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Synthesis and Spectrophotometric Study of Toxic Metals Extraction by Novel Thio-Based Non-Ionic Surfactant

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Published/Copyright: September 15, 2015
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Abstract

A new thio-based non-ionic surfactant 1-(3-chlorophenyl)-3-te-tradecanoylthiourea has been synthesized from potassium thiocyanate, tetradecanoyl chloride and 3-chloroanaline. The purity of the compound was characterized by techniques like 1H NMR, 13C NMR, and FT-IR. The compound was used to detect the toxic metals like copper, mercury and manganese by using UV-Visible spectrophotometric technique. The compound is able to act as a ligand as well to form micelles. Due to this the compound extracts these toxic metals in form of solubilization and complexation. The extracted metals settle down to the bottom in a water tank. The visible change in color with time proves the interaction of the compound with the metals. The compound having carbonyl as well as sulfur groups have soft corner to metal for complexation. This will be used to remove toxic metals from polluted soil and soft drinking surface and underground water. The surfactant is easily synthesized, very economical and environmentally acceptable. The CMC of the surfactant is also determined.

Kurzfassung

Ein neues nicht-ionisches Thiotensid (1-(3-Chlorophenyl)-3-tetradecanoylthiourea) wurde aus Kaliumthiocyant, Tetradecanolychlorid und 3-Chloranilin synthetisiert. Die Reinheit der Verbindung wurde mit 1H NMR, 13C NMR, and FT-IR bestimmt. Die Verbindung wurde eingesetzt, um toxische Metalle wie Kupfer, Quecksilber und Mangan mit der UV-Vis-Spektrophotometrie zu detektieren. Die Verbindung kann sowohl als Ligand agieren als auch Mizellen bilden. Daher kann man mit der Verbindung die toxischen Metalle extrahieren, in dem man sie einerseits komplexiert und andererseits solubilisiert. Dabei setzen sich die Metalle am Grund des Wassertanks ab. Die sichtbare Farbveränderung mit der Zeit belegt die Wechselwirkung der Verbindung mit den Metallen. Die Verbindung hat sowohl Cabonyl- als auch Schwefelhaltige Gruppen, weshalb das Molekül weiche Ecken für die Komplerierung hat. Dies wird für die Entfernung von toxischen Metallen aus verschmutzem Boden, Oberflächen- und Grundwässern ausgenutzt. Das Tensid lässt sich einfach synthetisieren und ist sowohl ökonomisch als auch ökologisch akzeptabel. Die CMC des Tensids wurde ebenfalls bestimmt.


*Correspondence address, Dr. Imdad Ullah, Department of Chemistry, Quaid-i-Azam University, 45320, Islamabad, Pakistan, Tel.: +92-51 90 64 21 10, Fax: +92-51 90 64 22 41, E-Mail:

Imdad Ullah (Gold medalist in M.Sc) is an assistant professor of Physical Chemistry in the government college of Khyber Pakhtunkhwa, Pakistan. He completed his Ph.D from the Department of Chemistry, Quaid-i-Azam University (QAU), Islamabad, Pakistan. Currently, he is visiting scholar status at the school of chemistry, -Monash University Clayton, VIC. Australia. He has synthesized more than fifty new thiourea-based surfactants and working on their environment friendly applications such as extraction of toxic metals and corrosion inhibitions.

Afzal Shah, an assistant professor in Quaid-iAzam University, received his Ph.D in physical Chemistry from QAU in 2010 under the indigenous Ph.D program launched by the Higher Education Commission, Pakistan. His research interests include elucidation of electrode reaction mechanism of biologically important molecules and development of new synthetic routes for the preparation of environmental friendly surfactants.

Musharaf Khan, lecturer in Biology in Federal college Mardan, Pakistan, received his PhD in biological science from Peshawar University, Pakistan. His research interest includes medicinal plants and taxonomy. He is also working on biosurfactants synthesis and their medicinal use in many drugs and foods.

Shahan Zeb Khan got his M. Sc. and M.Phil degrees from QAU. Islamabad. Currently he is doing PhD from QAU under the supervision of Dr. Zia-ur-Rehman. His research is focused on the synthesis and characterization of surfactants and medicinal applications of metal based compounds.

Zia-ur-Rehman earned his Ph.D from the Department of Chemistry, Quaid-i-Azam University, Islamabad in 2009 under the HEC indigenous program. Through a HEC IRSEP scholarship he studied in McGill University, Canada. Presently, he is assistant professor in the Department of Chemistry, Quaid-i-Azam University, Islamabad. His research interests include discovery of new metal-based anticancer drugs and their targeted delivery via loading in micelles of body compatible surfactants.

Amin Badshah is a professor in chemistry at Quaid-i-Azam University, Ismalabad, Pakistan. He has focused on the synthesis, characterization and applications of surfactants and medicinal compounds. His name is in the list of “Leading Scientists and Engineers of OIC Member States”, published by COMSTECH Secretariat, Islamabad, Pakistan.


References

1. Shah, A., Shah, A. H., Mahmood, S., Ullah, I. and Rehman, Z.: Cost effective procedures for efficient synthesis of environmental friendly surfactants. Tenside Surf. De.50 (2013) 160168. 10.3139/113.110243Search in Google Scholar

2. Jalal, H. and Seyed, H. B.: Determination of atorvastatin in human serum by salting out assisted solvent extraction and reversed-phase high-performance liquid chromatography–UV detection Arab. J. Chem.7 (2014) 8790. 10.1016/j.arabjc.2013.07.057Search in Google Scholar

3. Xiao, X. S., Kyung, N. H., Joong, K. C. and Eun, K. K.: Screening of surfactants for harmful algal blooms mitigation, Marine Pollution Bulletin48 (2004) 937945. 10.1016/j.morpolbul.2003.11.021Search in Google Scholar

4. Tibor, C., Esther, F. and Gyula, O.: Biological activity and environmental impact of anionic surfactants, Environment International28 (2002) 337348. Pll: SOI60-4120(02)00032-6.Search in Google Scholar

5. Ana, M. F., Uwe, H., Andreas, W. and Wolfgang, H. B.: New green surfactants for emulsion polymerization, Progress in Organic Coatings53 (2005) 246255. 10.1016/j.porgcoat.2004.12.011Search in Google Scholar

6. Ajay, S., JonathanD. V. H. and Owen, P. W.: Surfactants in microbiology and biotechnology: Part 2. Application aspects, Biotechnology Advances25 (2007) 99121. 10.1016/j.biotechadv.2006.10.004Search in Google Scholar

7. Abu, Z. M., Rudra, R. P. and Dickinson, W. T.: Effect of Application of Surfactants on Hydraulic Properties of Soils, Biosystems Engineering84 (2003) 363372. 10.1016/S1537-5110(02)00244-1Search in Google Scholar

8. Yan, Y. L. and Nicholas, L. A.: Applications of functional surfactants, Current Opinion in Colloid & Interface Science7 (2002) 267275. 10.1016/S1359-0294(02)00067-5Search in Google Scholar

9. Pradip and Beena, R.: Design of tailor-made surfactants for industrial applications using a molecular modelling approach, A: Physicochemical and Engineering Aspects205 (2002) 139148. 10.1016/S0927-7757(01)01153-0Search in Google Scholar

10. Yuan, L., Xinde, C., Ling, Z and Eduardo, A.: Biochar- and phosphate-induced immobilization of heavy metals in contaminated soil and water: implication on simultaneous remediation of contaminated soil and groundwater Environ Sci. Pollut. Res.10.1007/s11356-013-2423-1(2013)Search in Google Scholar

11. Sfaksi, Z., Azzouz, N. and Abdelwahab, A.: Removal of Cr(VI) from water by cork waste Arab. J. Chem.7 (2014) 3742. 10.1016/j.arabjc.2013.05.031Search in Google Scholar

12. Kanchi, S., Singh, P. and Bisetty, K.: Dithiocarbamates as hazardous remediation agent: A critical review on progress in environmental chemistry for inorganic species studies of 20th century Arab. J. Chem.7 (2014) 1125. 10.1016/j.arabjc.2013.04.026Search in Google Scholar

13. Veeraraj, A., Sami, P. and Raman, N.: Copper(II)complex of 3-cinnamalideneacetylacetone, Synthesis and characterization Proc. Indian Acad. Sci. (Chem. Sci.)112 (2000) 515521. 10.1007/BF02709284Search in Google Scholar

14. Javier, G., Africa, G. O., Juan, L. S., Jose, L. P., Luis, L., Maria, I. A. and Teofilo, R.: Synthesis and spectroscopic properties of copper(II) complexes derived from thiophene-2-carbaldehyde thiosemicarbazone Structure and biological activity of [Cu(C6H6N3S2)2]Journal of Inorganic Biochemistry75 (1999) 4554. PIIS0162-0134(99)31-8.10.1016/S0162-0134(99)00031-8Search in Google Scholar

15. Ardeshir, S., Mehrorang, G. and Hamed, G.: Potentiometric and Spectrophotometric Studies of Copper(II) Complexes of Some Ligands in Aqueous and Nonaqueous SolutionJournal of the Chinese Chemical Society54 (2007) 933940.10.1002/jccs.200700134Search in Google Scholar

16. Ana, D., Aurora, F., Noemí, G., Emilia, I. and Luis, M.: Determination of Critical Micelle Concentration of Some Surfactants by Three Techniques, Journal of Chemical Education74 (1997) 1227123. citeulike:6876827.Search in Google Scholar

17. Yun, H. S.: Preparation of organobentonite using nonionic surfactant, Chemosphere44 (2001) 989995. 0045-6535(200108)Search in Google Scholar

18. Saha, R., Nandi, R. and Saha, B.: Sources and toxicity of hexavalent chromium. J. Coord. Chem.64 (2011) 1782. 10.1080/00958972.2011.583646Search in Google Scholar

19. Basu, A., Ghosh, S. K., Saha, R., Ghosh, A., Mukherjee, K. and Saha, B.: Effect of Some Non Functional Surfactants and Electrolytes on the Hexavalent Chromium Reduction by Glycerol Tenside Surf. Det.50 (2013) 249. 10.3139/113.110152Search in Google Scholar

20. Samik, K. H. and Satya, P. M.: Determination of Critical Micelle Concentration (CMC) of Nonionic Surfactants by Donor–Acceptor Interaction with Iodine and Correlation of CMC with Hydrophile–Lipophile Balance and Other Parameters of the Surfactants, Journal of Surfactants and Detergents4 (2001) 303309. 10.1007/s11743-001-0184-2Search in Google Scholar

21. Aguiar, J., Carpena, P., Molina, B. J. A. and Carnero, R.: On the determination of the critical micelle concentration by the pyrene 1:3 ratio method, Journal of Colloid and Interface Science258 (2003) 116122). 10.1016/S0021-9797(02)00082-6Search in Google Scholar

22. Maria, V. F., Epaminondas, C. V., Nikolaos, S., Gill, M. E., George, B., Dimitrios, P. T. and Peter, J. H.: Critical Micelle Concentrations of Nonionic Surfactants in Organic Solvents: Approximate Prediction with UNIFAC, Journal of Colloid and Interface Science240 (2001) 277283. 10.1006/jcis.2001.7627Search in Google Scholar PubMed

23. Anna, M. and Boenna, R. R.: Prediction of Critical Micelle Concentration of Nonionic Surfactants by a Quantitative Structure – Property Relationship, Combinatorial Chemistry & High Throughput Screening13 (2010) 3944. 10.2174/138620710790218195Search in Google Scholar PubMed

24. Paweł, W.: The influence of the size of the hydrophilic group on the miscibility of zwitterionic and nonionic surfactants in mixed monolayers and micelles, Journal of Colloid and Interface Science316 (2007) 107113. 10.1016/j.jcis.2007.07.025Search in Google Scholar PubMed

25. Ullah, I., Naveed, A., Shah, A., Badshah, A., Rehman, Z., Shahzada, G. and Nadim, A.: High yield synthesis, detailed spectroscopic characterization and electrochemical fate of novel cationic surfactants. J Surfact Deterg.17 (2014) 243251. 10.1007/s11743-013-1511-zSearch in Google Scholar

26. Zaheer, M., Shah, A., Akhter, Z., Qureshi, R., Mirza, B. and TauseefM.: Synthesis, characterization, electrochemistry and evaluation of biological activities of some ferrocenyl Schiff bases. Bolte, M.; Appl. Organomet. Chem.25 (2011) 6169. 10.1002/aoc.1690Search in Google Scholar

27. Jain, W. and McLeod, C. W.: Rapid Sequential Determination of Inorganic Mercury and Methylmercury in Natural Waters by Flow-injection – Cold Vapor-Atomic-Fluorescence Spectrometry. Talanta39 (11) (1992) 15371542. 10.1039/AN9851000331Search in Google Scholar

28. Sladek, C., Gustin, M. S., Kim, C. S. and Biester, H.: Application of three methods for determining mercury speciation in mine waste. Geochemistry: Exploration, Environment, Analysis2 (2002) 369376. 10.1144/1467-787302-036Search in Google Scholar

29. Ullah, I., Sirajuddin, M., Khan, M., Shah, A. and Badshah, A.: Comparative Study on the Catalytic Performance of Metal Oxide Catalysts for Decomposition of Hydrogen Peroxide. J. Chem. Soc. Pak.35 (2013) 775782. 10.44127814Search in Google Scholar

30. Ghosh, A., Saha, R. and Saha, B.: Effect of CHAPS and CPC micelles on Ir(III) catalyzed Ce(IV) oxidation of aliphatic alcohols at room temperature and pressure. J. Ind. Eng. Chem.20 (2014) 345. 10.1016/j.molliq.2014.03.037Search in Google Scholar

31. Mukherjee, K., Saha, R., Ghosh, A., Ghosh, S. K. and Saha, B.: Efficient combination of promoter and catalyst for chromic acid oxidation of propan-2-ol to acetone in aqueous acid media at room temperature Spectrochim. Acta Part A.101 (2013) 294305. 10.1016/j.saa.2012.09.095Search in Google Scholar PubMed

Received: 2014-09-15
Accepted: 2014-11-03
Published Online: 2015-09-15
Published in Print: 2015-09-15

© 2015, Carl Hanser Publisher, Munich

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