Covalent attachment of phenyl and carboxyphenyl layers derived from diazonium salts onto activated charcoal for the adsorption of pesticides

Authors

  • Jeton Halili Department of Chemistry, FNMS, University of Prishtina
  • Fexhrie Salihu Department of Chemistry, FNMS, University of Prishtina
  • Avni Riza Berisha Department of Chemistry, FNMS, University of Prishtina http://orcid.org/0000-0002-3876-1345

DOI:

https://doi.org/10.20450/mjcce.2018.1442

Keywords:

organochlorine pesticides, adsorption, covalent modification, diazonium salts, grafting,

Abstract

The past and recent uncontrolled use of organochlorine pesticides imposes serious problems due to their adverse undesired effects in ecosystems. Finding new ways to dispose of these molecules is therefore mandatory. The covalent modification of activated charcoal powder (ACP) by substituted aryl groups can be achieved by reaction with aryl radicals obtained through the sonically induced dediazonation of diazonium salts. Seventeen organochlorine pesticides were adsorbed on ACP covalently grafted with phenyl and carboxyphenyl layers. The sorption percentages of the pesticides onto the carboxyphenyl modified ACPs [measured by GC-ECD (Gas Chromatography – Electron Capture Detector)] were in the range of 90–100% (DDT, δ-HCH, γ-HCH and endrin aldehyde), 80–90% (methoxychlor, endosulfan II, p,p-DDD and β-HCH) and 60–80% (α-HCH, DDE, endosulfansulfate, endrin, endosulfan I, aldrin, heptachlorepoxid, dieldrin and heptachlor). A tentative explanation is given for these differences based on steric effects.

References

G. Matthews, Pesticides: Health, Safety and the Environment, John Wiley & Sons, 2008.

DOI:10.1002/0470865687

Y. Li et al., Sources and pathways of selected organo-chlorine pesticides to the Arctic and the effect of pathway divergence on HCH trends in biota: A review, Science of the Total Environment, 342, 87–106 (2005). https://doi.org/10.1016/j.scitotenv.2004.12.027

M. El-Shahawi et al., An overview on the accumulation, distribution, transformations, toxicity and analytical methods for the monitoring of persistent organic pollutants, Talanta, 80, 1587–1597 (2010).

DOI:10.1016/j.talanta.2009.09.055

T. Ahmad et al., Removal of pesticides from water and wastewater by different adsorbents: A review, Journal of Environmental Science and Health, Part C 28, 231–271 (2010). https://doi.org/10.1080/10590501.2010.525782

R. Betarbet et al., Chronic systemic pesticide exposure reproduces features of Parkinson's disease, Nature Neuroscience, 3, 1301–1306 (2000). DOI:10.1038/81834

S. Mostafalou et al., Pesticides and human chronic diseases: evidences, mechanisms and perspectives, Toxicology and Applied Pharmacology, 268, 157–177 (2013). DOI:10.1016/j.taap.2013.01.025

M. Fontcuberta et al., Chlorinated organic pesticides in marketed food: Barcelona, 2001–06, Science of the Total Environment, 389, 52–57 (2008).

DOI: 10.1016/j.scitotenv.2007.08.043

D. H. Garabrant et al., DDT and related compounds and risk of pancreatic cancer, Journal of the National Cancer Institute, 84, 764–77 (1992).

https://doi.org/10.1093/jnci/84.10.764

M. Rodrigo et al., Electrochemically assisted remedi¬ation of pesticides in soils and water: A review, Chemical Reviews, 114, 8720–8745 (2014).

DOI: 10.1021/cr500077e

T. M. Phillips et al., Biodegradation of hexachloro-cyclohexane (HCH) by microorganisms, Biodegra¬dation, 16, 363–392 (2005).

DOI: 10.1007/s10532-004-2413-6

P. Abhilash et al., Remediation of lindane by Jatropha curcas L.: utilization of multipurpose species for rhizoremediation, Biomass and Bioenergy, 51, 189–193 (2013). DOI: 10.1016/j.biombioe.2013.01.028

G. Kyriakopoulos et al., Adsorption of pesticides on carbonaceous and polymeric materials from aqueous solutions: a review, Separation & Purification Reviews 35, 97–191 (2006).

https://doi.org/10.1080/15422110600822733

M. Delamar et al., Covalent modification of carbon surfaces by grafting of functionalized aryl radicals produced from electrochemical reduction of diazonium salts, Journal of the American Chemical Society, 114, 5883–5884 (1992). DOI: 10.1021/ja00040a074

A. Berisha et al., Electrode surface modification using diazonium salts, Electroanalytical Chemistry, CRC Press, 2015, pp.115–224. DOI: 10.1201/b19196-4

M. M. Chehimi, Aryl Diazonium Salts: New Coupling Agents and Surface Science, John Wiley & Sons, 2012.

D. Bélanger et al., Electrografting: a powerful method for surface modification, Chemical Society Reviews, 40, 3995–4048 (2011). DOI:10.1039/C0CS00149J

A. Berisha et al., Physisorption vs. grafting of aryldiazonium salts onto iron: A corrosion study, Electrochimica Acta, 56, 10762–10766 (2011).

DOI: 10.1016/j.electacta.2011.01.049

A. Berisha et al., Grafting of an aluminium surface with organic layers, RSC Advances, 6, 78369–78377 (2016). DOI: 10.1039/C6RA15313E

C. Saby et al., Electrochemical modification of glassy carbon electrode using aromatic diazonium salts. 1. Blocking effect of 4-nitrophenyl and 4-carboxyphenyl groups, Langmuir, 13, 6805–6813 (1997).

DOI: 10.1021/la961033o

M. Busson, et al., Photochemical grafting of diazonium salts on metals, Chemical Communications, 47, 12631–12633 (2011). DOI: 10.1039/C1CC16241A

C. Mangeney et al., Electroless ultrasonic func-tionalization of diamond nanoparticles using aryl diazonium salts, Diamond and Related Materials, 17, 1881–1887 (2008). DOI:10.1016/j.diamond.2008.04.003

F. Mirkhalaf, et al., Frequency effects on the surface coverage of nitrophenyl films ultrasonically grafted onto indium tin oxide, Langmuir, 27, 1853–1858 (2011). DOI: 10.1021/la104402z

J.-P. Jasmin et al., Straightforward grafting approach for cyclam-functionalized screen-printed electrodes for selective Cu (II) determination, Electrochimica Acta, 200, 115–122 (2016). DOI:10.1016/j.electacta.2016.03.141

C. Cannizzo et al., Calix [6] arene mono-diazonium salt synthesis and covalent immobilization onto glassy carbon electrodes, Tetrahedron Letters, 55, 4315–4318 (2014). DOI: 10.1016/j.tetlet.2014.06.043

J.-P. Jasmin et al., Fabrication and characterization of all-covalent nanocomposite functionalized screen-printed voltammetric sensors, Electrochimica Acta, 133, 467–474 (2014). DOI:10.1016/j.electacta.2014.04.069

P. A. Gauden et al., Estimating the pore size distribution of activated carbons from adsorption data of different adsorbates by various methods, Journal of Colloid and Interface Science, 273, 39–63 (2004).

DOI:10.1016/j.jcis.2003.08.033

E. Coulon et al., Electrochemical attachment of organic groups to carbon felt surfaces, Langmuir, 17, 7102–7106 (2001). DOI: 10.1021/la010486c

M. Gineys et al., Grafting of activated carbon cloths for selective adsorption, Applied Surface Science, 370, 522–527 (2016). DOI: 10.1016/j.apsusc.2015.11.257

A. Elyacoubi et al., Development of an amperometric enzymatic biosensor based on gold modified magnetic nanoporous microparticles, Electroanalysis, 18, 345–350 (2006). https://doi.org/10.1002/elan.200503418

B. Jin, et al., Multi-residue detection of pesticides in juice and fruit wine: A review of extraction and detection methods, Food Research International, 46, 399–409 (2012). DOI: 10.1016/j.foodres.2011.12.003

G. Socrates, Infrared and Raman Characteristic Group Frequencies: Tables and Charts, John Wiley & Sons, 2004. https://doi.org/10.1002/jrs.1238

A. P. Terzyk, Adsorption of biologically active compounds from aqueous solutions on to commercial unmodified activated carbons. Part V. The mechanism of the physical and chemical adsorption of phenol, Adsorption Science & Technology, 21, 539–585 (2003). https://doi.org/10.1260/0263617041514910

Y. Wei et al., Intrinsic wettability of graphitic carbon, Carbon, 87, 10–17(2015).

DOI:10.1016/j.carbon.2015.02.019

P. Auffinger et al., Halogen bonds in biological molecules, Proceedings of the National Academy of Sciences of the United States of America, 101, 16789–16794 (2004). DOI: 10.1073/pnas.0407607101

D. M. Packwood et al., pH-dependent wettability of carboxyphenyl films grafted to glassy carbon, Australian Journal of Chemistry, 64, 122–126 (2011).

https://doi.org/10.1071/CH10285

A. Noble, Partition coefficients (n-octanol—water) for pesticides, Journal of Chromatography, A 642, 3–14 (1993). DOI: 10.1016/0021-9673(93)80072-G

A. Paschke et al., Concentration dependence of the octanol/water partition coefficients of the hexachloro-cyclohexane isomers at 25 C, Chemical Engineering & Technology, 23, 666–670 (2000).

https://doi.org/10.1002/1521-4125(200008)23:8<666:: AID-CEAT666>3.0.CO;2-5

A. Durimel et al., pH dependence of chlordecone adsorption on activated carbons and role of adsorbent physico-chemical properties, Chemical Engineering Journal, 229, 239–249 (2013).

DOI:10.1016/j.cej.2013.03.036

K. Singh et al., Computational and experimental studies of molecularly imprinted polymers for organochlorine pesticides heptachlor and DDT, Current Analytical Chemistry, 8, 562–568 (2012).

DOI:10.2174/157341112803216807

C. B. Aakeröy et al., The C–H••• Cl hydrogen bond: does it exist?, New Journal of Chemistry, 23, 145–152 (1999). DOI:10.1039/A809309A

J. P. Lommerse et al., The nature and geometry of inter-molecular interactions between halogens and oxygen or nitrogen, Journal of the American Chemical Society, 118, 3108–3116 (1996). DOI:10.1021/ja953281x

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Published

2018-06-01

How to Cite

Halili, J., Salihu, F., & Berisha, A. R. (2018). Covalent attachment of phenyl and carboxyphenyl layers derived from diazonium salts onto activated charcoal for the adsorption of pesticides. Macedonian Journal of Chemistry and Chemical Engineering, 37(1), 71–78. https://doi.org/10.20450/mjcce.2018.1442

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Section

Materials Chemistry