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Cyclodextrins for remediation of soils contaminated with chlorinated organics

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Abstract

The effect of random methylated βCD (RAMEB) on the efficiency of various remediation technologies was studied in lab-scale model-experiments applying soil and groundwater originating from a site contaminated with trichloroethylene (TCE). The solubility of TCE was enhanced to tenfold in 10% solution of RAMEB compared to that in water. This solubilizing effect was utilized for remediation of the TCE contaminated soil using enhanced groundwater extraction and in situ TCE oxidation by ISCO (= in situ chemical oxidation). The effect of CD on TCE extraction from soil was studied using two technologies: ground-water extraction followed by air stripping or UV irradiation. The RAMEB-enhanced ISCO was applied directly to the water-saturated soil without water extraction or separation. The efficiency of air stripping of TCE (removal by bubbling air through the contaminated ground-water obtained by extraction) was decreased in the presence of RAMEB due to the volatility decreasing effect of complexation. The efficiency of the entire technology (extraction and air stripping together) was, however, enhanced as three times more TCE was dissolved, and more than twice as much could be removed when 5% RAMEB solution was applied instead of water. Similar results were obtained by UV irradiation. Although the complexation has a protective effect against degradation caused by irradiation, the efficiency of the technology (extraction and subsequent UV irradiation) is enhanced to approximately threefold, because more than 10 times higher TCE concentration was found in the extract using 20% RAMEB concentration. ISCO is based on Fe-catalyzed oxidation using hydrogen peroxide. The catalytic effect of RAMEB was observed only when it was applied together with Fe(II) salts. Without Fe(II) the effect of complex formation dominated. When hydrogen peroxide and FeSO4 were applied with RAMEB, over five times enhancement in TCE removal was obtained compared to the technology based on the addition of hydrogen peroxide and Fe(II) salts without RAMEB. This effect shows that the solubilizing effect on iron catalyst is at least as much or even more important than the solubilizing effect on TCE. The ternary complex formation with ferrous/ferric ion and TCE seems to be responsible for the enhanced efficacy.

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References

  1. Uemasu, I., Kushiyama, S., Aizawa, R.: Capture of volatile chlorinated hydrocarbons by aqueous solutions of branched cyclodextrins. J. Inclusion Phenom. Mol. Recognit. Chem. 25(1–3), 221–224 (1996)

    Article  CAS  Google Scholar 

  2. Berselli, S., Milone, G., Canepa, P., di Gioia, D., Fava, F.: Effects of cyclodextrins, humic substances, and rhamnolipids on the washing of a historically contaminated soil and on the aerobic bioremediation of the resulting effluents. Biotechnol. Bioeng. 88(1), 111–120 (2004)

    Article  CAS  Google Scholar 

  3. Hanna, K., Chiron, S., Oturan, M.A.: Coupling enhanced water solubilization with cyclodextrin to indirect electrochemical treatment for pentachlorophenol contaminated soil remediation. Water Res. 39(12), 2763–2773 (2005)

    Article  CAS  Google Scholar 

  4. Fenyvesi, E., Molnar, M., Leitgib, L., Gruiz, K.: Cyclodextrin-enhanced soil remediation technologies. Land Contam. Reclam. 17, 585–594 (2009)

    Article  Google Scholar 

  5. Agency for Toxic Substances and Desease Registry: http://www.atsdr.cdc.gov/substances/toxsubstance.asp?toxids=30 Accessed 6 June 2010

  6. Shirin, S., Buncel, E., van Loon, G.W.: The use of beta-cyclodextrins to enhance the aqueous solubility of trichloroethylene and perchloroethylene and their removal from soil organic matter—effect of substituents. Can. J. Chem. 81(1), 45–52 (2003)

    Article  CAS  Google Scholar 

  7. Boving, T.B., Brusseau, M.L.: Solubilization and removal of residual trichloroethene from porous media: comparison of several solubilization agents. J. Contam. Hydrol. 42(1), 51–67 (2000)

    Article  CAS  Google Scholar 

  8. McCray, J.E., Brusseau, M.L.: Cyclodextrin-enhanced in situ flushing of multiple-component immiscible organic liquid contamination at the field scale: analysis of dissolution behavior. Environ. Sci. Technol. 33(1), 89–95 (1999)

    Article  CAS  Google Scholar 

  9. Tick, G.R., Lourenso, F., Wood, A.L., Brusseau, M.L.: Pilot-scale demonstration of cyclodextrin as a solubility-enhancement agent for remediation of a tetrachloroethylene-contaminated aquifer. Environ. Sci. Technol. 37(24), 5829–5834 (2003)

    Article  CAS  Google Scholar 

  10. Kashiyama, N., Boving, T.B.: Hindered gas-phase partitioning of trichloroethylene from aqueous cyclodextrin systems: implications for treatment and analysis. Environ. Sci. Technol. 38(16), 4439–4444 (2004)

    Article  CAS  Google Scholar 

  11. Liang, C.J., Huang, C.F., Mohanty, N., Lu, C.J., Kurakalva, R.M.: Hydroxypropyl-beta-cyclodextrin-mediated iron-activated persulfate oxidation of trichloroethylene and tetrachloroethylene. Ind. Eng. Chem. Res. 46(20), 6466–6479 (2007)

    Article  CAS  Google Scholar 

  12. Liang, C., Lee, I.-L.: In situ iron activated persulfate oxidative fluid sparging treatment of TCE contamination—a proof of concept study. J. Contam. Hydrol. 100(3–4), 91–100 (2008)

    Article  CAS  Google Scholar 

  13. Shirin, S., Buncel, E., van Loon, G.W.: Effect of cyclodextrins on iron-mediated dechlorination of trichloroethylene—a proposed new mechanism. Can. J. Chem. 82(12), 1674–1685 (2004)

    Article  CAS  Google Scholar 

  14. Gruiz, K.: Reactor approach. Land Contam. Reclam. 17, 553–576 (2009)

    Article  Google Scholar 

  15. Gruiz, K., Molnar, M., Fenyvesi, E.: Evaluation and verification of soil remediation. In: Kurladze, G.V. (ed.) Environmental Microbiology Research Trends, pp. 1–58. Nova Science Publishers, Hauppauge (2008)

    Google Scholar 

  16. Fenyvesi, E., Gruiz, K., Verstichel, S., De Wilde, B., Leitgib, L., Csabai, K., Szaniszlo, N.: Biodegradation of cyclodextrins in soil. Chemosphere 60, 1001–1008 (2005)

    Article  CAS  Google Scholar 

  17. Szaniszlo, N., Fenyvesi, E., Balla, J.: Structure-stability study of cyclodextrin complexes with selected volatile hydrocarbon contaminants of soils. J. Incl. Phenom. Macrocycl. Chem. 53(3–4), 241–248 (2005)

    Article  CAS  Google Scholar 

  18. Molnár, M., Leitgib, L., Gruiz, K., Fenyvesi, E., Szaniszló, N., Szejtli, J., Fava, F.: Enhanced biodegradation of transformer oil in soils with cyclodextrin—from the laboratory to the field. Biodegradation 16(2), 159–168 (2005)

    Article  Google Scholar 

  19. Leitgib, L., Gruiz, K., Fenyvesi, E., Balogh, G., Murányi, A.: Development of an innovative soil remediation: “cyclodextrin-enhanced combined technology”. Sci. Total Environ. 392(1), 12–21 (2007). (2008)

    Google Scholar 

  20. Chu, W., Choy, W.: The study of lag phase and rate improvement of TCE decay in UV/surfactant systems. Chemosphere 41, 1199–1204 (2000)

    Article  CAS  Google Scholar 

  21. Tanimura, T., Yoshida, A., Yamazaki, S.: Reduced formation of undesirable by-products from photocatalytic degradation of trichloroethylene. Appl. Catal. B 61, 346–351 (2005)

    Article  CAS  Google Scholar 

  22. Szejtli, J.: Cyclodextrins and Their Inclusion Complexes. Akad Kiado, Budapest (1982)

    Google Scholar 

  23. Chen, G., Hoag, G.E., Chedda, P., Nadim, F., Woody, B.A., Dobbs, G.M.: The mechanism and applicability of in situ oxidation of trichloroethylene with Fenton’s reagent. J. Hazard. Mater. 87, 171–186 (2001)

    Article  CAS  Google Scholar 

  24. Tai, Y., Dempsey, B.A.: Nitrite reduction with hydrous ferric oxide and Fe(II): stoichiometry, rate, and mechanism. Water Res. 43, 546–552 (2009)

    Article  CAS  Google Scholar 

  25. Kohn, T., Livi, K.J., Roberts, A.L., Vikesland, P.J.: Longevity of granular iron in groundwater treatment processes: corrosion product development. Environ. Sci. Technol. 39(8), 2867–2879 (2005)

    Article  CAS  Google Scholar 

  26. Lindsey, M.E., Xu, G., Lu, J., Tarr, M.A.: Enhanced Fenton degradation of hydrophobic organics by simultaneous iron and pollutant complexation with cyclodextrins. Sci. Total Environ. 307, 215–229 (2003)

    Article  CAS  Google Scholar 

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Acknowledgments

The studies were supported by National Research and Technology Programme (MOKKA, NKFP-3-00020/2005).

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Fenyvesi, É., Balogh, K., Oláh, E. et al. Cyclodextrins for remediation of soils contaminated with chlorinated organics. J Incl Phenom Macrocycl Chem 70, 291–297 (2011). https://doi.org/10.1007/s10847-010-9839-8

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  • DOI: https://doi.org/10.1007/s10847-010-9839-8

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