In the Classroom

edited by

Resources for Student Assessment

John Alexander
University of Cincinnati
Cincinnati, OH 45221

Use of Chloroisocyanuarates for Disinfection of Water

Application of Miscellaneous General Chemistry Topics
Gabriel Pinto
Departamento de Ingeniera Qumica Industrial y del Medio Ambiente, E.T.S.I. Industriales, Universidad Politcnica de
Madrid, 28006 Madrid, Spain; gpinto@iqi.etsii.upm.es
Brian Rohrig
Aurora High School, Aurora, OH 44202

Chemistry often remains abstract and alien to students

and subsequently they are not motivated to study further.
There is evidence that students will better appreciate chemistry concepts if these concepts are applied to compounds
found in everyday lives. The idea of using a familiar context
with chemistry is common but not usually found in textbooks. Thus, chemistry teachers are always looking for examples of how chemical phenomena affect our lives (15),
and for novel problems that will stimulate students interest
once they have mastered the more routine skills.
This article describes a motivating and holistic approach
to the study of water chlorination. The compounds used, sodium dichloroisocyanurate (anhydrous and dihydrate) and
trichloroisocyanuric acid, seem mysterious to the students at
first, yet studying water chlorination allows students to focus on the versatility of the general chemistry concepts. This
paper represents a continuation of a research program intended to help university-level instructors include connections between students daily experience and chemical
principles taught in the classroom (611).
After an introduction to the subject, a series of questions is proposed to address various topics, including, formulation, molar mass, stoichiometry, chemical equations,
balanced equations, oxidation states, acidbase reactions, tautomerism, resonance, chlorinating products, and use of chlorine as a disinfectant.
Chlorine as a Disinfectant
Industry and commercial settings use the term chlorine
as a generic term for several different chlorine-containing
compounds. However, it is important that we develop the
habit of calling chemical compounds by their proper names,
otherwise students may think, for example, that the copper
in the blood stream is the same as metallic copper.
Chlorine is a disinfectant that has been used in water
treatment for a little more than a hundred years (12). Its use
as a disinfectant for drinking water and swimming pools is
widely known, as well as its use as a bleaching agent (13
16). The purpose of water disinfection is to destroy pathogenic organisms, thus preventing waterborne diseases such
as typhoid, cholera, dysentery, and hepatitis. Elemental chlorine dissolves slightly in water and disproportionates into
hypochlorous acid (HClO) and hydrochloric acid (HCl)

Cl2 + H2O

HClO + H + + Cl

(1)

Where the equilibrium constant (17) at 25 C is given by

HClO H + Cl
K =
4.5 104
Cl 2

(2)

HClO is a weak acid and it partially dissociates

HClO

H + + ClO

(3)

The corresponding dissociation constant (18), at 25 C is

H + ClO
Ki =
= 2.9 10 8
HClO

(4)

Hypochlorous acid is the principal water disinfectant.

It is widely used to kill bacteria and algae and is an effective
biocide since ClO is a strong oxidizing agent. Thus, chlorine as HClO is needed for sanitation and chlorine as ClO
is needed for oxidization. The disinfecting action is due to
both species, HClO and ClO, but not directly to the Cl2.
HClO, a weak acid, is not harmful to people. HCl, a strong
acid also produced by hydrolysis of the dissolved chlorine gas
(eq 1), is not harmful because of the low concentration produced.
The pH of water determines how much HClO dissociates into H and ClO, in accordance with eq 4, due to the
relationship
HClO
=
HClO + ClO

1
ClO

1+

HClO

1
K i (5)
1+ +
H

Chlorine is most efficient at pH of approximately 7.47.6.

In accordance with eq 5, at a high pH chlorine does not produce very much disinfectant, HClO; it is mostly in the form
of hypochlorite (plenty of oxidizing agent and low disinfectant). For example, at pH 7.0, 78% of the chlorine exists in
the active hypochlorous acid form, and increasing pH to 8.0
reduces the hypochlorous acid concentration to only 26%.

JChemEd.chem.wisc.edu Vol. 80 No. 1 January 2003 Journal of Chemical Education

41

In the Classroom

The hypochlorite ion is reduced to inactive chloride as

it functions as a biocide, following the reduction half-reaction
ClO + 2 H + + 2 e

Cl + H2O

(6)

Chlorine is available in a number of forms for water disinfecting effects (1921), mainly: chlorine gas (delivered as
a liquid in pressurized containers), chloroisocyanurates
(sodium dichloroisocyanurate or trichloroisocyanuric acid),
calcium hypochlorite, lithium hypochlorite, and sodium hypochlorite. These compounds provide free available chlorine,
that is, chlorine available in the forms of hypochlorous acid
and hypochlorite ions (22). Free available chlorine, known
by the acronym FAC in the water treatment industry, is a
measure of the oxidizing or biocidal power of the active chlorine in a compound expressed in terms of elemental chlorine,
usually referred to as percent by weight (20). Despite the fact
that the terms free and available mean almost the same
thing, the redundant term free available chlorine is widely
used in industry.
Combined available chlorine is chlorine existing in water in chemical combination with ammonia or organic nitrogen compounds such as amines and proteins. These
combined forms are known as chloramines, such as NH2Cl,
NHCl2, or NCl3. The chloramines do not exhibit any substantial sanitizing power and are actually the cause of some
unpleasant problems such as eye and skin irritation and strong
odor in pools (23). Chloramines are also known as combined
residual chlorine and should be kept to a minimum.
Table 1 gives the formula of chloroisocyanurates and the
corresponding FAC as found in several references (18, 20)
and in different labels of chlorinating products found currently in supermarkets. Chlorine products are required by law
to display on the label their chemical name and concentration. Thus the label of these products can be a source of questions for students.
Advantages and disadvantages of each type of chlorine
product for use as pool or spa water disinfectant or oxidant
can be evaluated by considering the properties, cost, and
safety (21). Ultraviolet light degrades chlorine by a photochemical reaction
2Cl2 + 2H2O

UV

(7)

4HCl + O2

In the absence of isocyanuric acid (1,3,5-triazine-2,4,6

(1H,3H,5H )-trione, see Figure 1) as a stabilizer, on a bright
sunny day 90% of the active chlorine can be destroyed by
sunlight in just 2 h. HClO and ClO are thought to closely
attach to one of the three bonding sites of the isocyanuric

acid molecule. As long as HClO and ClO remain attached,

they are not degraded by sunlight. Cyanuric acid stores chlorine in the form of HClO and releases it to do its work on
bacteria and algae. This compound and its chlorinated derivatives form a complex ionic and hydrolytic equilibrium
system, consisting of at least ten isocyanurate species (20).
Sodium dichloroisocyanurate (sodium 1,3-dichloro1,3,5-triazine-2,4-dione-6-oxide, see Figure 1), NaDCC, is
the only popular chlorine product that does not require the
addition of either a neutralizing chemical or isocyanuric acid,
because NaDCC solutions have a pH close to 7 and it supplies the proper ratio of both chlorine and stabilizer. Apart
from pools, the use of chlorine release tablets formulated using NaDCC to make up disinfectant solutions is well established throughout the world as a disinfectant for baby bottles
and other nursery equipment (24, 25), and for the daily disinfecting of soft hydrophilic contact lenses.
NaDCC, an oxidizing compound, dissociates into HClO
(free chlorine) and isocyanuric acid (stabilizer) in water, which
helps prevent sunlight from degrading the chlorine. The
NaDCC is highly efficient and yields a good performance
with no harm to humans. It is available in granular form or
as a tablet, sometimes in an effervescent base.
Trichloroisocyanuric acid (trichloro-1,3,5-triazinetrione),
TCC, is used mainly for pool water. It is highly acidic and
will corrode equipment and pool tile if improperly used. It
is necessary to add about 350 g of soda ash (the trade name
for sodium carbonate) for each kg of trichlor used. The addition of isocyanuric acid is not required.
Questions
The following questions cover various topics of general
chemistry that are related to the use of chloroisocyanurates
for chlorination of water. These questions are merely a starting point; the reader is encouraged to develop additional questions that will encourage students to apply chemical concepts
to the chlorination of water.

Question 1
Search the Internet, chemistry handbooks, organic chemistry books, or catalogs of chemicals to find the chemical
structure of NaDCC, TCC, and isocyanuric acid.
Question 2
When dissolved in water, NaDCC reacts to form hypochlorous acid and isocyanuric acid. Write the corresponding balanced reaction.
+

O
Table 1. Formulas and Free Available Chlorine, FAC,
of Common Chloroisocyanurates
Substance
Chlorine

Chemical Formula
Cl2

100

Sodium dichloroisocyanurate
(NaDCC)
Anhydrous

C3Cl2N3O3Na

6263

Dihydrate

C3Cl2N3O3Na2H2O

5556

C3Cl3N3O3

8991

Trichloroisocyanuric acid
(TCC)

42

Cl

Cl
N

FAC / wt. %

Na

O
Cl

N
N

H
N

N
N

Cl

Cl

Figure 1. Chemical structures of (a) sodium dichloroisocyanurate,

NaDCC; (b) trichloroisocyanuric acid, TCC; and (c) isocyanuric
acid .

Journal of Chemical Education Vol. 80 No. 1 January 2003 JChemEd.chem.wisc.edu

In the Classroom

Question 3
If the reaction of the previous question is a reduction
oxidation reaction, calculate the oxidation numbers of the
different atoms and identify the oxidizing and reducing
agents.
Question 4
Repeat questions 2 and 3 for TCC.
Question 5
Explain which species of the previous questions have
resonance structures or the possibility of tautomerism.
Question 6
Explain why the dissolution of NaDCC results in a almost neutral solution and the dissolution of TCC results in
an acidic solution.
Question 7
Deduce by stoichiometry the values of FAC for the compounds shown in Table 1.
Answers to Questions

Answer 1
The chemical structure of these compounds can be found
using several different sources (19, 20, 26). They are shown
in Figure 1.
Answer 2
C3H3N3O3(aq) + Na+(aq)
C3Cl2N3O3Na(s) + 2H2O(l)

+ ClO (aq) + HClO(aq)

(8)

Answer 3
To calculate the oxidation numbers of atoms in the
NaDCC, we can use the method as described by Halkides
(27). We can also consider the difference between valence
electrons of isolated atoms and the valence electrons of
bonded atoms as assigned by their electronegativity (28, 29)
shown in Figure 2. The oxidation state or number is the
charge on an atom in a molecule (or polyatomic ion) calculated on the assumption that bonding electrons between atoms are assigned to the more electronegative atom. Although
calculation is normally done by a set of rules that assumes
certain oxidation states for certain atoms, such as 2 for O,

2
+4

O
2

C
N
Cl

C3Cl3N3O3(s) + 3H2O(l)

3HClO(aq) + C3H3N3O3(aq)

(9)

The three atoms of N are reduced from 2 to 3, acting

as the oxidizing agent, and the three atoms of Cl act as reducing agent because they are oxidized from 0 to +1.

Answer 5
For isocyanuric acid and TCC, resonance has little importance because the other resonance structures, different from
those drawn in Figure 1, have more formal charges not equal
to zero, and thus have a smaller contribution to the resonance
hybrid. However, the dichloroisocyanurate anion that forms
NaDCC exhibits resonance, as exhibited in Figure 3.
This question can be used for clarifying the distinction
between formal charge and oxidation state (considered in
question 3). Formal charge is the charge of an atom in a compound calculated on the assumption that the electrons in each
bond are shared equally between the two atoms involved, and
thereby underestimates electron transfer. Oxidation state formalism, where electron transfer is overestimated, is a convenient tool for dealing with redox reactions. Formal charge
formalism can be used as a tool to evaluate and select the
best Lewis structure (29). It is important to realize that the
actual charge of the atoms in a compound lies somewhere
between these two descriptions. As can be noted with the
examples shown in this paper, oxidation numbers do not depend on the resonance form. It is also important to note, for
checking the correct assignment of charges, that the sum of
the oxidation states of all the atoms within a molecule must
be equal to zero. In a polyatomic ion, the sum of the charges
of all atoms must equal the net charge of the ion. The same
rule applies to formal charges.
Both structures shown in Figure 3 have the same contribution to the resonance hybrid. Other resonance structures
have more nonzero formal charges, and thus they have a
smaller contribution to the resonance hybrid.

+4

Cl

Answer 4

NaDCC is a special case as electronegativities of N and Cl

are the same; the electrons in each bond NCl must been
shared equally between the two atoms involved. The Pauling
electronegativities of O, N, Cl, C, and H, according to ref
30 are 3.5, 3.0, 3.0, 2.5, and 2.1, respectively.
Following the same procedure for the molecule of
isocyanuric acid, C3H3N3O3, we conclude that in eq 8 two
atoms of N are reduced from 2 to 3, and two atoms of Cl
are oxidized from 0 to +1 (in the form of HClO or ClO).
Thus, two N atoms act as oxidizing agent or oxidant and
the two Cl atoms act as reducing agent or reductant.

3
+4

O
2

Na

+1

Figure 2. Oxidation numbers for sodium dichloroisocyanurate.

Cl

Cl

N
N
Cl

N
N

Cl

Figure 3. Resonant structures of the dichloroisocyanurate anion.

JChemEd.chem.wisc.edu Vol. 80 No. 1 January 2003 Journal of Chemical Education

43

In the Classroom

Student Assessment column. One of us (G.P.) dedicates this

work to his children (Luca and Elisa), because, thanks to
them, disinfecting their baby bottles gave him the opportunity of knowing about the studied chlorinating compounds.

H
O

O
H

H
N

H
O

Literature Cited

Figure 4. Tautomeric forms of (a) isocyanuric acid and (b) cyanuric acid.

Isocyanuric acid tautomerizes with cyanuric acid, as illustrated in Figure 4. Lone pairs have been placed in the
structures in Figures 14, in order to facilitate the counting
of electrons.

Answer 6
As demonstrated in eq 8, the dissolution of NaDCC generates a weak acid and a buffer formed by HClO and ClO,
but the dissolution of TCC, as shown in eq 9, generates two
acids.
Answer 7
First it is necessary to calculate the molecular weights of
the chlorine-containing compounds: anhydrous NaDCC
(220.0 gmol), NaDCC dihydrate (256.0 gmol), TCC
(232.5 gmol), and isocyanuric acid (129.1 gmol). Examining the reaction of anhydrous NaDCC dissolution as described in eq 8 and the equivalence between chlorine and
hypochlorous expressed in eq 1, the FAC of 100.0 g of
NaDCC anhydrous is

2 mol ClO or HClO

mol NaDCC

100.0 g NaDCC

mol NaDCC
220.0 g NaDCC

mol Cl2

mol ClO or HClO

70.9 g Cl 2
= 64.5 g Cl 2

mol Cl 2

As seen in Table 1, the tabulated value of available

chlorine for this compound is 6263%, that is, slightly lower
than the obtained value. Proceeding in a similar way, the value
of FAC for 100.0 g of NaDCC dihydrate is 55.5 g and for
100.0 g of TCC the value is 91.6. In both cases these values
are also close to the tabulated values. For chlorine, FAC is
100% by definition.
Acknowledgments
The authors would like to gratefully recognize the financial support provided by the Fundacin Espaola para la
Ciencia y la Tecnologa (Spanish Foundation for Science and
Technology) under the Project Teaching/Learning of Chemistry and Everyday Life (Grant No. 17502/57-1F). Also, we
would like to thank the helpful comments of the reviewers
and especially John J. Alexander, editor of Resources for

44

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Journal of Chemical Education Vol. 80 No. 1 January 2003 JChemEd.chem.wisc.edu