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OCR for page 139
I The Chemistry of
Disinfectants in Water:
Reactions and Products
A major objective of this review of disinfectant chemistry is the
identification of likely by-products that might be formed through the use
of specific disinfectants. The review is part of a comprehensive study of
the possible health elects of contaminants in drinking water. The
prediction of possible products, which is attempted herein, is intended to
be a guide to those contaminants that might require removal or
toxicological evaluation; however, neither of these two aspects of the
overall study is discussed in this chapter.
While there is some current research on using combinations of
disinfectants sequentially, the chemical consequences and benefits of this
strategy are not yet clear. This subject has been omitted from the report.
Similarly the subcommittee did not review the chemical side benefits of
disinfection, such as removal of cyanides, phenols, and, possibly, many
other compounds, although these side benefits may be of considerable
Importance.
Although there is now a rapidly growing body of scientific literature
on chlorine by-products in drinking waters, comparable information for
other disinfectants is very scarce. The subcommittee believed that
reviewing chlorine by-products in detail, while saying little about other
disinfectants, could suggest (probably erroneously) that these alternate
disinfectants are free of the difficulties that are encountered with
chlorine. In an attempt to circumvent this problem, the subcommittee
found it necessary to broaden its information base by reviewing not only
data on potable water, but also studies on nonpotable water, such as
139
OCR for page 140
140 DRINKING WATER AND HEALTH
treated sewage effluents, and on synthetic model solutions, the data from
which might be applicable to potable waters. These studies on nonpota-
ble water shed light on the chemistry of disinfectants in drinking waters,
although it is obvious that many compounds produced in treated sewage
or in artificial laboratory experiments may never be found in drinking
waters. To avoid confusion, a clear distinction has been drawn
throughout this chapter between information acquired from actual
drinking waters and information derived from other sources.
A great deal of research on the chemistry of disinfectants is now in
progress. An attempt was made to ensure that this chapter was current
by contacting many scientists who are working in this field in the United
States and abroad. However, in an active field such as this, any review
can become rapidly outdated.
The chapter begins with a preliminary discussion of the character of
the natural organic substances from which by-products of organic
disinfectants are thought to originate. Subsequent sections describe the
chemistry of chlorine, chloramines, halogens (Br2 and I2), chlorine
dioxide, and, finally, ozone.
PRECURSOR COMPOUNDS AND THE HALOFORM REACTION
Since 1975, many investigators have assumed that the ubiquitous
appearance of chlorofo~ (CHCl3) and other THM's (trihalomethanes,
or haloforms) in chlorinated water can be explained by the mechanisms
involved in the "haloform reaction" and that the principal precursors of
THM's that are found in natural waters are humic substances. As
discussed subsequently in the section pertaining to chlorine chemistry,
the haloform reaction will proceed only if specific functional groups are
present in the available pool of organic compounds. It is likely that the
haloform reaction does occur when natural waters are chlorinated and
that humic substances provide the necessary functional groups, but it is
not certain that either of these postulates is true. For that reason, both
topics the haloform reaction and humic substances—merit further
. . .
alscusslon.
The Haloform Reaction
The terms "trihalomethanes" and "haloforms" are synonymous, but the
term "haloform reaction" is often misused in discussions of THM
formation in natural waters. In recent literature, it has been used to
mean any reaction between aqueous solutions of organic compounds
OCR for page 141
The Chemistry of Disinfectants in Water 141
and hypohalous acids that results in THM formation, but it actually has
a classic chemical definition that is more restrictive. In the future, the
expanded meaning may be preferred, but at present the term "haloform
reaction" is inappropriate from a strict chemical interpretation, unless
one is sure that the THM's are formed by reactions between hypohalous
acids and compounds containing acetyl groups or substituents that can
be converted to acetyl groups.
The classic haloform reaction, which is actually a series of well-defined
reactions, has been known since the 1800's (Fuson and Bull, 1934~. The
earliest studies were conducted with nonaqueous solvents, high concen-
trations of organic compounds, and chlorine gas, but research since 1974
has focused more on defining the reactions that yield THM's under
conditions that are closer to those more commonly encountered during
the treatment of drinking water supplies.
Compounds, or classes of compounds, with the general formula
CH3CHOHR or CH3COR, which includes ethanol, acetaldehyde,
methyl ketones, and secondary alcohols, can participate in the haloform
reaction. So may olefinic substances with the general structure
CH3CH=CR,R2, which will be oxidized by hypochlorous acid (HOC1)
first to secondary alcohols and then to methyl ketones. The site of attack
by chlorine is the carbon adjacent to the one bearing oxygen, and this
attack, wherein the hydrogen atoms are successively replaced by
chlorine, is preceded by a dissociation of one hydrogen (as H+) to
produce a carbanion ('H2-) that can react with C1(I), from hypochlo-
rous acid. Chlorine substitution continues until all hydrogen atoms on
the same carbon have been replaced. The final step involves a hydrolytic
cleavage of the trihalogenated carbon (the trichlorinated carbon, in this
example) to form the THM, which in this example would be chloroform
(Morris, 1975).
While it is well known that compounds containing acetyl groups are
reactants in the haloform reaction, methyl ketone (acetone, CH3COCH3)
itself is not a likely precursor during water treatment. According to
Morris and Baum (1978), who cited a study by Bell and Lidwell (1940),
the half-life for chloroform formation from acetone at pH 7 and room
temperature is nearly a year. Stevens et al. (1978) also discounted
acetone as a precursor of THM because of the slow reaction rate. The
rate-limiting step in the haloform reaction is the ionization that produces
carbanions, and, apparently, simple ketones are not representative of
those which react quickly to produce chloroform under conditions in
water treatment plants. Studies with model compounds, which are
discussed in the section pertaining to chlorine chemistry, have shown
OCR for page 142
142 DRINKING WATER AND HEALTH
that other types of compounds, including other ketones, may react more
rapidly than the simple ketones.
Humic Substances
As was mentioned previously, it is an attractive assumption that
naturally occurring humic substances, which are derived from the
structural components of living and decaying plants and/or soil
dissolution and runoff, provide the most ubiquitous source of haloform
precursors in natural water systems. Only limited information is
available concerning the structure of these complex natural products,
and it is not yet known whether all the major structural features have
been identified, if any structural differences exist among the hectic
substances in waters from different geographic areas, and if these
substances are closely or distantly related to soil humic and marine
humic materials.
The term "humic acid" is generic and refers to that fraction of soil
organic material that is soluble in alkaline solutions but insoluble in acid
and ethyl alcohol (Christman and Oglesby, 1971~. The fraction that is
soluble in acid is commonly labelled "fulvic acid," and that material
precipitated by acid but soluble in ethyl alcohol is "hymatomelanic
acid." Soils vary widely in their relative compositions of these acids, but
aquatic organic material behaves operationally as fulvic acid (Black and
Christman, 1963), which typically contains more oxygen and less
nitrogen than the humic acid fraction in both soil and aquatic organic
matter. Marine organic matter (including sedimentary material) is
derived largely from marine organisms and contains more sulfur than its
fresh water equivalent (Nissenbaum and Kaplan, 1972; Stuermer and
Harvey, 1978~. Christman and Oglesby (1971), Steelink (1977), Schnitzer
and Kahn (1972), and Dubach et al. (1964) have reported the presence of
carboxyl, phenolic and alcoholic hydroxyl, carboxyl, and methoxyl
functional groups in humic material. It would appear that the more
oxygenated fulvic acid fraction has a greater carboxyl acidity than the
humic acid fraction.
Whittaker and Likens (1973) estimated that 90~0 of the terrestrial
biospheric carbon (standing biomass) is tied up in woody tissue. Lignin is
a dominant (20~<~o) chemical entity in woody tissue. Because of its
refractory nature, it is probably a principal precursor of soil humus,
although a myriad of other natural products unquestionably contribute
to the complex pool of soil organic matter. Lignin itself is a mixed
polymer of guaiacyl (I), syringyl (II), end p-hydroxyphenylpropane (III)
aromatic moieties:
OCR for page 143
The Chemistry of Disinfectants in Water 143
c3 c3 c3
~ /[~\ ~
OCH3 CH3 O OCH3
OH OH OH
I II III
No other substitution patterns are known in nature and no other length
of alkyl side chain has been found in lignin from any source. Oxidative
degradation of lignin produces, therefore, only three aromatic substitu-
tion patterns (I, II, and III), although the relative amounts of each vaIy
among the gymnosperms, angiosperms, and the grasses. Intermonomeric
linkages in the lignin macromolecule are of both carbon-to-carbon and
ether linkage types. The largest single contributor is believed to be the
,8-4' ether configuration. Side-chain carbon atoms may be in various
states of oxygenation or unsaturation, and may contain methyl ketone,
allyl, and secondary alcohol configurations.
Significant changes occur in the humification process as reflected by
comparative functional group data for lignin and soil humic acid (Table
III- 1~.
This process, which is oxidative in nature, may strongly affect the
characteristics of aquatic humic matenal. Microbial mediation is
apparent when there is a marked decrease in methoxyl groups and
increases in phenolic hydroxyl and carboxyl acidity.
TABLE [it-] Comparative Functional Group Analysis
of Soil Humic Acid and Spruce Lignina
Group Content, mM/g
Functional Group
Soil
Humic Acid
Methoxyl
Total hydroxyl
Phenolic hydroxyl
Alcoholic hydroxyl
Carbonyl
Carboxyl
5.1
6.2
1.6
4.6
1.0
Trace 86.0
0.2
5.1
2.9
2.2
5.5
a From Christman and Oglesby, 1971.
OCR for page 144
144 DRINKING WATER AND HEALTH
The contribution of woody tissues to marine humus is not apparent
from the results of degradative experiments on marine fulvic acids, which
are considered to be autochthonous materials. Degradation of both soil
humic acid and aquatic humic material reflects a partial lignitic origin
(Table III-2), although a variety of other aromatic patterns (m-dihy-
droxy) and aliphatic chain lengths (C~ Cay) must result from other
natural product sources. The data in Table III-2 indicate key areas of
inadequacy in our knowlege of the chemical nature of aquatic Ohmic
substances. It is not possible to model natural aquatic humic material
with a desirable degree of chemical accuracy, and it certainly is not
possible to state that THM's, which appear in chlorinated water
containing humic substances, are derived by the classic haloform
reaction.
The ultimate concern for public health protection is, of course, the fact
that THM's are formed during the chlorination of drinking water
sources. Consequently, a discussion of chemical mechanisms may appear
to be rather academic. However, a precise understanding of the
mechanisms by which the THM's are formed may prove to be truly
beneficial by helping water utility personnel avoid the conditions during
treatment that promote the appearance of high concentrations of these
compounds in finished water. Studies with model compounds under
well-defined laboratory conditions have been useful in elucidating these
mechanisms and reaction conditions. Examples are given in the section
pertaining to chlorine chemistry.
CHLORINE
Chlorine has been the principal disinfectant of community water
supplies for several decades. Until recently, its use had never been
questioned seriously because the health benefits derived from it were so
obvious. Although an occasional taste-and-odor problem in finished
water was attributable to the reaction of chlorine with some substance in
the raw water, the events were usually intermittent, short-lived, and
presumably did not affect the public health. However, in 1974, Rook
(1974) in the Netherlands and Bellar et al. (1974) in the United States
reported that chlorine reacts with organic precursors that are found in
many source waters to produce a potential carcinogen, chloroform
(CHC13~.
In December 1974, Congress passed the Safe Drinking Water Act (PL
93-523), and in early 1975, the U.S. Environmental Protection Agency
(EPA) began an 80-city water supply survey the National Organics
Reconnaissance Survey (NORS) to determine the extent of the prob-
OCR for page 145
The Chemistry of Disinfectants in Water 145
lem (Symons et al., 1975~. As part of NORS, finished waters from five
cities (Miami, Florida; Seattle, Washington; Ottumwa, Iowa; Philadel-
phia, Pennsylvania; and Cincinnati, Ohio), which represented the major
types of water sources in the United States, were analyzed as thoroughly
as possible for all volatile organic compounds, i.e., those that can be
stripped from solution by purging with an inert gas (Coleman et al.,
19761. Seventy-two compounds were identified, 53% of them containing
one or more halogens. A later study, the EPA National Organic
Monitoring Survey (NOMS), included analyses of samples that had been
taken from the water supplies of 113 cities (Brass et al., 1977) on four
occasions over an 18-month period during 1976 and 1977. The source
waters of a few cities were examined, but most of the effort was directed
toward an analysis of finished waters for chloroform and 20 other
volatile organic compounds. In addition to the 21 compounds that were
ordinally selected, five others appeared frequently and were reported.
Since 1974, there have been numerous other surveys similar to NORS
and NOMS, but they have been more restricted in scope. In addition,
research activity has been intensified to isolate and identify the
precursors, products, and mechanisms that are associated with the
presence of potentially toxic organic compounds in both water and
wastewater. In December 1976, the EPA published a list of 1,259
compounds that had been identified in a variety of waters (including
industrial effluents) in Europe and in the United States (Shackelford and
Keith, 1976~. The agency is currently compiling a comprehensive register
of all data concerning the identification of organic pollutants in water.
Properties of Aqueous Chlorine
Various aspects of chlorine chemistry have been reviewed by Jolley et al.
(1978), Miller et al. (1978), Morris (1975, 1978), and Rosenblatt (1975~. A
synopsis of the basic principles will provide some understanding of the
various forms that chlorine can assume in water and the reactions that it
can undergo with certain types of compounds.
REACTIVE FORMS OF CHLORINE IN WATER
"Aqueous chlorine" is a misleading term because the active form of
chlorine that is present in treated water and wastewater is not the
gaseous chlorine molecule (C12) but, rather, a hydrolysis product,
hypochlorous acid (HOC1), which is formed from the reaction between
the chlorine molecule and water:
C12 + H2O = HOC1 + H+ + C1 `1)
OCR for page 146
146
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D :=
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331 333
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OCR for page 147
147
at
V\~.4
E9 -all= at i '-
j 5 a 3 ~, ~ ~ R
~ sac
a ~
°
a ~
- ~ ~ -
~ os
e ~— ~ ~ R
~ Is ~ ~ ~ ~
OCR for page 148
148 DRINKING WATER AND HEALTH
Hypochlorous acid, a weak acid, can ionize as follows:
HOC1 = H+ + OC1
(2)
The degree of ionization depends primarily on the pH and temperature
of the water. The concentration of hypochlorous acid and the hypochlor-
ite ion (OC1-) are approximately equal at pH 7.5 and 25°C.
Another form of chlorine, the hypochloronium acidium ion (H2OC1+),
is known to exist (Miller et al., 1978; Rosenblatt, 1975), but its
concentration would be extremely low in water at pH's between 5 and 9.
Still another form of chlorine, the chloronium (or chlorinium) ion (C1+),
has been proposed as an important reactant in aqueous solutions of
organic compounds (Carlson and Caple, 1978), although its existence is
disputed (Rosenblatt, 19751. Nevertheless, Morris (1978) pointed out
that "the reactant behavior of HOC1 with organic carbon and amino
nitrogen is as an electrophilic agent in which the chlorine atom takes on
partially the characteristics of C1+ and combines with an electron pair in
the substrate." Finally, Carlson and Caple (1978) mentioned that
another form of chlorine, the chlorine radical (Coo), may react in the light
to produce chlorine-substituted organic compounds when the parent
chlorine molecule is not lost by any other significant reaction pathway.
Rosenblatt (1975), citing others, described this form as "probably the
most selective chlorinating species of all."
Free chlorine species (HOC1, OC1-, C12, H2OC1+, C1+) will oxidize
both the bromide ion (Br~) and iodide ion (I-) to hypobromous and
hypoiodous acids (HOBr and HOI). This reaction, as will be discussed
later, is postulated to account for the presence of bromine- and iodine-
substituted organic compounds, particularly the mixed-halide haloforms,
in waters that had been disinfected by chlorination.
REACTIONS OF HYPOCHLOROUS ACID WITH ORGANIC COMPOUNDS
Chlorine reacts in solutions of organic compounds by one or more of
three basic mechanisms (Jolley et al., 1978; Miller et al., 1978; Morris,
1975; Morris, 1978), namely, addition, during which chlorine atoms are
added to a compound; oxidation; and substitution, during which
chlorine atoms are substituted for some other atom that is present in the
organic reactant. All three of these reactions involve hypochlorous acid
as an electrophile.
Only addition and substitution reactions produce chlorinated organic
OCR for page 149
The Chemistry of Disinfectants in Water 149
compounds. Oxidation reactions account for most of the "chlorine
demand" of natural waters and waste treatment effluents (Jolley et al.,
1978; Morris, 1975), but the end products are not chlorinated organic
compounds. That is not to say that those products cannot be harmful.
Miller et al. (1978) have mentioned that epoxides can be produced from
carbon-chlorinated compounds at pH values that are common in water
treatment plants (e.g., pH 9.5-10.5) where softening is practiced. To
illustrate, they describe the reaction between ethylene (COHN) and
hypochlorous acid, which yields ethylene chlorohydrin (ClCH2CH2OH)
as an intermediate. This hydrolyzes to form the epoxide, ethylene oxide
(C2H4O). Carlson and Caple (1978) mentioned one such reaction, in
which a mixture of chlorohydrins resulted from the reaction of oleic acid
[CH3(CH2~7CH=CH(CH2~7COOH] with hypochlorous acid. Presum-
ably, these would be converted to epoxides if the pH were to be
increased. Carlson and Caple also showed how a ubiquitous natural
compound, a-terpineol [CH3C6H4C(CH3~20H], could form epoxides
when reacted with hypochlorous acid. These reactions illustrate how
chlorination may result in the development of nonchlorinated products,
e.g., the epoxides, which may pose health risks. In instances such as those
just discussed, a chlorinated intermediate, which itself should be
evaluated toxicologically, is involved.
Chlorine By-Products Found in Drinking Water and Selected
Nonpotable Waters
The most frequently mentioned products of aqueous reactions between
chlorine and selected types of organic compounds are discussed in this
section. Special attention is given to the trihalomethanes (THM,s)
because of the current interest in them as potentially hazardous by-
products of chlorination in municipal water treatment facilities. The
specific reactions by which THM's are produced in chlorinated natural
waters are not well understood because the chemical structures of the
precursor organic compounds, which are thought to be primarily heroic
substances, are highly varied and extremely complex. A summary of the
relevant facts concerning these ubiquitous, natural organic substances is
presented in the section on precursors. The tea "haloform reaction" is
often mentioned as the mechanism by which THM's are produced when
natural waters are chlorinated. This has not been validated definitively in
actual water treatment systems. However, the reaction will be discussed
in conjunction with THM formation in natural waters because it is one
possible mechanism that has been described thoroughly in the literature.
OCR for page 240
240 DRINKING WATER AND H"LTH
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OCR for page 241
The Chemistry of Disinfectants in Water 241
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OCR for page 250
Representative terms from entire chapter:
chlorine dioxide
