OCR for page 29
Chemistry and Toxicity of Disinfection 29
able levels of chloroform. Resorcinol, as suggested earlier by Rook (1977),
consumed a large quantity of chlorine (7 moles per mole of resorcinol) and
rapidly produced 1 mole of chloroform. Similar results were produced with
their other model compounds, suggesting that chloroform is a primary re-
action product of chlorination of aquatic humic materials that contain sub-
structures similar to these model compounds. Other by-products produced
by their model compounds are shown in Table 3-1. High chlorine-to-carbon
ratios favored the production of nonvolatile hydrophilic by-products.
Boyce and Hornig (1983) studied chloroform production from chlorination
of 1,3-dihydroxyaromatic compounds and simple methyl ketones, which they
confirmed to be efficient at producing chloroform. With isotope labeling,
they unambiguously demonstrated that the C2 position of resorcinol is re-
sponsible for chloroform generation, as previously hypothesized by Rook
(1977) and Norwood et al. (19801. Boyce and Hornig (1983) further dem-
onstrated that the specific types of chlorinated products depend on both pH
and the relative concentrations of chlorine and substrate in solution. The by-
products that they obtained from resorcinol at various chlorine concentrations
and pH values are shown in Table 3-2 and confirm the previous observations
of Norwood et al. (1980) regarding by-products formed at neutral pH.
Based on these results and previous hypotheses of Moye (1967) and
Rook (1980), Boyce and Hornig proposed a comprehensive mechanism
for the conversion of 1,3-dihydroxyaromatic structures to chloroform by
aqueous chlorination. A portion of this proposed mechanism, modified
and reproduced in Figure 3-2, involves successive electrophilic attack of
chlorine to produce substituted resorcinols (I) with the eventual loss of
aromatic character to produce the intermediate pentachlororesorcinol (II).
This is followed by hydrolytic ring cleavage and a number of other sub-
stitution and hydrolysis reactions to produce chloroform and short-chain
chlorinated acids, in this case chloromatic acid (VI).
De Leer and Erkelens (1985) attempted to support the mechanism pro-
posed by Boyce and Hornig (1983) by synthesizing the proposed inter-
mediate pentachlororesorcinol according to the method of Zincke (1890)
and subjecting it to aqueous chlorination at neutral pH. Although the
chlorination of resorcinol and pentachlororesorcinol produced several iden-
tical products, large discrepancies were seen in apparent reaction rate,
chloroform production, and products, indicating that pentachlororesorcinol
is not a major intermediate. De Leer and Erkelens (1985) further concluded
that the principal reaction and most important side reaction are
C6H6O2 + 7C12 + 4H2O ~ CHC13 + CO2 + cis-HOOCCC1 = CHCOOH + 10HC1, and
C6H6O2 ~ cis-HOOCCC1 = CHCH2COOH + CO2 or CHC13,
but that many side reactions producing other chloroform precursors and
highly oxidized products occur.
OCR for page 30
30 DRINKING WATER AND HEALTH
TABLE 3-1 Reaction Products from Model Compounds and
Hypochlorous Acid (HOCl~a
Products Identified
Reactant At 0.5 Cl2/C
At 2.0 Cl2/C
1,3 DIHYDROXY
BENZENE
OH
OH
'JC1X(X=1-3)
HO OH
H
Cl,4~'C1
1 ~C1
O O
CHC13
CHC13
O O
11 11
HO-C-C=3C- C-OH
1 1
H C1
CC13COOH
3-METHOXY-4
HYDROXY
CINNAMIC ACID
CH=CHCOOH
CCH3
OH
CH=CHCOOH
LOCH
OH
r3
CH=CHCOOH
~C12
OCH3
OH
CH=CHC 1
OCH3
OH
CH=CHC 1
OCCIH3
OH
CHC
13
CHC13
CHC12COOH
CC13COOH
aFrom Norwood et al. (1980) with permission.
OCR for page 31
31
it:
. -
c~
-
o
~ -
o
no
Hi
1
to
-
x
o
. -
'e
· of
o
- <5
~ rat
V 0
°
Ct
O
so ._
~ X
._
~0
Cal
=, 1
~ O
o
. _
Ct
X
o
I
~ O
_Q ~
m x
En ~
TIC
C ~
O_
~O
Ct~
C)
i,, O
a
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X
0
of
o
~ /
-
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~O:V
o4o o 4o
~ 0
off
C:
_ ~_ ~
~ 0 ~ O 0 et
of 04o of o~
C: ~
_ ~
~ 0 ~ 0
off
o~o
V
_ ~_
C: o ~ o / ~
o~ 0~_ ~
-
v
OCR for page 32
32
1
_
o _
rT ~0
._
o
~ ~) ~
~ 3 o
\ / ~ ~ ~
@~5 i ~ ~ ~ ~
G ~ ~3~ on ~
~_ _
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~ ~ _ ~
Ott of
o
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Otto
.
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5~
rig
~ ~ °S 1
0~0 ~
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god
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O O
O O
o
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O O
a,
o
o
~ O
O O
11 11
O O
O O
^ ^
O O
O O
O O
^
O O O
OCR for page 33
33
~o
- o
o o
o
o
o
.
=
o
.
-
o
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o
.. 11
_ _
o o
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^ ^
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8
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11
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o
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o o
~ X
.;
o
. ~
o
.
o ~
~ o
:~ ~
.s ~ o
511 ~
~ E S ~
~ = ~ ~
~ C ~ o
o
_ ~ ~ ~ ~
5
o - ~ I
~= S Eo
~ ~ = 0 -
0 = ~ ~
~ &~t
o ~
o o
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E ~
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-
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e-
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^ o
OCR for page 34
34 DR! N K'NG WATER AN D H EALTH
OH
3 HOC1
OH
o
11
C 1 2CH CCC1 =CHCC 1 2CO2H
III
o
11
C 1 oCCCC 1 =CHCHC!
V
OH-(H+)+HOC 1
2 -CHC 1 3-20H
OH
I
C 1 lilts, 2 HOC
\j~ OH
o
0 1
C1~rJ~ I OH-(H+)+H2O
H~O:
II
OC _ C 1 3CCCC 1 =CHCC 1 2CO2H 2
IV
HO2CCC 1 =CHCO2H
VI
FIGURE 3-2 Abbreviation of mechanism proposed by Boyce and Hornig (1983) for the
aqueous chlorination of resorcinol (adapted from Norwood, 1985).
Thus, it appears from the above studies of model compounds that non-
selective aqueous chlorination of activated aromatic ring systems produces
not only chloroform (a volatile hydrophobic by-product) but many non-
volatile hydrophilic chlorinated aromatic by-products as well.
ISOLATED ACIDS
Working with isolated aquatic humic and fulvic acids, Christman and
co-workers (Christman et al. 1980, 1983, Johnson et al., 1982; Norwood
et al., 1983) identified more than 100 different chlorination products by
gas chromatographic/mass spectroscopic methods at a 4:1 chlorine-to-
carbon mole ratio. Some of these products are shown in Tables 3-1 and
3-2. Chlorination of several humic and fulvic acid samples from the same
source produced significant differences in product mixtures. A notable
difference was that most products of fulvic acid chlorination contained
chlorine, whereas most humic acid samples produced at high pH did not.
In both cases, however, the dominant chlorinated products were chloro-
form and chlorinated aliphatic acids, especially dichloroacetic acid (DCA),
trichloroacetic acid (TCA), chloroform, dichlorosuccinic acid, and di-
chloromalonic acid.
A variety of short-chain, nonvolatile aliphatic halogenated products
(listed by Norwood, 1985) result from the exposure of aquatic humic and
fulvic acids to chlorine:
OCR for page 35
Chemistry and Toxicity of Disinfection 35
Name
Trichloromethane
(chloroform)
Bromodichloromethane
Trichloroethanal
(chloral)
Chloroethanoic acid
(chloroacetic acid)
Dichloroethanoic acid
(dichloroacetic acid, DCA)
Trichloroethanoic acid
(trichloroacetic acid, TCA)
2,2-Dichloropropanoic acid
3,3-Dichloropropenoic acid
2,3,3-Trichloropropenoic acid
Dichloropropanedioic acid
(dichloromalonic acid, DCM)
Butanedioic acid
(succinic acid)
Chlorobutanedioic acid
(chlorosuccinic acid)
2,2-Dichlorobutanedioic acid
(a,cx-dichlorosuccinic acid,
DCS)
cis-Chlorobutenedioic acid
(chloromaleic acid)
cis-Dichlorobutenedioic acid
(dichloromaleic acid)
trans-Dichlorobutenedioic acid
(dichlorofumaric acid)
Molecular Formula
CHC13
CHBrcl2
CC13CHO
H2CClCO2H
HCC12CO2H
CC13CO2H
CH3CC12CO2H
CC12 = CHCO2H
CC12 = CClCO2H
HO2CCC12CO2H
HO2C(CH2~2CO2H
HO2CCH2CHClCO2H
HO2CCC12CH2CO2H
HO2CCH = CClCO2H
HO2CCC1 = CClCO2H
HO2CCC1= CClCO2H
The apparent dominance of C2-chlorinated acids is in agreement with the
findings of Quimby et al. (1980), who reported the tentative identification
of TCA and halogenated phenols after soil extract chlorination, and Rook
(1980), who found that DCA and TCA were the principal constituents in
methylene chloride extracts of Rotterdam drinking water after breakpoint
chlorination. However, no halogenated aromatic products were detected
after chlorination of actual aquatic humic and fulvic acids under high pH
conditions.
A large number of monobasic and dibasic unchlorinated aliphatic acids,
from oxalic up to the C27 monobasic fatty acid, were identified from the
humic acid fraction (Table 3-3~. Only a few of the dibasic acids were
associated with the fulvic acid fraction, and almost none of the monobasic
OCR for page 36
36 DRINKING WATER AND HEALTH
TABLE 3-3 Non-Chlorine-Containing Products of Aquatic Humic and
Fulvic Acidsa
Compound Class
Number
Identifiedb
Major Compounds
Benzenecarboxylic
acid
(Carboxyphenyl)-
glyoxylic acids
Monobasic acids
Dibasic acids
16
17
~ (COoH)n
nC= 1-5
COCOOH
~ (COoH)n
nd = 2-4
2H3C (CH2)n~OOH
ne = 7-25
HOOC-(CH2)n~OOH
n = 0-8
aFrom Norwood (1985) with permission.
bIncludes only the more confident identifications.
CAll possible isomers detected.
Several isomers detected in each case; identifications considered very tentative.
eNot all n values detected; some may have been below the detection limit.
acids were detected. The dibasic aliphatic acids are generally of low
molecular weight, containing 2 to 10 carbons. Most of these were detected
in relatively low yield. Aromatic acids were also detected, including mono-
benzoic to hexabenzoic acid in all isomers, as well as small quantities of
methyl-substituted aromatic acids (tentatively identified) and isomers of
(carboxyphenyl~glyoxylic acids (tentatively identified). These non-chlor-
ine-containing products of each acid are similar to the polybasic aromatic
and aliphatic acids reported from potassium permanganate (~InO4) ox-
idation (Christman et al., 1981; Liao et al., 19821.
Recently de Leer et al. (1985) subjected humic acid extracted from a
peat soil to aqueous chlorination under degradation-scale conditions (0.38 g
humic acid per liter of solution, pH 7.2, 24-hour reaction time, ambient
temperature, chlorine-to-carbon ratios of 0.39:1 and 3.35:11. The lower
chlorine-to-carbon mole ratio was chosen to represent typical drinking
water disinfection practice, while the higher ratio was chosen to maximize
product yields. Utilizing gas chromatography/mass spectrometry (GC/MS)
methods, structures were assigned to more than 100 products. The product
distribution was different for the two reaction mixtures.
The products detected in ether and ethyl acetate extracts of the acidified
high chlorine-to-carbon ratio aqueous reaction mixture were a series of
OCR for page 37
Chemistry and Toxicity of Disinfection 37
unchlorinated aliphatic monobasic and dibasic acids, aromatic carboxylic
acids, and chlorinated aliphatic monobasic and dibasic acids, both satu-
rated and unsaturated, that correspond well to those reported in the ex-
periments on isolated aquatic humic and fulvic acids (Tables 3-1 and
3-21. The predominant chlorinated compounds were DCA, TCA, and 2,2-
dichlorobutanedioic acid (c~,~-dichlorosuccinic acid), also in agreement
with the earlier findings.
Aqueous chlorination of humic acid derived from soil at a high chlorine-
to-carbon ratio (3.35:1) produced two new classes of compounds (Figure
3-3) (de Leer et al., 1985~. These were the cyano-substituted alphatic
monobasic acids, 3-cyanopropanoic acid and 4-cyanobutanoic acid, and
the chlorinated aromatic carboxylic acids, 4-chlorobenzoic acid, 2-chlo-
robenzoic acid, 2-chlorophenylacetic acid, 4-chlorophenylacetic acid, 2,6-
dichlorophenylacetic acid, and 2,4-dichlorophenylacetic acid. This con-
stituted the first definitive report of the production of chlorinated aromatic
compounds from the aqueous chlorination of humic material.
De Leer and coworkers (1985) found that a greater number of com-
pounds with higher boiling points were formed at the lower chlorine-to-
carbon ratio than at the higher ratio, although the classes of compounds
formed were similar. Also produced at the lower ratio was a group of
compounds termed "chlorofo~ precursors" because they contained a
trichloromethyl group adjacent to a group susceptible to further oxidation.
These structures, described above, may be divided into two groups: one
with the trichloromethyl group next to a hydroxyl group and the other
with the trichloromethyl group next to a carbonyl group conjugated with
a carbon-to-carbon double bond (Figure 3-31.
Holmbom et al. ~ 1 98 1 , 1 984) discovered a series of acids, the furanones,
in chlorinated kraft pulp waste. Recently, Hemming and colleagues (1986)
showed that low concentrations (~g/liter) of these compounds were formed
when aqueous humic and drinking water samples were chlorinated at 1: 1
chlorine-to-carbon weight ratios at pH 7. After chlorination, these non-
volatile compounds were concentrated and separated by high-pressure
liquid chromatography (HPLC). Almost all of the mutagenic activity in-
jected by chlorination was found to be in a relatively narrow HPLC frac-
tion. After methylation by CI and EI mass spectrometry, the major contributor
was tentatively identified as 3-chloro-4-(dichloromethyl)-5-hydroxy-2~5H)-
furanone. This same compound was also found by Meier et al. (1986~.
A number of studies have been conducted with commercial materials
of unknown origin sold as humic acid (Bull et al., 1982; Coleman et al.,
1984; Meier et al., 1983; Seeger et al., 1985~. These materials appear to
be European lignitic coal extract rather than soil or aquatic humic acid
(Malcolm and MacCarthy, 1986~. Chlorination products included chlo-
roacetonitriles, chloroketones, and chlorobenzenes (Coleman et al., 19841.
OCR for page 69
Chemistry and Toxicity of Disinfection 69
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70 OR ~ N K' NG WATER AN D ~ EALTH
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Representative terms from entire chapter:
humic acid
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