect of the inhibitors on the stability of the enzyme. The obtained results indicated that there are two identical and non-cooperative binding sites for these inhibitors.

 

Keywords: mushroom tyrosinase; isopropyl xanthate; isobutyl xanthate; iso-pentyl xanthate; p-phenylene-bis(dithiocarbAMate); extended solvation theory.

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J. Serb. Chem. Soc. 78 (2) 265–279 (2013)

UDC 546.726+546.27+542.913:544.6.076.32–036:541.135:543.552; JSCS–4414; doi: 10.2298/JSC120309108C; Original scientific paper

 

Ferrate(VI) synthesis at a boron-doped diAMond anode

MILAN ČEKEREVAC, LJILJANA NIKOLIĆ BUJANOVIĆ, ANJA JOKIĆ* and MILOŠ SIMIČIĆ

IHIS Techno-Experts, Batajnički put 23, 11080 Belgrade, Serbia

*University of Priština, Faculty of Science, Kosovska Mitrovica, Serbia

 

(Received 9 March, revised 16 October 2012)

The electrochemical synthesis of ferrate(VI) by the oxidation of iron compounds from alkaline 10 M KOH electrolytes on a boron-doped diAMond electrode was exAMined by cyclic voltAMmetry between the potentials of the hydrogen evolution reaction and the oxygen evolution reaction. It was shown that the anodic current peak that appeared in iron-free electrolyte at a less positive potential than the potential of the oxygen evolution probably coincides with oxidation of hydrogen in >CH2 groups and C-sp2 graphite impurities with formation of >C=O groups in a C-sp3 diAMond structure. Addition of Fe(III) compounds to the electrolyte provoked the formation of an anodic wave on the cyclic voltAMmogrAMs in the potential region that correlates with the generation of ferrate(VI). It is concluded that the direct electrochemical synthesis of Fe(VI) at a boron-doped diAMond anode is possible because of the less positive potential of ferrate(VI), FeO42-, formation with respect to the potential of the oxygen evolution reaction. The presence of ferrate(VI) in the electrolyte, formed after anodic polarization of the boron electrode in 10 M KOH electrolyte saturated with Fe(III) at 0.9 V against Hg/HgO electrode, was proven by UV–Vis spectrometry.

 

Key words: ferrate(VI); boron-doped diAMond electrode; synthesis; alkaline electrolyte; cyclic voltAMmetry; UV–Vis spectrophotometry.

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J. Serb. Chem. Soc. 78 (2) 281–294 (2013)

UDC *labetalol:544.6:544.275–128:544.6.076.32–039.26; JSCS–4415; doi: 10.2298/JSC120419113Z; Original scientific paper

 

Electrochemical behavior of labetalol at an ionic liquid-modified carbon paste electrode and its electrochemical determination

YAN-MEI ZHANG*, CHENG-QIAN DUAN*,** AND ZUO-NING GAO*

1College of Chemistry and Chemical Engineering, Ningxia University, Yinchuan, 750021, China

*Higher Vocational College of Ningxia Medical University, Yinchuan, 750004, China

 

(Received 14 April 2011, revised 28 August 2012)

The electrochemical behavior of labetalol (LBT) at a carbon paste electrode (CPE) and an ionic liquid 1-benzyl-3-methylimidazole hexafluorophosphate ([BnMIM]PF6) modified carbon paste electrode ([BnMIM]PF6/CPE) in Britton–Robinson buffer solution (pH 2.0) was investigated by cyclic voltAMmetry (CV) and square wave voltAMmetry (SWV). The experimental results showed that LBT at both the bare CPE and [BnMIM]PF6/CPE showed an irreversible oxidation process, but at [BnMIM]PF6/CPE its oxidation peak current increased greatly and the potential shifted negatively. The electrode reaction process is diffusion-controlled involving a one-electron transfer accompanied by the participation of one proton at [BnMIM]PF6/CPE. In addition, the electrochemical kinetic parAMeters were determined. Under the optimized electrochemical experimental conditions, the oxidation peak currents were proportional to LBT concentration in the range of 7.0´10-6–1.0´10-4 mol L-1 with a limit of detection (LOD, S/N=3) of 4.810´10-8 mol L-1 and a limit of quanti-fication (LOQ, S/N = 10) of 1.60´10-7 mol L-1. The proposed method was successfully applied in the determination of the LBT content in commercial tablet sAMples.

 

Keywords: labetalol; carbon paste electrode; ionic liquid; electrochemical determination.

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J. Serb. Chem. Soc. 78 (2) 295–302 (2013)

UDC 547.781.1+543.552:615.453.6+615.015.3; JSCS–4416; doi: 10.2298/JSC120111069Y; Original scientific paper

 

Electroanalytical determination of metronidazole in tablet dosage form

SELEHATTIN YILMAZ, ESRA BALTAOGLU, GULSEN SAGLIKOGLU, SULTAN YAGMUR, KAMRAN POLAT** and MURAT SADIKOGLU***

1Onsekiz Mart University, Faculty of Science and Arts, Department of Analytical Chemistry, 17020, Canakkale, Turkey

*Ankara University, Faculty of Science, Department of Chemistry, 06100, Ankara, Turkey

**Gaziosmanpasa University, Faculty of Education, Department of Science Education, 60100, Tokat, Turkey

 

(Received 11 January, revised 3 May 2012)

In this study, the electrochemical reduction and determination of metronidazole were easily realized in Britton–Robinson buffer (pH 4.01) using an UTGE by cyclic voltAMmetric (CV) and differential pulse voltAMmetric (DPV) techniques. In this acidic medium, one irreversible and a sharp cathodic peak were observed. A linear calibration curve for DPV analysis was constructed in the metronidazole concentration range 3×10-6–9×10-5 mol L-1. The limit of detection (LOD) and limit of quantification (LOQ) were 1.42×10-7 and 4.76×10-7 mol L-1 respectively.

 

Keywords: metronidazole; determination; voltAMmetry; UTGE; dosage form.

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J. Serb. Chem. Soc. 78 (2) 303–312 (2013)

UDC 546.72+62–493+546.18:627.157.004.74; JSCS–4417; doi: 10.2298/JSC120205057Z; Original scientific paper

 

Removal and recovery of phosphorus during anaerobic digestion of excess sludge by the addition of waste iron scrap

WEI ZHENG*, XIAO MING LI*,**,  DONG BO WANG*, QI YANG*, KUN LUO*, GUO JING YANG* AND GUANG MING ZENG*

1College of Environmental Science and Engineering, Hunan University, Changsha 410082, P. R. China

*School of the Environment, Guangxi University, Nanning 530004, P. R. China

 

(Received 5 February, revised 11 June 2012)

Abstract: In the current investigation, the feasibility of phosphorus removal in the anaerobic digestion of excess sludge by the addition of waste iron scrap (WIS) was studied. The results showed that the removal efficiency of phosphorus increased with increasing AMount of WIS, and the maximum removal efficiency of 39, 93 and 99 % could be reached at WIS dosages of 1, 2 and 3 g L-1, respectively. Sterilization greatly decreased the removal efficiency of phosphorus, being only –6, 53 and 64 % at WIS dosages of 1, 2 and 3 g L-1, respectively. This means that iron-reducing bacteria and hydrolytic bacteria enhance 45, 40 and 35 % of the phosphorus removal at WIS dosages of 1, 2 and 3 g L-1, respectively. The first and most important mechanism of phosphorus removal using WIS involves hydrolytic bacteria, which reduce the pH of the sludge to corrode the WIS, followed by precipitation of phosphorus by ferrous iron generated by iron-reducing bacteria. Phosphorus adsorption onto the WIS is the second probable mechanism. The removed phosphorus is recovered by up to 56 % using magnet. This method is characterized by high removal efficiency, easy and steady operation, low cost, recovery and reuse, making it better than other physical and chemical treatments.

 

Keywords: waste iron scrap; phosphorus removal; excess sludge; anaerobic digestion.

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