Hostname: page-component-cd9895bd7-mkpzs Total loading time: 0 Render date: 2024-12-22T22:36:25.940Z Has data issue: false hasContentIssue false
  • English
  • Français

Polarity Effect on Dichlorobenzene Sorption by Hexadecyltrimethylammonium-Exchanged Clays

Published online by Cambridge University Press:  28 February 2024

Guangyao Sheng  and
Stephen A. Boyd
Guangyao Sheng
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
Rights & Permissions [Opens in a new window]

Abstract

Core share and HTML view are not available for this content. However, as you have access to this content, a full PDF is available via the ‘Save PDF’ action button.

Sorptive properties of organoclays may be greatly influenced by the physicochemical properties of organic sorbates. Hexadecyltrimethylammonium(HDTMA) clays were prepared using a high-charge smectite (HDTMA-SAz-1), a low-charge smectite (HDTMA-SWy-2), and an illite (HDTMA-ILL). The resultant organoclays were used to sorb aqueous phase 1,2-dichlorobenzene (o-DCB), 1,3-dichlorobenzene (m-DCB), and 1,4-dichlorobenzene (p-DCB). Sorptive characteristics of these compounds were determined by their molecular polarities (o-DCB > m-DCB > p-DCB) and the HDTMA-clay interlayer distance. HDTMA-ILL was used for comparison to HDTMA-SAz-1 and HDTMA-SWy-2. All dichlorobenzene isomers were directly intercalated in the interlayers of HDTMA-SAz-1, causing interlayer expansion. o-DCB and m-DCB were not intercalated in the interlayers of HDTMA-SWy-2 at low concentrations, but intercalation occurred at higher concentrations, which caused interlayer expansion. The concentration needed to produce interlayer expansion depended on the solute molecular polarity, hence a higher concentration of m-DCB than o-DCB was required. p-DCB was sorbed primarily by the HDTMA phase on the external surfaces of HDTMA-SWy-2. In the presence of chlorobenzene (CB), p-DCB sorption by HDTMA-SWy-2 is greatly enhanced, owing to the interlayer expansion by CB and a cosolvent effect. Sorption of o-DCB resulted from both direct solvation-type interactions with HDTMA and partitioning into HDTMA. Such sorption results in double-sigmoid isotherms. m-DCB weakly solvates the HDTMA and partitions into the HDTMA, displaying either a double-sigmoid or a type-III isotherm depending on clay type. p-DCB lacks ability to solvate HDTMA and partitions into HDTMA as its sole mechanism, producing type-III isotherms. HDTMA-clays are potentially effective for treating dichlorobenzene-contaminated wastewater.

Keywords

CMS Clay SAz-1CMS Clay SWy-2DichlorobenzeneHDTMAOrganoclayPolaritySorption
Type
Research Article
Information
Clays and Clay Minerals , Volume 48 , Issue 1 , February 2000 , pp. 43 - 50
Copyright
Copyright © 2000, The Clay Minerals Society

References

Beall, G.W., 1985 Process for treating organics contaminated water .Google Scholar
Boyd, S.A. Lee, J.-E. and Mortland, M.M., 1988 Attenuating organic contaminant mobility by soil modification. Nature 333 345–347 10.1038/333345a0.CrossRefGoogle Scholar
Boyd, S.A. Mortland, M.M. and Chiou, C.T., 1988 Sorption characteristics of organic compounds on hexadecyltri-methylammonium-smectite. Soil Science Society of America Journal 52 652–657 10.2136/sssaj1988.03615995005200030010x.CrossRefGoogle Scholar
Boyd, S.A. Jaynes, W.F. Ross, B.S. and Baker, R.S., 1991 Immobilization or organic contaminants by organo-clays: Application to soil restoration and hazardous waste containment Organic Substances and Sediments in Water, Volume 1 Florida CRC Press, Boca Raton 181–200.Google Scholar
Brixie, J.M. and Boyd, S.A., 1994 Treatment of contaminated soils with organoclays to reduce leachable pentachlo-rophenol. Journal of Environmental Quality 23 1283–1289 10.2134/jeq1994.00472425002300060023x.CrossRefGoogle Scholar
Burris, D.R. and Antworth, C.P., 1992 In-situ modification of aquifer material by a cationic surfactant to enhance retardation of organic contaminants. Journal of Contaminant Hydrology 10 325–337 10.1016/0169-7722(92)90014-6.CrossRefGoogle Scholar
Chiou, C.T. Lee, J.-F. and Boyd, S.A., 1992 Comment on: The surface area of soil organic matter. Environmental Science and Technology 26 404–406 10.1021/es00026a028.CrossRefGoogle Scholar
Crocker, F.H. Guerin, W.E. and Boyd, S.A., 1995 Bioavailability of naphthalene sorbed to cationic surfactant-modified smectite clay. Environmental Science and Technology 29 2953–2958 10.1021/es00012a010.CrossRefGoogle ScholarPubMed
Gould, E.S., 1959 Mechanism and Structure in Organic Chemistry. New York Holt, Rinehart and Winston.Google Scholar
Gullick, R.W. and Weber, W.J. Jr. Gray, D.H. and Sawhney, B.L., 1996 Organic contaminant transport through clay liners and slurry walls Organic Pollutants in the Environment, Volume 8 Colorado The Clay Mineral Society, Boulder 95–136.Google Scholar
Harper, M. and Purnell, C.J., 1990 Alkylammonium mont-morillonites as adsorbents for organic vapors from air. Environmental Science and Technology 24 55–61 10.1021/es00071a004.CrossRefGoogle Scholar
Hayworth, J.S. and Burris, D.R., 1997 Nonionic surfactant-enhanced solubilization and recovery of organic contaminants from within cationic surfactant-enhanced sorbent zones. 1. Experiments. Environmental Science and Technology 31 1277–1283 10.1021/es960322w.CrossRefGoogle Scholar
Howard, P.H. and Meylan, W.M., 1997 Handbook of Physical Properties of Organic Chemicals. New York Lewis Publishers.Google Scholar
Jaynes, W.E. and Boyd, S.A., 1991 Hydrophobicity of si-loxane surfaces in smectites as revealed by aromatic hydrocarbon adsorption from water. Clays and Clay Minerals 39 428–436 10.1346/CCMN.1991.0390412.CrossRefGoogle Scholar
Jaynes, W.E. and Boyd, S.A., 1991 Clay mineral type and organic compound sorption by hexadecyltrimefhylammon-ium-exchanged clays. Soil Science Society of America Journal 55 43–48 10.2136/sssaj1991.03615995005500010007x.CrossRefGoogle Scholar
Kukkadapu, R.K. and Boyd, S.A., 1995 Tetramethylphos-phonium- and tetramethylammonium-smectites as adsorbents of aromatic and chlorinated hydrocarbons: Effect of water on adsorption efficiency. Clays and Clay Minerals 43 318–323 10.1346/CCMN.1995.0430306.CrossRefGoogle Scholar
Lee, J.-F. Crum, J.R. and Boyd, S.A., 1989 Enhanced retention of organic contaminants by soils exchanged with organic cations. Environmental Science Technology 23 1365–1372 10.1021/es00069a006.CrossRefGoogle Scholar
Lee, J.-F. Mortland, M.M. Boyd, S.A. and Chiou, C.T., 1989 Shape-selective adsorption of aromatic molecules from water by tetramethylammonium-smectite. Journal of Chemical Society, Faraday Transaction I 85 2953–2962 10.1039/f19898502953.CrossRefGoogle Scholar
Li, J. Smith, J.A. and Winquist, A.S., 1996 Permeability of earthen liners containing organobentonite to water and two organic liquids. Environmental Science and Technology 30 3089–3093 10.1021/es960172p.CrossRefGoogle Scholar
Nye, J.V. Guerin, W.E. and Boyd, S.A., 1994 Heterotrophic activity of microorganisms in soils treated with quaternary ammonium compounds. Environmental Science and Technology 28 944–951 10.1021/es00054a029.CrossRefGoogle ScholarPubMed
Pyda, M. and Kurzynski, M., 1982 Theory of sorption of gases on polymers. I. Conformational effects and the dou-ble-sigmoid shape of sorption isotherm. Chemical Physics 67 7–16 10.1016/0301-0104(82)88053-1.CrossRefGoogle Scholar
Pyda, M. and Kurzynski, M., 1983 Theory of sorption of gases on polymers. II. Effects of interchain secondary bonds. Chemical Physics 79 219–224 10.1016/0301-0104(83)85153-2.CrossRefGoogle Scholar
Rakhshandehroo, G.R. Wallace, R.B. Boyd, S.A. and Voice, T.C., 1998 Hydraulic characteristics of organomodified soils for use in sorptive zone applications. Soil Science Society of America Journal 62 5–12 10.2136/sssaj1998.03615995006200010002x.CrossRefGoogle Scholar
Sheng, G. Xu, S. and Boyd, S.A., 1996 Mechanism(s) controlling sorption of neutral organic contaminants by surfactant-derived and natural organic matter. Environmental Science and Technology 30 1553–1557 10.1021/es9505208.CrossRefGoogle Scholar
Sheng, G. Xu, S. and Boyd, S.A., 1996 Cosorption of organic contaminants from water by hexadecyltrimeth-ylammonium-exchanged clays. Water Research 30 1483–1489 10.1016/0043-1354(95)00303-7.CrossRefGoogle Scholar
Sheng, G. Wang, X. Wu, S. and Boyd, S.A., 1998 Enhanced sorption of organic contaminants by smectitic soils modified with a cationic surfactant Journal of Environmental Quality 27 806–814 10.2134/jeq1998.00472425002700040013x.CrossRefGoogle Scholar
Slabaugh, W.H. and Hiltner, P.A., 1968 The swelling of alkylammonium montmorillonites. Journal of Physical Chemistry 72 4295–4298 10.1021/j100858a060.CrossRefGoogle Scholar
Smith, J.A. and Jaffe, P.R., 1994 Benzene transport through landfill liners containing organophilic bentonite. Journal of Environmental Engineering 120 1559–1577 10.1061/(ASCE)0733-9372(1994)120:6(1559).CrossRefGoogle Scholar
Solomon, D.H. and Hawthorne, D.G., 1983 Chemistry of Pigments and Fillers. New York John Wiley and Sons.Google Scholar
Verschueren, K., 1983 Handbook of Environmental Data on Organic Chemicals. New York Van Nostrand Reinhold Company.Google Scholar
Wagner, J. Chen, H. Brownawell, B.J. and Westall, J.C., 1994 Use of cationic surfactants to modify soil surfaces to promote sorption and retard migration of hydrophobic organic compounds. Environmental Science and Technology 28 231–237 10.1021/es00051a008.CrossRefGoogle ScholarPubMed
Xu, S. and Boyd, S.A., 1995 Cationic surfactant adsorption by swelling and nonswelling layer silicates. Langmuir 11 2508–2514 10.1021/la00007a033.CrossRefGoogle Scholar
Xu, S. and Boyd, S.A., 1995 Alternative model for cationic surfactant adsorption by layer silicates. Environmental Science and Technology 29 3022–3028 10.1021/es00012a020.CrossRefGoogle ScholarPubMed
Xu, S. Sheng, G. and Boyd, S.A., 1997 Use of organo-clays in pollution abatement. Advances in Agronomy 59 25–62 10.1016/S0065-2113(08)60052-8.CrossRefGoogle Scholar