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Oxidative Degradation of Acetaminophen by

Permanganate in Neutral Medium-A Kinetic and
Mechanistic Pathway

S. Tabassum, S. Sabir, O. Sulaiman, M. Rafatullah, I. Khan & R. Hashim

To cite this article: S. Tabassum, S. Sabir, O. Sulaiman, M. Rafatullah, I. Khan & R. Hashim
(2011) Oxidative Degradation of Acetaminophen by Permanganate in Neutral Medium-A
Kinetic and Mechanistic Pathway, Journal of Dispersion Science and Technology, 32:2, 217-223,
DOI: 10.1080/01932691003656938

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Journal of Dispersion Science and Technology, 32:217–223, 2011
Copyright # Taylor & Francis Group, LLC
ISSN: 0193-2691 print=1532-2351 online
DOI: 10.1080/01932691003656938

Oxidative Degradation of Acetaminophen

by Permanganate in Neutral Medium-A Kinetic
and Mechanistic Pathway
S. Tabassum,1 S. Sabir,2 O. Sulaiman,1 M. Rafatullah,1 I. Khan,1 and
R. Hashim1
1
Division of Bio-Resource, Paper and Coatings Technology, School of Industrial Technology,
Universiti Sains Malaysia, Penang, Malaysia
2
Department of Chemistry, Aligarh Muslim University, Aligarh, U. P., India

The occurrence of pharmaceuticals in the environment is an emerging issue. Several studies

observed that the nonsteroidal antiinflammatory drug acetaminophen is ubiquitously present in
most of the surveyed surface waters, worldwide. This spectroscopic study presents the kinetics
and degradation pathways of oxidation of acetaminophen by permanganate in neutral medium.
The variables affecting the reactions were carefully investigated and the conditions were opti-
mized. The higher degradation rate was observed with increase in acetaminophen concentration
in the range of 0.4
103 to 9.7
103 min1. The retention time and UV-visible absorption
spectrum of the product were found to be identical to those of p-benzoquinone. The spectral
change in the course of reaction was observed in the region 400 nm to 700 nm and there was a
gradual decrease in absorption intensity at its kmax. Kinetic analysis of these results only gave
good linear plots, with regression coefficients >0.996, when they were fitted to a pseudo-first-
order reaction. The slope of log k versus 1/T also confirms the first-order dependence on the
reactant. Investigations of the reaction at different temperatures allowed the determination of
the activation parameters with respect to the slow step of proposed mechanism.
Keywords Acetaminophen, kinetic, oxidation, permanganate

INTRODUCTION information on the reaction as demonstrated by the results

In recent years, there has been growing interest on the
occurrence and fate of pharmaceuticals (antiinflamma-
tories, analgesics, betablockers, lipid regulators, antibio-
tics, antiepileptics, and estrogens) and active ingredients
in personal care products (PCPs) in the aquatic environ-
ment. These compounds and their bioactive metabolites
are continuously introduced in the environment via a
number of routes but mainly by both untreated and treated
wastewater.[1] The development of oxidation techniques for
achieving the reduction of water pollution has been pro-
posed.[2,3] The oxidation of organic reductants by KMnO4
in aqueous media has received considerable attention.[4–13]
Kinetic studies are important sources of mechanistic
Received 22 October 2009; accepted 14 November 2009.
The authors express their gratitude to the Chairman, Department
of Chemistry, Aligarh Muslim University, Aligarh, and Universiti
Sains Malaysia, Malaysia, for postdoctoral grant support and
providing the research facilities.
Address correspondence to S. Tabassum, Division of
Bio-Resource, Paper and Coatings Technology, School of Indus-
trial Technology, Universiti Sains Malaysia, 11800 Penang,
Malaysia. E-mail: tsalmachem@yahoo.com
referring to unsaturated acids both in aqueous[14–17] and
nonaqueous media.[18] Therefore, the MnO 4 oxidations
provide chemical kinetics with challenging mechanism to
possibilities due to the ability of Mn to exist in a multitude
of oxidation states.
Acetaminophen (paracetamol or N-(4-hydroxyphenyl)
acetamide or PAM) is regularly used as analgesic and
antipyretic drug, as material for the azo dyes production,
as photographic chemicals, and for chemical control of
Brown Tree snakes population. Levels of acetaminophen
of up to 6 mg=L have been detected in effluent waters from
sewage treatment plants[19] because of its hepatotoxicity[20]
and other side effects, concern has been raised about the
possible environmental impact of acetaminophen and
its (bio)degradation products, which may be toxic or
hazardous even in trace amounts.
Our investigations provide a detailed process-level
understanding of the oxidative degradation of acetamino-
phen by permanganate. The present study deals with the
title reaction to investigate the redox chemistry of
permanganate in such media and to arrive at a suitable mech-
anism for oxidation of acetaminophen by permanganate on

217
218 S. TABASSUM ET AL.
the basis of kinetic results. The specific objectives are a) to
examine reaction order, degradation rate and kinetic
behavior of acetaminophen in reaction with permanganate,
b) to demonstrate the extent of degradation, and c) to
investigate the reaction at different temperatures which
allows the determination of the activation parameters with
respect to the slow step. The overall mechanistic sequence
described here is consistent with product, mechanistic and
kinetic studies.
MATERIALS AND METHODS
Apparatus
Thermo spectronic Genesis 20 UV-visible spectrophoto-
meter with matched quartz cells was used to measure
absorbance. A high precision water bath was used to
control the heating temperature for color development.
Reagents and Standards
All reagents and chemicals used were of analytical
grade. Potassium permanganate (GR Grade, Merck
Limited, Mumbai, India) was prepared in deionized water.
The drug, paracetamol (Glaxo) used in the study.
Deionized water was used throughout the experiment.
Sample Solution of Acetaminophen
Two tablets were weighed and powdered. The powder
equivalent of 0.01 g of active ingredient was weighed
accurately, stirred well with deionized water for 30 min-
utes and filtered through Whatmann No. 42 filter paper
(Whatmann International Limited, Kent, UK). The resi-
due was washed well with deionized water for complete
recovery of the drug. The content of the drug was then
diluted to 50 ml. It was further diluted according to the
need and subjected to the degradation procedure for
acetaminophen.
Preparation of KMnO4 Solution
KMnO4 (0.040 gm) was quantitatively transferred into a
25 ml standard flask, and makeup with distilled water. The
solution of KMnO4 was stored in a dark glass bottle.
Potassium permanganate solution is freshly prepared.
Kinetic Procedure
The oxidation of acetaminophen by permanganate was
followed under pseudo-first-order conditions. The spectro-
photometric kinetic studies were performed on the basis of
the absorbance (optical density) noted at kmax (wavelength)
as a function of time. These reading were conveniently
made with a Genesis 20 spectrophotometer for relatively
slow reactions. The sample was withdrawn from the
thermo stated reaction mixture for measurement. The
reaction was initiated by mixing the required quantities
of acetaminophen and KMnO4 at desired temperature in
the range (25–55 C). The progress of the reaction was
observed spectrophotometrically by pipetting out aliquots
at different time intervals and measuring the change in the
absorbance at its kmax 525 nm. The first-order rate constants,
kobs were obtained from the plots of log (At  A1) versus
time (refer to Figure 2), where At refers to absorbance at
any time t and A1 is at infinite time which excludes the
absorbance of any Mn(VI) during the reaction.
In order to obtain spectroscopic characteristics of
intermediates or products formed during the reactions,
the reaction solution was successively scanned by a UV-vis
scan spectrophotometer.
RESULTS AND DISCUSSION
General Considerations
The limiting logarithmic method[21] was used for the
determination of the molar ratio between KMnO4 and
PAM in the reaction. This method depends on measuring
the optical densities of solutions of KMnO4 and PAM in
which the concentrations of the two species are varied.
The ratio may be found by plotting the logarithms of the
absorbance (A) of the two sets of solutions versus compo-
sition, one with constant KMnO4 concentration and
variable PAM concentration, the other with constant
PAM and variable KMnO4 concentration. The slope of
the curve in first case yields the number of moles of PAM
while that in second case give the number of moles of
KMnO4 and so the composition of the compound produced
can be evaluated. The molar ratio was found to be 1:2 for
PAM and KMnO4. To examine the effect of variables,
experiments were carried out under pseudo-first-order
conditions.
Degradation of ½MnO 4  and [Acetaminophen]
In order to investigate the kinetics of PAM-MnO 4
reaction, a series of experiments were carried out under
pseudo-first-order conditions. [PAM] is varied from
0.1
104 to 1.0
104 mol dm3 at constant ½MnO 4
0.6
103 mol dm3 (Table 1). The kobs [PAM] plot is
linear passing through the origin, indicating first-order
dependence on [PAM]; Figure 1 depicts the dependence
of kobs on [PAM] at constant ½MnO 4 . The pseudo-first-
order rate constants kobs, min1 were calculated from the
slopes of plots of log Abs versus time. The degradation
of permanganate is also shown, ½MnO 4  varied from
0.3
103 to 1.0
103 mol dm3, at constant [PAM]
0.5
104 mol dm3. It is observed that as the initial
½MnO 4  was increased, the value of kobs decreased
(Table 1). The abnormal behavior probably was due to
possible flocculation of colloidal particles.
 OXIDATIVE DEGRADATION OF ACETAMINOPHEN 219

TABLE 1 can be described with the following general rate equation:

Variation of pseudo-first-order rate constant (kobs) for the
oxidation of acetaminophen by ½MnO 4  at 525 nm, r ¼ 1=aðd ½PAM=dt ¼ k ½PAMx ½permanganatey ½1
Temp ¼ 35 C
When the concentration of [permanganate] is in excess,
103 ½MnO4 104 [PAM] Equation (1) can be simplified as Equations (2) and (3):
(mol dm3) (mol dm3) kobs
103 min1
r ¼ kobs ½PAMx ½2
0.1 0.5 8.8  0.009a
0.3 8.3  0.006
kobs ¼ k½permanganatey ½3
0.4 4.8  0.004
0.5 4.2  0.003
where r is a reaction rate, k the rate constant, [PAM] and
0.6 3.2  0.002
[permanganate] the concentrations of PAM and permanga-
0.7 3.2  0.002
nate, respectively. x and y are the orders of the reaction
0.8 2.7  0.002
with respect to each reactant. kobs is a pseudo-order rate
0.9 2.4  0.002
constant because [permanganate] is effectively constant
1.0 2.3  0.002
during the course of experiment. By varying the values of
0.6 0.1 0.4  0.000
[PAM] and measuring reaction rate, the order x with
0.2 2.1  0.001
respect to [PAM] can be simply determined by a log-log
0.4 2.5  0.002
form of Equation (2):
0.5 3.0  0.002
0.6 4.3  0.003 log r ¼ log kobs þ x log ½PAM ½4
0.7 4.8  0.004
0.8 6.3  0.004 In a similar way but varying initial concentration of
0.9 7.6  0.005 [permanganate] and measuring kobs, the order y with
1.0 9.7  0.004 respect to [permanganate] can be obtained by a log-log
a form of Equation (3):
Error limits are standard deviations.

log kobs ¼ log k þ y log ½permanganate ½5

Oxidation Kinetics
Kinetic experiments of oxidation of PAM with
permanganate were conducted at a constant temperature
of 25 C under dark conditions. As can be expected, the
plots of concentration versus time could be fitted to an
exponential curve in all cases. The degradation of PAM
To minimize the errors from competitive reaction that
may be induced using integral method, the initial rate
method was used to measure the rate parameters of reac-
tion. At the beginning of the reaction both of PAM and
permanganate concentrations are known. The PAM and
permanganate concentrations and the calculated rate
constants are summarized in Table 2. The two sets of
kinetic experiments were designed to calculate x and y
values for PAM oxidation. The first set of four experiments
was conducted with initial PAM concentrations varying

TABLE 2
Effect of [PAM] on the R0 for the oxidation of acetamino-
phen with ½MnO 4  ¼ 0.6
10
3
mol dm3, Temp ¼ 35 C
[PAM]
r0
103
104 mol  dm3 mol  dm3  min1 R

0.4 2.74 0.9853

0.5 3.30 0.9887
0.6 3.95 0.9882
0.7 4.24 0.9763
0.8 4.61 0.9834
0.9 5.00 0.9841
FIG. 1. Plot of kobs versus [PAM]; Reaction conditions: ½MnO4  ¼
0.6
103 mol dm3; Temperature ¼ 35 C. 1.0 5.23 0.9553
220 S. TABASSUM ET AL.

(0.4, 0.5, 0.6, and 0.7)
104 mol dm3. The initial per-
manganate concentration was fixed at 0.6
103 mol dm3
for all experiments. The initial reaction rates were determ-
ined as the tangent to the PAM concentration-time curve.
The rate at which PAM is degraded can be simply measured
when the other reactant, permanganate, is held essentially
constant throughout the experiment. In Figure 2, the log
of initial rates versus the log of the initial PAM is shown.
The slope of the calculated linear regression gave the rate
order x ¼ 0.8056 (1), indicating that the reaction is also
first-order reaction with respect to PAM concentration.
In the second set of four similar experiments, the initial
concentration of PAM was fixed at (0.5
104 mol dm3)
and PAM was reacted with permanganate ranging from
(0.3, 0.4, 0.5 and 0.7)
103 mol dm3. Figure 3 shows
the log of the pseudo-first-order rate constant (kobs) versus FIG. 3. Plot of kobs versus initial permanganate concentration at
the log of initial permanganate concentration. The slope of constant initial PAM concentration of 0.5
104 mol.dm3 at 35 C (kobs,
regression line is y ¼ 1.0864 (1), indicating that the reaction pseudo-first-order rate constant in min1; Permanganate0, initial
Permanganate concentration in mol  dm3).
is first-order with respect to the permanganate concentration.
From Figure 3, the rate constant for the overall reaction
can be calculated. The y-intercept of the gradient (5.9485)
is the antilog of the second order rate. Thus, Equation (1) relationship, indicating first order with respect to the PAM
can be rewritten as Equation (6). The results indicate that concentration. Similarly, at different initial dichromate con-
the overall reaction is a second-order reaction and first-order centrations, the log of permanganate=permanganateo versus
reaction with respect to both permanganate and PAM time also shows a linear relationship, demonstrating first
order with respect to the PAM concentration as well.
r ¼ 1:13
106 ½PAM ½permanganate ½6
Effect of Temperature on the Reaction Rate
The first-order reaction rate with respect to the initial
The effect of change in temperature was examined in the
PAM concentration is also confirmed in the log of PAM=
temperature range 25–55 C. As the temperature increases,
PAM0 versus time of four different initial PAM concentra-
the rate of the reaction should increase according to
tions. The slope of the linear regression shows a linear
Arrhenius equation. For the effect of change in temperature
on reaction rate, the Arrhenius equation was used to calculate
the various activation parameters of the reaction products:

ln k ¼ ln A  Ea =RT ½7

The rate constant k of the slowest step was obtained

FIG. 2. Plot of initial rates versus the initial concentration of PAM at
constant initial permanganate concentration of 0.6
103 mol dm3 at
35 C (r0, initial rate of reaction in mol dm3; PAM0, initial PAM concen-
tration in mol dm3).
from the slope of log Abs versus time plots at four differ-
ent temperatures with respect to different concentration of
[PAM] and ½MnO 4 . The energy of activation correspond-
ing to different rate constants obtained at varying tem-
peratures was calculated from the Arrhenius plot of log
k versus 1=T (Figure 4). It is found that a plot of ln k
against 1=T gives a straight line with negative slope. This
further confirms the first-order dependence on the reac-
tants. This also helped to deduce the kinetic rate
expression for the oxidation of the acetaminophen by pot-
assium permanganate.
Activation energy (Ea) can be calculated from the
slope (Ea=2.303 R) and A (pre-exponential factor) from
the intercept of the Arrhenius curve and found to be
23.9 kJ mol1 and 1.46091, respectively. The other activa-
tion parameters such as enthalpy, entropy and free energy
 OXIDATIVE DEGRADATION OF ACETAMINOPHEN 221

TABLE 3
Value of k (rate constant) calculated from slopes of log
absorbance versus time plots multiplied by 2.303. Reaction
Conditions: [PAM] ¼ 0.4
104 mol dm3,
½MnO 4  ¼ 0.6
10
3
mol dm3
Temp. (K) 1=T Slope k log k

298 0.00335 0.00079 0.0018113 2.74200

308 0.00324 0.00110 0.0025333 2.59631
318 0.00314 0.00161 0.0037078 2.43088
328 0.00304 0.00186 0.0042836 2.36819
Activation parameters: Ea ¼ 23.9 kJmol1.
DH# ¼ 21.4 kJmol1; DS# ¼ 225 JK1mol1; DG# ¼
1
88.4 kJmol .

FIG. 4. Arrhenius plot: log k versus 1=T for activation energy.
of activation of the reaction product were calculated
using Eyring equation:
k kb DS # DH # 1
log ¼ log þ  ½8
T h 2:303R 2:303R T
The plot log k=T versus 1=T (Figure 5) was linear with
correlation coefficient of 0.9841. DH# was evaluated from
the slope (DH#=2.303 R) and DS# from the intercept [log
(kb=h) þ DS#=2.303R] of the compiled Eyring plot. The
values of DH# and DS# were found to be 21.4 kJ mol1
and 225 JK1 mol1 respectively (Table 3). The Gibbs
free energy of activation was determined at 298 K and
found to be 88.4 kJ mol1 by using the following equation:
The negative entropy of activation is characteristic of the
existence of compact transition state. DS# suggests the for-
mation of an activated complex with a reduction in the
degrees of freedom of molecules. The fairly high positive
value of enthalpy (DH#) indicates that the transition state
is highly solvated. A meaningful mechanistic explanation of
the apparent values of DS# and DH# is not possible because
the kobs do not represent a single elementary kinetic step.
Electronic Spectra
The UV-visible spectra of the reacting solution over
the time are shown in Figure 6. The spectra show two

DG# ¼ DH#  TDS# ½9

FIG. 6. Spectral changes occurring during the oxidation of PAM by per-

manganate at initial PAM concentration of 0.4
104 mol  dm3 and
KMnO4 concentration of 0.6
103 mol  dm3 at 35 C, the top curve for
FIG. 5. Eyring plot: log k=T versus 1=T for DH# and DS#. t ¼ 0 minutes and the bottom for t ¼ 90 minutes.
222 S. TABASSUM ET AL.

absorption peaks at 400 nm and 525 nm at beginning of the

reaction. It shows a continuous decrease in the absorbance
at 525 nm which indicates that ½MnO 4  is used up to oxidize
the PAM in the reaction. The decrease in absorbance with
the course of reaction follows first-order fashion. Further,
there is a slight decrease in absorbance at 600 nm and
700 nm suggest that MnO2 4 and MnO3 4 apparently do
not form as reaction products. At a wavelength 450 nm,
the spectrum of the initial solution has the lowest absor-
bance and MnO 4 is almost transparent to source light.
The increase of absorbance at 450 nm with time indicates
the formation of a decomposition product of MnO 4.

Mechanism
Permanganate ion, MnO 4 , is a powerful oxidant, as it
exhibits many oxidation states; the oxidation was indicated
by the appearance of brown color in the reaction mixture
after the addition of oxidant. Oxidation of acetaminophen
was found to take place very quickly as observed by color
change of the reaction mixture from violet to red color and
then to orange color, as the reaction proceeds, slowly yel-
low turbidity develops, after keeping for a long time the SCH. 2. Oxidation-reduction pathways of PAM.

solution turns to colorless resulting in a brown precipitate.

This suggests that the product formed might have under-
gone further oxidation resulting in a lower oxidation state
of manganese, Mn (IV). There is a continuous decrease in
absorbance during the course of absorbance which indi-
cates degradation in the concentration of PAM. The degra-
dation pathway of PAM is shown in Scheme 1.
Many researchers[22,23] have proposed similar mech-
anism for one step, one electron transfer; the adsorption
of PAM on the surface of the colloidal MnO2 can be seen
from (Equation (5) in Scheme 2). The hydrogen bonding
between the –OH group of acetaminophen and MnO2 is
responsible for the formation of complex C. It has been
found[24–26] that C decomposes by a one step, one-electron
oxidation-reduction mechanism to Mn(III) and other pro-
ducts (Equation (5) in Scheme 2). Mn(III) is a strong oxi-
dant and is unstable with respect to disproportionation in
the presence of large amount of acetaminophen; it immedi-
ately gets converted into stable products (Equation (8) in
Scheme 2).
Product Analysis
After complete degradation of acetaminophen, which was
confirmed from no change in absorbance after 90 minutes,
the whole reaction mixture (acetaminophen ¼ 2
102
mol dm3 i.e., 0.120 gm in 50 ml distilled water and
KMnO4 ¼ 10
102 mol dm3 i.e., 0.400 gm in 25 ml dis-
tilled water) was extracted with 50 ml chloroform. The
chloroform layer was washed with 3
50 ml distilled water.
Chloroform was evaporated and the product obtained was
crystallized. The product obtained was compared with ben-
zoquinone by spot method.[27] Melting point of these crystals
was similar to that of benzoquinone (m.p. ¼ 114–116 C).
Sultan also suggested similar products by using different
oxidant.[28] Free radical formation was confirmed following
the literature method.[29] Product formation was further
supported by detection of ammonium ions in solution that
was verified by spot test.[28]

CONCLUSIONS
In this work, acetaminophen has been used as a model
SCH. 1. Degradation pathways of PAM. compound for the destruction of pharmaceutical industry
 OXIDATIVE DEGRADATION OF ACETAMINOPHEN
wastes. Acetaminophen is only partly degraded (to benzo-
quinone) rather than fully mineralized. Furthermore, since
the rate of mineralization depends linearly on substrate
concentration, the degradation method will be best suited
to relatively high strength wastes, and not to the very low
concentrations typical of incompletely degraded sewage
effluents. At present time, oxidative degradation of aceta-
minophen by KMnO4 is less expensive and probably
sufficiently rugged to be considered for long-term indus-
trial use. This permanganate oxidation can be effectively
used in the waste water treatment at the sites contaminated
by flouroquinolone antibiotics. Insoluble manganese
dioxide formed, provides advantages in the removal of phe-
nol and other organic contaminants from the waste water.
Although there has been no proof that very low amounts of
pharmaceuticals in natural waters have any adverse health
effects, they can produce toxic effects to aquatic organisms
and in the case of antimicrobials, the development of
multi-resistant strains of bacteria.[30] To avoid the danger-
ous accumulation of drugs in the aquatic environment,
research efforts are underway to develop more powerful
oxidation methods than those currently applied in waste-
water treatments for achieving their complete destruction.
Besides the practical implications of the research, these
results hold basic interest. Further work in our laboratory
is directed towards development and investigation of oxi-
dative material that can degrade acetaminophen more
effectively in assessing the ecological relevance of the
present study. The results of this investigation indicate that
acetaminophen of analgesic class is substantially degraded
under conditions yielding lower mass degradates.
REFERENCES
[1] Daughton, C.G. and Ternes, T.A. (1999) Environ. Health
Persp., 107: 907–938.
[2] Bautitz, I.R. and Nogueira, R.F.P. (2007) J. Photochem.
Photobiol. A, 187: 33–39.
[3] Nogueira, R.F.P. and Guimaraes, J.R. (2000) Water Res., 34:
895–901.
[4] Pode, J.S.F. and Waters, W.A. (1956) J. Chem. Soc., 717–724.
[5] Ladburry, J.W. and Cullis, C.F. (1958) Chem. Rev., 58: 403–438.
[6] Hasan, R.M., Mousa, M.A., and Wahdan, M.H. (1988)
J. Chem. Soc. Dalton Trans., 3: 605–609.
223
[7] Verma, R.S., Reddy, M.J., and Shastry, V.R. (1976) J. Chem.
Soc. Perkin Trans. II, 2: 469–472.
[8] Rao, V.S., Sethuram, B., and Rao, T.N. (1979) Int. J. Chem.
Kinet., 11: 165–173.
[9] Girgis, M.M., El-Shatoury, S.A., and Khalil, Z.H. (1985)
Can. J. Chem., 63: 3317–3321.
[10] Szammer, J. and Jaky, M. (1992) Int. J. Chem. Kinet., 24:
145–154.
[11] Perez-Benito, J.F., Arias, C., and Brillas, E. (1990) Int.
J. Chem. Kinet., 22: 261–287.
[12] Raju Khan, Z. and Kabir-ud-Din. (2005) Colloid Polym. Sci.,
284: 26–35.
[13] Arrizabalaga, A., Andres-ordax, F.J., Fernandez-Aranguiz,
M.Y., and Peche, R. (1997) Int. J. Chem. Kinet., 29: 181–185.
[14] Lee, D.G. (1982) In Oxidation in Organic Chemistry, Part D,
edited by W.S. Trahanovsky; New York: Academic Press;
pp. 147.
[15] Simandi, L.I. (1983) In The Chemistry of Functional Groups,
edited by S. Patai and Z Rappoport; Chichester, UK: Wiley
[16] Lee, D.G., Lee, E.J., and Brown, K.C. (1987) Phase Transfer
Catalysis; New Chemistry, Catalysis and Applications;
Washington, DC: ACS Symposium Series; American Chemi-
cal Society.
[17] Fatiadi, A.J. (1987) Synthesis, 106: 85–127.
[18] Perez-Benito, J.F. and Lee, D.G. (1987) J. Org. Chem., 52:
3239–3243.
[19] Daughton, C.G. and Ternes, T.A. (1998) Water Res., 32:
3245–3260.
[20] O’Brien, P.J., Khan, S., and Jatoe, S.D. (1991) Adv. Exp.
Med. Biol., 283: 51–64.
[21] Roso, J. (1964) Advanced Physiochemical Experiments;
London: Sir Issac Pitman and Sons.
[22] Mehrotra, R.N. (1968) J. Chem. Soc. B, 1123–1127.
[23] Rosenblatt, D.H., Davis, G.T., Hull, L.A., and Forbery,
G.D. (1968) J. Org. Chem., 33: 1649–1650.
[24] Fatiadi, A.J. (1976) Synthesis, 65: 133–167.
[25] Kotai, L., Kazinczy, B., Keszier, A., Holly, S., Gacs, I., and
Banerji, K.K. (2001) Z. Naturforsch, 56: 823–825.
[26] Khan, Z., Kumar, P., and Kabir-ud-Din. (2004) Colloids
Surf. A, 248: 25–31.
[27] Vogel, A.I.A. (1981) Textbook of Quantitative Chemical
Analysis; 5th ed.; London: Longman Group.
[28] Sultan, S.M. (1987) Talanta, 34: 605–608.
[29] Drummand, A.Y. and Waters, W.A. (1953) J. Chem. Soc.,
2836: 3119–3123.
[30] Balcioğlu, I.A. and O } tker, M. (2003) Chemosphere, 50:
85–95.