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ENVIRONMENT

INTERNATIONAL
ELSEVIER Environment International 28 (2002) 337-348
www.elsevier.com/locate/envint

Biological activity and environmental impact of anionic surfactants


Tibor Cserhati a,*, Esther Forgacs a, Gyula Oros b
alnstitute of Chemistry, Chemical Research Centre, Hungarian Academy o{Sciences, PO. Box 17, 1525 Budapest. Hungary
bpfant Protection Institute, Hungarian Academy of Sciences, Budapest, Hungary

Received I September 2001; accepted 22 April 2002

Abstract

The newest results concerning the biological activity and environmental fate of anionic surfactants are collected and critically evaluated.
The chemical and physicochemical parameters related to the biological activity and the field of application are briefly discussed. Examples on
the effect of anionic surfactants on the cell membranes, on the activity of enzymes, on the binding to various proteins and to other cell
components and on their human toxicity are presented and the possible mode of action is elucidated. The sources of environmental pollution
caused by anionic surfactants are listed and the methods developed for their removal from liquid, semiliquid and solid matrices are collected.
Both the beneficial and adversary effects of anionic surfactants on the environment are reported and critically discussed. It was concluded that
the role of anionic surfactants in the environment is ambiguous: they can cause serious environmental pollution with toxic effect on living
organisms; otherwise, they can promote the decomposition and/or removal of other inorganic and organic pollutants from the environment.
The relationship between their chemical structure, physicochemical parameters, biological activity and environmental impact is not well
understood. A considerable number of data are needed for the development of new anionic surfactants and for the successful application of
the existing ones to reduce the adversary and to promote beneficial effects.
© 2002 Elsevier Science Ltd. All rights reserved.

Keyword~: Anionic surfactants; Physicochemistry; Biological activity; Environmental impact

1. Chemistry and physicochemistry can decrease the energy of interaction and the energy of
solvation between a high variety of heterogeneous phases in
Anionic surfactants are amphipatic compounds consist- many technological processes and biological systems by
ing of a hydrophobic (alkyl chains of various length, adsorbing on oil-water (Staples et al., 2000), polystyrene-
alkylphenyl ethers, alkylbenzenes, etc.) and a hydrophilic water (Turner et al., 1999), and air- water (Hawerd and
part (carboxyl, sulfate, sulfonates, phosphates, etc). It has Warr, 2000) interfaces. In order to find materials for
been established many times that the hydrophobic and effective surfactant removal, the adsorption of anionic
hydrophilic parts readily interact with the polar and apolar surfactants on various solid surfaces have been extensively
substructures in marcomolecules such as proteins (Yamagu- studied. Thus, it has been established that sodium Iaury!
chi et a!., 1999; Xiao et al., 2000), and cellulose (Griffiths sulfate is readily adsorbed onto arsenic-bearing ferrihydrite
and Howe, 1998) or with the polar or apolar molecules in a (Quan eta!., 200 I), other surfactants have been adsorbed by
mixture of compounds (Chirila et a!., 2000; Von Berleps et layered double hydroxides (Pavan et a!., 2000), by hydro-
a!., 2000). Because of these interactions, anionic surfactants lytically stable metal oxides (Vovk, 2000). The adsorption
of anionic surfactant on solid surfaces (Somasundaran and
Huang, 2000; Rodriguez and Scamehom, 200 1) can modifY
Abbreviations: CD, cyclodextrin; CTAB, cetyl trimethyl ammonium
surface characteristic and electron transfer (Wang et a!.,
bromide; DTAB, dodecyltrimethylammonium bromide; LAS, linear alkyl- 2000a), can result in the formation of surface aggregates
benzene sulfonate; PAH, polyaromatic hydrocarbons; PEG, polyethylene- similarly to micelles (Luciani et al., 2001) and can increase
glycol; QSAR, quantitative structure-activity relationship; RDX, he- the film thickness of other adsorbed molecules (Churaev,
xahydro-1,3,5-trinitro-1,3,5-triazine; SDS, sodium dodecyl sulfate; TNT,
2000; Esumi et a!., 2000; Miyazaki et al., 2000).
2,4,6-trinitrotoluene.
' Corresponding author. Tel.: +36-1-1-325-7900; fax: +36-1-1-325-
7554.
E-mail address: forgacs@cric.chemres.hu (T. Cserhati).
Anionic surfactants not only change the surface charac-
teristics of solids by ad~orption but can also enhance the
solubility of sparingly soluble compounds in water (Harri-
-
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0160-4120/02/$ - see front matter © 2002 Elsevier Science Ltd. All rights reserved.
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338 T Cserh(/ti el a/. I Environmentlntemational 2/i (2002) 337- 34/i

sun l'l a!.. !999), and can reduce the resistance to mass undecyl sulfate per amino acid residues (Prieto et al., !993 ).
transfer (Vazquez et al., 20()() ). Anionic surfactants are The peptide fragment 828-848 of the envelop glycoprotein
present in monomeric fom1 in both apolar and polar solvents of human immunodeficiency virus (HIV) type I underwent a
at low concentration. At a higher concentration (critical transition from a random coil to an ordered conformation
micelle concentration, CMC), they form regular aggregates upon binding to negatively charged SDS micelles. It was
(micelles) (Joshi et al., I 999). CMC highly depends on the found that the interaction between the peptide and SDS is of
polarity ofthe solvent, on the structural characteristics of the exclusively electrostatic character with the six positively
surfactant molecule (Okano ct al., 2000; Jalali-Hemvi and charged arginines of the peptide acting as binding sites for
Konouz. 2000) and on the ion concentration of the solution SDS (Gawrisch et al.. 1993 ). This binding may explain that
(Talens~Alcsson, lli99). The hydrophobic part of anionic similar to other polyanions, anionic surfactants show in vitro
surfactants turns towards the bulk of the solvent in the case antiviral activity against HIV-1, HIV-2 and other enveloped
of apolar solvents (i.e. oil), the hydrophilic head groups tum viruses (Luscller-!Vlattli. 2000).
inside the micelles forming an environment that can readily Anionic surfactants influence enzyme activities by bind-
accommodate polar molecules such as water forming water- ing to the enzyme protein. The impact of anionic surfactants
in-oil type emulsions. In polar solvents, the situation is on enzyme activities has been extensively demonstrated.
reversed: head groups tum towards the bulk of solvent, Thus, it was proven that linear alkylbenzene sulfonate can
apolar substructures pointing towards the centre of the accumulate in the hepatic liposomes of the rat and can
micelle accommodating hydrophobic molecules (oil-in- inhibit the activity of the enzymes alkaline phosphatase and
water type emulsions). acid phosphatase (Bra gad in ct al.. 19% ). SDS inhibited the
Due to their favorable physicochemical characteristics, ATPase activity of ?-glycoprotein at very low concentra-
anionic surfactants are extensively used in many fields of tions while Triton X-100 stimulated at low concentration
technology and research. Anionic surfactants have been and inhibited the activity at higher concentrations (Doige ct
successfully employed for the enhancement of the efficacy aL 1993). Both anionic (SDS) and cationic detergents
of the active ingredient in pharmaceutical (Lawrence, l ':!94) caused the inhibition of lecithin/cholesterol acyltransferase
and agricultural formulations (Riechers et al., 1995), in with a water-soluble substrate, whereas the nonionic surfac-
biotechnological (Chang ct al.. 1904 l and in other industrial tant, Triton X-100, activated the enzyme (Bonelli and .Ionas.
processes (Czapla and Bart, 1999; ·rong ct aL 2000), and in 1993 ). SDS and cationic surfactants (DTAB) modified the
cosmetics (Reich and Robbins, 199 3 ). structure and enzymatic activity of jack bean urease (Hirai ct
al., 1993 ), and SDS activated latent potato leaf polyphenol
oxidase (Sanchez-Ferrer et aL 1993). It has been supposed
2. Biological activity that electrostatic interaction between the surfactant head
groups and ionic site in enzyme protein glucose oxidase
Anionic surfactants themselves show marked biological as well as hydrophobic interactions are involved in the bind-
activity too either by binding to various bioactive macro- ing of n-alkyltrimethylammoniumbromides and n-alkyl-
molecules such as starch (Merta and Stenius, 1999 ), proteins sulfates to the enzyme. Surfactants can activate or inhibit
(Nielsen ct al.. 2000), peptides and DNA (Marques et a!.. the enzyme depending on the surfactant concentration and
2000) or by inserting into various cell fragments (i.e. on the length of alkyl chain (Housaimlokh et a!., 1993).
phospholipid membranes) causing misfunction. The binding of anionic surfactants to phospholipids has
also been demonstrated. SDS increased the surface tension
2.1. Binding to proteins, peptides and membrane phospho- of phosphatidylcholine monolayers whereas CTAB
lipids inhibited the film formation below the critical micelle
concentration (Ah-Fal ct al., 1994).
The occurrence of binding of anionic surfactants to
proteins and peptides has been demonstrated many times. 2.2. Human toxicity
This binding may result in the alteration of the folding ofthe
polypeptide chain and the change of the surface charge of The amphoteric character of anionic surfactants facilitate
the molecule. The modification of structure and charge may their accumulation in living organisms. The negatively
lead to modified biological function too. charged head group can bind to the positively charged
It has been established that sodium dodecyl sulfate (SDS) molecular substructures by electrostatic forces while the
and the cationic ( cetyltrimethyl ammonium bromide, hydrophobic moiety may interact with the apolar parts of
CTAB) surfactants considerably influenced the dissociation, the target organs or organisms by hydrophobic forces. The
a-chymotryptic degradation and enteral absorption of insu- earlier results on the bioconcentration of surfactants were
lin hexamers whereas the nonionic surfactants Tween 80 previously collected and critically evaluated (Kloepper-
and polyoxyethylene 9 laurylether have a negligible effect Sams and Sijrn, 1994 ). ModifYing of protein structure and
(Shao et al., 1993 ). Equilibrium dialysis measurements misfunctioning of enzymes and phopholipid membranes by
indicated that insulin binds up to 2.7 molecules of sodium anionic surfactants causes toxic symptoms in organs and
T Cverhtiti eta/. I Environment lntemational 28 (2002) 337-348 339

animal and human organisms. Thus, the damaging effect of the drug (Seed her. 2000) or by influencing the adsorption
surfactants on human lymphocytes was reported the effect and absorption processes and the partition of drugs between
of cationic surfactants being the highest (Antoni and Szabo, hydrophobic and hydrophilic compartments in the organs
1982 ). Anionic surfactants mainly show eye and skin and organisms ( Yushmanov el al., 1994 ). The beneficial
irritation potentials. Because of the high number of surfac- effect of surfactants on the dissolution rate and release of
tants in contact with humans, many in vitro methods have various active ingredients has been frequently demonstrated
been developed for the prediction of the eye irritation (Sacrs et al., 1993 ). SDS and the nonionic surfactants Brij
potential of surfactants. Thus, the SIRC-NRU cytotoxicity 35 and polysorbate 80 increased the dissolution rate of
test revealed that nonionic surfactants have a lower toxic griseofulvin in PEG 3000 as carrier (Sjokkvist el a!.,
effect than cationic, anionic and amphoteric ones ( Ro~wet ct 1992), and SDS and DTAB (dodecyltrimethylammonium
aL I q92 l. According to another cytotoxicity test, the bromide) having a higher influence than Brij 35 (Alden ct
cytotoxicity order of surfactants determined on rabbit cor- a!.. 1993). SDS further enhanced the release of a highly
neal epithelial cells was cationic>anionic = amphoteric>non- water-soluble cationic medicinal compound (procain) from
ionic; however, Triton X-1 00 had a ranking similar to an inert, heterogeneous matrix probably by forming a
anionic surfactants (Grant et al., l9q2). The order oftoxicity complex by electrostatic interactions (Wells and Parrott
of surfactants determined with an ocular lens organ culture 1<)92 ). However, in the case of clofazimine analogues, the
was: benzalkonium chloride>cetylpyridinium bromide>Tri- effect of Triton-X -100 on the micellar solubilization was
ton-X-lOO>SDS>Geropon AC-78>Tween 20 (Sivak ct al., higher than that of SDS (Fahclelbom ct al., !993). Ionic
l 004 l. A study comparing two cytotoxicity tests for pre- surfactants influenced the distribution of the hormone
dicting ocular irritancy established that red blood cell lysis secretin between the hydrophobic and hydrophilic phases
test was predictive. Surfactants caused membrane disrup- of a water-in-oil-in-water multiple emulsion (Ohwaki ct al.,
tion; anionic and cationic surfactants were more toxic than 1993).
nonionic ones (Lewis ct al., 19q3). Anionic surfactants exert a considerable influence on the
Anionic surfactants also damage human skin as deter- pharmakokinetic parameters of drugs. It has been estab-
mined by differential scanning calorimetry and permeation lished that the effect of cationic and anionic surfactants on
studies. Interestingly, nonionic surfactants were able to the transdermal flux of methyl nicotinate was higher than
reduce the damaging effect of anionic surfactants; however, that of the nonionic surfactant tAshton et al., 1992), and
the molecular basis of the phenomenon has not been SDS improved the intestinal absorption of the anthelmintic
elucidated (Lagle ct a!.. !992). The dependence of the skin drug albendazole (Dd Estal et a!., 1993). The iontophoresis
irritancy potential of anionic surfactants on the molecular of hydrocortisone across hairless mouse skin has also been
structure was well established. The results indicated that the influenced by SDS (Wang et aL 2000b).
length of the alkyl chain of sodium alkyl sulfates has a
considerable impact on their skin irritating potential. C 18
compounds caused cell injury whereas ClO and Cl6 com- 4. Anionic surfactants in the environment
pounds caused more severe membrane destruction and
protein denaturation (Kotani ct al., 1904 ). Sodium Iaury I 4.1. Ground and waste waters: pollution and purification
sulfate causes more severe skin dehydration than dodecyl
trimethyl ammonium bromide; complete repair ofthe irritant Because of extensive application, a considerable amount
reaction was achieved 17 days after smfactant exposure of anionic surfactants are released in the environment
~Wilhelm et aL 1994). The test ofthe cutaneous toxicity of causing serious pollution of rivers (Oclokuma and ()kpok-
surfactants in normal human keratinocytes assessed by wa>ili, 1997) and sea (Raglimieri et al., 19~0; Romano and
cytotoxicity, arachidonic acid release and regulation of Ciarabetian, 1996) and can accumulate sludge sewage treat-
interleukin-la mRNA revealed that the effect of SDS was ment flow (Holt et a!.. 1995). The concentration of anionic
higher than that of the nonionic surfactants Triton-X-I 00 surfactants in rivers and lakes showed marked variation
and Tween 20 (Shivji et al., 1994). A quantitative structure- according to the season (Marcomini et aL, 2000) and the
activity relationship (QSAR) study revealed that the hydra- distance of residential districts ( lnaba and Amano, 19Xfl;
tion capacity of n-alkyl sulfates was closely correlated with l'v1uramoto et at., 1990; Souza and Wa>senmm. 1996 ), and it
the irritational potential, the maximum was found at C 12 depended heavily on the environmental conditions such as
analogue (Wilhelm c't al., 1993). the density of sea traffic ( Decemhrini et aL, 19<)5 ), the
intensity of offshore oil and gas exploration (Tkalin, 1993)
and the diurnal discharge of sewage (Kant in et al., 1981 ).
3. Adjuvant effects in pharmaceutical formulations The efficiency of the wastewater purification processes
concerning the concentration of alkyl sulfate detergents in
Anionic surfactants can considerably influence the bio- the effluent has to be controlled (Fendinger et aL 1992)
logical efficiency of the active ingredients in pharmaceutical because the incomplete purification of waste waters may
formulations (Gould et 2000 J either by direct binding to result in the contamination of the groundwater by anionic
340 T Cverluiti eta!. I Environment International 28 (2002) 337--348

detergents (Zoller. 1993). Many methods have been devel- transducer system is suitable for the evaluation of the
oped for the extraction and removal of anionic surfactants aerobic biodegradability of anionic sulfate and nonionic
from water by both physicochemical and microbiological ethoxylated surfactants. Surfactants were decomposed in
techniques. Physicochemical processes included the appli- 12 days at 25 oc except ethoxylates prepared from alcohols
cation of supported liquid membrane that removed effi- with a high degree of branching ( Diaz and Kravetz, 1995).
ciently linear alkylbenzene sulfonates from water at trace The biodegradability of anionic and nonionic surfactants
level (:V1iliotis cl. al., 1996 ), and various adsorption pro- under anaerobic conditions was also established in the
cesses. Thus, adsorption on activated carbon and coagula- automated pressure transducer system (Salanitro and Diaz,
tion/precipitation procedures have been tested for the J9Q5). The relationship between molecular structure of
removal of anionic and nonionic surfactants from waste- linear alkylbenzenesulfonates and their decomposition rate
water. It was found that the methods were more effective for in river water and sediments was determined. The data
anionic than for nonionic surfactants, the average removal indicated that decomposition followed a first-order kinetics,
being 67.4% and 31.7%, respectively (Atial:hi ct al., 1990). the half-life of mineralization being 15-33 h. The length of
Various destructive techniques have also been applied for alkyl chain, the position of the phenyl group did not
the removal of anionic surfactants from waters. The effect of influence the decomposition rate (Larson, 1990). The influ-
aqueous ozonation on the decomposition of anionic, cati- ence of salinity, temperature and the presence of sediment
onic and nonionic surfactants has been established many on the decomposition rate of sodium dodecylbenzene sul-
times. The results were earlier reviewed (Delanghe et al., fonate in seawater was investigated. It was concluded that
1991 ). The oxidative treatment of p-toluenesulfonic acid the effect of salinity is negligible but the degradation rate
using hydrogen peroxide has been reported too (Stoftler :md increased considerably with increasing temperature. The
LufL 1999). Gamma irradiation has also been proposed for presence of sediment also enhanced the rate of biodegrada-
the destruction of nonionic and anionic surfactants in tion probably due to the accumulation of surfactants and
industrial wastes (Perkowski d aL 1tJ?-\4 ). bacteria on the surface of the sediment (Quiroga ct aL
Because of simplicity and relatively low cost, a consid- 19R9). An extensive screening project resulted in the selec-
erable number of microbiological systems using various tion of alkyl sulfosuccinate-degrading bacteria more effi-
pure and mixed cultures and different fermentation condi- cient than those found in culture collections (Pruksova eta!.,
tions have been employed for the enhancement of the 199Sa ). The capacity of Comamonas terrigena N3H and C.
decomposition rate of surfactants. Because of the consid- terrigena N IC was the highest for the biodegradation of
erable quantity of anionic surfactants released in ground and alkyl sulfosuccinate surtactants (Proksovt1 et al... 1997). It
waste waters, the fate of this class of pollutants has been was found that the decomposition of dialkyl sulfosuccinates
extensively studied (White and Rus;;d!, !992). Thus, the followed first-order kinetics (Vrbanov~i et aL 1997). Bac-
successful stream periphytic biodegradation of C 1ralkyl teria (C. terrigena N3H) immobilized in polyurethane foam
sulfate at concentrations two orders of magnitude higher have also been successfully used for the biodegradation of
than usual was reported (Lee ct a!.. 1997). The rapid the anionic surfactants dihexyl sulfosuccinate and dioctyl
degradation of C 1ralkyl sulfate was also observed in a sulphosuccinate (Roig et aL 199?-\l. The highest decompo-
continuous-flow stream mesocosm (Gucke11 ct al., 1996) sition rate was found at pH 7.5 and at 50 oc temperature
and the use of the surfactant-degrading bacterium Pseudo- (Huska et al.. 1996a). Not only polyurethane foam but also
monas l2B immobilized in polyacrylamide gel (White and alginate gel was successfully employed for the immobiliza-
Thumas. !990; Thomas and White. 1990, 1991 ), glass tion of the strain C. terrigena N3H (Husb et al., 1996b,
support (Jerablwva et al., 1999), and polyurethane foam l997a). It was further established that starvation enhanced
( Roig et al., 1999) has been reported. However, another the biodegradation capacity of C. terrigena (T{lth et aL
study revealed that the ability of epilithic bacteria to degrade 199h; Huska et al., 1997b ). The decomposition process of
sulfonated surfactants was lower than their overall capacity anionic surfactants is not entirely understood. Not only the
to degrade other surfactants (Lee et at., 1995 ). The biode- biodegradation of the alkyl chain but also the desulfonation
gradation of alkyl sulfate surfactants in heterogeneous of linear alkylbenzenesulfonate surfactants and related com-
(water-sediment) environments has been studied in detail pounds by bacteria was reported (Ke11esz et aL 1994). It
(Russell et al., 199 l ). The results suggested that the surfac- was established that the hydrophobicity of the bacterial cell
tants adsorb to the river sediment, stimulating the simulta- is modified during the biodegradation of anionic surfactants
neous attachment of bacteria. The adsorption process ( 'v1archesi ct al., 1994a) and the first biodegradation product
accelerates the biodegradation of alkyl sulfate surfactants of SDS is dodecan-1-ol (Marchesi et al, 1994b;. The
(Marchesi et al., 199la,b: White, 199"). It has been further biodegradability of anionic surfactants is highly different;
established that the biodegradation of anionic surfactants therefore, the identification of persistent anionic surfactants
was more rapid in mixed cultures than in isolated ones. in sewage effluent is of considerable practical and theoret-
Bacteria preferably degraded the alkyl substructures of the ical importance (Cane and Duti!s, 1991 ). Various combined
surfactant molecules (Sigoillo1 and Nguyen. 1990: G!ludar chromatographic techniques identified the persistent anionic
et aL 1999). It was found that an automated pressure surfactants as linear alkylbenzene sulfonates, sulfophenyl-
T Cverluiti eta/. I Environment lntemationa/ 28 (20112) 337-348 341

carboxylated linear alkylbenzene sulfonates, tetralin and 4.3. Beneficial effects


indane sulfonates, and alkylphenol polyethoxylate carbox-
ylates (Field et al., 1992). Because of their amphoteric character, anionic surfac-
tants can adsorb on both hydrophobic and hydrophilic
4.2. Adsorption, desorption and leakage from solid matrices surfaces, can interact with hydrophobic and hydrophilic
molecules either by binding or by forming mixed micelles.
Pollution of solid matrices such as soil, sediment, etc. by The interactions can facilitate desorption of a wide range of
anionic surfactants has also been frequently demonstrated. polar and apolar environmental pollutants (Burris and Ant-
Because of their marked biological activity, the mechanism worth, 1992).
of adsorption, desorption and leakage of anionic surfactants
in soils and sediments has been studied in detail (Marchesi 4. 3.1. Enhancement (){ the desorption and leakage (){
ct al.. l 9\l I a) and the parameters influencing these phys- pesticides
icochemical parameters have been vigorously discussed. It The enhancement of desorption of pesticides by various
is generally accepted that advection and dispersion are the surfactants has been vigorously studied. Thus, a thin-layer
most important processes governing soil transport. How- chromatographic method was employed for the elucidation of
ever, it was indicated that capillary forces in dried soils may the effect of anionic, cationic and non ionic surfactants on the
have a considerable impact on the mobility of anionic mobility of the pesticides diazinon, atrazine, metolachlor and
surfactants (Zim ct aL 1993 ). The leakage of an alkyl ether acephate in soil. The results indicated that both the character
sulfate and a linear alkylbenzene sulfonate (LAS) surfactant of the surfactant and the hydrophobicity of the pesticide play
was studied using various soils. It was established that the a decisive role in the strength and selectivity of the effect
soil parameters exert a considerable influence on the mobi- (!\ rien7o ct al.. !995 ). Anionic surfactants may promote the
lity of the anionic surfactants tAllrcd ;md Brown, 19%). removal of pesticides form soil while carbon-rich wastes
Another study indicated that addition of SDS to the soil reduced the leakage ofthe same pesticides (lglcsias-Jimcnez
reduces the soil's hydraulic conductivity; the effect depends ct ul., 1997). It was established that not only the leakage but
on the concentration of SDS and on the clay content of the also the adsorption of pesticides on a sandy loam soil
soil (Liu and Roy. l 095). It was further found that anionic considerably depended on the character (anionic, cationic,
surfactants with twin head group are less liable to precipitate nonionic) and concentration of the surfactants and on the
and to adsorb to soil particle while their ability to soluble hydrophobicity of the pesticides (Iglesias-Jimenez ..;t a!..
organic contaminants is similar to the surfactants with a 1996 ). Anionic and cationic surfactants influence the adsorp-
single head group (Rouse ct aL 1993). The behavior of the tion strength of the pesticide carbofuran in soil, indicating
anionic surfactant, dodecylsulfate, in sediment and soil was that the addition of surfactants may influence the efficacy of
studied in detail. The results indicated the involvement of carbofuran to control nematodes (Singh. !994: Singh ..:t al.,
precipitation, micellization and micellar counterion binding 2000). Anionic surfactant not only modifies the desorption
in the adsorption. The relative importance of these phys- rate of pesticides but also accelerate their photocatalytic
icochemical processes markedly depended on the concen- decomposition as demonstrated on the case of the hydro-
tration of the surfactant (Jafvert and Heath, 1991 ). The phobic pesticide permethrin ( Hidaka ct aL 1992 ).
marked dependence of pH on the adsorption of sulfated
surfactants to a sandy soil has also been demonstrated 4.3.2. Enhancement ()/"the desorption and leakage of other
(Huang and van Bentschoten, 2000 ). A model was proposed environmental pollutants
for the description of the sorption of anionic surfactants on Surfactants can also be employed for the enhancement of
soils, sediments and sludges. Unfortunately, the model was the desorption of other environmental pollutants. Thus, the
not suitable for the prediction of desorption processes ( Di influence of anionic, cationic and nonionic surfactants on
Toro et aL I 'JlJO). desorption of the explosive trinitrotoluol (TNT) from soil
Because of the complexity of soil-surfactant systems, was compared. It was established that desorption-enhancing
the number of studies dealing with the decomposition of effect of SDS was higher than that of the cationic and
anionic surfactants adsorbed on solid matrices is fairly low. nonionic surfactants (Taha et al., l 'J97l. The influence of
High differences were observed between the adsorption SDS and hydroxypropyl- and methyH'>-cyclodextrin on the
capacity and biodegradability of surfactants in soil. Ethoxy- recovery of another explosive, hexahydro-1 ,3,5-trinitro-
lated anionic surfactants (sodium Iaury! ether sulfates) 1,3,5-triazine (RDX), from soil was also studied. The results
showed lower adsorption capacity than nonethoxylated proved that both cyclodextrins (CDs) and SDS increase the
anionic and nonionic surfactants; however, these surfactants water solubility of RDX. The effect of CDs was attributed to
were easily biodegradable (Sabatini et al.. I996 ). The their capacity to form inclusion complexes with the explo-
temperature also exerts a marked influence on the behavior sive (Hawari et al., 1996 ).
of anionic surfactants in soil. Thus, the half live of LAS in The enhancement of the dissolution of various halogen-
the soil strongly depended on the season being 5-25 days in ated pollutants and PAHs has been many times established.
summer and 68-117 days in winter (Litz et aL !087). Sodium dodecylbenzene sulfonate was more effective than
342 T Cserhati et a!. I Environment International 211 (2002) 337-3411

the nonionic surfactant Triton X-485 for the desorption of anionic surfactants can effectively enhance oil recovery in
pentachlorophenol adsorbed on soil particles (BaneJj i ct al., hot water flotation trom bitumen and tar sands (Schramm
1993 ). Anionic surfactants can form microemulsions with and Smith. 1987). Rhamnolipid surfactant consisting of two
various chlorocarbons, enhancing in this manner their sol- rhamnose sugar molecules bonded to one or two hydrox-
ubility in water and promoting soil remediation {Baran el3L ydecanoic acids modified the partition of a polar hexade-
1994 ). SDS enhanced also the apparent solubility of I ,2,4- cane in the subsurface (Tbanganumi and Shreve, !994 ). The
trichlorobenzene (DiVincenzo and Den teL 19i.Jii ), hexachlor- application of various surfactants in the oil industry has
obenzene and anthracene (Liu et al.. 1995) in the aqueous been discussed in detail and the influence of the physico-
phase of the soil (l'aya-Percz e1 ~1!., 1'1%). The efficacy of chemical characteristics of surfactants on their performance
anionic, cationic and nonionic surfactants to remove hazard- is emphasized (llall, 19~6).
ous organic compounds (I ,2,4-trichlorobenzene, aniline,
phenol and 2,4-dichlorophenol) from soil was compared. 4.3.3. Enhancement of the removal of inorganic pollutants
The data indicated that the performance of cationic surfac- Anionic surfactants may influence not only the mobility
tants was inferior to the other class of surfactants {Rajput ct of organic molecules in various systems but also that of the
aL 1994). The micellar solubilization of decahydronaphtha- inorganic ones. Thus, it has reported that the desorption of
lene, naphthalene and 1-naphtol by hexadecyl diphenyl oxide lead from soil particles can be increased by the addition of
and disulfonate were assessed. Semiequilibrium dialysis anionic surfactants (Huang ct a!.. 1997). SDS enhanced
proved that the effect of surfactants highly depended on the markedly the efficiency of the extraction of chromium from
type of contaminants (Rouse ct al., I 9Y5). The suitability of soil but the efficacy was lower than that of sodium phos-
anionic, cationic and nonionic surfactants and colloidal gas phate (Puis ct a!., 1994 ). The concentration of free cadmium
aphron suspensions was checked for the removal of naph- has been successfully reduced by complexing it with an
thalene from soil. Each adjuvant caused the increase of the anionic monorhamnolipid biosurfactant produced by Pseu-
removal of naphthalene (Roy ct aL !995). The partition of domonas aeruginosa ATCC9027 (Tan ct al., 1994 ). Anionic
pyrene, phenanthrene and naphthalene between dodecylsul- and cationic surfactants can also be employed to enhance
fate micelles and natural media (sediment and soil) was the efficiency of the removal of arsenic from high ionic
determined. The results indicated that the sorption potentials strength geothermal fluids by adsorptive bubble flotation
of the hydrophobic compounds are similar to surfactant (De and Thomas, 19X5 ). Anionic surfactants decreased the
micelles and natural media (.lafVcJi, 1991 ). The improvement uptake of various elements (Cd, Ni, AI, Ca, Mn) in the root
ofthe removal ofpolyaromatic hydrocarbons from soil with and top of water hyacinth (Eichhornia crassipes) but the
surfactant solution has also been proven ( Dur ct aL 2000a) underlying mechanism was not explained in detail (Mura-
and the heterogeneous dissolution of benzo(a)pyrene from moto and Oki, !9X4: Muramoto ct al.. llJX9 ).
solid deposit has been demonstrated (l)ur et al., 2000b). The
efficacy of micellar-enhanced ultrafiltration and air-stripping 4.3.4. Adsorption-increasing effect~
processes was tested for the recovery of hexadecyl diphen- Anionic surfactants not only facilitate the dissolution and
oxide disulfonate and dodecyl diphenoxide disulfonate removal of various environmental pollutants but they can
together with naphthalene and trichoroethylene. Both meth- increase adsorption under given conditions. Thus, anionic
ods successfully concentrated the surfactant-contaminant surfactants can increase the adsorption of tetrachloride,
systems but were not able to separate them 1Llpe eta! .. 1996). naphthalene and phenanthrene on the surface of aluminium
Surfactants can also be used for the removal of petro- oxide resulting in improved water pollution control (Park
chemical products from polluted soil. It was found that from and Jafte. 1993 ). Anionic surfactants coated on the surface
the 22 surfactants investigated, anionic ones showed the of alumina support considerably enhanced the sorption of
best performance, promoting the removal of diesel oil phenanthrene from water. The effect was higher with the
adsorbed in various soils. (Peters et a!., 1992). Anionic diphenyloxide disulfonates having a longer apolar alkyl
and nonionic surfactants have been successfully employed chain in the molecule (Sun and .Jaft~. ]99(, ). Phenanthrene
for the removal of residues of petroleum products from can also be removed from a soil-slurry by using anionic
shallow sandy aquifers {Abdul d al.. I990 ). It was further surfactant coated oxide support and separating the coated
proved that oily wastes pretreated with anionic surfactants oxides by magnetic separation technology (Park and Jaffe.
can enhance the dispersibility of oils in soil, resulting in 1995 ). SDS adsorbed on the surface of titanium dioxide
increased biodegradability (Rasiah and Voroney. 1993 ). A promoted the adsorption of 2-naphtol and Cu 2 + facilitating
combined technique was proposed for boosting the decom- their simultaneous removal (F.sumi et aL. 1998 ). SDS has
position rate of nonvolatile petroleum hydrocarbons in soiL also been adsorbed onto ferrihydrite and employed for the
The method employed the anionic surfactant guanidinium extraction of sparingly soluble organic compounds from
cocoate, hydrocarbon-degrading bacteria and the bulking water. The model compounds (toluene, trichloroethylene
agent vermiculite (Walter et al.. 1997). The presence of and p-xylene) were successfully removed form water at
petroleum contaminants has also influenced the biodegra- low pH. Desorption of both SDS and organic pollutants
dation of anionic surfactants 1Sarwar et a!.. 1q94 ). Natural occurred at higher pH (llolscn e1 aL, 199! l. It was further
T C~erhuti el a/. I Environment International 211 (2002) 337-34/1 343

confinned that adsorptive micellar floculation using SDS is show high differences according to type of the surfactants
a suitable technique for the removal of 2,4-dichlorophenoxy and the species under investigation (Lewis. 1990). The
acetic acid from solution ('l'all:ns-Aks~PJL 2001). effect of SDS on the duckweed Lemna minor L. depended
significantly on the concentration. SDS increased the rela-
4.3.5. Miscellaneous beneficial effects tive growth rate at lower concentrations but showed marked
It was established that sodium dodecylbenzenesulfonate inhibition and accumulation at higher concentrations (Dirli-
increases the efficiency of the precipitation flotation techni- gcn and Inee, 1905 ). Another study showed that increasing
que to remove fine particles from an aqueous medium concentration of anionic detergents and other organic com-
(Kubota d al., 1990). Anionic surfactant sodium Iaury! pounds resulted in the considerable enhancement of phyto-
sulfate enhanced markedly the photopotential and photo- plankton biomass, density and primary productivity in
current in a solar energy cell ~Khamesra et aL 1990). The polluted seas (Tkalin ct aL 1993 ). Anionic-nonionic sur-
influence of various types of surfactants on the mechanical factants mixtures used as oil dispersants showed marked
dewatering of highly decomposed fuel-farde peat was com- toxicity to the early life stages of topsmelt (Atherinops
pared. Cationic surfactants show marked positive effect, a[finis) and kelp (Macrocystis pyr(fera) (Singer et al.,
nonionic surfactants were ineffective and anionic ones ]9<)4).
exerted a negative impact on the dewatering process
(C'uoper et al., 19XX). 4.4.3. Toxicity towards invertebrates and crustaceans
Because of the considerable amount of anionic surfac-
4.4. Adversary effects tants released in water, the life cycle of aquatic animals has
also been influenced by the anionic surfactants. A QSAR
Much efforts were devoted for the evaluation of the study has been employed for the elucidation of the relation-
adversary effects of anionic surfactants on the environment. ship between the chronic toxicity of various surfactants and
The earlier results concerning the consumption of anionic other compounds towards the rotifer Brachionus calyciflo-
surfactants, their impact on marine environment, on the rus. Calculations indicated that toxicity increases with
coastal flora and their fate in wastewater treatment facilities increasing length of the alkyl chain within the different
have been previously reviewed ( Lesoucf et al., I ll93). Much classes of surfactants. The result suggests the involvement
efforts has been devoted to the elucidation of the relation- of hydrophobic interactive forces in the mode of action of
ship of the relationship between toxicity and molecular surfactants. In this instance, anionic surfactants exposed
parameters of anionic surfactants, the results considerably relatively low toxicity (Versteeg et al., 19<)7 ). Another study
depending on the surfactant-organism pair under investi- indicated that linear alkylbenzene sulfonate can inhibit the
gation. Thus, QSAR studies indicated that molecular lip- development of the soil-living collembolan Folsomia fime-
ophilicity exerts a considerable influence on the toxicity taria. The EC 50 values causing 10% inhibition were 185
(RobeJts, I')I) I), and the effect depends on both the char- mg/kg for frequency of molting, 163 for juvenile growth
acter of the polar head group and the length of apolar alkyl and 147 for reproductive effects (Holmstrnp and Krogh,
chain (Dyer ct al, 2000 ). 1996 ). The LC 50 values of SDS were determined for several
estuarine crustaceans. The data indicated that the sensitivity
4.4.1. Toxicity towards microorganisms of crustaceans towards SDS shows high variations: blue
The effect of SDS and Tween 80, a nonionic surfactant, crab (Callinectes sapidus) 9.8 mg/1; grass shrimp 34 mg/1
on the growth and nitrogen fixing capacity of the cyano- and mysids 48 mg/1 (Whiting et a!., 1996 ). The influence of
bacterium Gloeocapsa was compared. Both growth and alkyl ethoxylate sulfate and alkyl sulfate on various inver-
nitrogen fixation was inhibited at 50 ppm SDS and 500 tebrates and fish was determined. The results indicated that
ppm Tween 80. The results clearly prove that the toxicity of snails were not affected by surfactants, the sensitivity of
SDS considerably higher than that of the nonionic surfactant clams was the highest to the anionic surfactants (Belanger et
(fozum-Calgan and Atay-Ciuneyman. 1994 ). It was proved al., 1995a). It was found that high concentrations of alkyl
that dialkyl sulfosuccinates also influence the activity of sulfate and alkyl ethoxysulfate impaired the populations of
microorganisms. Thus, they stimulate respiration rate at low clams and mayfies in a stream mesocosm the no effect
concentration and inhibit it at higher concentrations. The concentrations being 224 and 251 mg/ml, respectively
ID 50 value depended markedly on the chemical structure of (Belanger et al., l995b ). Another study indicated that the
the surfactant ( CTrcgorovft et aL, l IJ')(J). Dialkyl sulfosucci- chronic and sublethal toxicity of surfactants to aquatic
nate anionic surtactants influence not only the respiration animals occur at very low concentrations such as 0.1 and
but also the activity of enzymes and the growth of the 0.002-40 mg/1, respectively U e\vi~. 1991 ). The effect of
degradative bacteria ( Proksov~i et aL 199Xb ). linear alkylbenzenesulfonates on the freshwater tubific spe-
cies Branchiura sowerby and Limnodrilus h(){fmeisteri was
4.4.2. Toxicity towards aquatic plants determined. It was established that the surfactant exerted a
The toxicity of anionic surfactants towards algae has considerable effect only on the number of cocoons (Castel-
been demonstrated. It has been found that the toxic effect lato and Negri~olo, 19119). The sensitivity of aquatic inver-
344 T Cserhati el a/. I Environment International 2R (2002) 337-348

tebrates show high variations both according to the species Acknowledgements


and the type of surfactants. Daphnia magna was found to be
the most sensitive. The acute toxicity values varied between This work was supported by the grant HP-206 from the
1.7 and 270 mg/1 for linear a1kylbenzene sulfonate, 1.0 and Ministry of Environmental Protection.
6.8 mg/1 for nonionic a1ky1ethoxylate, and 0.1 and 58 mg/1
for the cationic cetyl trimethyl ammonium chloride (Lewis
and Suprenant Jl)i\3: Verge~ and Moreno, 200(1).
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