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Solubilization of 4,4′-dibromodiphenyl ether under combined TX-100 and cosolvents

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Abstract

This paper is focused on the selection of cosolvents in the remediation of contaminated soils. The aim of this study was to investigate the combined effects of Triton X-100 (TX-100) and different cosolvents on the solubilization behavior of 4,4′-dibromodiphenyl ether (BDE-15) and the washing of BDE-15 from a contaminated soil. 1H NMR spectroscopies were used to elucidate the interactions among TX-100, cosolvents, and BDE-15 in aqueous micellar solution. Results showed that the solubility of BDE-15 was enhanced by the observed synergism among TX-100, BDE-15, and cosolvents, and the TX-100/dimethyl sulfoxide (DMSO) system exhibited the best performance in the solubilization of BDE-15. Similar synergism was further evidenced in the washing of BDE-15 from a contaminated soil. With 10 % (v/v) DMSO and 6.4 mM TX-100 solution added, considerable synergistic effect was achieved in TX-100/DMSO system, leading to the highest removal efficiency (92.9 %) of BDE-15 from the soil, relative to that of 67.3 % with TX-100 alone at the same concentration.

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References

  • Alexander S, Cosgrove T, Castle TC, Grillo I, Prescott SW (2012) Effect of temperature, cosolvent, and added drug on pluronic–flurbiprofen micellization. J Phys Chem B 116:11545–11551

    Article  CAS  Google Scholar 

  • Anon (2002) User Guide, SIMCA-P and SIMCA-P+ 10. Umetrics Umeå

  • Baglioni P, Kevan L (1987) Structural effects of alcohol addition to sodium dodecyl sulfate micelles studied by electron spin-echo modulation of 5-doxylstearic acid spin probe. J Phys Chem 91:1516–1518

    Article  CAS  Google Scholar 

  • Bernardez LA, Ghoshal S (2004) Selective solubilization of polycyclic aromatic hydrocarbons from multicomponent nonaqueous-phase liquids into nonionic surfactant micelles. Environ Sci Technol 38:5878–5887

    Article  CAS  Google Scholar 

  • Brusseau ML, Wang X, Hu Q (1994) Enhanced transport of low-polarity organic compounds through soil by cyclodextrin. Environ Sci Technol 28:952–956

    Article  CAS  Google Scholar 

  • Chaudhari P, Sharma P, Barhate N, Kulkarni P, Mistry C (2007) Solubility enhancement of hydrophobic drugs using synergistically interacting cyclodextrins and cosolvent. Curr Sci 92:1586–1591

    CAS  Google Scholar 

  • Chu W, Kwan C (2003) Remediation of contaminated soil by a solvent/surfactant system. Chemosphere 53:9–15

    Article  CAS  Google Scholar 

  • EPA U (2009) DecaBDE phase-out initiative. http://www.epa.gov/oppt/existingchemicals/pubs/actionplans/deccadbe.html

  • Fu J, Zhou Q, Liu J, Liu W, Wang T, Zhang Q, Jiang G (2008) High levels of heavy metals in rice (Oryzasativa L.) from a typical E-waste recycling area in southeast China and its potential risk to human health. Chemosphere 71:1269–1275

    Article  CAS  Google Scholar 

  • Graziano G, Lee B (2001) Hydration of aromatic hydrocarbons. J Phys Chem B 105:10367–10372

    Article  CAS  Google Scholar 

  • Jawitz JW, Dai D, Rao PSC, Annable MD, Rhue RD (2003) Rate-limited solubilization of multicomponent nonaqueous-phase liquids by flushing with cosolvents and surfactants: modeling data from laboratory and field experiments. Environ Sci Technol 37:1983–1991

    Article  CAS  Google Scholar 

  • Kawakami K, Oda N, Miyoshi K, Funaki T, Ida Y (2006) Solubilization behavior of a poorly soluble drug under combined use of surfactants and cosolvents. Eur J Pharm Sci 28:7–14

    Article  CAS  Google Scholar 

  • Li J-L, Chen B-H (2002) Solubilization of model polycyclic aromatic hydrocarbons by nonionic surfactants. Chem Eng Sci 57:2825–2835

    Article  CAS  Google Scholar 

  • Liu H, Zhou Q, Wang Y, Zhang Q, Cai Z, Jiang G (2008) E-waste recycling induced polybrominated diphenyl ethers, polychlorinated biphenyls, polychlorinated dibenzo-p-dioxins and dibenzo-furans pollution in the ambient environment. Environ Int 34:67–72

    Article  Google Scholar 

  • Lu GN, Dang Z, Tao XQ, Chen XP, Yi XY, Yang C (2007) Quantitative structure–activity relationships for enzymatic activity of chloroperoxidase on metabolizing organophosphorus pesticides. QSAR Comb Sci 26:182–188

    Article  CAS  Google Scholar 

  • Lu GN, Dang Z, Tao XQ, Yang C, Yi XY (2008) Estimation of water solubility of polycyclic aromatic hydrocarbons using quantum chemical descriptors and partial least squares. QSAR Comb Sci 27:618–626

    Article  CAS  Google Scholar 

  • Luning Prak DJ, Jahraus WI, Sims JM, MacArthur AHR (2011) An 1H NMR investigation into the loci of solubilization of 4-nitrotoluene, 2, 6-dinitrotoluene, and 2, 4, 6-trinitrotoluene in nonionic surfactant micelles. Colloid Surf A 375:12–22

    Article  CAS  Google Scholar 

  • Luo X-J, Liu J, Luo Y, Zhang X-L, Wu J-P, Lin Z, Chen S-J, Mai B-X, Yang Z-Y (2009) Polybrominated diphenyl ethers (PBDEs) in free-range domestic fowl from an e-waste recycling site in South China: levels, profile and human dietary exposure. Environ Int 35:253–258

    Article  CAS  Google Scholar 

  • Ma J, Kannan K, Cheng J, Horii Y, Wu Q, Wang W (2008) Concentrations, profiles, and estimated human exposures for polychlorinated dibenzo-p-dioxins and dibenzofurans from electronic waste recycling facilities and a chemical industrial complex in Eastern China. Environ Sci Technol 42:8252–8259

    Article  CAS  Google Scholar 

  • Masrat R, Maswal M, Dar AA (2013) Competitive solubilization of naphthalene and pyrene in various micellar systems. J Hazard Mater 244:662–670

    Article  Google Scholar 

  • Mata-Sandoval JC, Karns J, Torrents A (2002) Influence of rhamnolipids and Triton X-100 on the desorption of pesticides from soils. Environ Sci Technol 36:4669–4675

    Article  Google Scholar 

  • Millard JW, Alvarez-Nunez F, Yalkowsky S (2002) Solubilization by cosolvents: establishing useful constants for the log–linear model. Int J Pharm 245:153–166

    Article  CAS  Google Scholar 

  • Mulligan C, Yong R, Gibbs B (2001) Surfactant-enhanced remediation of contaminated soil: a review. Eng Geol 60:371–380

    Article  Google Scholar 

  • Ni K, Lu Y, Wang T, Kannan K, Gosens J, Xu L, Li Q, Wang L, Liu S (2013) A review of human exposure to polybrominated diphenyl ethers (PBDEs) in China. Int J Hyg Environ Health 216:607–623

    Article  CAS  Google Scholar 

  • Paria S (2008) Surfactant-enhanced remediation of organic contaminated soil and water. Adv Colloid Interf 138:24–58

    Article  CAS  Google Scholar 

  • Peng S, Wu W, Chen J (2011) Removal of PAHs with surfactant-enhanced soil washing: influencing factors and removal effectiveness. Chemosphere 82:1173–1177

    Article  CAS  Google Scholar 

  • Qiu M, Chen X, Deng D, Guo J, Sun G, Mai B, Xu M (2012) Effects of electron donors on anaerobic microbial debromination of polybrominated diphenyl ethers (PBDEs). Biodegradation 23:351–361

    Article  CAS  Google Scholar 

  • Rao KJ, Paria S (2008) Solubilization of naphthalene in the presence of plant−synthetic mixed surfactant systems. J Phys Chem B 113:474–481

    Article  Google Scholar 

  • Rouse J, Morita T, Furukawa K, Shiau B-J (2008) Solubilization of mixed polycyclic aromatic hydrocarbon systems using an anionic surfactant. Colloid Surf A 325:180–185

    Article  CAS  Google Scholar 

  • Ruelle P, Buchmann M, Nam-Tran H, Kesselring UW (1992) Enhancement of the solubilities of polycyclic aromatic hydrocarbons by weak hydrogen bonds with water. J Comput Aided Mol Des 6:431–448

    Article  CAS  Google Scholar 

  • Tittlemier SA, Halldorson T, Stern GA, Tomy GT (2002) Vapor pressures, aqueous solubilities, and Henry’s law constants of some brominated flame retardants. Environ Toxicol Chem 21:1804–1810

    Article  CAS  Google Scholar 

  • Wang Y, Jiang G, Lam PK, Li A (2007) Polybrominated diphenyl ether in the East Asian environment: a critical review. Environ Int 33:963–973

    Article  Google Scholar 

  • Wang Y, Luo C, Li J, Yin H, Li X, Zhang G (2011) Characterization of PBDEs in soils and vegetations near an e-waste recycling site in South China. Environ Pollut 159:2443–2448

    Article  CAS  Google Scholar 

  • Wang P, Zhang H, Fu J, Li Y, Wang T, Wang Y, Ren D, Ssebugere P, Zhang Q, Jiang G (2013) Temporal trends of PCBs, PCDD/Fs and PBDEs in soils from an E-waste dismantling area in East China. Environ Sci Process Impacts 15:1897–1903

    Article  CAS  Google Scholar 

  • Wei H, Zou Y, Li A, Christensen ER, Rockne KJ (2013) Photolytic debromination pathway of polybrominated diphenyl ethers in hexane by sunlight. Environ Pollut 174:194–200

    Article  CAS  Google Scholar 

  • Yang X-J, Dang Z, Zhang F-L, Lin Z-Y, Zou M-Y, Tao X-Q, Lu G-N (2013) Determination of decabrominated diphenyl ether in soils by soxhlet extraction and high performance liquid chromatography. Sci World J. doi:10.1155/2013/840376

  • Yogui G, Sericano J (2009) Polybrominated diphenyl ether flame retardants in the US marine environment: a review. Environ Int 35:655–666

    Article  CAS  Google Scholar 

  • Zana R, Yiv S, Strazielle C, Lianos P (1981) Effect of alcohol on the properties of micellar systems: I. Critical micellization concentration, micelle molecular weight and ionization degree, and solubility of alcohols in micellar solutions. J Colloid Interface Sci 80:208–223

    Article  CAS  Google Scholar 

  • Zhang F-L, Yang X-J, Xue X-L, Tao X-Q, Lu G-N, Dang Z (2013a) Estimation of n-octanol/water partition coefficients (log) of polychlorinated biphenyls by using quantum chemical descriptors and partial least squares. J Chem 2013. doi:10.1155/2013/740548

  • Zhang L, Li J, Zhao Y, Li X, Wen S, Shen H, Wu Y (2013b) Polybrominated diphenyl ethers (PBDEs) and indicator polychlorinated biphenyls (PCBs) in foods from China: levels, dietary intake, and risk assessment. J Agric Food Chem 61:6544–6551

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was financially supported by the National High Technology Research and Development Program of China (863 Program) (No. 2012AA06A203), the Program for New Century Excellent Talents in University (No. NCET-12-0199), the National Science Foundation of China (No. 21007017), the Science and Technology Innovation Program of Higher Education of Guangdong (No. 2013KJCX0015), the Program for Pearl River Young Talents of Science and Technology in Guangzhou (No. 2013J2200007), and the Fundamental Research Funds for the Central Universities (No. 2013ZZ063).

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Authors and Affiliations

  1. School of Environment and Energy, South China University of Technology, Guangzhou, 510006, People’s Republic of China

    Xingjian Yang, Guining Lu, Rui Wang, Chuling Guo, Hongliang Zhang & Zhi Dang

  2. The Key Lab of Pollution Control and Ecosystem Restoration in Industry Clusters, Ministry of Education, South China University of Technology, Guangzhou, 510006, People’s Republic of China

    Guining Lu & Chuling Guo

  3. The State Key Lab of Pulp and Paper Engineering, South China University of Technology, Guangzhou, 510640, People’s Republic of China

    Zhi Dang

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  1. Xingjian Yang
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  2. Guining Lu
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  3. Rui Wang
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  4. Chuling Guo
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  5. Hongliang Zhang
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Correspondence to Guining Lu or Zhi Dang.

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Responsible editor: Angeles Blanco

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Yang, X., Lu, G., Wang, R. et al. Solubilization of 4,4′-dibromodiphenyl ether under combined TX-100 and cosolvents. Environ Sci Pollut Res 22, 3856–3864 (2015). https://doi.org/10.1007/s11356-014-3639-4

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  • DOI: https://doi.org/10.1007/s11356-014-3639-4

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