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Abstract
The present study was used to probe the treatment of simulated wastewater containing cresols by Fenton process.
Experiments were conducted in a batch reactor to examine the effects of operating variables like pH, hydrogen peroxide
concentration (H2O2) and ferrous ion concentration (Fe2+) on chemical oxygen demand (COD) removal. The progress
of the degradation reaction was monitored by the decrease in COD content in the treated solution. The optimal reacting
conditions were experimentally determined and it was found to be [H2O2] 31.64 mM, [Fe2+] 0.90 mM for o- and p-
cresol while 0.72 mM for m-cresol at pH 3.070.2. The degradation efciency for cresol isomers was as high as 82%
within 120 min at optimum conditions. A pseudo-rst-order kinetic model was adopted to represent the Fenton
oxidation for cresols. The mineralization rate for cresols obeys the following sequence: m-4p-4o-. Maximum
degradation occurred at 30 1C for the temperature range of 2050 1C studied. The global activation energy for the rst-
order reaction was estimated to be in the range of 12.9016.25 kJ/mol. Air/nitrogen did not play an active role in
completely mineralizing the organic intermediates at the experimental conditions adopted. Irrespective of the position
of methyl group in o-, m- or p-position, the maximum dissolved organic carbon (DOC) removal efciency was 42%.
Only 2/5th of cresol was mineralized to CO2 by Fenton process. The results showed that the cresols were completely
oxidized and degraded into lower molecular weight aliphatic acids. Among the acids, acetic and oxalic acids were
identied as the major products formed during the degradation.
r 2005 Elsevier Ltd. All rights reserved.
Keywords: Cresols; Fentons reagent; Oxidation; Acetic acid; Oxalic acid; Mineralization
0043-1354/$ - see front matter r 2005 Elsevier Ltd. All rights reserved.
doi:10.1016/j.watres.2005.05.011
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V. Kavitha, K. Palanivelu / Water Research 39 (2005) 30623072 3063
The high oxidation potential of dOH radical because of the possibility of mineralizing the target
(E o 2:8 V), can oxidize organic substrates and miner- pollutants. Zheng et al. (1993) reported on ozonation of
alize them to CO2 and H2O. An exhaustive list of cresol isomers with the rate constant for o-, m- and p-
various classes of organic compounds, which can be cresol were 32 240, 60 870 and 45 460 M1 s1. Hetero-
treated by Fenton process was reviewed by Gogate and geneous photocatalytic oxidation using ultraviolet light/
Pandit (2004) and Neyens and Baeyens (2003). The titanium dioxide (UV/TiO2) was applied to treat cresols
coupled Fenton system with ultrasound cavitation was (Wang et al., 1998). Complete removal of cresols
studied by Lin and Ma (2000) using 2-chlorophenol, occurred within 2.5 h. Photo oxidation of creosote
where more than 99% of chlorophenol was decom- components containing xylenols using TiO2 and on
posed. Heterogeneous Fenton systems like Fezeolite goethite were studied by Terzian and Serpone (1995) and
(FeZSM-5) and Felaponite-based nanocomposite by Mazellier and Bolte (2000), respectively. Among
(FeLap-RD), where iron is coated on a solid support different AOPs, homogeneous Fenton process is one of
to use it for the degradation studies of phenol the powerful oxidative treatments available at room
(Fajerwerg et al., 1997) and reactive red HE-3B (Feng temperature and pressure with dOH radical as the
et al., 2003), respectively. reactive species. Recently, the role of dOH radical in
Cresols represent classes of chemical phenolic com- degrading organic compounds has been questioned and
pounds used extensively in resin manufacturing, herbi- ferrate species [Fe(OH)3(H2O)4]+ has been suggested,
cide like dinitro-o-cresol (DNOC), pharmaceuticals, which follows a non-radical mechanism for Fenton
tricresylic acid and surfactants. Wastewater from these oxidation (Bossmann et al., 1998). Since the products of
industries together with coal-conversion unit and both dOH and ferrate degradation pathways cannot be
petrochemicals (Shivaraman and Pandey, 2000) contain distinguished (Goldstein et al., 1993), the classical
high concentration of cresol. These compounds possess interpretation of dOH radical as the oxidizing species
a signicant threat to environment, as they are toxic and in Fenton oxidation has been discussed here.
refractory in nature. Cresols are classied by USEPA as Most of the previous studies were focused on the
persistent, priority, toxic chemical and the quantitative potential viability of Fenton oxidation to destroy cresols
structureactivity relationship (QSAR) shows chronic in aqueous solution. The operating parameters like
effects at 12 mg/L (Callahan et al., 1979). The LC50 for H2O2 concentration, Fe2+ ion concentration and pH,
cresols towards Salmonid sh, which is the most which are pertinent for the oxidation reaction, were
sensitive environmental species, is 6.28.4 mg/L. studied. However, there have not been extensive studies
Treatment methods available for destructing cresols that explicitly deal on the effect of gaseous atmosphere
include biological, chemical and electrochemical oxida- and temperature at the same experimental conditions. In
tions. Microbial degradation of cresols was investigated a way, these parameters could be important in inuen-
by Ahamad and Kunhi (1999) using Psuedomonas sp. cing the Fenton oxidation. In this paper, the effects of
and the rate of degradation of three cresol isomers was the above parameters together with quantifying the
in the order of o-cresolop-cresolom-cresol. Longer reaction byproducts formed during the degradation were
retention time, usually in days to oxidize the organic examined in order to understand the overall reaction
compound, is one of the drawbacks in biological mechanism involved in Fenton oxidation of cresols.
oxidation systems. Electrochemical oxidation of cresols
on Ti/TiO2RuO2IrO2 and carbon cathode was studied
by Rajkumar and Palanivelu (2003) using chloride as a 2. Materials and methods
supporting electrolyte. The formation of halogenated
organic compounds during the electrolytic oxidation 2.1. Chemicals
requires carbon polishing as a post-treatment of
electrolytic treated wastewater before discharging. Analytical grade reagents, o-, m-, p-cresols were
Thermal decomposition of cresols at 460 1C was purchased from CDH, India. All chemicals were used
experimented by Martino and Savage (1997) and as received without any further purication and the
Martino et al. (1995) resulting in the formation of stock solutions of cresols were prepared in 0.1 M NaOH.
intermediates like hydroxybenzaldehyde, indanone and The initial concentration of cresols used during the
CO2. High cost involved in maintaining supercritical experimental runs was 200 mg/L. Stock solution of H2O2
conditions and formation of toxic and higher molecular at 6.76.8 N was prepared by diluting 30% w/v of
weight compounds leads to the emergence of new cost- peroxide (Qualigens) with distilled water and maintained
effective and clean technologies for treating cresol- at acidic pH. Analytical grade ferrous sulphate hepta
bearing wastewater. hydrate (FeSO4 7H2O, CDH) was used as a source of
Advanced oxidation processes (AOPs) are commonly iron and the stock solution was maintained at 90 mM
used for remediating wastewaters contaminated with Fe2+ ion in 0.1 M H2SO4. All stock solutions were
recalcitrant organic pollutants. The methods are attractive stored in light resistant pyrex glass bottles, refrigerated
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3064 V. Kavitha, K. Palanivelu / Water Research 39 (2005) 30623072
at 4 1C. Standards like sodium acetate, sodium oxalate time for acetic and oxalic acids, respectively. Samples
(BDH) used for ion-chromatograph (IC) system and were treated with 6 N NaOH, ltered through 0.2 mm
potassium hydrogen phthalate (BDH) for dissolved Gelman acrodisc before injecting into the column. The
organic carbon (DOC) analyses were the highest-grade H2O2 concentration in the stock solution and in samples
analytical reagents. Sodium hydroxide (1 N) and sul- was determined by standard iodometric titration method
phuric acid (1 N) were used for pH adjustments. described in Jeffery et al. (1989).
70
3.5
60 3.2.2. Effect of initial H2O2 concentration on degradation
3 of cresols
Final pH
50
2.5 Hydrogen peroxide plays the role of an oxidizing
40 agent in Fenton process. The effect of change in H2O2
2
concentration on degradation efciency for cresol
30
1.5 isomers is depicted in Fig. 2. The concentration of
DE-o-cresol DE-p-cresol
20 DE-m-cresol pH-o-cresol H2O2 was varied from 0 to 50 mM at room conditions
pH-p-cresol pH-m-cresol 1
10
while keeping the Fe2+ ion concentration at 0.8 mM and
0.5
pH at 3.070.2. The degradation efciency increases
0 0 with increasing H2O2 concentration, due to incremental
2 2.5 3 3.5 4 4.5 5 6 d
OH radical produced by the reaction as shown in
Initial pH
Eq. (1). Maximum degradation efciency was attained
Fig. 1. Effect of initial pH on degradation efciency for cresols. at 31.64 mM for all the cresol isomers studied. Further
DE and pH represents the degradation efciency and nal pH addition of H2O2, did not improve the degradation
curves for the cresols studied (conditions: [Cresols] 1.85 mM, efciency, may be due to self-decomposition of H2O2 as
[H2O2] 25.8 mM, [Fe2+] 0.8 mM). in Eq. (4). Moreover, the excess H2O2 react with ferric
ion (Fe3+) to form weaker hydroperoxyl radical (HO2 )
as presented in Eqs. (5) and (6), which is not as active as
p-nitrophenol (Ma et al., 2000) and p-hydroxybenzoica- d
OH radical towards cresols degradation
cid (Rivas et al., 2001). It may, therefore, be suggested
that the optimum pH obtained is the most ideal pH 2H2 O2 ! 2H2 O O2 ; (4)
(3.070.2) for the generation of dOH radical rather than
specic to a particular organic substrate. The drop in Fe3 H2 O2 ! Fe2 HO2 H ; (5)
degradation efciency at pH44.0, is due to precipita-
tion of Fe(OH)3, which lowers the concentration of free d
OH H2 O2 ! HO2 H2 O: (6)
soluble iron species available for reacting with peroxide.
Hence, lesser concentration of dOH radical is generated From the results it can be drawn that maximum
for oxidizing cresols and consequently the degradation degradation occurred with H2O2 to cresol molar ratio of
efciency decreases. Besides, the oxidation potential of approximately 17. The stoichiometric amount of H2O2
d
OH radical decreases with increasing pH. Bossmann et required for total mineralization of cresol isomers was
al. (1998) reported the oxidation potential for the redox
couple dOHaq/H2O is 2.59 V at pH 0 and decreased to
1.64 V at pH 14.0. On the other hand, at very low pH 90
values (o 2.0) the reaction is slowed down due to
the formation of complex species [Fe(H2O)6]2+, which 80
Degradation efficiency (%)
70
Eq. (10) becomes
ln C cr =C cr;t0 k0cr t. (11)
DE-o-cresol
60 DE-m-cresol The kinetics of total mineralization of cresols has been
DE-p-cresol followed by measuring the residual DOC. Pseudo-rst-
order rate constant for cresol isomers can be obtained
50 through a linear least-square t of mineralization data to
Eq. (11) and is presented in Fig. 4. The rate constant for
40 o-, m- and p-cresol are 0.0075, 0.0086 and 0.0081 min1,
respectively. The mineralization data reveals that among
the cresol isomers, increasing rate of mineralization
30 follows the sequence of o-op-om-cresol, which is in
0 0.2 0.4 0.6 0.8 1
accordance with the results observed by Zheng et al.
Fe2+ ion concentration (mM) (1993) during the degradation of cresols by ozone. Half-
Fig. 3. Effect of initial Fe2+ ions concentration on degradation life (t1=2 ) values for cresols can be calculated by applying
efciency for cresols (conditions: [Cresols] 1.85 mM, the corresponding rate constant values to Eq. (12) and
pH 3.070.2, [H2O2] 31.64 mM). found to be 92.40, 80.88 and 85.55 min for o-, m- and
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2.1 1.8
o - cresol m - cresol 2
1.6 p - cresol
1.8 1.8
1.4 1.6
1.5
1.2 1.4
-ln (Ct/C0)
-ln (Ct/C0)
-ln (Ct/C0)
1.2 1 1.2
1
0.9 0.8
0.8
0.6
0.6 0.6
0.4
0.4
0.3
0.2 0.2
0 0 0
0 20 40 60 0 10 20 30 40 50 60 0 10 20 30 40 50 60
Time (min) Time (min) Time (min)
Fig. 5. Temperature dependence on Fenton oxidation for cresols [conditions as in Fig. 4 ((~), (), (m), and (K) 20, 30, 40 and
50 1C, respectively)].
Table 1
Pseudo-rst-order rate constant (min1) for cresols at different temperatures
-3.1 100 14
DE-Air DE-Nitrogen
ym-cresol = -1.5528x + 1.452
DE-Normal DO-Air
12
-3.7 6
40
4
-3.9
20
2
-4.1
0 0
0 1 5 10 15 30 45 60 90 120
-4.3 Time (min)
3 3.1 3.2 3.3 3.4 3.5
(1/T)*103 (K-1) Fig. 7. Effect of gaseous atmosphere on degradation efciency
for o-cresol (conditions: [o-cresol] 1.85 mM, pH 3.070.2,
Fig. 6. Arrhenius plot of Fenton oxidation rate constants for [H2O2]/[Fe2+] 35).
cresols.
3.5. Effect of gaseous atmosphere on degradation of o- solution for o-cresol is shown in Fig. 7. At normal,
cresol air and in nitrogen-saturated solutions, the degradation
efciency for o-cresol remained same. In nitrogen-
Kinetic plot on the decrease in COD in the solution as saturated solution, the initial degradation efciency was
a function of time for normal, air and nitrogen-saturated less compared to normal and air-saturated conditions.
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V. Kavitha, K. Palanivelu / Water Research 39 (2005) 30623072 3069
take place but rather the parent cresol compounds were were accumulated during the progress of the reaction
drastically altered as shown by change in sign of the and the oxidation did not proceed further to complete
oxidation state from high negative to positive values. conversion to CO2. Sedalk and Andren (1991) reported
The average oxidation state for the treated solution has a contrasting role of these acids in Fenton oxidation by
a value close to 2.5 (is a value representative of highly forming potentially stable complexes like ferric oxalate
oxidized substance) indicating that the byproducts and ferric acetate. In this way, the intermediates formed
formed during the degradation of cresol were highly (oxalic acid and acetic acid) preclude further oxidation
oxidized and less toxic in nature. reactions by deactivating Fe2+ ion in dOH radical
The peroxide was consumed as the reaction proceeded production. Bigda (1995) also reported on the refractory
for the generation of dOH radical, which ultimately nature of these acids towards Fenton oxidation.
resulted in the degradation of cresols. It was found that The measured DOC when compared to the calculated
the concentration of peroxide decreased from the initial DOC (carbon equivalent of the detected intermediates)
value of 1075 mg/L to around 725700 mg/L within indicated more than 92% residual carbon in cresol
5 min, where only 910% mineralization occurred oxidation was accounted for oxalic acid and acetic acid.
resulting in the peroxide consumption of 3034%. At The results imply that majority of the aromatic organic
the end of the reaction, only 5055 mg/L of peroxide was carbon in cresol was converted into aliphatic com-
left in the reacting solution. Considering the detection pounds namely oxalic acid and acetic acid suggesting
limit for peroxide measurement is about 90 mg/L, it may they were the nal products formed during Fenton
be regarded that almost all the peroxide was utilized oxidation for cresol isomers irrespective of the position
during the degradation studies. of methyl substituent on aromatic phenolic ring.
Analysis of possible intermediate products indicates
the presence of oxalic acid and acetic acid during the
degradation of all cresol isomers and is illustrated in
Fig. 9. The concentration of oxalic acid and acetic acid 4. Conclusions
increased as the reaction proceeded and reached a steady
value after 60 min of the reaction time. Kang et al. Treatment of simulated wastewater containing cresols
(1999) and Hess et al. (2003) reported the presence of by Fenton process has been taken into consideration in
oxalic acid during the degradation of dinitrophenol and the present study. On the basis of the results obtained,
nitro aromatic compounds by Fenton process. A the following conclusions have been made:
substantial amount of acetic acid was formed during
the initial stages of the reaction indicating the possible
The optimum operating conditions for Fenton
cleavage of alkyl group in the phenolic ring. Both oxalic oxidation of cresol isomers were 31.64 mM [H2O2],
acid and acetic acid were formed almost in same amount 0.90 mM [Fe2+] for o- and p-cresol while 0.72 mM
(on weight basis) and their values ranged from 110 to for m-cresol at an initial pH of 3.070.2. Under these
142 mg/L. As it is evident from Fig. 9, both these acids conditions, maximum degradation of 82% was
observed for all the cresol isomers.
1.8 2.5
Fenton process was modeled into pseudo-rst-order
Ox-o-cresol Ox-m-cresol kinetics, since peroxide and Fe2+ ion are in excess
1.6 Ox-p-cresol Ac-o-cresol
concentration to the substrate. The rate of miner-
Ac-m-cresol Ac-p-cresol
1.4 2 alization obeys the following sequence: m-4p-4o-
cresol with t1=2 values ranging from 80.88 to
Acetic acid (Ac, mM)
Oxalic acid(Ox, mM)
and acetic acid were quantitatively identied. These Jeffery, G.H., Bassett, J., Mendham, J., Denney, R.C., 1989.
ring cleaved products were the main components Vogels Textbook of Quantitative Chemical Analysis.
contributing for the residual organic matter in the ELBS, Singapore, pp. 394395.
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pounds, requires alternative treatment methods like Hydrogen Peroxide and Derivatives, vol. 30. Royal Society
of Chemistry, Cambridge, UK.
applying UV light to Fenton system (photo-Fenton)
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