Abiotic association of phthalic acid esters with humic acid of a sludge landfill

Abstract

The abiotic association between phthalic acid esters (PAEs) and humic substances (HS) in sludge landfill plays an important role in the fate and stability of PAEs. An equilibrium dialysis combined with ¹⁴C-labeling was used to study the abiotic association of two abundant PAEs (diethyl phthalate and di-n-butyl phthalate) with humic acid (HA) isolated from a sludge landfill with different stabilization times and different molecular weights. Elemental analysis and Fourier Transform Infrared Spectrophotometer (FTIR) suggested that high K_A value of HA was related to the high aromatic content and large molecular weight of HA. The results indicated that the association strength of PAEs with HA depended on both the properties of the PAEs and the characteristics of HA. The K_A values of the association were strongly dependent on solution pH, and decreased dramatically as the pH was increased from 3.0 to 9.0. The results suggested that non-specific hydrophobic interaction between PAEs and HA was the main contributor to the association of the PAEs with HA. The interactive hydrogen-bonds between the HA and the PAEs molecules may also be involved in the association.

Keywords

abiotic association / phthalic acid esters (PAEs) / humic acid / sludge / landfill

References

[1] Yuan S Y, Liu C, Liao C S, Chang B V. Occurrence and microbial degradation of phthalate esters in Taiwan river sediments. Chemosphere, 2002, 49(10): 1295-1299

[2] Alatriste-Mondragon F, Iranpour R, Ahring B K. Toxicity of di-(2-ethylhexyl) phthalate on the anaerobic digestion of wastewater sludge. Water Research, 2003, 37(6): 1260-1269

[3] Teil M J, Blanchard M, Chevreuil M. Atmospheric fate of phthalate esters in an urban area (Paris-France). The Science of the Total Environment, 2006, 354(2-3): 212-223

[4] Zhu J, Phillips S P, Feng Y L, Yang X. Phthalate esters in human milk: concentration variations over a 6-month postpartum time. Environmental Science & Technology, 2006, 40(17): 5276-5281

[5] Bauer M J, Herrmann R. Estimation of the environmental contamination by phthalic acid esters leaching from household wastes. The Science of the Total Environment, 1997, 208(1-2): 49-57

[6] Liu H, Liang Y, Zhang D, Wang C, Liang H C, Cai H S. Impact of MSW landfill on the environmental contamination of phthalate esters. Waste Management (New York, N.Y.), 2010, 30(8-9): 1569-1576

[7] Wang J L, Liu P, Qian Y. Biodegradation of phthalate acid ester by acclimated activated sludge. Environment International, 1996, 22(6): 737-741

[8] Stales C A, Peterson D R, Parkerton T F, Adams W J. The environmental fate of phthalate esters: a literature review. Chemosphere, 1997, 35(4): 667-749

[9] Zeng F, Cui K, Xie Z, Wu L, Luo D, Chen L, Lin Y, Liu M, Sun G. Distribution of phthalate esters in urban soils of subtropical city, Guangzhou, China. Journal of Hazardous Materials, 2009, 164(2-3): 1171-1178

[10] Cai Q Y, Mo C H, Wu Q T, Zeng Q Y. Polycyclic aromatic hydrocarbons and phthalic acid esters in the soil-radish (Raphanus sativus) system with sewage sludge and compost application. Bioresource Technology, 2008, 99(6): 1830-1836

[11] Haitzer M, Hoss S, Traunspurger W, Steinberg C. Relationship between concentration of dissolved organic matter (DOM) and the effect of DOM on the bioconcentration of benzo[a]-pyrene. Aquatic Toxicology (Amsterdam, Netherlands), 1999, 45(2-3): 147-158

[12] Cho H H, Park J W, Liu C C K. Effect of molecular structures on the solubility enhancement of hydrophobic organic compounds by environmental amphiphiles. Environmental Toxicology and Chemistry /SETAC, 2002, 21(5): 999-1003

[13] Müller M B, Fritz W, Lankes U, Frimmel F H. Ultrafiltration of nonionic surfactants and dissolved organic matter. Environmental Science & Technology, 2004, 38(4): 1124-1132

[14] Clapp C E, Mingelgrin U, Liu R, Zhang H, Hayes M H B. A quantitative estimation of the complexation of small organic molecules with soluble humic acids. Journal of Environmental Quality, 1997, 26(5): 1277-1281

[15] Vinken R, Schaffer A, Ji R. Abiotic association of soil-borne monomeric phenols with humic acids. Organic Geochemistry, 2005, 36(4): 583-593

[16] Chai X L, Shimaoka T, Guo Q, Zhao Y C. Characterization of humic and fulvic acids extracted from landfill by elemental composition, 13C CP/MAS NMR and TMAH-Py-GC/MS. Waste Management, 2008, 28(5): 896-903

[17] Lu X Q, Hanna J V, Johnson W D. Source indicators of humic substances: an elemental composition, solid state ¹³C CP/MAS NMR and Py-GC/MS Study. Applied Geochemistry, 2000, 15(7): 1019-1033

[18] Polak J, Sułkowski W W, Bartoszek M, Papiez W. Spectroscopic studies of the progress of humification processes in humic acid extracted from sewage sludge. Journal of Molecular Structure, 2005, 744-747: 983-989

[19] Gauthier T D, Shane E C, Guerin W F, Seitz W R, Grant C L. Fluorescence quenching method for determining equilibrium constants for polycyclic aromatic hydrocarbons binding to dissolved humic materials. Environmental Science & Technology, 1986, 20(11): 1162-1166

[20] Enfield C G, Bengtsson G, Lindqvist R. Influence of macromolecules on chemical transport. Environmental Science & Technology, 1989, 23(10): 1278-1286

[21] Kopinke F D, Poerschmann J, Stottmeister U. Sorption of organic pollutants on anthropogenic humic matter. Environmental Science & Technology, 1995, 29(4): 941-950

[22] Zhu D Q, Hyun S, Pignatello J J, Lee L S. Evidence for π-π electron donor-acceptor interactions between π-donor aromatic compounds and π-acceptor sites in soil organic matter through pH effects on sorption. Environmental Science & Technology, 2004, 38(16): 4361-4368

[23] Chin Y P, Aiken G R, Danielsen K M. Binding of pyrene to aquatic and commercial humic substances: the role of molecular weight and aromaticity. Environmental Science & Technology, 1997, 31(6): 1630-1635

RIGHTS & PERMISSIONS

Higher Education Press and Springer-Verlag Berlin Heidelberg