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A RESEARCH PROPOSAL ON THE KINETICS OF DEGRADATION OF SODIUM LAUROYLSARCOSINATE IN THE PRESENCE OF FENTONS REAGENT

BY

OLORUNYOMI JOSEPH FUNSO

SUPERVISOR: DR. O. OWOYOMI

SEPTEMBER, 2012

TABLE OF CONTENT CONTENT TITLE ABSTRACTS INTRODUCTION AND LITERATURE REVIEW EXPERIMENTAL SECTION AND PROPOSED METHOD OF RESULT ANALYSIS REFERENCES PAGE 1 3 4 8 18

ABSTRACTS This work will be carried out in order to study the kinetics of degradation of sodium lauroylsarcosinate in the presence of Fentons reagent at low pH and a temperature of 250C in aqueous medium at predetermined times. Studies have revealed that the rate of biodegradation of surfactants largely depends on whether the condition is aerobic or anaerobic as some tend to be persistent under anaerobic conditions, also with the possibility of toxic byproducts being involved. However with advanced oxidation processes such Fentons reaction, there is a complete oxidation of the surfactant to stable inorganic compounds. In this study, the Fentons reagents will be used in varying concentrations but which are much higher than the initial concentrations of the surfactant. To follow-up the rate of degradation, the surfactants concentrations will be determined spectrophotometrically using methylene blue (a cationic dye). The surfactant-dye interaction would have been previously studied using the methods of continuous variation and conductometry in the premicellar regions of the surfactant in order to determine the stoichiometry of the interaction. However, the rate law will be determined from the degradation studies.

INTRODUCTION AND LITERATURE REVIEW Surfactants have been defined as a diverse group of compounds that are designed to have cleaning or solubilization properties (Guang-Guo, 2005; Mousavi et. al., 2011). They generally consist of a polar head group (which may or may not be charged but is well solvated in water), and a nonpolar hydrocarbon tail (which is not easily dissolved in water). A simple classification of surfactants is based on the nature of the polar head. The main classes have been identified as ionic, nonionic, amphoteric and Germini surfactants (Tadros, 2005). All surfactants exhibit the tendency to self-associate in order to produce an aggregation polymer called micelle at the surfactant concentration known as Critical Micelle Concentration (CMC). For this reason, surfactants have been used to perform various functions in some processes or products, in contrast to other organic chemicals that may be used to produce another chemical or product (Rosen, 2004). For instance, the catalytic ability of surfactants for some reactions has been well established (Olanrewaju et. al., 2007; Samiey and Ashoori, 2011), surfactants are used in dispersing dyes of low solubility in the textile and printing industry (Sabina and Span, 2000; Petra, 2004; Halide and Kartal, 2007) and the possible use of surfactants to effect and accelerate the degradation of the toxic pollutant, Polycyclic Aromatic Hydrocarbon has been reported (Li and Chen, 2009). BIODEGRADATION OF SURFACTANTS Since surfactants are used on a large-scale basis from everyday household use to industrial cleaning and textile manufacturing, there are concerns regarding their effects, particularly their biodegradability in the environment and their toxicity to marine organisms. The different types of surfactants that are now in use are of different rate of biodegradation in the environment.
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Guang-Guo (2006) noticed that while most classes of surfactants readily biodegrade under aerobic conditions, some are persistent under anaerobic conditions. Tadros (2004) drew attentions to the factors upon which the rate of biodegradation depends: surfactant concentration, the pH of the environment, temperature, solubility of the surfactant in water (as the soluble ones are more readily biodegradable than the less soluble ones which accumulate in the lipid compartment of the organism) and the degree of branching of the alkyl chain in the hydrophobic part of the surfactant (since extensive branching tends to reduce the rate of biodegradation due to steric hindrance, preventing the surfactant molecule from getting close to the active site of the enzyme). EFFECTS OF SURFACTANTS AND THEIR BIODEGRADATION PRODUCTS ON LIVING ORGANISMS It is a known fact that surfactants pose threat to the aquatic environment (Mehrvar and Venhuis, 2004; Guang-Guo, 2005). Even at low concentrations, they reduce the surface tension of water, and therefore may increase the adsorption of organic compounds such as pesticides and phenols on the skin and membranes of aquatic animals and humans (Othman et. al., 2012). Lee et. al., (2000) opined that in addition to the toxicity and aesthetic problems that they cause; they also bring about the obstruction of air transportation from air to water. Surfactants become more dangerous to aquatic lives when they biodegrade to produce harmful intermediates and by-products. For instance, alkylphenols (nonylphenol and octylphenols) which are degradation products of alkylphenol polyethoxylates- a class of widely used nonionic surfactant-have been reported to have estrogenic effects and also possess the ability to bioaccumulate in aquatic organisms in anaerobic environments(Guang-Guo, 2005). The

eventual conversion of a surfactant into stable inorganic compounds will generally involve several successive transformations which would depend on the conditions of the environment. ADVANCED OXIDATION PROCESSES The numerous factors upon which complete biodegradation of surfactants depend have led to people to use the advanced oxidation processes which convert any organic compound to stable inorganic compounds. Mehrvar and Venhuis (2004) discussed some advanced oxidation techniques as follows: a. Photocatalytic Degradation of Surfactants: This method uses a catalyst that is chemically and biologically inert, easily recovered and reusable in the presence of ultra-violet radiation to oxidize organic pollutants, most especially surfactants. A compound that is normally used for this purpose is titanium (IV) oxide, TiO2. The rate of reaction is found to be dependent on the adsorption of the surfactant on the surface of the catalyst in addition to other optimum conditions (pH and temperature). The process has been found to be successful in mineralization of surfactants except for the fact that takes a long time (5 hours to degrade 80% of initial linear alkylbenzene sulphonate at a =254nm). A more efficient technique is the use of hydrogen peroxide instead of

titanium (IV) oxide to oxidize surfactant. b. Wet Air Oxidation of Surfactants: This degradation technique is suitable for the treatment of organic or inorganic pollutants dissolved in water. It is dependent on high temperatures and pressures operating in the range of 1743200C and 2.1720.7 MPa, respectively. At high enough temperatures and pressures, the solubility of oxygen increases and provides the driving force for oxidation. The source of oxygen is either

compressed air or pure oxygen. The high pressures are required to keep the water in a liquid state. Wet Air Oxidation provides the same oxidative ability as flame combustion but at much lower temperatures. c. Sonochemical Oxidation of Surfactants: This technique uses high-frequency sound wave at high temperatures and pressure to cause homolysis of water to produce radicals (H. and OH.). The attack of the surfactant molecules by the radicals and thermal decomposition are the main oxidation pathways. The rates of degradation depend on the surfactants initial concentration. d. Fentons Treatment of Surfactant: The Fentons system used in treating a wide variety of organic pollutants consist of Fe2+ combined with hydrogen peroxide H2O2 under acidic condition. It has been efficiently used as a chemical process for wastewater treatment (Hassan et. al., 2008).The Fentons reagent can generate a huge amount of hydroxyl radical with powerful oxidizing ability which attacks the organic substrate. It is highly efficient but this depends mainly on the hydrogen peroxide concentration, Fe2+/H2O2 ratio, pH and reaction time. When compared with other advanced oxidation methods, it is better because its raw materials are cheaper, it does not require expensive instrumentation and it generates a greater amount of oxidants. The widely accepted mechanism for the reaction is as follows: +
. .

+ +

+ +

(Hassan et. al., 2008)

THE SCOPE OF THIS WORK The surfactant that will be used in this study is Sodium lauroylsarcosinate (which would thereafter be referred to as SNa)

O O N ONa+

N-lauroylsarcosine, Sodium salt

Sodium lauroylsarcosinate is a surfactant used in a wide range of personal care products such as in the making of toothpaste and in the cosmetic industry. However, like other surfactants, it has some environmental effects. Anwal et. al. (1983) reported its disruptive effect on the outer membrane of Pseudomonas cepacia by altering the fluidity of the outer membrane of the organism. The degradation of the surfactant will be carried out in the presence of Fentons reagents (Fe (II)/H2O2 system) under specific conditions of pH, temperature and at predetermined times. To monitor the rate of degradation, the surfactant concentration will be determined spectrophometrically as earlier described by Smith (1963) and then later by Koga et.al. (1995) and Kotchi et.al. (2010). AIM OF THE STUDY This work will be aimed at studying the kinetics of degradation of sodium lauroylsarcosinate in the presence of Fentons reagent.

OBJECTIVES 1. The method of continuous variation will be used to study the interaction between methylene blue, a cationic dye with the surfactant. 2. Conductometric technique will also be used to study the surfactant-dye interaction and this technique will be compared with the first one in order to assess the interaction. 3. Fentons oxidation of the surfactant will be studied and the rate law for the process will be derived.

EXPERIMENTAL SECTION AND PROPOSED METHOD OF RESULT ANALYSIS In wastewater analysis and anionic surfactant degradation studies, several techniques such as microbial sensor, amperometric biosensor, ion-pair formation with insitu flow injection analysis using dynamic surface tension detection and chromatography have been used to determine the surfactant content of a given reaction mixture (Pal et. al, 2005; Hassan et. al, 2008), but these require expensive instrumentation. A simplified spectrophotometric method using

methylthioninium chloride also known as methylene blue (MBCl), a cationic dye, will be used in the extraction and determination of residual surfactant content in the reaction mixture. This method relies on the understanding that any surfactant molecule present forms an ion-pair with the cationic dye and this can be extracted in a suitable organic solvent (Koga et. al., 1995; Kotchi et. al., 2010).
N

S+ Cl-

Methylthioninium chloride

Reagents: FeSO4.7H2O, H2O2 ,Methylene Blue, Sodium N-Lauroylsarcosine, Chloroform, H2SO4 and NaOH (to control the pH of the Fentons reaction)

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The Interaction between Methylene Blue (MBCl) and Sodium lauroylsarcosinate (SNa) Two methods will be employed in studying the interaction between MBCl and SNa in order to determine their stoichiometric composition in the ion-pair and ion-pair formation constant (Kf). These are Jobs method of continuous variation and Conductometric technique. Jobs Method of Continuous variation: This method was initially used to study and determine the formula and the formation constants of transition metal complexes in solution. It was originally described by Ostromisslenski in 1911; the principles were outlined by Denison in 1912, but the method was named after Paul Job who in 1928 published a detailed application of the technique to study a wide range of coordination compounds. This method has been used by researchers to study the dye-surfactant interaction in recent time (Petra and Span, 1999; Sinem and Melda, 2003; Petra, 2004). Where only one complex is important and the measured experimental property depends linearly on concentration, the method is capable of yielding both the stoichiometric composition and the association constant of the complex. (Petra and Span, 1999) Preparation of Solutions for the Determination of Stoichiometry of the Ion-Pair: Equimolar stock solutions of MBCl and SNa of concentrations in the premicellar regions of SNa such that 10 , 5.0 10 , 7.0 10 and = respectively would be prepared = 1.0 10 ,and 9.0 10 , 3.0 .

The Critical Micelle Concentration (CMC) of SNa is 1.457 10

(Venkataraman

and Subrahmanyam, 1985). The temperature of 250C would be maintained throughout this study. The absorbance of the solutions of the dye would be taken in order to determine its
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molar extinction coefficient( ). Both solutions of MBCl and SNa would be mixed in a 10 ml flask in varying volume ratios such that unit volume of SNa is added to ( ) unit volume of

MBCl solution. A series of ten mixed solutions are prepared from each pair of MBCl and SNa stock solutions. The absorbance A of the mixtures would be taken and recorded. Determination of Stoichiometric ratio of MBCl and SNa in the Ion-Pair Formed: The stoichiometry is determined by plotting the corrected absorbance A of particular mixtures against the volume ratio of the surfactant. A represents the difference between the

measured absorbance Aexp and the theoretical absorbance Athe: = (1)

The theoretical absorbance is the absorbance of the mixture if no reaction has occurred in the solution, so that: = (1 ) + (2)

Where d and s are the molar extinction coefficients of the dye and surfactant respectively, and are the stock concentration of the dye and surfactant respectively and is the volume

ratio of the surfactant in the mixture. existing in the solution. = +

represents the sum of absorbances of all species

(3)

Where ds is the molar extinction coefficient of the dye-surfactant complex (the ion-pair) and Cds is the concentration of the ion-pair; and dye molecules respectively.
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and

are the concentrations of the free surfactant

If the absorbances are measured in the visible region of the electromagnetic spectrum where the surfactant would show no absorption, then we could calculate the corrected absorbance as: = (1 ) (4) against the volume fraction of = corresponding to the

Studies have revealed that the plot of corrected absorbance, the surfactant is a curve with a maximum or minimum at

combining ratio of the dye and surfactant in the complex (Petra and Span, 1999; Sinem and Melda, 2003; Petra, 2004). Determination of Equilibrium Constant of the Ion-Pair: Schaeppi-Treadwells Method Schaeppi-Treadwells Method is a derivative of Jobs method of continuous various which will be used in determining the ion-pair formation constant. It is a suitable method when only one stable complex is formed; however the method depends on the stoichiometric composition of the complex (Petra, 2004). Supposing there is a 1:1 formation of ion-pair between the cationic dye and the anionic surfactant; then the equilibrium constant is: +
Kf

(5)

The Kf can be obtained from the plot of corrected absorbance, of the surfactant . The measured at =

against the volume fraction


0

is compared to theoretical

which is to

derived by extrapolation of the linear parts of the curve to their intersection. The ratio of
0

represents the degree of association, (1-). = (1 )

(6)

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Where is the degree of unassociated ions; since the dye and the surfactant are of equal concentration, then as: =[
[ ][ ] ]

, then the equilibrium constant expression can now be written

( ( )

(7)

is the concentration of the dye and surfactant in a 1:1 ratio.

Conductometric Approach to Studying Dye-Surfactant Interaction: In order to study the ionpair formation between MBCl and SNa, the conductivity measurement would be done at the premicellar concentrations of the surfactant and at low concentration of the dye. The specific conductivities of the surfactant and the dye in the absence of the surfactant would be taken for about thirty different concentrations. The specific conductivity of the dye-surfactant system as a function of the surfactant concentration would be taken. To obtain the dye-surfactant system, a solution of the dye would be used to prepare the concentrated stock solution of the surfactant. All measurement would be taken at 250C. Determination of Equilibrium Constant: If we assume a 1:1 ion-pair formation, then the equilibrium reaction would be: +
K

(8)

In order to determine concentration of free and bound surfactant and dye ions as well as the value of the equilibrium constant, the measured conductivity which is the sum of the contribution of all free ions in the solution cannot be solely depended upon. A theoretical

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model which describes the condition within the solution must be applied. This model has been previously used by Bracko and Span (2001), Halide and Kartal (2005), Sibel and Duman (2006) and more recently Nora (2012) to study various surfactant-dye interaction conductometrically. The model assumes that the cationic dye MB+ and the anionic surfactant S- form a nonconducting ion-pair in the solution. Based on Kohlrauschs law, we know that: and Where and = = + + (9a)

(9b)

are the equivalence conductances of the dye and surfactant , , and are the equivalent ionic conductances

respectively at infinite dilution;

at infinite dilution. values can be determined experimentally from the specific conductivities of the surfactant and the dye by converting them to equivalent conductance using:

(10)

Where C is the molar concentration; the values of can be determined by plotting against . The intercept of the plot on the -axis is the . Using the values of and

from the literature, one can write: + = + ( + ) (11)

Then the equilibrium constant can be expressed as:

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[ [ ] [

] ]

(12)

Where[

], [

] and [

] are the concentrations of ion-pair, free dye and surfactant

ions respectively. The concentrations of the free ions cannot be easily determined and so, they are expressed in terms of [ ] and [ [ [ ] , the total dye and surfactant concentrations respectively, so that ] =[ ] =[ ] +[ ] and ] (13a) (13b)

] + [

The observed specific conductivity surfactant interaction. = +

can be expressed as sum of specific conductivity of if there were no surfactant-dye

and the specific conductivity of the dye

(14)

This means that before the ion-pair formation, the surfactant-dye interaction is negligible, and then; 10 = [ ] + [ ] + [ ] + [ ] (15)

But with the formation of ion-pair, a decrease in the concentration of free ions occur and so equation (14) can be written in terms of the concentration of the conducting species, free ions. 10 = [ ] + [ ] + [ ] + [ ] (16)

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Since the ion-pair is a non-conducting specie, then equations (13a) and (13b) can be rearranged to give the concentration of the free ions in terms of the total concentration of the dye and the ion-pair. [ [ ] =[ ] =[ ] [ ] and ] (17a) (17b)

] [

Equations (17a) and (17b) can be inserted into equation (16) in order to obtain:
10 = ([ ] [ ])+ [ ] + ([ ] [ ]) + [ ]

(18) Subtracting equation (18) from (15) cancels out the total concentration terms and yields the specific conductivity of the ion pair: 10 So that =[ ]( + ) (19)

is the difference between the theoretical and measured specific conductivities at a

givien surfactant concentration. Kohlrauschs law for infinite dilute solution of an electrolyte can be applied to equation (19) to obtain: 10 Where [ ]( + )=[ ] (20) value

is the equivalent conductance of the ion-pair at infinite dilution,

would be determined experimentally by measuring the specific conductivities of the dye and surfactants.

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The equilibrium constant can be calculated by inserting equations (17a) and (17b) into equation (12): =
[ ([ ] [ ] )([ ] ] [ ])

(21)

The Gibbs free energy for the ion-pair formation at 250C can be calculated as: = THE FENTONS REACTION The degradation studies of Sodium lauroylsarcosinate will be done at relatively lower concentration of the surfactant than the oxidant concentrations in order to be able to monitor the reaction rate. The initial concentrations will be at proportions [H2O2]0=100[SNa]0=2[Fe2+]0 at a constant temperature of 250C and a pH of 3. Procedure: An acidified water (pH=3) is used to prepare the surfactant at very low concentration (below its CMC) and the Iron (II) tetraoxosulphate (VI) salt. Hydrogen peroxide is freshly prepared in an amber bottle before the start of any experiment. The reaction takes place in 500 ml vessels that are opaque to light. A calculated volume of Fe2+ solution prepared is added to the solution of the surfactant and the mixture is then agitated with the aid of magnetic stirrer. 25 ml of this mixture is taken before the H2O2 is added. This corresponds to the concentration of the surfactant at time t=0. A known volume of H2O2 is then added to the remainder. To monitor the reaction progress, 25 ml of the sample after the H2O2 has been added is taken at various times (t= 1, 5, 15, 30, 45, 60, 90, 120 minutes). The H2O2 is only added at the beginning of the reaction. Each sample is neutralized by a known amount of sodium
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(22)

hydroxide to stop the reaction at the predetermined time. All samples are brought back to the working temperature for analysis. The reaction can be repeated at varying concentrations of the H2O2 and Fe2+ but at constant [SNa]0 in order study the effect of varying Fenton's reagent concentration on the oxidation of the surfactant. Analysis of the Samples: Alkaline solutions of chloroform and methylene blue would be added to each sample. The biphasic solution formed is then shaken thoroughly to ensure the distribution of the components throughout the organic and aqueous phases. The dye molecules should form ion-pairs with the residual surfactant molecules in the solution. It has been shown in an equilibrium studies of anionic surfactants (AS) with methylene blue, and their associated ion-pair AS-MB in water and chloroform phases, that both AS and MBCl molecules alone are never transferred to the chloroform phase but are rather associated forming an ion-pair AS-MB (Koga et. al., 1999). On this basis, the absorbance of the solution (in the chloroform phase) is then measured at a .

Determination of Surfactant concentration in the Samples: The absorbance of the chloroform phase is related to the surfactant concentration. This relationship can be determined by drawing a calibration profile. To obtain this, different standard solutions of surfactants are prepared and each is added to a chloroform- MBCl system. The mixture is agitated; the ion-pair extracted into the organic phase and the absorbance measurement is made. A plot of absorbance against the varying concentration of the surfactant gives the relationship between the measured absorbance and the concentration of the surfactant.

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Determination of Rate Law: the data obtained would be used to determine the rate law of the reaction.

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