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Adsorption of Dinitrophenol Herbicides From Water by Montmorillonites

Published online by Cambridge University Press:  01 January 2024

Guangyao Sheng ,
Cliff T. Johnston ,
Brian J. Teppen  and
Stephen A. Boyd
Guangyao Sheng
Affiliation:
Department of Crop, Soil and Environmental Sciences, University of Arkansas, Fayetteville, Arkansas 72701, USA
Cliff T. Johnston
Affiliation:
Department of Agronomy, Purdue University, West Lafayette, Indiana 47907, USA
Brian J. Teppen
Affiliation:
Department of Crop and Soil Sciences, Michigan State University, East Lansing, Michigan 48824, USA
Stephen A. Boyd*
Affiliation:
Department of Crop and Soil Sciences, Michigan State University, East Lansing, Michigan 48824, USA
*
*E-mail address of corresponding author: [email protected]
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Abstract

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The adsorption of two dinitrophenol herbicides, 4,6-dinitro-o-cresol (DNOC) and 4,6-dinitro-o-sec-butyl phenol (dinoseb), by two reference smectite clays (SWy-2 and SAz-1) was evaluated using a combination of sorption isotherms, Fourier transformation infrared (FTIR) spectroscopy, X-ray diffraction (XRD) and molecular dynamic simulations. Clays were subject to saturation with various cations, and charge reduction. The DNOC adsorption decreased with increasing pH indicating that DNOC was primarily adsorbed as the neutral species. The FTIR spectra of DNOC-clay films showed that DNOC molecules are oriented parallel to the clay surface. Interlayer cations have a strong effect on adsorption depending largely on their hydration energies. Weakly hydrated cations, e.g. K+ and Cs+, resulted in greater sorption compared to more strongly hydrated cations such as Na+ or Ca2+. Lower hydration favors direct interactions of exchangeable cations with -NO2 groups of DNOC and manifests optimal interlayer spacings for adsorption. In the presence of sorbed DNOC, an interlayer spacing for K-SWy-2 of between 12 and 12.5 Å was maintained regardless of the presence of water. This d-spacing allowed DNOC molecules to interact simultaneously with the opposing clay layers thus minimizing contact of DNOC with water. The charge density of clays also affected sorption by controlling the size of adsorption domains. Accordingly, DNOC adsorption by low-charge clay (K-SWy-2) was much higher than by high-charge clay (K-SAz-1) and Li-charge reduction greatly enhanced dinoseb adsorption by K-SAz-1. Steric constraints were also evident from the observation that adsorption of DNOC, which contains a methyl substituent, was much greater than dinoseb, which contains a bulkier isobutyl group. Adsorption of DNOC by K-SAz-1 was not affected in the presence of dinoseb, whereas dinoseb adsorption was greatly reduced in the presence of DNOC.

Keywords

AdsorptionClayOrientationPesticideSteric Effect
Type
Research Article
Information
Clays and Clay Minerals , Volume 50 , Issue 1 , February 2002 , pp. 25 - 34
Copyright
Copyright © 2002, The Clay Minerals Society

References

Bailey, G.W. White, J.L., Gunther, F.A. and Gunther, J.D., (1970) Factors influencing the adsorption, desorption, and movement of pesticides in soil Residue Reviews — Residues of Pesticides and other Foreign Chemicals in Foods and Feeds. Vol. 32 New York Springer-Verlag 29 92.Google Scholar
Boyd, S.A. Jaynes, W.F. and Mermut, A.R., (1994) Role of layer charge in organic contaminant sorption by organo-clays Layer Charge Characteristics of 2:1 Silicate Clay Minerals Boulder, Colorado Clay Minerals Society 48–77 CMS Workshop Lectures, Vol. 6.Google Scholar
Boyd, S.A. Sheng, G. Teppen, B.J. and Johnston, C.T., (2001) Mechanisms for the adsorption of substituted nitrobenzenes by smectite clays Environmental Science & Technology 35 4227–4234 10.1021/es010663w.Google Scholar
Brindley, G.W. and Ertem, G., (1971) Preparation and solvation properties of some variable charge montmorillonites Clays and Clay Minerals 19 399–404 10.1346/CCMN.1971.0190608.Google Scholar
Chiou, C.T. and Meyers, R.A., (1998) Soil sorption of organic pollutants and pesticides Encyclopedia of Environmental Analysis and Remediation New York John Wiley & Sons 4517 4554.Google Scholar
Chiou, C.T. Peters, L.J. and Freed, V.H., (1979) A physical concept of soil-water equilibria for nonionic organic compounds Science 206 831–832 10.1126/science.206.4420.831.Google Scholar
Chiou, C.T. Porter, P.E. and Schmedding, D.W., (1983) Partition equilibria of nonionic organic compounds between soil organic matter and water Environmental Science & Technology 17 227–231 10.1021/es00110a009.Google Scholar
Chiou, C.T. Kile, D.E. Rutherford, D.W. Sheng, G. and Boyd, S.A., (2000) Sorption of selected organic compounds from water to a peat soil and its humic acid and humin fractions: potential sources of the sorption nonlinearity Environmental Science & Technology 34 1254–1258 10.1021/es990261c.Google Scholar
Green, R.E. and Guenzi, W.D., (1974) Pesticide-clay-water interactions Pesticides in Soil and Water Madison, Wisconsin Soil Science Society of America 3 37.Google Scholar
Gundl, T. and Small, G., (1993) Mineral contributions to atrazine and alachlor sorption in soil mixtures of variable org anic carbon and clay content Journal of Contaminant Hydrology 14 117–128 10.1016/0169-7722(93)90034-P.Google Scholar
Haderlein, S.B. and Schwarzenbach, R.P., (1993) Adsorption of substituted nitrobenzenes and nitrophenols to mineral surfaces Environmental Science & Technology 27 316–326 10.1021/es00039a012.Google Scholar
Haderlein, S.B. Weissmahr, K.W. and Schwarzenbach, R.P., (1996) Specific adsorption of nitroaromatic explosives and pesticides to clay minerals Environmental Science & Technology 30 612–622 10.1021/es9503701.Google Scholar
Hassett, J.J. Banwart, W.L. Wood, S.G. and Means, J.C., (1981) Sorption of x-naphathol: Implications concerning the limits of hydrophobic sorption Soil Science Society of America Journal 45 38–42 10.2136/sssaj1981.03615995004500010008x.Google Scholar
Jaynes, W.F. and Boyd, S.A., (1990) Trimethylphenylammonium-smectite as an effective adsorbent of water soluble aromatic hydrocarbons Journal of the Air & Waste Management Association 40 1649–1653 10.1080/10473289.1990.10466811.Google Scholar
Jaynes, W.F. and Boyd, S.A., (1991) Hydrophobicity of siloxane surfaces in smectites as revealed by aromatic hydrocarbon adsorption from water Clays and Clay Minerals 39 428–436 10.1346/CCMN.1991.0390412.Google Scholar
Johnston, C.T., Oliveira, M.F.D., Teppen, B.J., Sheng, G. and Boyd, S.A. (2001) Spectroscopic study of nitroaromatic-smectite sorption mechanisms. Environmental Science & Technology (in press).Google Scholar
Karickhoff, S.W., (1984) Organic pollutant adsorption in aqueous systems Journal of Hydraulic Engineering 110 707–735 10.1061/(ASCE)0733-9429(1984)110:6(707).Google Scholar
Karickhoff, S.W. Brown, D.S. and Scott, T.A., (1979) Sorption of hydrophobic pollutants on natural sediments Water Research 13 241–248 10.1016/0043-1354(79)90201-X.Google Scholar
Kleineidam, S. Rugner, H. Ligouis, B. and Grathwohl, P., (1999) Organic matter facies and equilibrium sorption of phenanthrene Environmental Science & Technology 33 1637–1644 10.1021/es9806635.Google Scholar
Laird, D.A., Meyer, M.T. and Thurman, E.M., (1996) Interactions between atrazine and smectite surfaces Herbicite Metabolites in Surface Water and Groundwater Washington, D.C. American Chemical Society 86–100 10.1021/bk-1996-0630.ch008 ACS Symposium Series 630 .Google Scholar
Laird, D.A. Barriuso, E. Dowdy, R.H. and Koskinen, W.C., (1992) Adsorption of atrazine on smectites Soil Science Society of America Journal 56 62–67 10.2136/sssaj1992.03615995005600010010x.Google Scholar
Leboeuf, E.J. and Weber, W.J. Jr, (1997) A distributed reactivity model for sorption by soils and sediments. 9. Sorbent organic domains: discovery of a humic acid glass transition and an argument for a polymer-based model Environmental Science & Technology 31 1697–1702 10.1021/es960626i.Google Scholar
Lee, J.-F. Mortland, M.M. Chiou, C.T. Kile, D.E. and Boyd, S.A., (1990) Adsorption of benzene, toluene, and xylene by two tetramethylammonium-smectites having different charge densities Clays and Clay Minerals 39 113–120 10.1346/CCMN.1990.0380201.Google Scholar
MacEwan, D.M.C. Wilson, M.J., Brindley, G.W. and Brown, G., (1980) Interlayer and intercalation complexes of clay minerals Crystal Structures of Clay Minerals and Their X-ray Identification London Mineralogical Society 197 248.Google Scholar
Maple, J.R. Hwang, M.-J. Stockfish, T.P. Dinur, U. Waldman, M. Ewig, C.S. and Hagler, A.T., (1994) Derivation of Class II force fields. I. Methodology and quantum force field for the alkyl functional group and alkane molecules Journal of Computational Chemistry 15 162–182 10.1002/jcc.540150207.Google Scholar
Margulies, L. Rozen, H. and Banin, A., (1988) Use of X-ray powder diffraction and linear dichloism methods to study the orientation of montmorillonite clay particles Clays and Clay Minerals 36 476–479 10.1346/CCMN.1988.0360514.Google Scholar
Mortland, M.M., Huang, P.M. and Schnitzer, M., (1986) Mechanisms of adsorption of non-humic organic species by clay Interactions of Soil Minerals with Natural Organics and Microbes Madison, Wisconsin Soil Science Society of America 59–76 Special Publication 17 .Google Scholar
MSI, Cerius2 Molecular Simulation Software (2000) San Diego, California MSI, Inc. Release 4.2.Google Scholar
Pelmenschikov, A. and Leszczynski, J., (1999) Adsorption of 1,3,5-trinitrobenzene on the siloxane sites of clay minerals: Ab initio calculations of molecular models Journal of Physical Chemistry B103 6886–6890 10.1021/jp990091q.Google Scholar
Pignatello, J.J. and Xing, B., (1996) Mechanisms of slow sorption of organic chemicals to natural particles Environmental Science & Technology 30 1–11 10.1021/es940683g.Google Scholar
Prost, R. and Chaussidon, J., (1969) The infrared spectrum of water adsorbed on hectorite Clay Minerals 8 143–149 10.1180/claymin.1969.008.2.03.Google Scholar
Sawhney, B.L. and Singh, S.S., (1997) Sorption of atrazine by Al- and Ca-saturated smectite Clays and Clay Minerals 45 333–338 10.1346/CCMN.1997.0450304.Google Scholar
Sheng, G. Johnston, C.T. Teppen, B.J. and Boyd, S.A., (2001) Potential contributions of smectite clays and organic matter to pesticide retention in soils Journal of Agricultural and Food Chemistry 49 2899–2907 10.1021/jf001485d.Google Scholar
Teppen, B.J. Rasmussen, K. Bertsch, P.M. Miller, D.M. and Schäfer, L., (1997) Molecular dynamics modeling of clay minerals. 1. Gibbsite, kaolinite, pyrophyllite, and beidellite Journal of Physical Chemistry B101 1579–1587 10.1021/jp961577z.Google Scholar
Weissmahr, K.W. Haderlein, S.B. and Schwarzenbach, R.P., (1997) In situ spectroscopic investigations of adsorption mechanisms of nitroaromatic compounds at clay minerals Environmental Science & Technology 31 240–247 10.1021/es960381+.Google Scholar
Weissmahr, K.W. Haderlein, S.B. and Schwarzenbach, R.P., (1998) Complex formation of soil minerals with nitroaromatic explosives and other π-acceptors Soil Science Society of America Journal 62 369–378 10.2136/sssaj1998.03615995006200020012x.Google Scholar
Xia, G. and Ball, W.P., (2000) Polanyi-based models for the competitive sorption of low-polarity organic contaminants on a natural sorbent Environmental Science & Technology 34 1246–1254 10.1021/es9812453.Google Scholar