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The Effect of Salts on Ozone Oxidation Processes

a a a b b
Marc A. Boncz , Harry Bruning , Wim H. Rulkens , Han Zuilhof & Ernst J. R. Sudhlter
a
Wageningen University and Research Centre, Subdepartment of Environmental Technology ,
Wageningen, the Netherlands
b
Wageningen University and Research Centre, Laboratory of Organic Chemistry ,
Wageningen, the Netherlands
Published online: 18 Jan 2007.

To cite this article: Marc A. Boncz , Harry Bruning , Wim H. Rulkens , Han Zuilhof & Ernst J. R. Sudhlter (2005) The Effect of
Salts on Ozone Oxidation Processes, Ozone: Science & Engineering: The Journal of the International Ozone Association, 27:4,
287-292, DOI: 10.1080/01919510591006382

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 Ozone: Science and Engineering, 27: 287292
Copyright # 2005 International Ozone Association
ISSN: 0191-9512 print / 15476545 online
DOI: 10.1080/01919510591006382
The Effect of Salts on Ozone Oxidation Processes
Marc A. Boncz,1 Harry Bruning,1 Wim H. Rulkens,1 Han Zuilhof,2 and Ernst J. R. Sudholter2
1
Wageningen University and Research Centre, Subdepartment of Environmental Technology, Wageningen, the Netherlands
2
Wageningen University and Research Centre, Laboratory of Organic Chemistry, Wageningen, the Netherlands
Downloaded by [The University of British Columbia] at 11:15 14 October 2014
Much research on ozone oxidation is performed using
model wastewaters, containing a number of organic com-
pounds to be degraded. In some cases they contain low
concentrations of inorganic buffers to stabilize the pH during
the experiments. In practical applications, however, salts and
detergents may be present as well. The effect of such com-
pounds on the process has to be investigated to prevent
unexpected results in pilot- or full-scale applications. To
quantify these effects, experiments have been performed on
model waste waters in the absence and the presence of high
concentrations of several inorganic salts. The oxidation
selectivity in these experiments was interpreted using
Hammett free-energy relationships. The effect of the differ-
ent salt concentrations on the oxidation selectivity when
considering reactions in the bulk of the liquid was seen to
be small. This implicates the design of an ozone-based oxida-
tion system can often be based on literature or calculated
data regarding reaction rates. However, the effect of
increased salt concentrations on ozone solubility and bubble
size distribution may have implications for the reactor design,
as these factors affect the mass transfer efficiency.
Keywords Ozone, Salt effect, Chloride, Phosphate, Sulfate,
Nitrate, Ozone Solubility, Hammett-relationships
INTRODUCTION
Most of the research on ozonation of waste waters is
done on aqueous model systems, containing no other
compounds than the organic compounds to be degraded
(Alaton et al., 2002; Beltran et al., 2000). In some cases
low concentrations of inorganic buffers or higher concen-
trations of carbonate, serving as a radical scavenger, are
present. In practical applications however, other com-
pounds, such as salts and detergents, will be present as
well. In the pulp and paper industry for instance, where
ozone can be used to remove color from the process water
Address correspondence to Marc A. Boncz, Rue Madressilua
156, Caranda Boeque II, Campo Grande, 79032-380, Brazil, E-
mail: marc.boncz@wur.nl
Ozone: Science and Engineering
(Archibald and RoyArcand, 1997), large amounts of cal-
cium, sulfate and carbonate (up to several grams per liter)
will be present. In the tanker cleaning industry, detergents
were seen to be the most frequently used chemicals
(Boncz, 2002; EPA, 1998). The effect of these salts on the
process has to be investigated in order to be able to design
installations, which can be applied effectively in practice.
Salts can affect the ozone oxidation process in two
ways: physically and chemically. Physical changes occur
in ozone solubility and ozone mass transfer. A change in
ozone solubility can be observed in salt-containing solu-
tions, as mentioned by Rischbieter et al. (2000) and
Sotelo et al. (1989). The presence of a salt generally low-
ers the solubility of a gas. This effect can be quantified by
the Sechenov relation for solutions containing moderate
concentrations of salts (up to 2 M) (Rischbieter et al.,
2000):

 X
log H=H0 KS salt
1

Here H is Henrys law constant as observed for the gas,
H0 Henrys law constant under P standard conditions, KS
the Sechenov constant, and [salt] the total salt concen-
tration. Typical values for KS are between 0.1 M1 and
0.5 M1, depending on the compound. Using these data it
can be shown that a 0.5 M salt concentration can already
lead to a decrease of the ozone solubility by 50%, as
shown in Figure 1.
Salts can also influence the size distribution of gas
bubbles in a bubble column (Christenson and
Yaminsky, 1995; Walker et al., 2001). Above the so-called
transition concentration, electrolytes largely inhibit bubble
coalescence, resulting in a lower average bubble diameter.
This leads to increased mass transfer rates, resulting in
changing ozone oxidation kinetics (Christenson and
Yaminsky, 1995).
A more important effect of inorganic salts on the
ozone oxidation process however is caused by chemical
reactions. Carbonate ions are well-known species for
August 2005 287
 8.0
Na 2SO 4
7.0
MgSO 4
6.0
5.0 Ca(NO3) 2

H/H0
4.0 NaCl
3.0 KCl
2.0
1.0
0.0
0.0 0.5 1.0 1.5 2.0
salt concentration (M)

FIGURE 1. Effect of salts on the solubility of ozone in an aqueous solution (Rischbieter et al., 2000).

scavenging the radicals involved in the ozone decomposi- HO H2 PO4  ! OH H2 PO4 k < 1:2  107 M1 s1
tion (Boncz, 2002; Rischbieter et al., 2000; Sotelo et al., 6

Downloaded by [The University of British Columbia] at 11:15 14 October 2014

1989). The two reactions responsible for the radical

scavenging effect are given below:
HO CO3 2 ! OH CO3  k 4:2  108 M1 s1
2

O2  CO3  ! CO3 2 O2 k 7:5  108 M1 s1
3

These reactions result in a catalytic decrease of the
hydroxyl radical concentration and consequentially in a
loss of efficiency and a relatively higher share of the direct
oxidation mechanism (Christenson and Yaminsky, 1995;
Walker et al., 2001).
Radical scavenging reactions of other anions, compar-
able to the reactions [2] and [3], are a possibility that
might affect ozone-oxidation selectivity. Unfortunately,
very few literature data could be found on the scavenging
effect by such reactions of other inorganic salts (like
nitrate, phosphate, and sulfate).
Liao reported a small radical scavenging effect by
chloride (Liao et al., 2001). Schmelling et al. found no
radical scavenging effect using nitrate, chloride, or borate
(Schmelling et al., 1997). Tanaka found no significant
effect of chloride in the ozone oxidation of ammonia in
seawater (Tanaka and Matsumura, 2002). Finally,
Hoigne reported that sulfate, phosphate, nitrate, chlor-
ide are extremely slow in reacting with HO; their scaven-
ging effect can generally be neglected (Hoigne, 1998).
This is consistent with all but the first of the following
reaction rates being considerably slower than reaction [2]
(Farhataziz and Ross, 1977):
HO PO4 3 ! OH PO42 k < 1  107 M1 s1
7

Sotelo et al. (1989), however, reported a decrease in
ozone decomposition rate due to radical scavenging, not
only by carbonate, but also by phosphate and sulfate at
moderate and elevated pH. No reference was made to
regeneration of the scavenging inorganic anions, in reac-
tions comparable to the one in equation [3].
At low pH, however, phosphate and chloride were
found to increase the ozone decomposition rate (Sotelo
et al., 1989). Due to the direct reaction between ozone
and the chloride anion, the half-life time of ozone was
reduced by a factor of 2 in the presence of 0.1 M NaCl.
The following reactions and reaction-rate constants were
reported (Haag and Hoigne, 1983):
O3 Cl ! O2 OCl  k1 0:003 M1 s1 8

O3 OCl ! 2 O2 Cl  k2 110 M1 s1 9

Simulating ozone decomposition in the presence of chlor-
ide using these two reactions could explain the reduction
in ozone lifetime as observed by Sotelo to a great extent,
as shown in Figure 2.
Although, based on literature, salt effects cannot be
excluded completely, we do not expect to find any sig-
nificant effect of them. Experiments were performed to
verify if the selectivity of ozone oxidation in systems
containing increased salt concentrations is indeed com-
parable to the selectivity of the ozone oxidation in solu-
tions of a lower ionic strength.

HO Cl ! ClOH k 8:9  107 M1 s1 4

EXPERIMENTAL
HO NO3 ! OH NO3  k < 5  105 M1 s1 The effect of moderate salt concentrations on the selec-
5
tivity of the ozone-oxidation was investigated using

288 Ozone: Science and Engineering August 2005


1.00
0.80
[O 3]t / [O 3]0
0.60
0.40
0.20
0.00
0.00 10.00 20.00 30.00 40.00 50.00
time (min.)
FIGURE 2. Simulation of ozone decomposition in water at pH = 6
in the presence of different concentrations of Cl, taking into
account (i) a simplified OH initiated decomposition pathway and
(ii) reactions (7) and (8). Data points are experimental data from
Sotelo (1989). Curves are fitted to data points, using k1 = 0.003
Downloaded by [The University of British Columbia] at 11:15 14 October 2014
M-1S-1 and k2 = 110 M-1S-1.
comparative experiments with a model system, consisted
of p-methoxy benzoic acid, p-methyl benzoic acid, ben-
zoic acid, p-chloro benzoic acid and p-nitro benzoic acid,
as described before (17), but in the presence of a moder-
ately high concentration (0.5 M) of a specified salt.
Comparative experiments were used, as they allow for
determination of reaction rates independent of rate lim-
itations imposed by mass transfer rates, and independent
of slight variations of the ozone concentration in the
ozone/oxygen gas mixture fed to the reactor (Munoz
and Sonntag, 2000).
As it was demonstrated that salts can have both a
(small) radical scavenging and an initiating effect,
depending on the pH, experiments were performed
under both acidic and basic conditions. The pH values
were chosen to guarantee comparable reactions to take
place: using these conditions the experiments were per-
formed at a pH of 2.4, well below the pKAs of all but one
of the acidic compounds (and still allowing 50% depro-
tonization of the most acidic benzoic acid) or at a pH
clearly above the pKAs of all acidic compounds (at
pH = 10.4). In the experiments performed under basic
conditions a radical mechanism was aimed at, so the
presence of carbonate in the reactor was prevented. A
selection of relevant data regarding these compounds is
given in Table 1.
TABLE 1. Acidity Constants and Hammett s Substituent Parameters for the Acids under Study
Compound
p-Methoxy benzoic acid
p-Methyl benzoic acid
Benzoic acid
p-Chloro benzoic acid
Ozone: Science and Engineering
The experiments were performed as follows: in a closed
0.00
reactor (see Figure 3), 1500 ml of the desired salt solution was
0.05
brought, and adjusted to the desired pH using H2SO4 (caus-
0.10
0.50
ing an additional loading with sulfate of around 0.002 M).
Salt solutions (0.5 M) were prepared from K2SO4, KNO3, or
K2HPO4, respectively. Consequentially, the reactor contents
were thermostated at 15 oC and saturated with ozone, pro-
duced from pure oxygen (HoekLoos gases, NL) by a Sorbios
GSG 001 ozone generator (Sorbios GmbH, Berlin,
60.00
Germany) and introduced at a controlled rate using a mass
flow controller (Brooks Instruments, Veenendaal, NL).
The pH was kept constant by automatic addition (using a
LH Fermentation auto-titrator, LH Fermentation,
Maindenhead, UK) of solutions of 1 M HCl or a 1.5 N
NaOH/Ca(OH)2 (1.25:0.125 M:M) solution. After saturation
a 20.00 ml sample was withdrawn to determine the initial
ozone concentration using the indigo method (Bader and
Hoigne, 1981). Then, 50 ml of a stock solution containing a
total of 30 mM of the mixture of the five organic compounds
(competition experiment) was injected to start the experi-
ment. The pH of the reaction mixture was monitored and
kept constant automatically by addition of a 1.5 N NaOH/
Ca(OH)2 (1.25:0.125 M:M) solution. Ca(OH)2 was used to
prevent the accumulation of carbonate in the alkaline solu-
tion, as this anion may reduce the amount of radicals in the
solution. In addition to using Ca(OH)2 in the alkaline solu-
tion used for the automatic pH regulation, the storage vessel
in which this solution was kept vented through Ca(OH)2
pellets.
At selected time intervals, 20.00 ml samples were taken
from this reactor and brought into 50.00 ml volumetric flasks
containing an acidic buffer and a small, but known, amount
of indigo-trisulfonate, to quench any ozone present in the
sample and to allow for determination of the dissolved
ozone concentration. Consequentially, demineralized
water was supplemented to 50.00 ml. Concentrations of
the individual compounds were measured by means of
HPLC using a 10 cm Chromspher C18 column as men-
tioned in earlier publications (Boncz, 2002; Boncz et al.,
1999). The mobile phase was a gradient, starting as a 15:85
mixture of methanol containing 2% demineralized water
and a buffer containing 1.47 mM sodium acetate, 19.58
mM acetic acid, and 4.84 mM triethylamine in deminera-
lized water, at a flow of 0.5 ml/min. Over time (20 min) the
percentage of the methanol/demineralized water mixture
increased at a constant rate to 30% v/v, to change back at
pKA (19) sp (20) sp+ (20)
4.47 0.27 0.78
4.36 0.17 0.31
4.19 0.00 0.00
3.98 0.23 0.11
August 2005 289
 pH

O3

pH controller
mass flow
controller basic and acidic
solutions
ozone
generator vent

spectro-
pump
photometer
thermostating
coil ( 15 oC)
H 2O 2
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oxygen gas

pH-electrode
magnetic stirrer

FIGURE 3. Schematic drawing of the experimental setup (Boncz, 2002).

the end of the analysis. Detection was performed using a
Kratos Analytical 783 UV detector (Kratos, Manchester,
UK) at wavelengths of 218, 227, and 247 nm. A Varian
DMS 100 spectrophotometer (Varian, Palo Alto, CA,
USA) was used to measure the concentration of ozone in
the off-gas of the reactor (to determine the amount of ozone
needed for a certain degree of oxidation) and to measure the
concentration of indigo trisulfonate in the samples.
RESULTS AND DISCUSSION
The effect of different salt concentrations on the oxi-
dation selectivity was quantified using Hammett free-
energy relationships, in the same way as published before
(Boncz, 2002). The sensitivity of the reaction mechanism
to substituent effects, r, being r = d log(k/k0)/d s, was
taken as a measure of reaction selectivity. Relative reac-
tion rates (k/k0) were determined in competition experi-
ments, thus eliminating the effect of the ozone
concentration from the experimentally determined reac-
The decrease of selectivity in the presence of phosphate
can be in agreement with a stimulation of ozone dissocia-
tion by phosphate as mentioned by Sotelo et al. (1989), if
this dissociation mechanism involves a radical mechan-
ism. The result may be affected however by the large error
in the determination of the reaction rate of p-nitro ben-
zoic acid in this experiment. The reduction of the selec-
tivity in the presence of sulfate, is not supported by
literature data. Hence it cannot be concluded that the
anions studied significantly affect the selectivity of the
ozone oxidation by increasing the share of radical reac-
tions under acidic conditions.
blank
nitrate
0.80 phosphate
0.60 sulphate
0.40 chloride
0.20
log(k/k0)

tion rates. Under both acidic and basic reaction condi- 0.00
tions, the effect of the presence of the different salts on -0.20
-0.40
this selectivity was seen to be small.
-0.60
The experiments at low pH involve a direct oxidation (by -0.80
O3) only. At a pH of 2.4, ozone decomposition by the -1.00
hydroxyl-anion initiated mechanism (Staehelin and Hoigne, -1.00 -0.50 0.00 0.50 1.00
1985) can be considered negligible. As can be seen in Figure +
4, nitrate and chloride hardly affect the selectivity of the
ozone oxidation. A decrease in selectivity (indicated by a FIGURE 4. Hammett-plot showing the effect of four different salts
smaller slope r in the Hammett-plot correlating log(k/k0) (0.5 M) on the selectivity of the oxidation of mixtures of the five
benzoic acids mentioned in Table 1 with ozone at pH = 2.4.
with s;r = 0.38 vs r = 0.65 in the blank) is only seen in
Reference (k0) is benzoic acid.
the presence of sulfate and phosphate.

290 Ozone: Science and Engineering August 2005


0.20 blank
nitrate
0.10 phosphate
sulphate
0.00
-0.4 -0.2 0.0 0.2 0.4 0.6 0.8
-0.10
log(k/k0)
-0.20
-0.30
-0.40
-0.50
FIGURE 5. Hammett-plot showing the effect of four different salts
(0.5 M) on the selectivity of the oxidation of mixtures of the five
benzoic acids mentioned in Table I with ozone at pH = 10.4.
Reference (k0) is benzoic acid.
Downloaded by [The University of British Columbia] at 11:15 14 October 2014
The second set of experiments was performed under basic
conditions, to maximize radical formation from ozone.
Radical scavenging by carbonate was prevented by use of
the NaOH/Ca(OH)2 solution for the automatic pH control.
The results show that no increases in selectivity were
observed, implicating that the different anions, unlike car-
bonate, do not act as radical scavengers (Figure 5).
In the presence of nitrate, the selectivity decreases even
more: r = 0.25 vs = 0.33 in the blank. This could
indicate participation of nitrate in the radical reaction
scheme, in agreement with findings from Fichter (1942),
although the reaction rate constant for the reaction of the
nitrate anion with the hydroxyl radical (reaction [4]) is
not high, especially when compared to the reaction rate
constant of reaction [2].
CONCLUSIONS
When taking available literature into account, one can
hardly expect any effect of the presence of inorganic
anions on the selectivity of the ozone-oxidation of
organic compounds. In some cases (mainly at low pH),
inorganic anions may stimulate ozone dissociation and
perhaps radical formation. In such cases, a decrease of
oxidation selectivity will occur. In more basic solutions
inorganic anions may act as radical scavengers and thus
cause an increase in oxidation selectivity. This increase in
selectivity however, will be accompanied by a loss of
efficiency, as the radicals removed from the system by
scavenging reactions do not contribute to the oxidation
process.
Competition experiments performed under acidic con-
ditions showed no decrease in selectivity by the presence
of nitrate. As was expected from the findings of Sotelo, a
small decrease in selectivity was observed in the presence
of 0.5 M of phosphate. A comparable decrease in selec-
tivity was observed in the presence of sulfate. No loss of
selectivity occurred in the presence of chloride, however.
Ozone: Science and Engineering
The oxidation reactions under basic conditions show a
lower selectivity than those at a low pH due to the larger
contribution of radical degradation pathways. In the pre-
sence of the anions used in this study, the selectivity of the
oxidation increases marginally, indicating that these
anions, unlike the carbonate anion, do not act as signifi-
cant radical scavengers. The exception is nitrate, where
interaction with the radical mechanism is suspected.
Overall, it can be aagreed that the conclusions with
regard to the selectivity and efficiency of the process,
drawn from experiments in low ionic strength model sys-
tems, can be maintained when these processes are to be
used on waste waters containing intermediate concentra-
tions of salts.
REFERENCES
1. Alaton, I. A., A. Kornmuller, and M. R. Jekel, Ozonation of Spent
Reactive Dye-Baths: Effect of HCO3/CO32 Alkalinity, J. Environ.
Eng. ASCE, 128(8):689696 (2002).
2. Beltran, F. J., J. F. Garcia Araya, F. J. Rivas, P. Alvarez, and
E. Rodriguez, Kinetics of Competitive Ozonation of Some
Phenolic Compounds Present in Wastewater from Food
Processing Industries, Ozone Sci. Eng., 22(2):167183 (2000).
3. Archibald, F. and L. RoyArcand, The Use of Ozone to Decolorize
Residual Direct Paper Dyes in Kraft Paper Machine Whitewater,
Ozone Sci. Eng., 19(6):549565 (1997).
4. EnvironmentalProtectionAgency,DevelopmentDocumentforProposed
Effluent Limitations Guidelines and Standards for the Transportation
Equipment Cleaning Category, US-EPA, Office of Water, Report
Number:EPA-821-B-98-011,1998,Washington,DC,USA.
6. Rischbieter, E., H. Stein, and A. Schumpe, Ozone Solubilities in
Water and Aqueous Salt Solutions, J. Chem. Eng. Data, 45(2):338
340 (2000).
7. Sotelo, J. L., F. J. Beltran, F. J. Benitez, and J. Beltran-Heredia,
Henrys Law Constant for the Ozone-Water System, Water Res.,
23(10):12391246 (1989).
8. Christenson, H. K. and V. V. Yaminsky, Solute Effects on Bubble
Coalescence, J. Phys. Chem., 99:10420 (1995).
9. Walker, A. B., C. Tsouris, D. W. DePaoli, and K. T. Klasson,
Ozonation of Soluble Organics in Aqueous Solutions Using
Microbubbles, Ozone Sci. Eng., 23(1):7787 (2001).
10. Sotelo, J. L., F. J. Beltran, M. Gonzalez, and J. Dominguez, Effect
of High Salt Concentrations on Ozone Decomposition in Water,
J. Environ. Sci. Health Pt A Environ. Sci. Eng., 24(7):823842 (1989).
11. Liao, C. H., S. F. Kang, and F. A. Wu, Hydroxyl Radical
Scavenging Role of Chloride and Bicarbonate ions in the H2O2/
UV Process, Chemosphere, 44(5):11931200 (2001).
12. Schmelling, D. C., K. A. Gray, and P. V. Kamat, The Influence of
Solution Matrix on the Photocatalytic Degradation of TNT in TiO2
Slurries, Water Res., 31(6):14391447 (1997).
13. Tanaka, J. and M. Matsumura, Kinetic Studies of Removal of
Ammonia from Seawater by Seawater by Ozonation, J. Chem.
Technol. Biotechnol., 77(6):649656 (2002).
14. Hoigne, J. Chemistry of Aqueous Ozone and Transformation of
Pollutants by Ozonation and Advanced Oxidation Processes, in The
Handbook of Environmental Chemistry. J. Hrubec, Editior. Springer
Verlag: Berlin, Germany, pp. 83141 (1998).
15. Farhataziz and A. B. Ross, Selected Specific Rates of Reactions of
Transients of Water in Aqueous solution, III: Hydroxyl Radical and
Perhydroxyl Radical and Their Radical Ions, (Washington, DC,
USA: U.S. Government Printing Office, 1977), 122 pages.
16. Haag, W. R. and J. Hoigne, Ozonation of Water Containing
Chloride or Chloramines, Water Res., 17:486493 (1983).
August 2005 291
 17. Boncz, M. A., H. Zuilhof, H. Bruning, E. J. R. Sudholter, and
W. H. Rulkens, Linear Structure-Reactivity Relations in the
Advanced Oxidation of Organic Compounds, in Proceedings of the
14th Ozone World Congress, Dearborn, Michigan: International
Ozone Association, (1999).
18. Munoz, F. and C. V. Sonntag, Determination of Fast Ozone
Reactions in Aqueous Solution by Competition Kinetics, J. Chem.
Soci. Perkin Trans., 2(4):661664 (2000).
19. Tratnyek, P. G. and J. Hoigne, Oxidation of Substituted Phenols in
the Environment: A QSAR Analysis of Rate Constants For Reaction
with Singlet Oxygen, Environ. Sci. Technol., 25:15961604 (1991).
Downloaded by [The University of British Columbia] at 11:15 14 October 2014
292 Ozone: Science and Engineering
20. Hansch, C. and A. Leo, Substituent Constants for Correlation
Analysis in Chemistry and Biology, in Substituent Constants for
Correlation Analysis in Chemistry and Biology. New York: John
Wiley & Sons (1979).
21. Bader, H. and J. Hoigne, Determination of Ozone in Water by the
Indigo Method, Water Res., 14:449456 (1981).
22. Staehelin, J. and J. Hoigne, Decomposition of Ozone in Water in the
Presence of Organic Solutes Acting as Promoters and Inhibitors of
Radical Chain Reactions, Environ. Sci. Technol., 19:12061213 (1985).
23. Fichter, F., Organische Elektrochemie, (Dresden, Germany:
Theodor Steinkopff Verlag, 1942), 259 pp.
August 2005