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Solubility and reactivity of surfactant-enhanced alkaline hydrolysis of organophosphorus pesticide DNAPL

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Abstract

The study presented in this paper evaluated the effectiveness of surfactants in enhancing mass removal of organophosphorus pesticides (OPPs) from soil under highly alkaline conditions and potential for enhancing in situ alkaline hydrolysis for treatment of OPPs, particularly parathion (EP3) and methyl parathion (MP3). In control and surfactant experiments, hydrolysis products EP2 acid, MP2 acid, and PNP were formed in non-stoichiometric amounts indicating instability of these compounds. MP3 and malathion were found to have faster hydrolysis rates than EP3 under the conditions studied. All surfactants evaluated increased solubility of OPPs under alkaline conditions with four nonionic alcohol ethoxylate products providing the greater affect over the polyglucosides, sulfonate, and propionate surfactants evaluated. The alcohol ethoxylates were shown to provide substantial mass removal of OPPs from soil. Hydrolysis rates were typically slower in the presence of surfactant, despite the relatively higher aqueous concentrations of OPPs; this was likely due to micellar solubilization of the OPPs which were therefore less accessible for hydrolysis. The results of this study support the use of surfactants for contaminant mass removal from soil, particularly under alkaline conditions, and may have implications for use of some surfactants in combination with other technologies for treatment of OPPs.

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References

  1. Amos BK, Daprato RC, Hughes JB, Pennell KD, Löffler FE (2007) Effects of the nonionic surfactant tween 80 on microbial reductive dechlorination of chlorinated ethenes. Environ Sci Technol 41:1710–1716

  2. Bondgaard M, Hvidbjerg B, Ramsay L (2012) Remediation of pesticide contamination by in situ alkaline hydrolysis - a new soil remediation technology. In: Proceedings of the eight international conference on remediation of chlorinated and recalcitrant compounds. Battelle Memorial Institute, Monterey, Califonia

  3. Chu W, Chan KH, Choy WK (2006) The partitioning and modelling of pesticide parathion in a surfactant-assisted soil-washing system. Chemosphere 64:711–716. https://doi.org/10.1016/j.chemosphere.2005.11.028

  4. Chuan-Yu Q, Yong-Sheng Z, Wei Z (2014) The influence zone of surfactant-enhanced air sparging in different media. Environ Technol 35(9–12):1190–1198. https://doi.org/10.1080/09593330.2013.865060

  5. Dave BP, Ghevariya CM, Bhatt JK, Dudhagara DR, Rajpara RK (2014) Enhanced biodegradation of total polycyclic aromatic hydrocarbons (TPAHs) by marine halotolerant Achromobacter xylosoxidans using Triton X-100 and β-cyclodextrin--a microcosm approach. Mar Pollut Bull 79:123–129. https://doi.org/10.1016/j.marpolbul.2013.12.027

  6. Di Palma L (2003) Experimental assessment of a process for the remediation of organophosphorous pesticides contaminated soils through in situ soil flushing and hydrolysis. Water Air Soil Pollut 143:301–314. https://doi.org/10.1023/A:1022890529765

  7. Dugan PJ, Siegrist RL, Crimi ML (2010) Coupling surfactants/cosolvents with oxidants for enhanced DNAPL removal: a review. Remediat J 20:27–49. https://doi.org/10.1002/rem

  8. Fan G, Cang L, Fang G, Zhou D (2014) Surfactant and oxidant enhanced electrokinetic remediation of a PCBs polluted soil. Sep Purif Technol 123:106–113. https://doi.org/10.1016/j.seppur.2013.12.035

  9. Han X, Balakrishnan VK, Buncel E (2007) Alkaline degradation of the organophosphorus pesticide fenitrothion as mediated by cationic C12, C14, C16, and C 18 surfactants. Langmuir 23:6519–6525. https://doi.org/10.1021/la063521u

  10. Hasegawa M, Shau B, Sabatini D et al (2000) Surfactant-enhanced subsurface remediation of DNAPLs at the former naval air station alameda, California. In: Wickramanayake G, Gavaskar A, Gupta N (eds) Treating dense nonaqueous-phase liquids (DNAPLs): remediation of chlorinated and recalcitrant compounds. Battelle Press, Columbus, OH, pp 219–226

  11. Hoag G, Collins J (2011) Soil remediation method and composition

  12. Jafvert CT, Strathmann J (2000) Innovative surfactant/cosolvent technologies for removal of NAPL and sorbed contaminants from aquifers. In: Tedder DW, Pohland F (eds) EMERGING TECHNOLOGIES IN HAZARDOUS WASTE MANAGEMENT 8. KLUWER ACADEMIC/PLENUM PUBL, 233 SPRING ST, NEW YORK, NY 10013 USA, pp 93–108

  13. Ketelaar JAA (1950) Chemical studies on insecticides II - the hydrolysis of OO′-diethyl- and -dimethyl-O″-p-nitrophenyl thiophosphonate (parathion and dimethylparathion (E 605)). Recl des Trav Chim des Pays-Bas 69:649–658

  14. Li Z, Hanlie H (2008) Combination of surfactant solubilization with permanganate oxidation for DNAPL remediation. Water Res 42:605–614. https://doi.org/10.1016/j.watres.2007.08.010

  15. Londergan J, Meinardus H, Mariner P et al (2001) DNAPL removal from a heterogeneous alluvial aquifer by surfactant-enhanced aquifer remediation. Gr Water Monit Remediat 21:57–67

  16. Menendez-Vega D, Gallego JLR, Pelaez AI et al (2007) Engineered in situ bioremediation of soil and groundwater polluted with weathered hydrocarbons. Eur J Soil Biol 43:310–321. https://doi.org/10.1016/j.ejsobi.2007.03.005

  17. Mirgorodskaya AB, Valeeva FG, Lukashenko SS et al (2012) Dicationic surfactant based catalytic systems for alkaline hydrolysis of phosphonic acid esters. Kinet Catal 53:206–213

  18. Mulligan C, Yong R, Gibbs B (2001) Surfactant-enhanced remediation of contaminated soil: a review. Eng Geol 60:371–380. https://doi.org/10.1016/S0013-7952(00)00117-4

  19. Pennell KD, Abriola LM, Weber WJ (1993) Surfactant-enhanced solubilization of residual dodecane in soil columns. 1. Exper Inves 27:2332–2340

  20. Pennell KD, Cápiro NL, Walker DI (2013) Surfactant and cosolvent flushing. In: Kueper B, Stroo HF, Ward H (eds) Chlorinated solvent source zone remediation. Springer, New York, NY, pp 353–394

  21. Perelo LW (2010) Review: in situ and bioremediation of organic pollutants in aquatic sediments. J Hazard Mater 177:81–89. https://doi.org/10.1016/j.jhazmat.2009.12.090

  22. Ramsburg C, Abriola L, Pennell K, Löffler FE, Gamache M, Amos BK, Petrovskis EA (2004) Stimulated microbial reductive dechlorination following surfactant treatment at the bachman road site. Environ Sci Technol 38:5902–5914

  23. Seebunrueng K, Santaladchaiyakit Y, Soisungnoen P, Srijaranai S (2011) Catanionic surfactant ambient cloud point extraction and high-performance liquid chromatography for simultaneous analysis of organophosphorus pesticide residues in water and fruit juice samples. Anal Bioanal Chem 401:1703–1712. https://doi.org/10.1007/s00216-011-5214-x

  24. Seebunrueng K, Santaladchaiyakit Y, Srijaranai S (2012) Study on the effect of chain-length compatibility of mixed anionic-cationic surfactants on the cloud-point extraction of selected organophosphorus pesticides. Anal Bioanal Chem 404:1539–1548. https://doi.org/10.1007/s00216-012-6209-y

  25. Sharma SR, Singh RP, Ahmed SR (1985) Effect of different saline, alkaline salts, fertilizers, and surfactants on the movement of some phosphorus-containing pesticides in soils. Ecotoxicol Environ Saf 10:339–350. https://doi.org/10.1016/0147-6513(85)90080-6

  26. Shrivastava A, Ghosh KK (2008) Micellar effects on hydrolysis of parathion. J Dispers Sci Technol 29:1381–1384. https://doi.org/10.1080/01932690802313063

  27. Suchomel EJ, Ramsburg CA, Pennell KD (2007) Evaluation of trichloroethene recovery processes in heterogeneous aquifer cells flushed with biodegradable surfactants. J Contam Hydrol 94:195–214. https://doi.org/10.1016/j.jconhyd.2007.05.011

  28. Torres LG, Ramos F, Avila Ma, Ortiz I (2012) Removal of methyl parathion by surfactant-assisted soil washing and subsequent wastewater biological treatment. Journal of Pesticide Science 37(3):240–246. https://doi.org/10.1584/jpestics.D11-024

  29. Tsai T, Kao C, Yeh T, Liang S, Chien H (2009) Application of surfactant enhanced permanganate oxidation and bidegradation of trichloroethylene in groundwater. J Hazard Mater 161(1):111–119. https://doi.org/10.1016/j.jhazmat.2008.03.061

  30. USEPA (2014) Estimation programs interface (EPI). In: http://www.epa.gov/oppt/exposure/pubs/episuite.htm

  31. Wattanaphon HT, Kerdsin A, Thammacharoen C et al (2008) A biosurfactant from Burkholderia cenocepacia BSP3 and its enhancement of pesticide solubilization. J Appl Microbiol 105:416–423. https://doi.org/10.1111/j.1365-2672.2008.03755.x

  32. Yeh DH, Pennell KD, Pavlostathis SG (1999) EFFECT OF TWEEN SURFACTANTS ON METHANOGENESIS AND MICROBIAL REDUCTIVE DECHLORINATION OF HEXACHLOROBENZENE. Environ Toxicol Chem 18:1408. https://doi.org/10.1897/1551-5028(1999)018<1408:EOTSOM>2.3.CO;2

  33. Zeng Q, Tang H, Liao B, Zhong T, Tang C (2006) Solubilization and desorption of methyl-parathion from porous media: a comparison of hydroxypropyl-beta-cyclodextrin and two nonionic surfactants. Water Res 40:1351–1358. https://doi.org/10.1016/j.watres.2006.01.036

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Acknowledgments

Acknowledgments go to the NorthPestClean project team for funding and fruitful discussions of the study. In addition to the authors of this paper, it includes Anja Melvej Hermansen, Børge Hvidbjerg, Kaspar Rüegg, and Lars Ernst from Region Midtjylland. From Meijer, Erik Petrovskis is acknowledged. Bo Breinbjerg from Cheminova A/S is gratefully acknowledged for help with the chemical analysis of soil and water samples.

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Correspondence to Jens Muff.

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Muff, J., MacKinnon, L., Durant, N.D. et al. Solubility and reactivity of surfactant-enhanced alkaline hydrolysis of organophosphorus pesticide DNAPL. Environ Sci Pollut Res 27, 3428–3439 (2020). https://doi.org/10.1007/s11356-019-07152-0

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Keywords

  • Surfactant
  • In situ remediation
  • Alkaline hydrolysis
  • Organophosphorus pesticides
  • DNAPL
  • Parathion