Surfactant-enhanced remediation of organic contaminated soil and water.

Surfactant based remediation technologies for organic contaminated soil and water (groundwater or surface water) is of increasing importance recently. Surfactants are used to dramatically expedite the process, which in turn, may reduce the treatment time of a site compared to use of water alone. In fact, among the various available remediation technologies for organic contaminated sites, surfactant based process is one of the most innovative technologies. To enhance the application of surfactant based technologies for remediation of organic contaminated sites, it is very important to have a better understanding of the mechanisms involved in this process. This paper will provide an overview of the recent developments in the area of surfactant enhanced soil and groundwater remediation processes, focusing on (i) surfactant adsorption on soil, (ii) micellar solubilization of organic hydrocarbons, (iii) supersolubilization, (iv) density modified displacement, (v) degradation of organic hydrocarbon in presence surfactants, (vi) partitioning of surfactants onto soil and liquid organic phase, (vii) partitioning of contaminants onto soil, and (viii) removal of organics from soil in presence of surfactants. Surfactant adsorption on soil and/or sediment is an important step in this process as it results in surfactant loss reduced the availability of the surfactants for solubilization. At the same time, adsorbed surfactants will retained in the soil matrix, and may create other environmental problem. The biosurfactants are become promising in this application due to their environmentally friendly nature, nontoxic, low adsorption on to soil, and good solubilization efficiency. Effects of different parameters like the effect of electrolyte, pH, soil mineral and organic content, soil composition etc. on surfactant adsorption are discussed here. Micellar solubilization is also an important step for removal of organic contaminants from the soil matrix, especially for low aqueous solubility organic contaminants. Influences of different parameters such as single and mixed surfactant system, hydrophilic and hydrophobic chain length, HLB value, temperature, electrolyte, surfactant type that are very important in micellar solubilization are reviewed here. Microemulsion systems show higher capacity of organic hydrocarbons solubilization than the normal micellar system. In the case of biodegradation of organic hydrocarbons, the rate is very slow due to low water solubility and dissolution rate but the presence of surfactants may increase the bioavailability of hydrophobic compounds by solubilization and hence increases the degradation rate. In some cases the presence of it also reduces the rate. In addition to fundamental studies, some laboratory and field studies on removal of organics from contaminated soil are also reviewed to show the applicability of this technology.

[1]  R. V. Nauman,et al.  Micellar Weights of and Solubilization of Benzene by a Series of Tetradecylammonium Bromides. The Effect of the Size of the Charged Head1a , 1964 .

[2]  S. Biggs,et al.  Adsorption Kinetics and Structural Arrangements of Cetylpyridinium Bromide at the Silica-Aqueous Interface , 2001 .

[3]  B. Chowdhry,et al.  Polycyclic aromatic hydrocarbon extraction from a coal tar-contaminated soil using aqueous solutions of nonionic surfactants , 1999 .

[4]  K. Hayes,et al.  Refinement of the density-modified displacement method for efficient treatment of tetrachloroethene source zones. , 2004, Journal of contaminant hydrology.

[5]  S. Paria,et al.  Adsorption of Non-ionic Surfactants onto Sand and Its Importance in Naphthalene Removal , 2007 .

[6]  D. Sabatini,et al.  Properties of food grade (edible) surfactants affecting subsurface remediation of chlorinated solvents. , 1995, Environmental science & technology.

[7]  S. Boyd,et al.  Cation exchange chemistry of hexadecyltrimethylammonium in a subsoil containing vermiculite , 1994 .

[8]  T. Sobisch,et al.  Effect of additives on biodegradation of PAH in soils , 2000 .

[9]  S. Paria,et al.  A review on experimental studies of surfactant adsorption at the hydrophilic solid-water interface. , 2004, Advances in colloid and interface science.

[10]  Mark A. Schlautman,et al.  Partitioning of Hydrophobic Organic Compounds to Sorbed Surfactants. 1. Experimental Studies , 1998 .

[11]  D. Sabatini,et al.  Net-Average Curvature Model for Solubilization and Supersolubilization in Surfactant Microemulsions , 2003 .

[12]  Partyka,et al.  Adsorption Mechanism of Conventional and Dimeric Cationic Surfactants on Silica Surface: Effect of the State of the Surface. , 1999, Journal of colloid and interface science.

[13]  Ponisseril Somasundaran,et al.  Adsorption of Alkyltrimethylammonium Bromides on Negatively Charged Alumina , 1997 .

[14]  P. Rao,et al.  Adsorption of anionic and nonionic surfactant mixtures from synthetic detergents on soils. , 2006, Chemosphere.

[15]  Robert C. Knox,et al.  Surfactants for ground water remediation , 1999 .

[16]  M. Mills,et al.  Solubilization of naphthalene and methyl-substituted naphthalenes from crude oil using biosurfactants , 1997 .

[17]  F. Tokiwa Solubilization behavior of sodium dodecylpolyoxyethylene sulfates in relation to their polyoxyethylene chain lengths , 1968 .

[18]  Andrew Klimek,et al.  The use of surfactants for in situ extraction of organic pollutants from a contaminated aquifer , 1991 .

[19]  Microbial mineralization of organic compounds in an acidic agricultural soil: Effects of preadsorption to various soil constituents , 1996 .

[20]  A. Graciaa,et al.  Improving solubilization in microemulsions with additives. 2. Long chain alcohols as lipophilic linkers , 1993 .

[21]  Kurt D. Pennell,et al.  Surfactant-enhanced solubilization of residual dodecane in soil columns. 1. Experimental investigation , 1993 .

[22]  P. Somasundaran,et al.  ADSORPTION BEHAVIOR OF ALKYLARYLETHOXYLATED ALCOHOLS ON SILICA , 1991 .

[23]  L. Thibodeaux,et al.  Relationships between micelle-water and octanol-water partition constants for hydrophobic organics of environmental interest , 1989 .

[24]  Ji-won Yang,et al.  Surfactant-enhanced electrokinetic removal of phenanthrene from kaolinite. , 2007, Journal of hazardous materials.

[25]  Catherine N. Mulligan,et al.  Surfactant-enhanced remediation of contaminated soil: a review , 2001 .

[26]  S. Ghoshal,et al.  Micellar solubilization of naphthalene and phenanthrene from nonaqueous-phase liquids. , 2002, Environmental science & technology.

[27]  Alexander T. Florence,et al.  Surfactant Systems: Their chemistry, pharmacy and biology , 1983 .

[28]  S. Boyd,et al.  Heterotrophic activity of microorganisms in soils treated with quaternary ammonium compounds. , 1994, Environmental science & technology.

[29]  Lowell A. Douglas,et al.  Soils and the Environment, An Introduction , 1993 .

[30]  W. Weber,et al.  Solubilization of nonaqueous phase liquid hydrocarbons in micellar solutions of dodecyl alcohol ethoxylates. , 1994, Environmental science & technology.

[31]  Clarence A. Miller,et al.  Effect of micellar solubilization on biodegradation rates of hydrocarbons , 1993 .

[32]  T. Gao,et al.  Synergism in binary mixtures of surfactants 12. Mixtures containing surfactants with two hydrophilic and two or three hydrophobic groups , 1994 .

[33]  M. Drach,et al.  Theoretical modelling of self assembly of zwitterionic surfactants at the silica/water interface , 2005 .

[34]  J. A. V. BUTLER,et al.  Theory of the Stability of Lyophobic Colloids , 1948, Nature.

[35]  K. Valsaraj,et al.  Aqueous solubility enhancement and desorption of hexachlorobenzene from soil using a plant-based surfactant , 1997 .

[36]  S. Partyka,et al.  Investigations of First Adsorption Step of Cationic Dimeric (Gemini) Surfactants onto Silica Surfaces by Analytical and Calorimetric Methods , 2001 .

[37]  R. Luthy,et al.  Inhibition of phenanthrene mineralization by nonionic surfactants in soil-water systems , 1991 .

[38]  K. Shinoda,et al.  The solubilization of hydrocarbons in aqueous solutions of nonionic surfactants , 1967 .

[39]  J. Th. G. Overbeek,et al.  Theory of the stability of lyophobic colloids , 1955 .

[40]  T. Feijtel,et al.  Terrestrial risk assessment for linear alkyl benzene sulfonate (LAS) in sludge-amended soils. , 1998, Chemosphere.

[41]  D. Doulia,et al.  Effect of nonionic surfactants on the solubilization of alachlor. , 2006, Journal of hazardous materials.

[42]  K. Mittal,et al.  Solution Chemistry of Surfactants , 1979 .

[43]  Tiberg,et al.  Nature of the Adsorption of Zwitterionic Surfactants at Hydrophilic Surfaces , 1996, Journal of colloid and interface science.

[44]  J. Karns,et al.  Influence of rhamnolipids and triton X-100 on the biodegradation of three pesticides in aqueous phase and soil slurries. , 2001, Journal of agricultural and food chemistry.

[45]  D. Sabatini,et al.  Microemulsion formation and detergency with oily soils: I. Phase behavior and interfacial tension , 2003 .

[46]  D. Grasso,et al.  Micellar desorption of polynuclear aromatic hydrocarbons from contaminated soil , 2001 .

[47]  V. Seredyuk,et al.  Micellization and adsorption properties of novel Zwitterionic surfactants , 2001 .

[48]  G. Shreve,et al.  Effect of anionic biosurfactant on hexadecane partitioning in multiphase systems. , 1994, Environmental science & technology.

[49]  A. Abd‐Allah,et al.  Biodegradation of anionic surfactants in the presence of organic contaminants , 1998 .

[50]  B. Moudgil,et al.  Mechanisms of nonionic polymer adsorption on oxide surfaces , 1998 .

[51]  I. A. Rahman,et al.  Strengthening of hydrophobic bonding and the increase in the degree of micellar ionization by amphiphiles and the micelle-water distribution coefficient as a function of the surfactant chain length in sodium alkyl sulfates , 1985 .

[52]  J. Lee,et al.  Attenuating organic contaminant mobility by soil modification , 1988, Nature.

[53]  Xiaoyan Song,et al.  Solvent effect on the aggregate of fluorinated gemini surfactant at silica surface. , 2006, Journal of colloid and interface science.

[54]  S. Rehfeld Solubilization of benzene in aqueous cetyltrimethyl ammonium bromide measured by differential spectroscopy , 1971 .

[55]  A. M. Jacobson,et al.  Biodegradation of naphthalene in aqueous nonionic surfactant systems , 1995, Applied and environmental microbiology.

[56]  R. Maier,et al.  Pseudomonas aeruginosa rhamnolipids: biosynthesis and potential applications , 2000, Applied Microbiology and Biotechnology.

[57]  Jan Carmeliet,et al.  A multi-objective optimization framework for surfactant-enhanced remediation of DNAPL contaminations. , 2006, Journal of contaminant hydrology.

[58]  D. Sabatini,et al.  Supersolubilization in Chlorinated Hydrocarbon Microemulsions: Solubilization Enhancement by Lipophilic and Hydrophilic Linkers , 2000 .

[59]  R. Miller,et al.  Effect of a Pseudomonas rhamnolipid biosurfactant on cell hydrophobicity and biodegradation of octadecane , 1994, Applied and environmental microbiology.

[60]  A. Dobson,et al.  Effect of surfactants on fluoranthene degradation by Pseudomonas alcaligenes PA-10 , 2006, Applied Microbiology and Biotechnology.

[61]  Lizhong Zhu,et al.  Enhanced desorption of phenanthrene from contaminated soil using anionic/nonionic mixed surfactant. , 2007, Environmental pollution.

[62]  K. Hayes,et al.  Use of a surfactant-stabilized emulsion to deliver 1-butanol for density-modified displacement of trichloroethene. , 2003, Environmental science & technology.

[63]  W. M. Lee,et al.  Enhanced naphthalene solubility in the presence of sodium dodecyl sulfate: effect of critical micelle concentration. , 2001, Chemosphere.

[64]  K. H. Tan Environmental Soil Science , 1994 .

[65]  T. Ahmed,et al.  Modeling the influence of nonionic surfactants on biodegradation of phenanthrene , 1999 .

[66]  P. Jaffé,et al.  Bioavailability of Hydrophobic Compounds Partitioned into the Micellar Phase of Nonionic Surfactants , 1996 .

[67]  Robert W. Peters,et al.  Surfactant Foam/Bioaugmentation Technology for In Situ Treatment of TCE-DNAPLs , 1998 .

[68]  K. Urano,et al.  Adsorption of surfactants on sediments , 1984 .

[69]  D. N. Johnson,et al.  Efficient, near-complete removal of DNAPL from three-dimensional, heterogeneous porous media using a novel combination of treatment technologies. , 2004, Environmental science & technology.

[70]  Minhee Lee,et al.  Application of nonionic surfactant-enhanced in situ flushing to a diesel contaminated site. , 2005, Water research.

[71]  S. Partyka,et al.  Adsorption of Dimeric (Gemini) Surfactants at the Aqueous Solution/Silica Interface☆ , 1998 .

[72]  A. Tiehm Degradation of polycyclic aromatic hydrocarbons in the presence of synthetic surfactants , 1994, Applied and environmental microbiology.

[73]  F. Wagner,et al.  Effect of the addition of microbial surfactants on hydrocarbon degradation in a soil population in a stirred reactor , 2004, Applied Microbiology and Biotechnology.

[74]  K. Stadnicka,et al.  Adsorption isotherms of homologous alkyldimethylbenzylammonium bromides on sodium montmorillonite. , 2003, Journal of colloid and interface science.

[75]  G. E. Jones,et al.  Mineralization of phenanthrene by a Mycobacterium sp , 1988, Applied and environmental microbiology.

[76]  L. Wesson,et al.  DOWFAX surfactant components for enhancing contaminant solubilization , 2000 .

[77]  Yanli Sun,et al.  Effects of mixed surfactants on the volatilization of naphthalene from aqueous solutions. , 2007, Journal of hazardous materials.

[78]  James A. Smith,et al.  Surfactant-Enhanced Remediation of a Trichloroethene-Contaminated Aquifer. 2. Transport of TCE , 1998 .

[79]  E. Ron,et al.  Enhancement of Solubilization and Biodegradation of Polyaromatic Hydrocarbons by the Bioemulsifier Alasan , 1999, Applied and Environmental Microbiology.

[80]  Kun Yang,et al.  Sorption of sodium dodecylbenzene sulfonate by montmorillonite. , 2007, Environmental pollution.

[81]  Lizhong Zhu,et al.  Solubilization of pyrene by anionic-nonionic mixed surfactants. , 2004, Journal of hazardous materials.

[82]  Glenn O. Brown,et al.  Anionic surfactant transport characteristics in unsaturated soil , 1996 .

[83]  D. Sabatini,et al.  Alcohol-free diphenyl oxide disulfonate middle-phase microemulsion systems , 2000 .

[84]  Seung-Woo Jeong Evaluation of the use of capillary numbers for quantifying the removal of DNAPL trapped in a porous medium by surfactant and surfactant foam floods. , 2005, Journal of colloid and interface science.

[85]  Catherine N. Mulligan,et al.  Remediation with surfactant foam of PCP-contaminated soil , 2003 .

[86]  G. G. Stokes "J." , 1890, The New Yale Book of Quotations.

[87]  Koide,et al.  Adsorption and Adsolubilization by Monomeric, Dimeric, or Trimeric Quaternary Ammonium Surfactant at Silica/Water Interface , 1996, Journal of colloid and interface science.

[88]  Kun Yang,et al.  Minimizing losses of nonionic and anionic surfactants to a montmorillonite saturated with calcium using their mixtures. , 2005, Journal of colloid and interface science.

[89]  S. Boyd,et al.  Cationic Surfactant Sorption to a Vermiculitic Subsoil via Hydrophobic Bonding. , 1995, Environmental science & technology.

[90]  Kun Yang,et al.  Solubilization of DNAPLs by mixed surfactant: reduction in partitioning losses of nonionic surfactant. , 2006, Chemosphere.

[91]  Richard G. Luthy,et al.  SOLUBILIZATION OF POLYCYCLIC AROMATIC HYDROCARBONS IN MICELLAR NONIONIC SURFACTANT SOLUTIONS , 1991 .

[92]  S. Paria,et al.  Solubilization of naphthalene by pure and mixed surfactants , 2006 .

[93]  R. Luthy,et al.  Distribution of nonionic surfactant and phenanthrene in a sediment/aqueous system. , 1994, Environmental science & technology.

[94]  R. Luthy,et al.  Sorption and Transport Kinetics of a Nonionic Surfactant through an Aquifer Sediment. , 1995, Environmental science & technology.

[95]  M. Nydén,et al.  Adsorption of zwitterionic gemini surfactants at the air–water and solid–water interfaces , 2002 .

[96]  W. C. Anderson Innovative site remediation technology , 1993 .

[97]  M. Brusseau,et al.  Adsorption of a multicomponent rhamnolipid surfactant to soil , 2000 .

[98]  S. Paria,et al.  Effects of Chain Length and Electrolyte on the Adsorption of n-Alkylpyridinium Bromide Surfactants at Sand-Water Interfaces , 2006 .

[99]  D. Janssen,et al.  Facilitated transport of a PAH mixture by a rhamnolipid biosurfactant in porous silica matrices , 2000 .

[100]  S. P. Moulik,et al.  Gemini surfactants: A distinct class of self-assembling molecules , 2002 .

[101]  K. Hayes,et al.  A Multicomponent Analysis of the Sorption of Polydisperse Ethoxylated Nonionic Surfactants to Aquifer Materials: Equilibrium Sorption Behavior , 1997 .

[102]  S. Boyd,et al.  Cationic Surfactant Adsorption by Swelling and Nonswelling Layer Silicates , 1995 .

[103]  Y. H. Shen Sorption of non-ionic surfactants to soil: the role of soil mineral composition. , 2000, Chemosphere.

[104]  Fang Li,et al.  The Adsorption of Gemini and Conventional Surfactants onto Some Soil Solids and the Removal of 2-Naphthol by the Soil Surfaces. , 2001, Journal of colloid and interface science.

[105]  J. Zimmerman,et al.  Partitioning of Ethoxylated Nonionic Surfactants into Nonaqueous-Phase Organic Liquids: Influence on Solubilization Behavior , 1999 .

[106]  William A. Telliard,et al.  PRIORITY POLLUTANTS I-A PERSPECTIVES VIEW , 1979 .

[107]  C. Treiner,et al.  Micellar solubilization of 1-pentanol in binary surfactant solutions: a regular solution approach , 1987 .

[108]  H. Govers,et al.  Sorption of linear alcohol ethoxylates on suspended sediment , 1996 .

[109]  C. Goudar,et al.  Competitive substrate biodegradation during surfactant-enhanced remediation , 1999 .

[110]  O. Shibata,et al.  Solubilization of Benzene, Naphthalene, Anthracene, and Pyrene in Dodecylammonium Trifluoroacetate Micelles , 1994 .

[111]  M. Alexander,et al.  Surfactants at low concentrations stimulate biodegradation of sorbed hydrocarbons in samples of aquifer sands and soil slurries , 1992 .

[112]  M. Alexander,et al.  Use of surfactants and slurrying to enhance the biodegradation in soil of compounds initially dissolved in nonaqueous-phase liquids , 1995, Applied Microbiology and Biotechnology.

[113]  W. Klein,et al.  Sorption of nonpolar and polar compounds to soils: Processes, measurements and experience with the applicability of the modified OECD-Guideline 106 , 1991 .

[114]  R. Luthy,et al.  Sorption of non-ionic surfactants onto soil , 1992 .

[115]  Catherine N Mulligan,et al.  Environmental applications for biosurfactants. , 2005, Environmental pollution.

[116]  R. Grim,et al.  REACTION OF DIFFERENT CLAY MINERALS WITH SOME ORGANIC CATIONS , 1947 .

[117]  M. Brusseau,et al.  Biosurfactant-enhanced solubilization of NAPL mixtures. , 2001, Journal of contaminant hydrology.

[118]  J. Westall,et al.  Sorption of linear alkylbenzenesulfonates on sediment materials , 1999 .

[119]  D. Sabatini,et al.  Coalescence and solubilization kinetics in linker-modified microemulsions and related systems , 2003 .

[120]  A. Tiehm,et al.  Surfactant-Enhanced Mobilization and Biodegradation of Polycyclic Aromatic Hydrocarbons in Manufactured Gas Plant Soil , 1997 .

[121]  W. N. Townsend An Introduction to the Scientific Study of the Soil , 1928, Nature.

[122]  James A. Smith,et al.  Effect of ten quaternary ammonium cations on tetrachloromethane sorption to clay from water , 1990 .

[123]  J. Villeneuve,et al.  Adding sodium dodecyl sulfate and Pseudomonas aeruginosa UG2 biosurfactants inhibits polycyclic aromatic hydrocarbon biodegradation in a weathered creosote-contaminated soil , 1996, Applied Microbiology and Biotechnology.

[124]  J. Zimmerman,et al.  Partitioning of ethoxylated nonionic surfactants in water/NAPL systems: Effects of surfactant and NAPL properties , 2000 .

[125]  C. Peters,et al.  Bioavailability of Mixtures of PAHs Partitioned into the Micellar Phase of a Nonionic Surfactant , 1998 .

[126]  S. Grimberg,et al.  Kinetics of phenanthrene dissolution into water in the presence of nonionic surfactants. , 1995, Environmental science & technology.

[127]  Ali Mahfoodh,et al.  Solubilization of naphthalene and pyrene by sodium dodecyl sulfate (SDS) and polyoxyethylenesorbitan monooleate (Tween 80) mixed micelles , 2006 .

[128]  A. Bielefeldt,et al.  Aqueous chemistry and interactive effects on non-ionic surfactant and pentachlorophenol sorption to soil. , 2003, Water research.

[129]  Jae-Woo Park,et al.  Solubilization of PAH mixtures by three different anionic surfactants. , 2002, Environmental pollution.

[130]  Yang,et al.  Influence of a Nonionic Surfactant (Triton X-100) on Contaminant Distribution between Water and Several Soil Solids. , 2000, Journal of colloid and interface science.

[131]  P. Somasundaran,et al.  Adsorption of surfactants and polymers at the solid-liquid interface , 1997 .

[132]  C. T. Chiou,et al.  Water solubility enhancements of DDT and trichlorobenzene by some surfactants below and above the critical micelle concentration , 1989 .

[133]  T. Cserháti,et al.  Structural Requirements for the Membrane Damaging Effect of Non Homologous Series of Nonionic Tenzides. Structural Requirements for the Biological Activity of Tenzides , 1984 .

[134]  L. Koopal,et al.  Adsorption of cationic surfactants on silica. Comparison of experiment and theory , 1997 .

[135]  K. Hayes,et al.  Pilot-scale demonstration of surfactant-enhanced PCE solubilization at the Bachman Road site. 1. Site characterization and test design. , 2005, Environmental science & technology.

[136]  T. Gu,et al.  Hemimicelle formation of cationic surfactants at the silica gel–water interface , 1987 .

[137]  W. Inskeep,et al.  Sorption of nonionic organic compounds in soil-water systems containing a micelle-forming surfactant. , 1995, Environmental science & technology.

[138]  E. Seagren,et al.  Combined effects of pH and biosurfactant addition on solubilization and biodegradation of phenanthrene , 2004, Applied Microbiology and Biotechnology.

[139]  Kurt D. Pennell,et al.  Surfactant-enhanced solubilization of residual dodecane in soil columns. 2. Mathematical modeling , 1993 .

[140]  K. Hayes,et al.  Implications of alcohol partitioning behavior for in situ density modification of entrapped dense nonaqueous phase liquids. , 2002, Environmental Science and Technology.

[141]  C. Jafvert,et al.  Solubilization of non-polar compounds by non-ionic surfactant micelles , 1994 .

[142]  Lizhong Zhu,et al.  Efficiency of surfactant-enhanced desorption for contaminated soils depending on the component characteristics of soil-surfactant--PAHs system. , 2007, Environmental pollution.

[143]  D. Sabatini,et al.  Microemulsion formation and detergency with oily soils: III. Performance and mechanisms , 2005 .

[144]  Gary A. Pope,et al.  A new concept: the use of neutrally-buoyant microemulsions for DNAPL remediation , 1998 .

[145]  P. Carey,et al.  Examination of the adsorption of ethylene oxide–propylene oxide triblock copolymers to soil , 1999 .

[146]  Cass T. Miller,et al.  Physicochemical Transport Processes Affecting the Removal of Residual DNAPL by Nonionic Surfactant Solutions , 1996 .

[147]  Kamy Sepehrnoori,et al.  Simulation of surfactant-enhanced aquifer remediation , 1994 .

[148]  David R. Burris,et al.  In situ modification of an aquifer material by a cationic surfactant to enhance retardation of organic contaminants , 1992 .

[149]  Bing‐Hung Chen,et al.  Solubilization of selected polycyclic aromatic compounds by nonionic surfactants , 2006 .

[150]  R. Podoll,et al.  Sorption of water-soluble oligomers on sediments. , 1987, Environmental science & technology.

[151]  M. Brusseau,et al.  Effect of clays, metal oxides, and organic matter on rhamnolipid biosurfactant sorption by soil. , 2007, Chemosphere.

[152]  M. Sakai,et al.  Solubilization of Benzene, Naphthalene, Anthracene, and Pyrene in 1-Dodecanesulfonic Acid Micelle , 1995 .

[153]  P. H. Pritchard,et al.  Response of fluoranthene-degrading bacteria to surfactants , 1998, Applied Microbiology and Biotechnology.

[154]  Suiling Wang,et al.  An evaluation of surfactant foam technology in remediation of contaminated soil. , 2004, Chemosphere.

[155]  D. Myers Surfactant Science and Technology , 1988 .

[156]  K. Rathfelder,et al.  Pilot-scale demonstration of surfactant-enhanced PCE solubilization at the Bachman Road site. 2. System operation and evaluation. , 2005, Environmental science & technology.

[157]  Rosén,et al.  Adsorption of Gemini and Conventional Cationic Surfactants onto Montmorillonite and the Removal of Some Pollutants by the Clay. , 2000, Journal of colloid and interface science.

[158]  D. Sabatini,et al.  Separation of Organic Compounds from Surfactant Solutions: A Review , 2007 .

[159]  C. A. Ramsburg,et al.  Density-modified displacement for DNAPL source zone remediation: density conversion and recovery in heterogeneous aquifer cells. , 2002, Environmental science & technology.

[160]  J. Foght,et al.  Effect of Emulsan on Biodegradation of Crude Oil by Pure and Mixed Bacterial Cultures , 1989, Applied and environmental microbiology.

[161]  S. Boyd,et al.  Sorption Characteristics of Organic Compounds on hexadecyltrimethylammonium‐Smectite , 1988 .

[162]  R. Luthy,et al.  Effects of nonionic surfactants on the solubilization and mineralization of phenanthrene in soil–water systems , 1992, Biotechnology and bioengineering.

[163]  William C. Anderson Soil Washing/Soil Flushing , 1994 .

[164]  Lizhong Zhu,et al.  Solubilization of DNAPLs by mixed surfactant: synergism and solubilization capacity. , 2006, Journal of hazardous materials.

[165]  Kyoung-Woong Kim,et al.  A Biosurfactant-Enhanced Soil Flushing for the Removal of Phenanthrene and Diesel in Sand , 2004, Environmental geochemistry and health.

[166]  Lizhong Zhu,et al.  RETRACTED: Micellar solubilization of TCE and PCE by mixed surfactant: Effects of surfactant partitioning and DNAPL mixing , 2007 .

[167]  W. Rulkens,et al.  Microbiological aspects of surfactant use for biological soil remediation , 1997, Biodegradation.

[168]  G. K. Williams,et al.  Structure-activity relationships for sorption of linear alkylbenzenesulfonates. , 1987, Environmental science & technology.

[169]  Lizhong Zhu,et al.  Enhanced desorption and biodegradation of phenanthrene in soil-water systems with the presence of anionic-nonionic mixed surfactants. , 2007, Journal of hazardous materials.

[170]  Andrew G. Glen,et al.  APPL , 2001 .

[171]  K. Urum,et al.  Crude oil contaminated soil washing in air sparging assisted stirred tank reactor using biosurfactants. , 2005, Chemosphere.

[172]  E. Voudrias,et al.  Behavior and fate of linear alkylbenzene sulfonate in different soils , 1998 .

[173]  J. Karns,et al.  Influence of rhamnolipids and triton X-100 on the desorption of pesticides from soils. , 2002, Environmental science & technology.

[174]  S. Biggs,et al.  Adsorption of 12-s-12 gemini surfactants at the silica-aqueous solution interface , 2003 .

[175]  Kun Yang,et al.  A multi-component statistic analysis for the influence of sediment/soil composition on the sorption of a nonionic surfactant (Triton X-100) onto natural sediments/soils. , 2003, Water research.

[176]  F. Menger,et al.  GEMINI SURFACTANTS : SYNTHESIS AND PROPERTIES , 1991 .

[177]  K. Reddy,et al.  Surfactant-enhanced electrokinetic remediation of polycyclic aromatic hydrocarbons in heterogeneous subsurface environments , 2005 .

[178]  Nagamune Nishikido Mixed micelles of polyoxyethylene-type nonionic and anionic surfactants in aqueous solutions , 1977 .

[179]  J. Karns,et al.  Effect of rhamnolipids produced by Pseudomonas aeruginosa UG2 on the solubilization of pesticides , 2000 .

[180]  D. Sabatini,et al.  Minimizing surfactant losses using twin-head anionic surfactants in subsurface remediation , 1993 .

[181]  Fredric M. Menger,et al.  Gemini surfactants: a new class of self-assembling molecules , 1993 .

[182]  Dickson L. S. Liu Enhancement of PCBs biodegradation by sodium ligninsulfonate , 1980 .

[183]  M. Brusseau,et al.  Effects of Rhamnolipid Biosurfactants on Removal of Phenanthrene from Soil , 1998 .

[184]  M. Alexander,et al.  Effect of surfactants at low concentrations on the desorption and biodegradation of sorbed aromatic compounds in soil , 1991 .

[185]  Li,et al.  Effects of Chain Length and Structure of Cationic Surfactants on the Adsorption onto Na-Kaolinite. , 1999, Journal of colloid and interface science.

[186]  C. Cunningham,et al.  Effect of biosurfactants on crude oil desorption and mobilization in a soil system. , 2005, Environment international.

[187]  S. Paria,et al.  Solidification/Stabilization of Organic and Inorganic Contaminants using Portland Cement: A Literature Review , 2006 .

[188]  J. Mcbain,et al.  Solubilization of Insoluble Organic Liquids by Detergents , 1946 .

[189]  E. Ruckenstein,et al.  Molecular Theory of Microemulsions , 2000 .

[190]  Craig Taylor,et al.  A Controlled Field Test of Surfactant‐Enhanced Aquifer Remediation , 1996 .

[191]  P. Dorn,et al.  Sorption of an alcohol ethoxylate surfactant to natural sediments , 1996 .

[192]  C. T. Chiou,et al.  A Physical Concept of Soil-Water Equilibria for Nonionic Organic Compounds , 1979, Science.

[193]  T. Gibson,et al.  Laboratory studies of surfactant-enhanced washing of polychlorinated biphenyl from sandy material , 1991 .

[194]  J. Lee,et al.  Enhanced retention of organic contaminants by soils exchanged with organic cations , 1989 .

[195]  S. Boyd,et al.  Alternative model for cationic surfactant adsorption by layer silicates. , 1995, Environmental science & technology.

[196]  Abdel-Mohsen Onsy Mohamed,et al.  Principles of Contaminant Transport in Soils , 1992 .

[197]  T. A. Hatton,et al.  Solubilization of polycyclic aromatic hydrocarbons by poly(ethylene oxide-propylene oxide) block copolymer micelles: effects of polymer structure , 1992 .

[198]  Jeffrey H. Harwell,et al.  Surfactants and subsurface remediation , 1992 .

[199]  Miss A.O. Penney (b) , 1974, The New Yale Book of Quotations.

[200]  C. A. Ramsburg,et al.  Density-modified displacement for dense nonaqueous-phase liquid source-zone remediation: density conversion using a partitioning alcohol. , 2002, Environmental science & technology.

[201]  S. Tao,et al.  Interactions of organic contaminants with mineral-adsorbed surfactants. , 2003, Environmental science & technology.

[202]  O. Yenigün,et al.  Sorption of Anionic Surfactants SDS, AOT and Cationic Surfactant Hyamine 1622 on Natural Soils , 2002 .

[203]  Meifang Zhou,et al.  Screening commercial surfactants suitable for remediating DNAPL source zones by solubilization. , 2000 .

[204]  Nagashima,et al.  Adsorption of Sodium n-Decylbenzenesulfonate onto Alumina: Relationships between Macro- and Microscopic Behavior. , 1999, Journal of colloid and interface science.

[205]  C. T. Chiou,et al.  Partition equilibriums of nonionic organic compounds between soil organic matter and water. , 1983, Environmental science & technology.

[206]  D. Rubingh In: Solution Chemistry of Surfactants , 1979 .

[207]  Gary A. Pope,et al.  Anionic surfactant remediation of soil columns contaminated by nonaqueous phase liquids , 1999 .

[208]  C. Peters,et al.  Solubilization of PAH Mixtures by a Nonionic Surfactant , 1998 .

[209]  E. Campos,et al.  Anaerobic digestion of linear alkyl benzene sulfonates: biodegradation kinetics and metabolite analysis. , 2005, Chemosphere.

[210]  R. Miller,et al.  Evidence from Liposome Encapsulation for Transport-Limited Microbial Metabolism of Solid Alkanes , 1989, Applied and environmental microbiology.

[211]  Kibbey,et al.  A Predictive Numerical Thermodynamic Model of Mixed Nonionic Surfactant Sorption in Natural Systems , 1998, Journal of colloid and interface science.

[212]  Gary F. Bennett,et al.  Manual for spills of hazardous materials : Technical Services Branch, Environmental Protection Service, Environment Canada, March 1984, approx. 600 pages, no price given. , 1986 .

[213]  J. Westall,et al.  Sorption of Nonionic Surfactants on Sediment Materials , 1997 .

[214]  Lizhong Zhu,et al.  Solubilization and biodegradation of phenanthrene in mixed anionic-nonionic surfactant solutions. , 2005, Chemosphere.

[215]  C. Breuil,et al.  Effects of lipids, fatty acids, and other detergents on bacterial utilization of hexadecane. , 1980, Canadian journal of microbiology.

[216]  M. S. Rodríguez-Cruz,et al.  A comparative study of adsorption of an anionic and a non-ionic surfactant by soils based on physicochemical and mineralogical properties of soils. , 2005, Chemosphere.

[217]  E. Ruckenstein,et al.  Locus of solubilization of benzene in surfactant micelles , 1984 .

[218]  James A. Smith,et al.  Surfactant-enhanced remediation of a trichloroethene-contaminated aquifer. 1. Transport of triton X-100 , 1997 .

[219]  M. Abe,et al.  Interaction between anionic surfactants and oil dyes in the aqueous solutions , 1985 .

[220]  D. Sabatini,et al.  Transport and remediation of subsurface contaminants : colloidal, interfacial, and surfactant phenomena , 1992 .

[221]  S. Partyka,et al.  Influence of the Chemical Surface State of Silica on Adsorption Process of Conventional Cationic and Gemini Surfactants: Thermodynamic Investigations , 2001 .

[222]  S. Partyka,et al.  Micellization and adsorption of a zwitterionic surfactant: N-dodecyl betaine—effect of salt , 1996 .

[223]  T. Cserháti,et al.  Effect of non-ionic tensides on the growth of some soil bacteria , 1991, Applied Microbiology and Biotechnology.

[224]  Jiantao Yang,et al.  Remediation of Petroleum-Contaminated Loess Soil by Surfactant-Enhanced Flushing Technique , 2005, Journal of environmental science and health. Part A, Toxic/hazardous substances & environmental engineering.

[225]  K. Shinoda,et al.  Conditions to produce so-called microemulsions: Factors to increase the mutual solubility of oil and water by solubilizer , 1973 .

[226]  W. Maier,et al.  Effect of Rhamnolipids on the Dissolution, Bioavailability, and Biodegradation of Phenanthrene , 1997 .

[227]  Robert C Knox,et al.  Field demonstration of surfactant-enhanced solubilization of DNAPL at Dover Air Force Base, Delaware. , 2006, Journal of contaminant hydrology.

[228]  O. Ward,et al.  Effect of surfactant solubilization on biodegradation of polychlorinated biphenyl congeners by Pseudomonas LB400 , 1999, Applied Microbiology and Biotechnology.

[229]  A. Graciaa,et al.  Improving Solubilization in Microemulsions with Additives. 1. The Lipophilic Linker Role , 1993 .

[230]  K. Hayes,et al.  Micellar solubilization of nonaqueous phase liquid contaminants by nonionic surfactant mixtures: Effects of sorption, partitioning and mixing , 1998 .

[231]  R. Miller,et al.  Rhamnolipid (biosurfactant) effects on cell aggregation and biodegradation of residual hexadecane under saturated flow conditions , 1997, Applied and environmental microbiology.

[232]  D. L. Prak,et al.  Solubilization of polycyclic aromatic hydrocarbon mixtures in micellar nonionic surfactant solutions. , 2002, Water research.

[233]  D. L. Prak,et al.  Solubilization Rates of n-Alkanes in Micellar Solutions of Nonionic Surfactants , 2000 .

[234]  Raina M. Miller-Maier,et al.  Biosurfactant (Rhamnolipid) Sorption and the Impact on Rhamnolipid-Facilitated Removal of Cadmium from Various Soils under Saturated Flow Conditions , 1998 .

[235]  D. L. Prak Solubilization of nitrotoluenes in micellar nonionic surfactant solutions. , 2007, Chemosphere.

[236]  M. Schwuger,et al.  Detergents in the environment , 1997 .

[237]  Ibrahim M. Banat,et al.  Biosurfactants production and possible uses in microbial enhanced oil recovery and oil pollution remediation: a review , 1995 .

[238]  M. S. Rodríguez-Cruz,et al.  Study of the desorption of linuron from soils to water enhanced by the addition of an anionic surfactant to soil-water system. , 2003, Water research.

[239]  L. Torres,et al.  Washing of Soil Contaminated with PAHs and Heavy Petroleum Fractions Using Two Anionic and One Ionic Surfactant: Effect of Salt Addition , 2004 .

[240]  C D Cox,et al.  Micellar solubilization of polynuclear aromatic hydrocarbons in coal tar-contaminated soils. , 1995, Environmental science & technology.

[241]  K. Valsaraj,et al.  Nutrient and surfactant enhancement for the biodegradation of chlorinated hydrocarbons in the wastewater from a Louisiana Superfund site , 1998 .

[242]  I. Ivshina,et al.  Microbial surfactants and their use in field studies of soil remediation , 2002, Journal of applied microbiology.

[243]  L. Abriola,et al.  Solubilization of Dodecane, Tetrachloroethylene, and 1,2-Dichlorobenzene in Micellar Solutions of Ethoxylated Nonionic Surfactants , 1997 .

[244]  Y. H. Shen Preparations of organobentonite using nonionic surfactants. , 2001, Chemosphere.

[245]  Kenichiro Koga,et al.  The hydrophobic effect , 2003 .

[246]  P. Kralchevsky,et al.  Kinetics of solubilization of n-decane and benzene by micellar solutions of sodium dodecyl sulfate. , 2002, Journal of colloid and interface science.

[247]  J. Obbard,et al.  Evaluation of an elevated non-ionic surfactant critical micelle concentration in a soil/aqueous system. , 2002, Water research.

[248]  S. Rehfeld Solubilization of benzene in aqueous sodium dodecyl sulfate solutions measured by differential spectroscopy , 1970 .

[249]  N. Yoshida,et al.  Thermodynamics and kinetics of solubilization of naphthalene into anionic micelles , 2000 .

[250]  R. Efroymson,et al.  Biodegradation by an Arthrobacter Species of Hydrocarbons Partitioned into an Organic Solvent , 1991, Applied and environmental microbiology.

[251]  Shirley Dex,et al.  JR 旅客販売総合システム(マルス)における運用及び管理について , 1991 .

[252]  R. Doong,et al.  Solubilization and mineralization of polycyclic aromatic hydrocarbons by Pseudomonas putida in the presence of surfactant. , 2003, Journal of hazardous materials.

[253]  Lizhong Zhu,et al.  Synergistic solubilization of polycyclic aromatic hydrocarbons by mixed anionic-nonionic surfactants. , 2003, Chemosphere.

[254]  S. Biggs,et al.  The influence of chain length and electrolyte on the adsorption kinetics of cationic surfactants at the silica-aqueous solution interface. , 2003, Journal of colloid and interface science.

[255]  R. Miller,et al.  Enhanced octadecane dispersion and biodegradation by a Pseudomonas rhamnolipid surfactant (biosurfactant) , 1992, Applied and environmental microbiology.

[256]  Robert Levine,et al.  Performance Monitoring of MNA Remedies for VOCs in Ground Water: A Framework , 2005 .

[257]  J. Park,et al.  Partitioning of naphthalene to gemini surfactant-treated alumina. , 2000, Chemosphere.

[258]  P. Lafrance,et al.  Conditions for effective removal of pyrene from an artificially contaminated soil using Pseudomonas aeruginosa 57SJ rhamnolipids. , 2005, Environmental pollution.

[259]  Jeffrey H. Harwell,et al.  Surfactant selection for enhancing ex situ soil washing , 1999 .

[260]  D. Fuerstenau Equilibrium and Nonequilibrium Phenomena Associated with the Adsorption of Ionic Surfactants at Solid–Water Interfaces , 2002 .

[261]  R. E. Brown,et al.  Evaluation of ethoxylated alkylsulfate surfactants for use in subsurface remediation , 1996 .

[262]  T. Sun,et al.  Adsorption of linear alkylbenzene sulfonate (LAS) on soils , 1996 .

[263]  E. Vansant,et al.  The Exchange of Alkylammonium Ions on Na-Laponite , 1978 .

[264]  D. Sabatini,et al.  Integrated design of surfactant enhanced DNAPL remediation: efficient supersolubilization and gradient systems , 2000 .

[265]  Xiaoyan Song,et al.  Adsorption of hexyl-α,ω-bis(dodecyldimethylammonium bromide) gemini surfactant on silica and its effect on wettability , 2006 .

[266]  J. Wong,et al.  Effect of surfactants on solubilization and degradation of phenanthrene under thermophilic conditions. , 2004, Journal of environmental quality.

[267]  P. Jaffé,et al.  Biodegradation Kinetics of Phenanthrene Partitioned into the Micellar Phase of Nonionic Surfactants , 1996 .