Abiotic association of phthalic acid esters with humic acid of a sludge landfill
Xiaoli CHAI, Yongxia HAO, Xin ZHAO, Guixiang LIU, Ying ZHU, Rong JI, Jun WU, Huanhuan TONG, Youcai ZHAO
Abiotic association of phthalic acid esters with humic acid of a sludge landfill
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 KA 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 KA 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.
abiotic association / phthalic acid esters (PAEs) / humic acid / sludge / landfill
[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
CrossRef
Pubmed
Google scholar
|
[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
CrossRef
Pubmed
Google scholar
|
[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
CrossRef
Pubmed
Google scholar
|
[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
CrossRef
Pubmed
Google scholar
|
[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
CrossRef
Pubmed
Google scholar
|
[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
CrossRef
Pubmed
Google scholar
|
[7] |
Wang J L, Liu P, Qian Y. Biodegradation of phthalate acid ester by acclimated activated sludge. Environment International, 1996, 22(6): 737-741
CrossRef
Google scholar
|
[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
CrossRef
Google scholar
|
[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
CrossRef
Pubmed
Google scholar
|
[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
CrossRef
Pubmed
Google scholar
|
[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
CrossRef
Google scholar
|
[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
CrossRef
Pubmed
Google scholar
|
[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
CrossRef
Pubmed
Google scholar
|
[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
CrossRef
Google scholar
|
[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
Pubmed
|
[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
CrossRef
Google scholar
|
[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
CrossRef
Google scholar
|
[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
CrossRef
Google scholar
|
[20] |
Enfield C G, Bengtsson G, Lindqvist R. Influence of macromolecules on chemical transport. Environmental Science & Technology, 1989, 23(10): 1278-1286
CrossRef
Google scholar
|
[21] |
Kopinke F D, Poerschmann J, Stottmeister U. Sorption of organic pollutants on anthropogenic humic matter. Environmental Science & Technology, 1995, 29(4): 941-950
CrossRef
Pubmed
Google scholar
|
[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
CrossRef
Pubmed
Google scholar
|
[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
CrossRef
Google scholar
|
/
〈 | 〉 |