Eur. J. Lipid Sci. Technol.

104 (2002) 293–299 293

Zoran S. Petrović a, Epoxidation of soybean oil in toluene with

Alisa Zlatanić a, Charlene
C. Lavaa, Snežana
Sinadinović-Fišerb
a Pittsburg State University,
Kansas Polymer
Research Center,
Pittsburg, KS, USA
b Faculty of Technology,
University of Novi Sad,
Novi Sad, Yugoslavia
peroxoacetic and peroxoformic acids – kinetics
and side reactions
The kinetics of the epoxidation of soybean oil and the extent of side reactions were
studied at 40, 60 and 80 °C. Epoxidation was carried out in toluene with “in situ ”
formed peroxoacetic and peroxoformic acid and in the presence of an ion exchange
resin as the catalyst. The reaction was found to be first-order with respect to the dou-
ble bond concentration. At higher temperatures and at higher conversions a deviation
from the first-order kinetics was observed. The rate constants for the epoxidation with
peroxoacetic acid were 0.118 (h–1) at 40 °C, 0.451 (h–1) at 60 °C and 1.278 (h–1) at
80 °C, while those for peroxoformic acid were 0.264, 0.734, and 1.250 (h–1). The acti-
vation energy was found to be 54.7 kJ/mol for the epoxidation with peroxoacetic acid
and 35.9 kJ/mol for that with peroxoformic acid. Three factors indicated that side reac-
tions did not occur on a large scale: The absence of an OH band in the IR spectra, the
formation of less than 2% of higher molecular weight products from gel permeation
chromatography and the selectivity values between 0.9 and 1.

Keywords: Epoxidation, kinetics, soybean oil, peroxoacetic, peroxoformic.

1 Introduction caused by acetic acid suggesting that acetic acid is more

Epoxidation of vegetable oils on an industrial scale is
most frequently carried out with peroxoacetic and peroxo-
formic acids, the products being used as PVC plasticiz-
ers. Typical conversions of double bonds to epoxy groups
are about 90%. Epoxidation may be carried out to reach a
maximum conversion (epoxy yield), especially if the prod-
uct is to be used for further chemical transformations. On
the other hand epoxidation may be employed to obtain a
product in the most economical way, e.g. aiming at the
suitable for the preparation of epoxidized oils [2]. The ki-
netics of the epoxidation of vegetable oils with peroxo-
acetic acid were studied under different conditions [3–8]
whereas most of the kinetic studies with peroxoformic
acid were carried out on the epoxidation of rubbers
[9–12]. It was found that the kinetic parameters for the
epoxidation of natural rubber were identical to those for
the epoxidation of palm olein methyl esters [1]. Our aim
was to compare the epoxidation rates of soybean oil with
those of the two acids and analyze the extent and type of

highest conversion rate but not necessarily at the highest
conversion. The kinetics for each individual set of condi-
tions differ. In our study, we selected the synthesis in so-
lution in order to minimize side reactions and to obtain a
high epoxy yield.
The objective of this work was to find the conditions for a
maximum epoxy yield and to compare the kinetics of the
epoxidation with peroxoformic and peroxoacetic acids
formed “in situ”, as well as to analyze the type and extent
of side reactions. We were particularly concerned with the
polymerization reaction as a result of the ring opening,
since it contributes considerably to the increase of viscos-
ity. It is known that epoxidation in solution is preferable if
the minimization of side reactions is desired [1]. The ring
opening caused by formic acid in the presence of isobu-
tanol was found to be a thousand times faster than that
Correspondence: Zoran Petrović, Pittsburg State University,
Kansas Polymer Research Center, 1501 S. Joplin Street, Pitts-
burg, KS 66762, USA. Phone: 316-235-4928, Fax: 316-235-4919;
e-mail: zpetrovi@pittstate.edu
Research Paper
side reactions. In this work, we compared the kinetics of
the epoxidation of soybean oil in toluene with peroxo-
acetic and peroxoformic acid generated “in situ” in the
presence of an ion exchange resin as catalyst. The mea-
sured kinetic parameters were the rate constants at 40,
60 and 80 °C and the activation energies. The extent of
side reactions that may have taken place was determined
by titration, Fourier Transform Infrared Spectroscopy
(FTIR), gel permeation chromatography (GPC) and vis-
cosity measurements.
2 Materials and methods
2.1 Materials
Soybean oil of RBD grade (refined, bleached, deodor-
ized) and of an iodine number of 125 (Hanus) was ob-
tained from Archer Daniels Midland Company (Decatur,
USA). Glacial acetic acid (certified A.C.S. Plus) from
Fisher Scientific (Pittsburgh, PA, USA), formic acid
(95–97%) from Aldrich (Milwaukee, WI, USA) and a 30%
(w/w) solution of hydrogen peroxide from Sigma (St.

© WILEY-VCH Verlag GmbH, 69451 Weinheim, 2002 0931-5985/2002/0505-0293 $17.50+.50/0

294 Petrović et al.
Louis, MO, USA) were used. Amberlite IR–120 in acid
form was purchased from Supelco (Bellefonte, PA, USA),
toluene (HPLC grade), ethyl acetate (HPLC grade), and
sodium sulfate anhydrous from Fisher Scientific.
2.2 Methods
A FTIR Perkin-Elmer spectrophotometer, model Spec-
trum-1000 (Perkin-Elmer, Norwalk, CT, USA), was used
to follow the formation of epoxy groups, the disappear-
ance of double bonds and the formation of hydroxyl
groups (side reactions). GPC is a technique used to sep-
arate the molecules according to their sizes, and was
found to be well suited to follow the formation of dimers
or trimers from the side reactions during synthesis. Wa-
ters GPC model 510, equipped with three Styragel HR
Waters columns (covering molecular weights range
102–106) and differential refractometer model 410 (Waters,
Milford, MA, USA), with tetrahydrofuran as the eluent was
used to follow the molecular weight increase (polymeriza-
tion side reactions). The flow rate of tetrahydrofuran was
1 ml/min at room temperature. Viscosity was measured at
30 °C with a Rheometric Dynamic Stress Rheometer,
model SR–500 (Rheometric Scientific, Inc., Piscataway,
NJ, USA), with parallel plates of 25 mm in diameter,
having a gap of 0.200 mm.
2.2.1 Synthesis
Each synthesis was carried out in a 500-ml three-necked
round-bottom flask equipped with a thermometer sensor,
a mechanical stirrer, and a septum, pierced with an injec-
tion needle to equalize pressure. The whole apparatus
was kept in a water bath to maintain the respective tem-
perature of 40, 60 and 80 ± 0.5 °C. Thus, the temperature
was measured inside the reaction vessel and in the water
bath. 100 g (0.49 mol) of soybean oil, 50 ml of toluene,
25.00 g of Amberlite, and either 15.00 g (0.25 mol) of
glacial acetic acid or 11.80 g (0.25 mol) of formic acid
were added into the round-bottom flask. With agitation,
83.70 g (0.74 mol) of 30% H2O2 were added slowly
through a separatory funnel during half an hour. This pre-
caution was taken to prevent overheating of the system
due to the exothermic nature of epoxidation reactions. An
ice water bath was prepared to cool off the reaction if
needed. Samples were taken out of the reaction vessel
every hour.
To purify the samples, the solution was first dissolved in
ethyl acetate. The Amberlite was filtered off, and the fil-
trate was poured into a separatory funnel. The washing
with warm water was repeated until the pH was neutral.
The oil phase was further dried above anhydrous sodium
sulfate and then filtered. The solvent was removed using
a rotary evaporator, first with the help of a water vacuum
pump and then under high vacuum. The purified samples
Eur. J. Lipid Sci. Technol. 104 (2002) 293–299
spread on a NaCl plate were analyzed using FTIR to
check the disappearance of the double bonds at
3009 cm–1 and the formation of the epoxy groups (dou-
blet at 822 cm–1 and 833 cm–1). The iodine value, as the
measure of concentration of double bonds, was deter-
mined using the Hanus method [13], and the epoxy oxy-
gen content was measured according to a standard pro-
cedure for oils and fats [14].
3 Results and discussion
“In situ” epoxidations were carried out in the molar ratio of
1:0.5:1.5 – double bonds : organic acid : hydrogen perox-
ide. The detailed mechanism of the peracid formation dur-
ing epoxidation with in situ formed peroxoacetic acid is
given in a previous paper of us [3]. While organic acid is
converted to peroxoacid and then regenerated, hydrogen
peroxide is consumed in the process and the excess of
50 mol-% relative to double bonds was considered rea-
sonable. The amount of toluene used was 43.9 wt-%
relative to the weight of soybean oil. Ion exchange resin
was added in an amount of 25 wt-% relative to the sum
of the weights of organic acid and 30% H2O2 solution.
Two series of epoxidations were carried out at three
different temperatures (40, 60 and 80 °C), one with per-
oxoacetic acid and the other one with peroxoformic acid.
The samples of the first series are designated as SB-
PAA40, SBPAA60 and SBPAA80, where SB stands for
soybean, PAA for peroxoacetic acid and the number for
the temperature. Corresponding samples with peroxo-
formic acid were designated as SBPFA40, SBPFA60 and
SBPFA80.
The variations of the iodine values and the epoxy oxygen
contents with reaction time for epoxidations with perox-
oacetic acid and peroxoformic acid at the three applied
temperatures are presented in Figs. 1 and 2. The iodine
value is a measure of the concentration of double bonds
Fig. 1. Comparison of iodine values vs. time for the epox-
idation of soybean oil with peroxoacetic and peroxoformic
acid at 40, 60 and 80 °C.
Eur. J. Lipid Sci. Technol. 104 (2002) 293–299 Epoxidation of soybean oil in toluene 295
k1
AA + H2O2 i PAA + H2O (1)
k2
k1
DB + PAA i EO + AA (2)

where AA is acetic acid; PAA is peracetic acid, DB is dou-

ble bond, EO is epoxy group and k1, k2 and k3 are reaction
rate constants.

The first reaction is the acid-catalyzed formation of per-

oxoacetic (or peroxoformic) acid from acetic (or formic)
acid, while the second is the uncatalyzed epoxidation of
unsaturated soybean oil with the peroxoacid. At the same
time, the side reactions, such as epoxy ring opening
Fig. 2. Comparison of the epoxy oxygen content vs. time
for the epoxidation of soybean oil with peroxoacetic and (reactions with the acid or water) followed by the dimer-
peroxoformic acid at different temperatures. ization of already formed hydroxy and/or acetoxy com-
pounds, may proceed. A range of possibly occurring side
products is given in Fig. 3.
present. For the epoxidation with peroxoacetic acid, the
conversion of double bonds was very fast at 80 °C Polymerization reactions are especially detrimental since
(Fig. 1). In that case the final epoxy content was already they increase the viscosity of the product considerably.
reached after 3 h. At 60 °C it was reached after 9 h, Polymerization of epoxides in the presence of acids
whereas even after 12 h a significant double bond con- (cationic polymerization) is a well-established route to re-
centration was still present at 40 °C. Epoxidations with generate epoxy resins. In the case at issue the first step,
peroxoformic acid followed the same trend. It appears, the attack of a proton on an epoxy group, leads to the
however, that with peroxoformic acid a somewhat higher formation of hydroxyl and acetyl or formyl groups. If the
epoxy content was obtained at 60 °C than at 80 °C. Fig. 1 reaction stops at that stage, a polyol is formed. A hydrox-
shows that at 40 °C and 60 °C the epoxidation of soy- yl group may react further with an epoxy group to give in-
bean oil followed by the conversion of double bonds was ternal ethers or oligomeric ethers (dimers) as shown in
faster in the presence of peroxoformic acid than in that of Fig. 4.
peroxoacetic acid, but at 80 °C the peroxoacetic acid was
more efficient than the peroxoformic one. Comparing the
changing epoxy oxygen content with time of the two acids
at different temperatures entails also the just mentioned
conclusion (Fig. 2). With peroxoformic acid a higher
epoxy yield was obtained at 60 °C than at 80 °C. Howev-
er, the reaction rate was lower. Whereas the maximum
epoxy yield obtained was almost the same for both per-
oxoacids at 80 °C, the rate of achieving it appeared to be
higher with peroxoacetic acid than with peroxoformic
acid. The conclusion is that at lower temperatures (40 and
60 °C) peroxoformic acid is more efficient for “in situ”
epoxidation than peroxoacetic acid, while at the higher Fig. 3. Possible side reactions of epoxy group.
temperature (80 °C) peroxoacetic acid is at least as effi-
cient if not more efficient than peroxoformic acid. There is
good reason to suppose that due to the very high activity
of the formic acid some hydrogen peroxide is decom-
posed, and thus the system is depleted of oxygen fairly
early on. Hence the reaction is slowed down. In other
words, this temperature is too high for an epoxidation with
peroxoformic acid. Consequently, only the initial stage of
the reaction was taken into account for the kinetic studies.

“In situ” epoxidation is characterized by two main reac-

tions involving formation of peroxoacids (1) and formation
of epoxides (2) as exemplified with peroxoacetic acid: Fig. 4. Schematic representation of dimer formation.
296 Petrović et al.
Selectivity (S) is a measure for the amount of side reac-
tions occurring during epoxidation, it gives the relative
yield of epoxides and was calculated as:
S = (EO/EOm)/([IV0–IV]/IV0)
where EO (%) is the experimentally determined content of
epoxy oxygen in 100 g of oil, IV is the iodine value, IV0 is
the initial iodine value and EOm (%) is the content of
epoxy oxygen in 100 g of oil at complete conversion, cal-
culated as:
EOm = [(IV0/2AJ)/100 + (IV0/2Aj) · A0] · A0 · 100
where AJ = 126.9045 and A0 = 16.0000. For IV0 =
125 is EOm = 7.3
Plots of selectivity vs. time for epoxidations with peroxo-
acetic and peroxoformic acid at the three temperatures
are depicted in Figs. 5 and 6. Higher values of selectivity
were observed at lower temperatures and at the begin-
ning of the epoxidation. Selectivity values higher than 1
can be explained by the fact that the epoxy oxygen con-
tent is low and the relative error is high (5–10%) at low
concentrations of epoxy groups. This phenomenon is
more pronounced for the slowest reaction at 40 °C, as in
this case only about 30% of epoxy groups are formed af-
ter 3 h with PAA. Otherwise, the selectivity values are be-
tween 0.9 and 1, they indicate a relatively low extent of
side reactions. With peroxoacetic acid, the selectivity
values at 60 and 80 °C are the same within the experi-
mental error, suggesting that the epoxidation should be
rather carried out at 80 °C, the temperature allowing for a
higher reaction rate (Fig. 5). However, the selectivity val-
ues for peroxoformic acid are lower at 80 °C than at 60 °C
(Fig. 6), indicating that a lower temperature is preferable
to prevent an undesirable extent of side reactions.
During the epoxidation IR spectroscopy was used to fol-
low the disappearance of double bonds and the formation
of epoxy groups with time, but also to detect the presence
of any OH (and/or C=O) group(s), which would indicate
the formation of side reaction products. The absence of
Fig. 5. Selectivity vs. time for the epoxidation with per-
oxoacetic acid at different temperatures.
Eur. J. Lipid Sci. Technol. 104 (2002) 293–299
Fig. 6. Selectivity vs. time for the epoxidation with per-
oxoformic acid at different temperatures.
the OH band in the IR spectra of the epoxidized oils,
obtained from both peroxoacetic and peroxoformic acid,
indicated a negligible occurrence of ring-opening reac-
tions and thus a negligible formation of hydroxyl groups
and/or hydroxyacetate byproducts.
In almost all GPC graphs, a peak from a higher molecular
weight compound (dimer, since higher oligomers were not
observed) appeared at shorter retention times than the
main peak for the epoxidized soybean oil (ESBO). The
relative areas of the two peaks are presented in Tab. 1.
The degree of dimerization increased with time, but the fi-
nal amount of dimers was less than 2%. Thus GPC analy-
sis showed that higher molecular weight products result-
ing from polymerization side reactions during the epoxi-
dation with both organic acids at all temperatures never
exceeded 2%. It should be emphasized that when a dimer
is created an intermolecular ether bond is formed only be-
tween two epoxy groups although 8–9 groups are present
altogether. Thus, if only one intermolecular bond is formed
in 100 triglyceride molecules, the dimer area amounts to
2%. The extent of intramolecular bonds cannot be esti-
mated since it only causes a lower epoxy yield and does
not promote a molecular weight increase. Besides FTIR is
not sensitive enough to detect such low conversions.
Since the probability of intramolecular and intermolecular
reactions is the same, it can be concluded that intramole-
cular reactions also occur only to a minor degree. Tab. 1
shows that dimer formation increases with temperature
and reaction time and that it is slightly higher with peroxo-
formic acid than with peroxoacetic acid. Nevertheless, all
values are very low.
The extent of side reactions that may occur during epoxi-
dation was also assessed by viscosity measurements.
The viscosity for soybean oil with IV = 125 is 58 mPa s at
30 °C while the viscosity of the completely epoxidized
soybean oil is about 210 mPa s. The conversion of dou-
ble bonds to epoxy groups leads to an increased viscosi-
ty. However, if hydroxyl groups are formed, the viscosity
Eur. J. Lipid Sci. Technol. 104 (2002) 293–299 Epoxidation of soybean oil in toluene 297

Tab. 1. Analysis of the GPC results of epoxidized soybean oils with peroxoacetic and peroxoformic acids.
Sample Temperature [°C] Time [h] area of ESBO [%] area of dimer [%]
SBPAA40 4 99.5 0.5
40 8 99.5 0.5
12 99.2 0.8
SBPAA60 4 99.4 0.6
60 8 99.0 1.0
12 98.8 1.2
SBPAA80 3 98.7 1.3
80 6 98.4 1.6
9 98.2 1.8
12 97.3 2.7
SBPFA40 4 99.4 0.6
40 8 99.3 0.7
12 98.8 1.2
SBPFA60 2 99.3 0.7
60 5 99.1 0.9
9 98.9 1.1
12 98.5 1.5
SBPFA80 2 99.0 1.0
80 5 98.5 1.5
9 97.8 2.2
12 97.9 2.1

increase is significantly higher [15] (the viscosity of the
polyol, depending on the number of hydroxyl groups and
substituents on the adjacent carbon atom, is typically
above 2000 mPa s for 3 OH groups per molecule).
The presence of dimers and trimers in the polyol drives
viscosity to about 4000 mPa s. Acetic and formic acids
achieved almost complete conversion in about 3 h at
80 °C judging by the time when the final viscosity was
reached. When viscosity is plotted against conversion, all
values for the different reaction temperatures and the dif-
ferent peroxoacids fell on the same line (Fig. 7) indicating
that there was no considerable difference in side reac-
tions.
3.1 Kinetics of epoxidation
The above-mentioned results were used to determine the
reaction order of the epoxidations carried out with perox-
oacetic and peroxoformic acids formed “in situ”, and also
to determine the activation energies for the applied ex-
perimental conditions. The general form of the rate equa-
tion for the conversion of double bonds by peroxoacetic
acid (epoxidation reaction 2) may be written as:

Fig. 7. Change of viscosity with conver-

sion of double bonds into epoxide groups.
298 Petrović et al.
–d[DB]/dt = k3 [DB]n1[PAA]n2 (3)
where [DB] and [PAA] are molar concentrations of double
bonds and peroxoacetic (or peroxoformic) acid, respec-
tively; k3 is a rate constant (see eq. 2), n1 and n2 are the
reaction orders with respect to the double bonds and per-
oxoacetic or peroxoformic acid.
If it is assumed that epoxidation is pseudo first order with
respect to the double bonds as well as to the peroxoacetic
acid and if the rate constant is defined as k = k3 [PAA], the
rate equation for pseudo first order can be written as:
–d[DB]/dt = k[DB] (4)
The rate data for the epoxidation with peroxoacetic acid
are fitted in equation (4). And the latter is also used for the
kinetics data of the epoxidation with peroxoformic acid,
PFA, except that the rate constant in that case is defined
as k = k3 [PFA]. Hence, after integration, equation (4) be-
comes:
Eur. J. Lipid Sci. Technol. 104 (2002) 293–299
ln([DB]0/[DB]) = kt (5)
The slope of the plot of ln([DB]0/[DB]) vs. reaction time
points to a pseudo first reaction order. The results of the
rate constant determinations for epoxidations with perox-
oacetic and peroxoformic acid at three temperatures are
shown in Figs. 8 and 9. The kinetics of the epoxidation
with peroxoacetic acid followed first order kinetics for fair-
ly high conversions. Consequently, they result in a linear
dependency and the straight lines in Figs. 8 and 9 indi-
cate that the epoxidation with both acids is a pseudo first
order reaction with respect to the double bond disappear-
ance in the early stages of the reaction. In contrast the
epoxidation with peroxoformic acid at 80 °C the final con-
version was reached incredibly fast and thus this reaction
exhibited non-linear dependencies. In other words, this
epoxidation did not follow first order kinetics at higher
conversions. Activation energy for the epoxidation process
was determined from the rate constants at different tem-
Fig. 8. Determination of the pseudo
rate constants for the epoxidation of
soybean oil with peroxoacetic acid at
40, 60 and 80 °C.
Fig. 9. Determination of the pseudo
rate constants for the epoxidation of
soybean oil with peroxoformic acid at
40, 60 and 80 °C.
Eur. J. Lipid Sci. Technol. 104 (2002) 293–299
Fig. 10. Determination of the activation energies for the
epoxidation of soybean oil with peroxoacetic and peroxo-
formic acids.
peratures assuming their Arrhenius-type temperature de-
pendence. The activation energies for epoxidation with
both peroxoacetic and peroxoformic acid were calculated
from the slope of the ln(k) vs. 1/T dependencies (Fig. 10).
The value of the activation energy for peroxoacetic acid
(54.7 ± 2.1 kJ/mol) is higher than that for peroxoformic
acid (35.9 ± 5.2 kJ/mol). Our values for the activation
energy of the epoxidation in toluene with peroxoacetic
and peroxoformic acid are lower than those found by Gan
et al. [1] for the epoxidation of palm oil methyl esters with
peroxoacetic acid (63 kJ/mol) or for the epoxidation of
natural rubber [11] with peroxoformic acid (55 kJ/mol).
4 Conclusions
The epoxidation of soybean oil was carried out in a
toluene solution with in situ formed peroxoacetic and per-
oxoformic acid as oxidizing agents, in order to study ki-
netics and extent of side reactions. The kinetic parame-
ters were determined at 40, 60 and 80 °C. The rate con-
stants for the epoxidation with peroxoacetic acid were
0.118 (h–1) at 40 °C, 0.451 (h–1) at 60 °C and 1.278 (h–1)
at 80 °C, while those for peroxoformic acid were 0.264,
0.734, and 1.250 (h–1). The activation energy of the epox-
idation was found to be 54.7 kJ/mol for peroxoacetic acid
and 35.9 kJ/mol for peroxoformic acid. It was found that
the extent of side reactions was minimal with peroxo-
acetic acid in the entire temperature range and somewhat
higher with peroxoformic acid at 80 °C.
Acknowledgements
This material is based upon work supported by the Co-
operative State Research, Education and Extension Ser-
vice, U.S. Department of Agriculture, under Agreement
No. 99-35504-7873 and PSU/NSF-REU Program.
Epoxidation of soybean oil in toluene 299
References
[1] L. H. Gan, S. H. Goh, K. S. Ooi: Kinetic studies of epoxida-
tion and oxirane cleavage of palm olein methyl esters. J.
Am. Oil Chem. Soc. 69 (1992) 347–351.
[2] F. A. Zaher: Vegetable Oil as Alternative Fuel for Diesel-
Engines – A Review. Grasas y aceites 41 (1990) 82–91.
[3] S. Sinadinović-Fišer, M. Jankoviæ , Z. S. Petroviæ: Kinetics
of “In Situ” Epoxidation of Soybean Oil in Bulk Catalyzed by
Ion Exchange Resin. J. Am. Oil Chem. Soc. 78 (2001)
725–731.
[4] T. C. Chou, J. Y. Chang: Acetic-acid as an Oxygen Carrier
Between Two Phases for Epoxidation of Oleic-acid. Chem.
Eng. Commun. 41 (1986) 253–266.
[5] P. J. M. delaCuesta, E. R. Martinez, A. J. Medina, J. A. Gar-
cia, V. R. Cortes: Epoxidation in liquid phase of corn oil with
isopropylbenzene hydroperoxide. Influence of variables.
Kinetic study. Grasas y aceites 39 (1988) 1–7.
[6] T. W. Findley, D. Swern, J. T. Scanlan: Epoxidation of
Unsaturated Fatty Materials with Peracetic Acid in Glacial
Acetic Acid Solution. J. Am. Chem. Soc. 67 (1945) 412–
414.
[7] B. Rangarajan, A. Havey, E. A. Grulke , P. D. Culnan: Kinet-
ic Parameters of A Two-Phase Model for In-Situ Epoxidation
of Soybean Oil. J. Am. Oil Chem. Soc. 72 (1995) 1161–
1169.
[8] J. Wisniak , E. Navarrete: Epoxidation of Fish Oil. Ind. Eng.
Chem. Prod. Res. Develop. 9 (1970) 33–41.
[9] B. George, S. Abraham, M. M. Mathew: Epoxidation of
natural rubber latex stabilized with a nonionic surfactant.
Ind. J. Nat. Rubber Res. 5 (1992) 179–187.
[10] X. Hang, H. Yang: Model for Cascade Continuous Epoxida-
tion Process. J. Am. Oil Chem. Soc. 76 (1999) 89–92.
[11] L. H. Gan, S. C. Ng: Kinetic studies of the performic acid
epoxidation of natural rubber latex stabilized by cationic
surfactant. Eur. Polym. J. 22 (1986) 573–576.
[12] S. Roy, C. S. S. Namboodri, B. R. Maiti, B. R. Gupta:
Kinetic modeling of the epoxidation of natural rubber with
in-situ-formed peracid. Polym. Eng. Sci. 33 (1983) 92–96.
[13] C. Paquot, A. Hautfenne: Determination of Iodine Value
(I.V.). The Hanus Method in IUPAC, Applied Chemistry Divi-
sion, Commission on Oils Fats and Derivatives: Standard
Methods for the Analysis of Oils, Fats and Derivatives,
Blackwell Scientific Publications, London (UK) 1987.
[14] C. Paquot, A. Hautfenne: Determination of Epoxy-Group
Oxygen in IUPAC, Applied Chemistry Division, Commission
on Oils Fats and Derivatives: Standard Methods for the
Analysis of Oils, Fats and Derivatives, Blackwell Scientific
Publications, London (UK) 1987.
[15] A. Guo, Y. Cho, Z. S. Petrović: Structure and Properties of
Halogenated and Nonhalogenated Soy-Based Polyols. J.
Polym. Sci. A: Polym. Chem. 38 (2000) 3900–3910.
[Received: September 6, 2001; accepted: February 15, 2002]