International Journal of Organic Chemistry, 2011, 1, 224-232
doi:10.4236/ijoc.2011.14033 Published Online December 2011 (
Copyright © 2011 SciRes. IJOC
Synthesis of Chlorinated Bicyclic Adduct as Biocids for
Sulfate-Reducing Bacteria
Mona A. Youssif, Nahla A. Mansour, Azza M. Mazrouaa, Mohamed A. Shenashen
Egyptian Petroleum Research Institute, Ca iro , Egypt
Received June 21, 2011; revised August 28, 2011; accepted September 12, 2011
Synthesis of bicyclic systems containing chlorine atoms, and/or ether groups in aromatic rings can be con-
sidered as an important method for building bicyclic system and production of new adducts. One of the most
important types in the cycloaddition reaction is the Diels-Alder reaction (1,4 cycloaddition). In the present
investigation a new ether of allylic type (dienophile) p-allyl bromo phenol was prepared and its structure was
confirmed by molecular weight determination, refractive index, infrared spectra, and density. A new adduct
was obtained by means of 1,4 cycloaddition reaction of hexachlorocyclopentadiene (HCP) and the new pre-
pared dienophile. The reaction takes place without using solvent, catalysts, or elimination of any compound.
The effect of variations in temperature, initial molar ratio and reaction duration were studied to determine the
optimum conditions of the reaction. The optimum conditions reached were reaction temperature recorded
140˚C, initial molar ratio diene: dienophile was 3:1 and the reaction duration time reached 6 h. Under these
optimum conditions the maximum yield was 78%. The new adduct revealed very high biological effect as
sulfate-reducing bacteria (SRB).
Keywords: 1,4 Cycloaddition, Hexachlorocyclopentadiene, Adduct and Sulfate-Reducing Bacteria (SRB)
1. Introduction
The Diels-Alder reaction is an organic chemical reaction
(specially,a cyclo-addition) between a conjugated diene
and substituted alkene, commonly termed (the dienophile)
to form a substituted cyclohexene system [1,2]. The Di-
els-Alder reaction is generally considered the “Monalisa”
of reaction in organic chemistry since it requires very lit-
tle energy to create the very useful cyclohexene ring [3-
5]. Due to the high degree of regio-and stero selectivity
(due to the concerted mechanism), the Diels-Alder reac-
tion is a very powerful reaction and widely used in syn-
thetic organic chemistry [5,6]. The reaction is usually
thermodynamically favorable due to the conversion of 2π
bonds into new stronger (б) bonds. Diels-Alder reaction
is favored by electron withdrawing groups on the electro-
philic dienophile and by electron donating groups on the
nuclophilic diene. The diene components in Diels-Alder
reaction can be an open-chain or cyclic type, it can have
many different kinds of substituents. It must be able to
exsit in the cis conformation [2,5]. Cyclic dienes that are
premantly in the s-cis conformation are exceptionally
reactive in Diels-Alder reactions. Cyclic dienes that are
permanently in the s-trans conformation will not undergo
the Diels-Alder reaction at all [2,5]. Dienophiles in D-A
reaction do not react with equal case. The reactivities of
the dienophiles depend on the structure, i.e the kind and
the position of the substituents of the dienophiles mole-
cules. The greater number of the electron attracting sub-
stituents on the double or triple bonds, the more abil- ity
of the olefins or acetylenes to be react as dienophiles
[2,7,8]. The D-A reaction is reversible one, and many ad-
ducts dissociate into their components at quite low tem-
perature. In this case better yield are obtained by using
an excess of one of the reactants, or solvent from which
the adduct separates readily [2]. Hexachlorocyclopenta-
diene (HCP) and/or its derivatives have been used in
diene synthesis since 1954. It has been found that they
could be considered as a good dienes which may be used
in the diene synthesis due to the importance of its ad-
ducts with various type of dienophiles, as they have very
important applications and great role in the industial
fields [9,10]. (HCP) can be adding to certain dienophiles
under certain conditions. Several studies are carried out to
compare the reactivity of the dienophiles of allylic type in
D-A reaction 1,4 cyclo-addition with (HCP) [9,11-15].
Sulfide production by sulfate-reducing bacteria (SRB) is
a major concern for the petroleum industry since it is
toxic and corrosive and causes plugging due to the for-
mation of insoluble iron sulfides [16-18]. A number of
methods for controlling sulfide production in different oil
production facilities had been proposed in order to redu-
ce activity of SRB [19-21]. However, most of methods
are usually inefficient because of microbial resistance or
they might be a risk to human health and environment.
The sulfate reducing bacteria (SRB) are the most destruct-
tive microorganisms in anaerobic minimum concentra-
tion inhibition MIC. These bacteria having the ability to
oxidize sulfur compounds, it reduce sulphate to sulphide
and promote formation of sulphide film, i.e., their char-
acteristic form of respiration uses sulphate and results in
sulphide formation [22]. According to Iverson, apart
from H2S, SRB also produces a highly corrosive pho-
sphides containing metabolite at pH = 3 that enhances the
dissolution of the metal under anaerobic conditions [23].
Many chemical compounds have the ability to inhibit the
growth and metabolism of microorganisms or to kill
them [24]. The aim of the work is synthesis of chlorin-
ated bicyclic adduct which may be used as biocides for
Sulfate-Reducing Bacteria.
2. Experiment
2.1. Materials
Para bromophenol: (C6H5BrO) M.Wt. 173.01 g·mol1,
Density 1.84 g·mL1, M.p. 64˚C - 68˚C, B.p. 235˚C - 236˚C.
Allyl bromide: (C3H5Br) M.Wt. 120.99 g·mol1, Density
1.398 g·mL1, M.p. –119˚C, B.p. 71˚C.
Anhydrous (K2CO3): M.Wt. 183.205 g·mol1, Density
2.29 g·mL1, M.p. 891˚C, B.p. decomposes.
Acetone: M.Wt. 58.08 g·mol1, Density 0.7925 g·mL1,
M.p. 95˚C, B.p. 56˚C - 57˚C.
NaOH: M.Wt. 39.997 g·mol1, Density 2.13 g·mL1,
M.p. 318˚C, B.p. 1388˚C.
Anhydrous (MgSO4): M.Wt. 120.366 g/mol, Density
2.66 g/cm3, M.p. 1124˚C.
Hexach loroc yclop entad ien e (HCP): (diene) B.p. 239˚C/
753 mm, density at 25˚C, 1.7179 g/mol, M.wt. 272.7,
viscosity at 35˚C, 5.04 Cp and 1.5626.
2.2. Methods
1) Infrared spectroscopy (IR)
The IR analysis was carried out using a FTIR spec-
trometer at wavelengths from 500 - 4000 cm–1 and
transmittance % from 30 - 100.
2) Nuclear Magnetic Resonance (NMR)
Proton NMR spectra in deuterated CHCL3 containing
tetramethyl silane as an internal standard were recorded
in an A varian instrument division EM-390 90M HZ NMR
3) Density
The density was measured at the Egyptian Petroleum
Research Institute (EPRI) using Instrument: 6890 plus G.
Preparation of Allyl P-bromophenylether:
One mole of para bromophenol, one mole of allyl bro-
mide, one mole of anhydrous K2CO3 and 150 gm of ace-
tone were mixed together in a round flasket. The reaction
mixture was refluxed for 12 - 14 hours with stirring. The
mixture kept to be cool. Potassium bromide was separa-
ted by filtration. Cold water and ether were added to the
reaction liquid and the organic layer was separated [9,
The resulting organic layer was washed with brine
(NaOH 10%), and then dried over anhydrous MgSO4.
After removing the drying agent by filtration all the un-
desirable materials were distilled off. The new allyl
ether was collected under subatmospheric pressure of
(20 - 23) mmHg, at 152˚C, in a yield of 75% wt. The
new ether has the following properties: average mo-
lecular weight: 213.4 g, colour: pale oily yellow liquid,
solubility: soluble in CCl4, xylene, = 1.4508 and
d25 = 0.9432. The infrared spectrum is given in Figure 1.
which indicates that: the transmission absorbance could
be due to: C-Br at 660 cm–1, -CH bending aromatic at
813 - 997 cm–1, -CO ether at 1235 cm–1 , C=C aromatic
at 1421, CH2 bending at 1484 cm–1 , C=C aliphatic at
1692 cm–1, para aromatic subs. At 1742 - 1866 cm–1,
CH2 stretching sym. At 2857 cm–1, CH asym. at 2919,
and CH-Aromatic sym. at 3078.
Synthesis of 1,2,3,4,7,7, Hexachloro 5 parabromoph-
enoxymethyl bicyclo 2,2,1heptene-2:
In a round bottomed 50 ml flask, 0.075 mole (13.6 gm)
of HCP was mixed with 0.025 mole of allyl p-bromo-
phenylether. The flask was stoppered carefully and pla-
ced in an oil bath for a constant reaction time of 6 hours
at each of evaluated temperature (90˚C - 160˚C). The
condensation reaction was carried out without using sol-
vents or catalysts. The flask was removed from the oil
bath, cooled, and opened. The unreacted diene, dieno-
phile as well as the adduct were separated from the reac-
tion mixture by careful fraction distillation. This was
carried out under subatmospheric pressure of (20 - 23)
mmHg [9,13-25].
After three days the adduct was obtained in its past
form, then recrystallization took place using (1:3) mix-
ture hexanemethylene chloride. The new adduct was pre-
pared in its pure form as white yellowish needles, soluble
in benzene, DMF and chloroform. Average molecular
weight (486.7 gm), m.p. 120˚C - 122˚C, the infrared
spectra-I.R. Figure 2 which indicat that the transmission
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Copyright © 2011 SciRes. IJOC
absorbance could be due to C-Br at 593 cm–1, C-Cl at
676 cm–1 ,C-H bending aromatic at 803 cm–1, C-O ether
at 1230 cm–1, CH2 aliphatic at 1482 cm–1, C=C (endo
form) at the ring at 1595 cm–1, 1701-1860 due to para
subistitution of aromatic ring, CH2 symmetrical stretching
at 2867 cm–1, 2916cm–1 due to CH symmetrical stretch-
ing .The H–1NMR analysis of the new adduct (Figure 3)
which reveals the presence of peaks at 1.124 - 1.261
doublet of doublet, and 3.346 (multiple) due to bicyclic
proton. This indicates that, the reaction (1,4) cyclo-addi-
tion was carried out, and the bicyclic compound was
formed. The H–1 NMR at 4.582 is due to the protons at
(-OCH2). While the H-1NMR peaks at 6.796 - 6.954, ppm
and at 7.349 - 7.469 are due to protons of aromatic ring
(P-substitution). The elemental analysis of the new adduct
is given in Table 1.
Figure 1. I. R. of the prepared ether.
Figure 2. I. R. of the new chlorinated adduct.
Figure 3. HNMR of the new chlorinated adduct.
Table 1. Elemental analysis of adduct.
pound Theoretical
Adduct 34.56 34.21 1.85 1.52 - Nil
The same experimental trend was repeated in order to
know the effect of both: molar ratio diene: dienophile
from 1:1 to 5:1 at fixed temperature of 140˚C, and fixed
reaction time of 6 hours and the effect of duration time of
the reaction from one to eight hours, at fixed temperature
(140˚C), and fixed molar ratio diene:dienophile (3:1).
The results are shown in Tables 2-4, and Figures 4-6.
3. Results and Discussion
This study is one of an extended of several research work
which based on (D-A) 1,4 cyclo-addition reaction using
HCP and/or its derivatives with new prepared dienophile
of allylic ether structure to produce a new halogenated
allylic ether adduct. The effects of variation of: tempera-
ture, molar ratio (diene:dienophile), and the duration ti-
me reaction were studied to determined the optimum con-
ditions at which the maximum yield could be obtained.
The results are given Tables 2-4, Figures 4-6.
3.1. Effect of Temperature
The study of the effect of the temperature variation on the
product yield was carried out at the range of (90 - 160)˚C
Table 2. Effect of variation of temperature on the yield
wt% Dials-Alder reaction of (HCP) with Allyl p-bromophe-
Temp. ˚C 90 100 110 120 130 140 150 160
Yield wt%3849 59 67 74 78 75 63
Table 3. Effect of variation of reaction time on the yield
wt% Dials-Alder reaction of (HCP)with Allyl p-bromoph-
Tim/hr 1 2 3 4 5 6 7 8
Yield wt% 32 46 58 68 75 78 78 78
Table 4. Effect of variation of molar ratio diene:dinophile
on the yield wt% Dials-Alder reaction of (HCP) with Allyl
p-bromophenylether .
Ratio diene:dinophile 1:1 2:1 3:1 4:1 5:1
Yield wt% 48 72 78 78 78
at fixed reaction time at 6 hours and fixed molar ratio of
3:1 diene:dienophile. Figure 4 shows that the product
yield increases with increasing the temperature up to
140˚C at which a maximum yield (78%) by weight was
obtained, Tab le 2. As it is known the adduct formation is
a combination or an association reaction in which two
double bonds from dienes and one bond from the dieno-
phile are involved. These bonds formation need some
heating to be activated [26,27]. The optimum tempera-
ture for this activetion seems to be 140˚C.
Copyright © 2011 SciRes. IJOC
Figure 4. Effect of variations in the reaction temperature on
the yield wt%in the Diels-Alder reaction of HCP with Allyl
p-bromophenylether . (Fixed Criteria: Molar ratio, diene:di-
enophile 3:1, Duration time 6 hours).
Figure 5. Effect of variations in the reaction time on the yie-
ld wt% in the Diels-Alder reaction of HCP with Allyl p-
bromophenylether. (Fixed Criteria: Molar ratio, diene: die-
nophile 3:1, Temp.: 140˚C).
Figure 6. Effect of variations in molar ratio diene:dinophile
on the yield wt% in the Diels-Alder reaction of HCP with
Allyl p-bromophenylether. (Fixed Criteria: Duration time 6
hours, Temp.: 140˚C).
Table 2 and Figure 4 show that up to 140˚C (part AB
of the Figure), the rise of the temperature accelerated the
adduct formation as indicated by the increase in the yield
formation. The results indicated that the initial reaction
rate was high and about 50% of the theoretical yield was
obtained at 100˚C after 6 hours. Raising the temperature
from 100˚C to 140˚C, has fastened the reaction rate but
the actual increase in the yield was not significant. This
is apparently due to stimulation of the back reaction as
temperature rise from 100˚C to 140˚C and the equilib-
rium is reached between the main and the back reaction.
Above 140˚C the rise of temperature accelerated the
back reaction gradually rather than the main reaction,
hence the percent weight of the yield decreases (part BC
of the Figure). This is may be expected from a non cata-
lytic reaction especially when it is an elementary reaction
that take place at one step only, as in chain reaction.
Hence farther increase in the temperature decreases the
product yields sharply. This is may be due to the forma-
tion of undesirable by product [9,13,14,26].
90100 110120 130 140 150 160 170 180 190 200
Yi eld
Yield %
eratu re
Temperature (˚C)
3.2. Effect of Reaction Duration
The effect reaction time on the product yield was studied
over the range of one to eight hours at fixed reaction
temperature of 140˚C, and fixed molar ratio diene:die-
nophile 3:1, (Figure 5) and Table 3. Figure 5 shows that
the product yield increases gradually, and as the reaction
proceed up to 6 hours where the equilibrium is reached
between the main and the back reaction.
Yield %
It was found that in the first hours about 30% of the
theoretical yield was obtained. At this condition there is
much concentration of diene and enough to dienophile to
make the reaction proceed markedly. After the first hour,
there is still much of diene concentration in the reaction
medium, and there is a decrease in the dienophile con-
centration, hence it is to be expected that the reaction
slows down considerably during the second hour so that
only about 14% of the theoretical yield was produced com-
pared to the 32% during the first hour. After the second
hour of the reaction, and with the further continuous de-
crease in dienophile concentration in the reaction medi-
um, the adduct formation continued slowing down. This
indicates a pesudo first order reaction with respect to the
dienophile as the diene is always present in excess in the
reaction medium than stoichemetric. Figure 5 shows,
that at an interval of 4 to 6 hours the yield increases with
the reaction time, but slowly. Further increase in the re-
action time (than 6 hours) has no effect on the product
yield. This may be due to the formation of side reaction
Yield %
3.3. Effect of Molar Ratio
Data in Table 4, Figure 6 show that the effect of reac-
tant ratio (diene:dienophile) on the product yield was
studied over range of 1:1 to 5:1 of at fixed temperature of
Copyright © 2011 SciRes. IJOC
140˚C, and fixed reaction time of 6 hours. It was found
that at equimolar ratio of reactants about (50%) of the
theoretical yield was obtained. When was doubling the
initial ratio of the diene under the same conditions about
(70%) of the theoretical yield was obtained. At (3:1)
mole ratio of diene:dienophile 78% of the product yield
was obtained. Further increase in the initial molar ratio
of the diene has no effect on the reaction rate. This is
indicated that, this increase of the ratio of the diene does
not affect the rate of the adduct formation, although it may
be promote polymerization reaction leading to the produc-
tion of resin. This is in concordance with [9,13,14,26].
It is known that the adduct formation reaction takes
place between one molecule of diene and one molecule
of dienophile. Data in Table 4 show that an initial equi-
molar ratio of reactance seems to be the best ratio for such
reaction to be proceeding with a good rate. How- ever, the
presence of electron withdrawing chlorine atom in the
diene molecule decreases the electron density at the dou-
ble bonds, leading to a decrease in the reactivity of diene.
So it must be need, for a much of diene in the reaction me-
dium, in the form of a higher initial molar ratio of diene.
The D-A reaction of HCP and p-bromo allyl ether is
an exothermic reaction which takes place under autoge-
netic pressure (closed system) to facilitate the reaction
rate in absence of solvent or catalyst. The better yield is
obtained by using an excess of one of component (di-
ene). This is compatible with (Carrutuners). The new
ether (dienophile) is prepared and characterized by av-
erage molecular weight (213.4 g), density (0.9432) and
infrared spectra Figure 1. The new adduct was prepared
in its pure form as white yellowish needles and its
structure was confirmed by molecular weight, IR Fig-
ure 2 and H1 NMR spectra Figure 3 and elemental
analysis Table 1.
To compare the effect of kind of the substituent in the
dienophilic molecule of allylic structure on (D-A) 1,4
cycloaddition with (HCP). The following explanation is
carried out. The maximum product yield in this present
work is relatively higher than that obtained in the previ-
ous work [26], although the two dienophiles are the same
allylic structure. This implies that, the reason is related to
kind of the substituent in the dienophile molecule has the
major effect on the electron density of the terminal dou-
ble bond (alpha position) of the side chain, and conse-
quently on the product yield.
Our explanation is that the presence of methyl group in
ref [25] which has an electron donating activator group
(has +M, +I effect) which pushes the electron by means
of mesomeric effect to the benzylic ring, and consequen-
tly by resonance to the terminal alkenyl double bond.
Consequently the reactivity of the dienophilic olefin to
react in the (D-A) 1,4 cyclo-addition relatively decreas-
ing. Whereas in the present work the bromine atom in the
dienophilic molecules has (–I, +M) effect due to the fact
that when there is a conflict between the mesomeric ef-
fect (M) and inductive effect (I), the conflict between the
mesomeric effect predominates in most cases, except in
case of halogens, the (–I) effect is more powerful than
(+M) effect. So, the bromine atom pulls the electrons
from the adjacent benzylic carbon, then by resonance it
pulls the electron from the alkenyl double bond. Thus the
electron density on the terminal double bond of the al-
kynl chain decreases. So it increase the reactivity of the
olefinic molecule (dienophile) to be reactive and the
(D-A) 1,4 cyclo addition is more predominates than the
previous work [25].
On the other hand study of (D-A) 1,4 cycloaddition
was carried out using dimethoxy tetrachloro cyclopeta-
diene (DMTCP), which is a drevative of HCP, with p-
chloro-allylether [9]. It was found that, the maximum
yield is (84.6) at optimum conditions (120˚C, 5 hours
and 2:1 molar ratio diene:dienophile). The maximum
yield in the previous study is higher than the present one.
Although the two dienophiles in the studies share the
same allylic structures, their substituent’s in the two di-
enophiles are approximately of equal activity, and their
positions in the dienophilic molecules are in the same (P-
positions). So the difference in the product yields is re-
lated to the nature of the diene molecule: the presence of
two electron donating groups (methoxy groups) in the
study (10) increase the electron density on the double
bond of the diene molecule, and thus it increases its reac-
tivity. Whereas the presence of six chlorine atoms in
HCP diene molecule decreases the electron density on its
double bond, and hence its reactivity decreases compare-
ing to the other diene (DMTCP). This conclusion is in
concordance with that mentioned in ref [9,13].
3.4. Antibacterial Activity
As a result of the numerous problems caused by sulfate
reducing bacteria in oil and gas production operations,
aggressive measures have been taken to monitor and
control bacterial populations. Measurements of bacterial
growth are not usually considered until after corrosion
failures point due to microbial induced corrosion. By the
time microbial induced corrosion is discovered, exten-
sive and costly damage to the operating systems has of-
ten already occurred [28]. The antibacterial activities of
the synthesized compound was tested against sulfur re-
ducing bacteria Desulfomonas p igra. The biocidal activi-
ties of the synthesized compound against SRB strain
were investigated at different concentrations using the
serial dilution method, Table 5. Both the minimum in-
hibitory concentrations (MIC) and the lethal concentra-
Copyright © 2011 SciRes. IJOC
Table 5. The antibacterial activities of the synthesized com-
Concentration SRB Count (colony/ml sample)
10–1 00.00
10–2 00.00
10–3 00.00
10–4 268
10–5 4.98 × 103
Control 7.72 × 103
tions (LC) was detected, the results are shown in Table 5.
The minimum inhibitory concentration (MIC) is the
lowest concentration of the compound that didn’t show
microbial growth [29]. This means that, the lower the
MIC value of a compound, the higher is its activity. The
adduct is efficient compound since its MIC value is
(0.00073), and has three lethal concentration val- ues
(10–1 and 10–2, 10–3).
King [30] has showing greater impacts of 2,4-DBP on
aerobic bacteria, and the behavior of these compounds as
potent uncouplers of oxidative phosphorylation [31,32].
Antibiotic activity towards microbes and meiofauna [30,
33-37] and nephrotoxic and hepatotoxic activity in higher
organisms [38,39] have previously been documented for
bromophenols and other brorninated metabolites. The in-
hibition pattern for sulfate reduction suggests that sul-
fate-reducing bacteria are sensitive bromo phenols, though
not to the extent noted for aerobes. The effect of bromo-
phenols on sulfate reduction appears to be tempered by the
rapid dehalogenation bromophenols under anoxic condi-
tions [30,40]. The interaction between adduct molecules
and cellular membrane causes, a strong damage of the
selective permeability of these membranes which disturbs
the metabolic pathway within the cytoplasm.
4. Conclusions
A new dienophile had been allylic type (Allyl P-
bromophenylether) was prepared and its structure had
been confirmed.
The Diels-A1, 4-addition reaction has been studied
using a diene, H.Cl.C.D., and dienophile, allyl P-
The condensation reaction took place under pressure
without catalyst or solvent.
Reaction conditions were studied including, tem-
perature 90˚C - 160˚C, reactant molar ratio 1:1 to 5:1,
and reaction time 1to 8 hours.
The structure of the new adduct was confirmed by;
molecular weight, H1 NMR and IR spectra.
The optimum conditions for maximum product yield
were found to be as following; temperature = 140˚C,
reactant molar ratio = 3:1 with a reaction time of six
Maximum adduct yield was = 78%.
The new adduct revealed very high effect as sul-
fate-reducing bacteria (SRB).
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