Abstract
Humic acid (HA) and water play an important role in polycyclic aromatic hydrocarbons (PAHs) adsorption and biodegradation in soil. In this work, molecular dynamics (MD) and electrostatic potential surfaces (EPSs) simulations are conducted to research the contribution of quartz surface, leonardite humic acid (LHA), and water to PAH adsorption. The adsorption energies between PAHs and LHA are much higher than that between PAHs and quartz. Simulation shows that the hydroxyl and carboxyl groups’ attraction by LHA is the main adsorption force between PAHs and LHA. The π-π interaction between PAHs and LHA also contributes to the adsorption process. In addition, the mobility of water on quartz surface is much higher than that of LHA. Water should be regarded as an adsorbate in the system as well as PAHs. However, the presence of water has a remarkable negative effect on the adsorption of PAHs on LHA and quartz. The bridging effect of water could only enhance the stability of the aggregation system. The adsorption contribution of quartz and LHA to PAHs in the soil model tends to 0 if the water layer reaches 2.0 nm.
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Ahangar AG, Smernik RJ, Kookana RS, Chittleborough DJ (2008) Separating the effects of organic matter–mineral interactions and organic matter chemistry on the sorption of diuron and phenanthrene. Chemosphere 72:886–890. https://doi.org/10.1016/J.CHEMOSPHERE.2008.03.059
Ahmed AA, Thiele-Bruhn S, Aziz SG, Hilal RH, Elroby SA, al-Youbi AO, Leinweber P, Kühn O (2015) Interaction of polar and nonpolar organic pollutants with soil organic matter: sorption experiments and molecular dynamics simulation. Sci Total Environ 508:276–287. https://doi.org/10.1016/j.scitotenv.2014.11.087
Antao SM, Hassan I, Wang J, Lee PL, Toby BH (2008) State-of-the-art high-resolution powder X-ray diffraction (HRPXRD) illustrated with Rietveld structure refinement of quartz, sodalite, tremolite, and meionite. Can Mineral 46:1501–1509. https://doi.org/10.3749/canmin.46.5.1501
Aquino AJA, Tunega D, Schaumann GE, Haberhauer G, Gerzabek MH, Lischka H (2009) Stabilizing capacity of water bridges in nanopore segments of humic substances: a theoretical investigation. J Phys Chem C 113:16468–16475. https://doi.org/10.1021/jp9054796
Arias-Estévez M, Fernández-Gándara D, García-Falcón M, García-Río L, Mejuto J et al (2007) Sorption of PAHs to colloid dispersions of humic substances in water. Bull Environ Contam Toxicol 79:251–254. https://doi.org/10.1007/S00128-007-9022-0
Bartolomé N, Hilber I, Schulin R, Mayer P, Witt G, Reininghaus M, Bucheli TD (2018) Comparison of freely dissolved concentrations of PAHs in contaminated pot soils under saturated and unsaturated water conditions. Sci Total Environ 644:835–843. https://doi.org/10.1016/j.scitotenv.2018.06.359
Bell KY, Leboeuf EJ (2013) Influence of temperature and macromolecular mobility on sorption of TCE on humic acid coated mineral surfaces. Chemosphere 90:176–181. https://doi.org/10.1016/J.CHEMOSPHERE.2012.05.112
Berns AE, Philipp H, Narres H-D, Burauel P, Vereecken H, Tappe W (2008) Effect of gamma-sterilization and autoclaving on soil organic matter structure as studied by solid state NMR, UV and fluorescence spectroscopy. Eur J Soil Sci 59:540–550. https://doi.org/10.1111/j.1365-2389.2008.01016.x
Buchmann C, Bentz J, Schaumann GE (2015) Intrinsic and model polymer hydrogel-induced soil structural stability of a silty sand soil as affected by soil moisture dynamics. Soil Tillage Res 154:22–33. https://doi.org/10.1016/j.still.2015.06.014
Chahal MK, Harsh JB, Flury M (2016) Translocation of fluoranthene in porous media by advancing and receding air–water interfaces. Colloids Surf A Physicochem Eng Asp 492:62–70. https://doi.org/10.1016/j.colsurfa.2015.12.012
Cheng M, Zeng G, Huang D, Lai C, Xu P, Zhang C, Liu Y (2016) Hydroxyl radicals based advanced oxidation processes (AOPs) for remediation of soils contaminated with organic compounds: a review. Chem Eng J 284:582–598. https://doi.org/10.1016/j.cej.2015.09.001
Chianese S, Fenti A, Iovino P, Musmarra D, Salvestrini S (2020) Sorption of organic pollutants by humic acids: a review. Molecules 25:918. https://doi.org/10.3390/MOLECULES25040918
Chin Y-P, Aiken GR, Danielsen KM (1997) Binding of pyrene to aquatic and commercial humic substances: the role of molecular weight and aromaticity. Environ Sci Technol 31:1630–1635. https://doi.org/10.1021/es960404k
Chiou CT, Shoup TD (1985) Soil sorption of organic vapors and effects of humidity on sorptive mechanism and capacity. Environ Sci Technol 19:1196–1200. https://doi.org/10.1021/ES00142A010
Dai Z-W, Ling J, Huang X-J, Wan L-S, Xu Z-K (2011) Molecular simulation on the interactions of water with polypropylene surfaces. J Phys Chem C 115:10702–10708. https://doi.org/10.1021/jp201040g
Daniel NRR, Uddin SMM, Harper RJ, Henry DJ (2019) Soil water repellency: a molecular-level perspective of a global environmental phenomenon. Geoderma 338:56–66. https://doi.org/10.1016/j.geoderma.2018.11.039
El-Mufleh A, Béchet B, Grasset L, Rodier C, Gaudin A et al (2012) Distribution of PAH residues in humic and mineral fractions of sediments from stormwater infiltration basins. J Soils Sediments 13:531–542. https://doi.org/10.1007/s11368-012-0586-x
Feng H, Zhang H, Cao H, Sun Y, Zhang A, Fu J (2018) Application of a novel coarse-grained soil organic matter model in the environment. Environ Sci Technol 52:14228–14234. https://doi.org/10.1021/acs.est.8b03116
Gan S, Lau EV, Ng HK (2009) Remediation of soils contaminated with polycyclic aromatic hydrocarbons (PAHs). J Hazard Mater 172:532–549. https://doi.org/10.1016/j.jhazmat.2009.07.118
Gao Y, Zygourakis K (2019) Kinetic study of the pyrolytic treatment of petroleum contaminated soils. Ind Eng Chem Res 58:10829–10843. https://doi.org/10.1021/acs.iecr.9b01494
Garcia-Falcón MS, Pérez-Lamela C, Simal-Gandara J (2004) Strategies for the extraction of free and bound polycyclic aromatic hydrocarbons in run-off waters rich in organic matter. Anal Chim Acta 508:177–183. https://doi.org/10.1016/j.aca.2003.11.065
García-Falcón MS, Soto-González B, Simal-Gándara J (2006) Evolution of the concentrations of polycyclic aromatic hydrocarbons in burnt woodland soils. Environ Sci Technol 40:759–763. https://doi.org/10.1021/ES051803V
Golding CJ, Smernik RJ, Birch GF (2005) Investigation of the role of structural domains identified in sedimentary organic matter in the sorption of hydrophobic organic compounds. Environ Sci Technol 39:3925–3932. https://doi.org/10.1021/es048171h
Grathwohl P (1990) Influence of organic matter from soils and sediments from various origins on the sorption of some chlorinated aliphatic hydrocarbons: implications on Koc correlations. Environ Sci Technol 24:1687–1693. https://doi.org/10.1021/ES00081A010
Guggenberger G, Pichler M, Zech W (1996) Influence of sample pretreatment on the extractability of polycyclic aromatic hydrocarbons (PAH) from forest floor horizons. Z Pflanzenernähr Bodenkd 159:405–407. https://doi.org/10.1002/jpln.1996.3581590415
Ji H, Wu G, Zi M, Chen D (2016) Microsecond molecular dynamics simulation of methane hydrate formation in humic-acid-amended sodium montmorillonite. Energy Fuel 30:7206–7213. https://doi.org/10.1021/acs.energyfuels.6b01544
Johnson WP, Amy GL (1995) Facilitated transport and enhanced desorption of polycyclic aromatic hydrocarbons by natural organic matter in aquifer sediments. Environ Sci Technol 29:807–817. https://doi.org/10.1021/es00003a032
Jr LTS, Varnum JM, Jansen SA (1999) Conformational modeling of a new building block of humic acid: approaches to the lowest energy conformer. Environ Sci Technol 33:546–552. https://doi.org/10.1021/ES9805324
Karapanagioti HK, Kleineidam S, Sabatini DA, Grathwohl P, Ligouis B (2000) Impacts of heterogeneous organic matter on phenanthrene sorption: equilibrium and kinetic studies with aquifer material. Environ Sci Technol 34:406–414. https://doi.org/10.1021/es9902219
Keiluweit M, Kleber M (2009) Molecular-level interactions in soils and sediments: the role of aromatic pi-systems. Environ Sci Technol 43:3421–3429. https://doi.org/10.1021/ES8033044
Keller KS, Olsson MHM, Yang M, Stipp SLS (2015) Adsorption of ethanol and water on calcite: dependence on surface geometry and effect on surface behavior. Langmuir 31:3847–3853. https://doi.org/10.1021/LA504319Z
Kim S-J, Kwon J-H (2010) Determination of partition coefficients for selected PAHs between water and dissolved organic matter. CLEAN - Soil Air Water 38:797–802. https://doi.org/10.1002/clen.201000113
Kim P-G, Roh J-Y, Hong Y, Kwon J-H (2017) Effects of soil water saturation on sampling equilibrium and kinetics of selected polycyclic aromatic hydrocarbons. Chemosphere 184:86–92. https://doi.org/10.1016/j.chemosphere.2017.05.170
Kleestorfer K, Vinek H, Jentys A (2001) Structure simulation of MCM-41 type materials. J Mol Catal A Chem 166:53–57. https://doi.org/10.1016/S1381-1169(00)00463-5
Komy ZR, Shaker AM, Heggy SEM, El-Sayed MEA (2014) Kinetic study for copper adsorption onto soil minerals in the absence and presence of humic acid. Chemosphere 99:117–124. https://doi.org/10.1016/J.CHEMOSPHERE.2013.10.048
Kubicki JD, Apitz SE (1999) Models of natural organic matter and interactions with organic contaminants. Org Geochem 29:911–927. https://doi.org/10.1016/S0146-6380(99)00075-3
Kuppusamy S, Thavamani P, Venkateswarlu K, Lee YB, Naidu R, Megharaj M (2017) Remediation approaches for polycyclic aromatic hydrocarbons (PAHs) contaminated soils: technological constraints, emerging trends and future directions. Chemosphere 168:944–968. https://doi.org/10.1016/j.chemosphere.2016.10.115
Liu Z, Lee C (2006) Drying effects on sorption capacity of coastal sediment: the importance of architecture and polarity of organic matter. Geochim Cosmochim Acta 70:3313–3324. https://doi.org/10.1016/J.GCA.2006.04.017
Meleshyn A, Tunega D (2011) Adsorption of phenanthrene on Na-montmorillonite: a model study. Geoderma 169:41–46. https://doi.org/10.1016/j.geoderma.2010.09.018
Mikutta R, Kleber M, Kaiser K, Jahn R (2005) Organic matter removal from soils using hydrogen peroxide, sodium hypochlorite, and disodium peroxodisulfate. Soil Sci Soc Am J 69:120–135. https://doi.org/10.2136/sssaj2005.0120
Mulliken RS (1955) Electronic population analysis on LCAO–MO molecular wave functions. II. Overlap populations, bond orders, and covalent bond energies. J Chem Phys 23:1841–1846. https://doi.org/10.1063/1.1740589
Niederer C, Goss K-U (2007) Quantum chemical modeling of humic acid/air equilibrium partitioning of organic vapors. Environ Sci Technol 41:3646–3652. https://doi.org/10.1021/ES062501B
Nosé S (1984) A unified formulation of the constant temperature molecular dynamics methods. J Chem Phys 81:511–519. https://doi.org/10.1063/1.447334
Orsi M (2014) Molecular dynamics simulation of humic substances. Chem Biol Technol Agric 1:10. https://doi.org/10.1186/S40538-014-0010-4
Perdew JP, Yue W (1986) Accurate and simple density functional for the electronic exchange energy—generalized gradient approximation. Phys Rev B 33:8800–8802. https://doi.org/10.1103/PhysRevB.33.8800
Petrov D, Tunega D, Gerzabek MH, Oostenbrink C (2017) Molecular dynamics simulations of the standard leonardite humic acid: microscopic analysis of the structure and dynamics. Environ Sci Technol 51:5414–5424. https://doi.org/10.1021/acs.est.7b00266
Phillips KL, Di Toro DM, Sandler SI (2011) Prediction of soil sorption coefficients using model molecular structures for organic matter and the quantum mechanical COSMO-SAC model. Environ Sci Technol 45:1021–1027. https://doi.org/10.1021/es102760x
Piccolo A, Conte P, Trivellone E, van Lagen B, Buurman P (2002) Reduced heterogeneity of a lignite humic acid by preparative HPSEC following interaction with an organic acid. Characterization of size-separates by Pyr-GC-MS and 1H-NMR spectroscopy. Environ Sci Technol 36:76–84. https://doi.org/10.1021/es010981v
Plimpton S (1995) Fast parallel algorithms for short-range molecular dynamics. J Comput Phys 117:1–19. https://doi.org/10.1006/jcph.1995.1039
Pontevedra-Pombal X, Rey-Salgueiro L, García-Falcón MS, Martínez-Carballo E, Simal-Gándara J, Martínez-Cortizas A (2012) Pre-industrial accumulation of anthropogenic polycyclic aromatic hydrocarbons found in a blanket bog of the Iberian Peninsula. Environ Res 116:36–43. https://doi.org/10.1016/j.envres.2012.04.015
Preston CM (1996) Applications of NMR to soil organic matter analysis: history and prospects. Soil Sci 161:144–166. https://doi.org/10.1097/00010694-199603000-00002
Radian A, Mishael Y (2012) Effect of humic acid on pyrene removal from water by polycation-clay mineral composites and activated carbon. Environ Sci Technol 46:6228–6235. https://doi.org/10.1021/ES300964D
Ravindra K, Sokhi R, Grieken RV (2008) Atmospheric polycyclic aromatic hydrocarbons: source attribution, emission factors and regulation. Atmos Environ 42:2895–2921. https://doi.org/10.1016/j.atmosenv.2007.12.010
Rey-Salgueiro L, García-Falcón MS, Martínez-Carballo E, González-Barreiro C, Simal-Gándara J (2008) The use of manures for detection and quantification of polycyclic aromatic hydrocarbons and 3-a[a]pyrene in animal husbandry. Sci Total Environ 406:279–286. https://doi.org/10.1016/j.scitotenv.2008.07.059
Rey-Salgueiro L, Martínez-Carballo E, Cid A, Simal-Gándara J (2017) Determination of kinetic bioconcentration in mussels after short term exposure to polycyclic aromatic hydrocarbons. Heliyon 3:e00231. https://doi.org/10.1016/J.HELIYON.2017.E00231
Rey-Salgueiro L, Martínez-Carballo E, Merino A, Vega JA, Fonturbel MT, Simal-Gandara J (2018) Polycyclic aromatic hydrocarbons in soil organic horizons depending on the soil burn severity and type of ecosystem. Land Degrad Dev 29:2112–2123. https://doi.org/10.1002/LDR.2806
Rutherford DW, Chiou CT (1992) Effect of water saturation in soil organic matter on the partition of organic compounds. Environ Sci Technol 26:965–970. https://doi.org/10.1021/es00029a015
Saparpakorn P, Kim JH, Hannongbua S (2007) Investigation on the binding of polycyclic aromatichydrocarbons with soil organic matter: a theoretical approach. Molecules 12:703–715. https://doi.org/10.3390/12040703
Schaumann GE (2006) Soil organic matter beyond molecular structure part II: amorphous nature and physical aging. J Plant Nutr Soil Sci 169:157–167. https://doi.org/10.1002/JPLN.200521791
Schaumann GE, Bertmer M (2008) Do water molecules bridge soil organic matter molecule segments? Eur J Soil Sci 59:423–429. https://doi.org/10.1111/j.1365-2389.2007.00959.x
Schaumann GE, Thiele-Bruhn S (2011) Molecular modeling of soil organic matter: squaring the circle? Geoderma 166:1–14. https://doi.org/10.1016/J.GEODERMA.2011.04.024
Schulten HR, Leinweber P (1999) Thermal stability and composition of mineral-bound organic matter in density fractions of soil. Eur J Soil Sci 50:237–248. https://doi.org/10.1046/j.1365-2389.1999.00241.x
Schulten H-R, Schnitzer M (1997) The chemistry of soil organic nitrogen: a review. Biol Fertil Soils 26:1–15. https://doi.org/10.1007/S003740050335
Shailaja MS, D’Silva C (2003) Evaluation of impact of PAH on a tropical fish, Oreochromis mossambicus using multiple biomarkers. Chemosphere 53:835–841. https://doi.org/10.1016/S0045-6535(03)00667-2
Shaker AM, Komy ZR, Heggy SEM, El-sayed MEA (2012) Kinetic study for adsorption humic acid on soil minerals. J Phys Chem A 116:10889–10896. https://doi.org/10.1021/JP3078826
Simonson RW (1991) Soil science - goals for the next 75 years. Soil Sci 151:7–18. https://doi.org/10.1097/00010694-199101000-00003
Sui H, Li L, Zhu X, Chen D, Wu G (2016) Modeling the adsorption of PAH mixture in silica nanopores by molecular dynamic simulation combined with machine learning. Chemosphere 144:1950–1959. https://doi.org/10.1016/j.chemosphere.2015.10.053
Sun H, Ren P, Fried JR (1998) The COMPASS force field: parameterization and validation for phosphazenes. Comput Theor Polym Sci 8:229–246. https://doi.org/10.1016/S1089-3156(98)00042-7
Sutton R, Sposito G, Diallo MS, Schulten HR (2005) Molecular simulation of a model of dissolved organic matter. Environ Toxicol Chem 24:1902–1911. https://doi.org/10.1897/04-567R.1
Thiele-Bruhn S (2010) Biophysico-chemical processes involving natural nonliving organic matter in environmental systems - edited by Senesi, N., Xing, B. & Huang, P.M. Eur J Soil Sci 61: 437–438. https://doi.org/10.1111/J.1365-2389.2010.01231.X
Wild SR, Jones KC (1995) Polynuclear aromatic hydrocarbons in the United Kingdom environment: a preliminary source inventory and budget. Environ Pollut 88:91–108. https://doi.org/10.1016/0269-7491(95)91052-M
Wu G, He L, Chen D (2013) Sorption and distribution of asphaltene, resin, aromatic and saturate fractions of heavy crude oil on quartz surface: molecular dynamic simulation. Chemosphere 92:1465–1471. https://doi.org/10.1016/j.chemosphere.2013.03.057
Wu G, Zhu X, Ji H, Chen D (2015) Molecular modeling of interactions between heavy crude oil and the soil organic matter coated quartz surface. Chemosphere 119:242–249. https://doi.org/10.1016/j.chemosphere.2014.06.030
Yuan T, Marshall WD (2007) Optimizing a washing procedure to mobilize polycyclic aromatic hydrocarbons (PAHs) from a field-contaminated soil. Ind Eng Chem Res 46:4626–4632. https://doi.org/10.1021/ie070119h
Zhang W-Z, Chen X-Q, Zhou J-M, Liu D-H, Wang H-Y et al (2013) Influence of humic acid on interaction of ammonium and potassium ions on clay minerals. Pedosphere 23:493–502. https://doi.org/10.1016/S1002-0160(13)60042-9
Zhang R, Yan W, Jing C (2015) Experimental and molecular dynamic simulation study of perfluorooctane sulfonate adsorption on soil and sediment components. J Environ Sci 29:131–138. https://doi.org/10.1016/j.jes.2014.11.001
Zhao T, Xu G, Yuan S, Chen Y, Yan H (2010) Molecular dynamics study of alkyl benzene sulfonate at air/water interface: effect of inorganic salts. J Phys Chem B 114:5025–5033. https://doi.org/10.1021/jp907438x
Zhuo S, Huang Y, Hu J, Liu H, Jiang J (2008) Computer simulation for adsorption of CO2, N2 and flue gas in a mimetic MCM-41. J Phys Chem C 112:11295–11300. https://doi.org/10.1021/jp803428n
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The authors thank the Shanghai Sailing Program (No. 19YF1410800) for supporting this work.
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Zhao, N., Ju, F., Pan, H. et al. Molecular dynamics simulation of the interaction of water and humic acid in the adsorption of polycyclic aromatic hydrocarbons. Environ Sci Pollut Res 27, 25754–25765 (2020). https://doi.org/10.1007/s11356-020-09018-2
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DOI: https://doi.org/10.1007/s11356-020-09018-2