374 Eur. J. Lipid Sci. Technol.

2011, 113, 374–379

Research Article
An initial study on the formation of 3-MCPD
esters during oil refining

Karel Hrncirik and Gerrit van Duijn

Unilever R&D Vlaardingen, Vlaardingen, The Netherlands

Oil refining is essential for ensuring quality and safety of oils and fats. However, during the deodorization
step of the refining process, the oil is exposed to high temperatures and changes in the lipid matrix may
occur leading to the formation of 3-chloropropane-1,2-diol (3-MCPD) esters and possibly other
processing by-products. This study was initiated to address the limited understanding on the
formation of 3-MCPD ester in oil refining. The impact of refining conditions, both at pilot-plant
and industrial scale, were investigated by subjecting palm and rapeseed oils to different refining
treatments. The experiments showed that 3-MCPD esters and glycidyl esters were formed during
the deodorization of palm oil, but not rapeseed oil. The level of 3-MCPD esters in the refined palm
oils (3.5–4.9 mg/kg) was independent of the deodorization conditions. No correlation was found
between the level of 3-MCPD esters formed and the content of the potential precursors, partial
acylglycerols and chlorides. In contrast, the formation of glycidyl esters was affected by the
deodorization conditions (both temperature and residence time). Higher levels of glycidyl esters
(up to 3.8 mg/kg) were found in palm oil deodorized at temperatures above 2308C.

Keywords: Chloropropanediols / Deodorization / Edible oils / Glycidyl ester / 3-MCPD ester

Received: October 22, 2010 / Revised: December 6, 2010 / Accepted: December 21, 2010
DOI: 10.1002/ejlt.201000317

1 Introduction of ‘purified’ oils enabled the development and the introduc-

Since ancient times, oils and fats have been used for food
preparation. Next to their nutritional contribution, they serve
as a heat transfer medium at elevated temperatures (e.g. in
frying), they improve the mouth-feel and give texture and
flavour to a wide range of foodstuffs. Until the industrial
revolution in the 19th century, oils and fats were purified
by simple decanting and sometimes filtration. After 80 years
of development, the purification process changed in the
1900s to a combination of neutralization with lye, bleaching
with active clay and deodorization at high temperature under
vacuum with steam. This refining process improved taste,
appearance and keepability of the product and hence allowed
the use of oils and fats with a ‘natural’ strong off-taste and/or
dark colour like cottonseed oil, palm oil, etc. The availability
Correspondence: Dr. Karel Hrncirik, Unilever R&D Vlaardingen,
Department of Fat Technology, Olivier van Noortlaan 120, 3133 AT
Vlaardingen, The Netherlands
E-mail: karel.hrncirik@unilever.com
Fax: þ31-10-4606000
Abbreviations: 3-MCPD, 3-chloropropane-1,2-diol; FFA, free fatty acid;
RSD, relative SD
tion of oil modification technologies, such as hydrogenation
and interesterification. Later, the development of improved
analytical techniques showed that the basic refining process
together with subsequent modifications and improvements
also reduces the levels of many of the contaminants (metals,
polyaromatic hydrocarbons and pesticide residues) present in
the crude oil [1].
However, the high temperature during deodorization may
also cause modification of the TAG matrix and reactions of
TAGs with other components present in the oil. The best
known example of a TAG modification is the cis–trans isomer-
ization, which occurs in oils containing high levels of PUFA at
temperatures above 2208C [2]. Recently, the formation of
3-chloropropane-1,2-diol (3-MCPD) esters and glycidyl
esters (Fig. 1) has been reported as other undesirable reac-
tions occurring during refining.
3-MCPD esters represent a class of food-borne contami-
nants that are mainly formed during high-temperature proc-
essing of fat-based matrices. They were first detected by
Velı́šek et al. [3] in acid-hydrolysed vegetable proteins. In
1983, 3-MCPD esters were found in rapeseed oils adulter-
ated with aniline and refined with hydrochloric acid [4] and
two decades later their occurrence was reported in various
processed foods [5, 6], including refined oils [7]. Large

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Eur. J. Lipid Sci. Technol. 2011, 113, 374–379
R2
O
Cl O were not disclosed. Nevertheless, the principles of the main
R1
3-chloropropane-1,2-diol (3-MCPD): R 1, R 2 = H
1-acyl-3-chloropropan-2-ol: R 1 = Ac; R2 = H
2-acyl-3-chloropropan-1-ol: R 1 = H; R 2 = Ac
1,2-diacyl-3-chloropropane: R1, R 2 = Ac
O centrifuge. The oil was subsequently washed by in-line water
O by filtration. Deodorization by continuous process was
R performed at different temperatures (details are given in
2,3-epoxy-1-propanol (glycidol): R = H
1-acyl-2,3-epoxypropane: R = Ac
Figure 1. Structure of 3-MCPD and glycidyl esters.
variations of 3-MCPD ester levels have been observed
between oils of different origin but also amongst the oils of
the same kind; refined olive oil and palm oil have been shown
to be particularly prone to elevated levels [7, 8]. It is not
clear to what extent the inconsistency in reported levels of
3-MCPD esters in refined oils can be attributed to intrinsic
compositional variation of the crude oils, different processing
conditions or analytical methodologies used. Since refined
oils are used in various food products (either as ingredients or
as a medium during the manufacturing), there is a great
interest in understanding the formation of 3-MCPD esters
in the oil refining process and exploring the possibilities of an
effective mitigation. There is only limited information in the
literature about the subject [7–9].
The present study was designed to investigate the impact of
the major refining routes (physical and chemical refining), and
in particular deodorization conditions, on the formation of
3-MCPD esters. Two different types of oil (palm and
rapeseed) were refined at both pilot-plant and industrial scale,
taking into account the content of potential precursors of
3-MCPD esters in the crude oils, notably partial acylglycerols.
2 Material and methods
2.1 Samples and materials
Samples of bleached (see Section 2.2.2), neutralized/
bleached (see Section 2.1.1), and fully refined palm and
rapeseed oils were obtained from refineries of several com-
panies who were members of the FEDIOL organization.
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An initial study on the formation of 3-MCPD esters 375
2.2 Industrial scale oil refining processes
It is reasonable to expect minor differences amongst the
refining processes performed at different refineries, in
particular in equipment, dosage levels of processing aids
and process conditions (e.g. time, temperature); these details
refining steps are identical and are described below.
2.2.1 Chemical refining
Crude palm oil or degummed rapeseed oil was neutralized in
a continuous industrial line equipped with in-line phosphoric
acid and lye dosing followed by soapstock separation in a
dosing, followed by separation of the wash water by a centri-
fuge. The neutralized oil was bleached in a continuous
process with a residence time of around 20 min followed
Section 3).
2.2.2 Physical refining
Crude palm oil or acid degummed rapeseed oil was bleached
with a phosphoric or citric acid pre-treatment (needed to
agglomerate residual phospholipids or metals) before dosing
of bleaching earth. The agglomerates were then removed by
filtration together with the bleaching earth prior to the
continuous deodorization step.
2.3 Pilot plant deodorization
Deodorization trials were carried out in a 75 kg pilot plant
batch deodorizer at temperatures of 180 or 2308C (tempera-
tures above 2308C could not be applied because of the safety
limit of the pilot plant steam generator). Oil was heated to the
target temperature within 25–40 min. The deodorization
process was run for 5 h (this time greatly exceeds the regular
time applied in refineries) at a pressure 3–4 mbar with a
steam (deionized and degassed water) dosage of 1% w/w.
The deodorizer was equipped with a special device to take
samples during the process without breaking the vacuum
allowing sampling (1 kg) at regular intervals.
2.4 Analytical methods
Two different methods were used for the determination of
3-MCPD esters. The sum of 3-MCPD esters and glycidyl
esters (generally called ‘3-MCPD esters and related com-
pounds’) was determined by the method of Weißhaar [10].
The method based on the modification of the former one [10],
in which sodium chloride solution was substituted by
ammonium sulphate solution in the salting out step, was used
for the specific analysis of 3-MCPD esters. From the difference
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376 K. Hrncirik and G. van Duijn Eur. J. Lipid Sci. Technol. 2011, 113, 374–379

between the results obtained by these two methods the con- 3-MCPD-E Glycidyl-E
tent of glycidyl esters was calculated and expressed as glycidol 5.0
after multiplying the difference by a factor 0.67 (a ratio 4.5
between a molar mass of glycidol and 3-MCPD). This 4.0
quantification assumes that glycidol is converted to
3.5

3-MCPD completely in the sample preparation and that
glycidyl esters are the only compounds being converted into
3-MCPD. It has been previously discussed that such an
indirect estimation of glycidyl ester levels is associated with
a relative uncertainty [11, 12], however, at the time when this
study was conducted, that approach (adopted by several
groups working on a similar subject) was the only option
to estimate the amount of glycidyl esters in refined oils. In
order to be able to compare our results with the results of
those other studies we decided to apply the same analytical
methodology. All determinations were performed in duplicate,
and gave repeatability with a relative SD (RSD) below 10%.
The content of inorganic chlorides in oil was determined
by ion chromatography after solid-phase extraction clean up.
Each sample was analysed in triplicate, the repeatability had
an RSD < 5%.
Standard methods were used for the determination of free
fatty acid (FFA) [13], hydroperoxides [14] and partial acyl-
glycerols [15]. The repeatability of these determinations,
performed in duplicate, had an RSD < 3%.
3 Results and discussion
3.1 Pilot plant deodorization experiment
Samples of bleached palm oil and rapeseed oil were obtained
from four different oil refineries across Europe. Table 1 pro-
vides the basic chemical parameters relevant for this study.
Fatty acid profiles (data not shown), free acidity and the
content of partial acylglycerols were typical for these
materials. The initial level of 3-MCPD esters in bleached
and neutralized/bleached palm oil was 1.7 and 1.5 mg/kg,
respectively, while glycidyl esters were not found. Pre-treated
rapeseed oil samples did not contain 3-MCPD or glycidyl
esters. The chloride content in palm oil and rapeseed oil
samples was comparable (2–6 mg/kg).
The formation of 3-MCPD esters and glycidyl esters was
studied during the batch deodorization performed at two
different temperatures (180 or 2308C) over time (up to
5 h). The levels of 3-MCPD esters and glycidyl esters found
in chemically and physically refined palm oils are shown in
Conc. [mg/kg]
3.0
2.5
2.0
1.5
1.0
0.5
0.0
180, 180, 180, 230, 230, 230,
1h 3h 5h 1h 3h 5h
Temp [ºC], time [h]
Figure 2. Formation of 3-MCPD esters and glycidyl esters in neu-
tralized/bleached palm oil deodorized at different time and tempera-
ture (Section 2.1.1).
Figs. 2 and 3, respectively. 3-MCPD esters and glycidyl esters
were not found in rapeseed oil samples (limit of quantification
0.15 mg/kg). This is in agreement with the results for physi-
cally refined rapeseed oil reported by Zelinková et al. [7],
although more recently, a mean value of 3-MCPD esters
calculated for a set of refined rapeseed oils (refining con-
ditions unspecified) was reported to be 0.4 mg/kg [8].
Irrespective of the type of oil pre-treatment used
(dry bleaching versus neutralization/bleaching) and the deo-
dorization conditions, the levels of 3-MCPD esters were
similar in all samples of deodorized palm oil (3.5–4.7 mg/
kg). In contrast, the formation of glycidyl esters did show a
dependence on the temperature of the deodorization process.
At 1808C up to only 0.5 mg/kg of glycidyl esters was formed
irrespective of the duration, whereas at 2308C the formation
was more pronounced (up to 2.1 mg/kg) and increased the
most over time. The levels of 3-MCPD and glycidyl esters
found in this study fall within the variation reported for a set
of refined palm oil and palm oil-based fats (1.0–5.8 mg/kg for
true 3-MCPD esters and 0.3–6.3 mg/kg for glycidyl esters)
using the same methodology [8].
Other chemical parameters were also monitored in deo-
dorized samples. As expected, no changes in fatty acid and
acylglycerol profile were found (data not shown). Peroxide

Table 1. Chemical characterization of pre-treated oils used for pilot-plant deodorization experiment

Sample Free acidity (%) MAGs (%) DAGs (%) Chlorides (mg/kg)

Palm oil, bleached; supplier A 6.5 0.6 8.8 3.6

Palm oil, neutralized/bleached; supplier A 0.25 0.3 8.5 4.2
Rapeseed oil, bleached; supplier C 0.80 1.2 0.7 2.7
Rapeseed oil, neutralized/bleached; supplier D 0.07 1.0 0.6 5.9

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Eur. J. Lipid Sci. Technol. 2011, 113, 374–379 An initial study on the formation of 3-MCPD esters 377

3-MCPD-E Glycidyl-E these samples were comparable with those obtained by deo-
5.0 dorization carried out at the pilot plant scale.
4.5 The analytical results of 3-MCPD esters and glycidyl
4.0 esters in palm oils refined at industrial scale (with the deodor-
ization performed at 240–2658C and residence time at these
3.5
Conc. [mg/kg]

temperatures about 1 h) were plotted together with the

3.0
results obtained in pilot plant (also chosen after one hour)
2.5 against the deodorization temperature (Fig. 4).
2.0 The concentrations of 3-MCPD esters found (3.2–
1.5 4.9 mg/kg) were comparable to those found in samples deo-
1.0 dorized in the batch process at lower temperatures (180–
0.5 2308C) suggesting that the deodorization temperature within
the range 180–2658C does not have significant impact on the
0.0
formation of 3-MCPD esters. By contrast, a steep increase of
180, 180, 180, 230, 230, 230,
glycidyl ester levels (up to 3.8 mg/kg) was observed with
1h 3h 5h 1h 3h 5h
increasing temperature. The temperature increase from
Temp [ºC], time [h] 180 to 2308C had a relatively limited effect on the formation
of glycidyl esters for a deodorization period of one hour
Figure 3. Formation of 3-MCPD esters and glycidyl esters in
(an increase below 0.3 mg/kg), whilst further temperature
bleached palm oil deodorized at different time and temperature
(Section 2.2.2). increase above 2308C (at industrial scale) led to higher levels
of glycidyl esters.
These findings are in agreement with the results of
value was reduced in all cases to below 0.2 meq O2/kg within Weißhaar and Perz [8], who found a limited increase of
1 h of deodorization. Reduction of FFAs in the processed oils glycidyl ester levels when the deodorization temperature
was dependant on the deodorization conditions. High increased from 210 to 2308C, but a considerable increase
amount of FFA in bleached palm oil (6.5%) was successfully (glycidyl esters levels up to 4.4 mg/kg) when the temperature
reduced by deodorization at 2308C to 1.5% after 1 h and to was elevated further to 2508C. Similarly, Franke et al. [9]
<0.1% after 3 h. A temperature of 1808C was not sufficient modified the conditions of lab-scale deodorization and inves-
to remove FFA from the oil, even after 5 h only 20% of the tigated the impact on the formation of 3-MCPD (and
FFA present in the bleached oils was removed. Similar results glycidyl) esters. Although the analytical methodology used
were found for rapeseed oil. did not allow to distinguish between 3-MCPD and glycidyl
esters, a similar trend can be deduced from their data. The
3.2 Comparison with industrial scale samples authors found just a moderate increase within the tempera-
ture range 180–2408C, but further temperature increase to
Samples of fully refined palm and rapeseed oils, collected 2708C nearly doubled the content of ‘3-MCPD and related
from several oil refineries, were refined at different con- compounds’ in the deodorized oil, most likely due to the
ditions. More details of the refining processes and basic increase of glycidyl ester level.
chemical characterization of the samples are given in
Table 2. FFA content was below 0.15%, the level of 3.3 Formation of 3-MCPD and glycidyl esters
DAGs ranged from 6.7 to 10.9 and 0.7 to 1.2% for palm
oil and rapeseed oil, respectively. The chloride content varied The formation of 3-MCPD esters and glycidyl esters have
within the range 3–10 mg/kg. Based on this characterization, very different time and temperature dependencies and it

Table 2. Chemical characterization of fully refined oils obtained by refining process at industrial-scale

Sample Free acidity (%) MAGs (%) DAGs (%) Chlorides (mg/kg)

Palm oil, bleached/deodorized (2408C); supplier B 0.05 0.4 10.9 3.4

Palm oil, bleached/deodorized (2608C); supplier B 0.05 0.4 7.8 5.2
Palm oil, bleached/deodorized (2658C); supplier A 0.05 0.2 7.2 4.6
Palm oil, neutralized/bleached/deodorized (2658C); supplier A 0.05 0.1 6.7 3.2
Rapeseed oil, bleached/deodorized; supplier C 0.15 0.9 0.7 4.0
Rapeseed oil, bleached/deodorized; supplier D 0.10 1.7 0.8 9.8
Rapeseed oil, neutralized/bleached/deodorized; supplier C 0.07 1.0 0.8 3.7
Rapeseed oil, neutralized/bleached/deodorized; supplier D 0.10 1.8 1.2 4.1

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378 K. Hrncirik and G. van Duijn
12.0
10.0
Conc. [mg/kg]..
8.0
6.0
4.0
2.0
0.0
150 175 200 225 250 275 300
Temp [ºC]
Figure 4. Effect of deodorization temperature on the formation of 3-
MCPD esters and related compounds in deodorized palm oil.
Symbol ‘T’ represents levels of 3-MCPD esters, symbol ‘&’
represents levels of 3-MCPD esters and related compounds (the
sum of 3-MCPD and glycidyl esters). Samples deodorized at 180
and 2308C were obtained at the pilot plant scale after 1 h deodoriza-
tion. The details of analytical methodology used are given in
Section 2.4.
therefore seems probable that they are formed by different
pathways. 3-MCPD esters reach steady levels within 1 h
(even at relatively low temperature) and the levels appear
to be independent of deodorization conditions. On the other
hand, increased deodorization temperatures and prolonged
deodorization times enhance the formation of glycidyl esters.
Several groups tentatively reported a positive correlation
between the content of partial acylglycerols and the level of
glycidyl esters formed. In fact, particularly high concen-
trations of glycidyl esters found in oils based mainly on
DAGs led even to the withdrawal of these oils from the
market in September 2009 (Kao Corporation: Kao to
Temporarily Refrain from Selling Econa Products.
Electronic citation 2009. http://www.kao.com/jp/en/corp_
news/2009/20090916_002.html). Nevertheless, it remains
unclear what makes certain oils (palm oil in particular) prone
to the formation of 3-MCPD esters. The level of partial
acylglycerols, namely DAGs, is relatively high in palm oil
(typically 5–9%); however, no clear correlation between the
levels of true 3-MCPD esters and level of DAGs has been
demonstrated so far. In this present study there was no
appreciable formation of 3-MCPD esters in the samples of
rapeseed oil which, although different in composition to palm
oil, is also notably much lower in DAG levels.
Self-evidently another precursor of 3-MCPD esters is
chlorine. Due to the low levels of inorganic chlorides occur-
ring in oils (Tables 1 and 2), it was reasonable to have
expected that the chloride concentration may be a limiting
factor for the level of 3-MCPD esters formed. In this study,
no effect of the different initial concentrations of inorganic
chlorides in bleached oils was found. In addition, no decrease
ß 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Eur. J. Lipid Sci. Technol. 2011, 113, 374–379
of chloride levels during deodorization was observed and all
samples still contained substantial amount of chlorides
after the deodorization (palm oil 2.7–5.2 mg/kg, rapeseed oil
3.7–9.8 mg/kg). As inorganic chlorides do not decrease during
the deodorization process it is likely that other chlorinated
compounds are involved in the formation of 3-MCPD esters.
4 Conclusions
3-MCPD esters and glycidyl esters are formed during the
deodorization step of the refining process due to the effect of
high temperature. The level of 3-MCPD esters seems to be
independent of the refining conditions (both the type of oil
pre-treatment used, i.e. bleaching versus neutralization/
bleaching, and the deodorization conditions) and is primarily
determined by the oil type. No correlation was found between
the levels of possible precursors (DAGs and inorganic
chlorides) and the levels of 3-MCPD esters formed. On
the other hand, the levels of formation of glycidyl esters were
shown to be affected by the parameters of the deodorization
process.
The results suggest that the mitigation of glycidyl ester
formation through optimized refining may be more promising
than the mitigation of 3-MCPD ester formation. Limiting the
level of glycidyl esters formed during deodorization by
decreasing the deodorization temperature (or the residence
time) may be feasible assuming the operation can be opti-
mized in such a way that other contaminants and FFAs are
sufficiently removed from the oil. This would pose a sub-
stantial challenge for the oil processors. Further extensive
work is required to test other mitigation strategies, such as a
pre-treatment of the crude oil and/or a potential modification
of the initial steps of oil refining, namely degumming, neutral-
ization and bleaching. It is clear that further progress on such
mitigation strategies for 3-MCPD and glycidyl esters would
be enhanced by the elucidation of the formation mechanisms
and the identification of the critical precursors.
This work has been carried out in co-operation with members of the
FEDIOL Contaminant Working Group. These members have
supported us by organizing the shipment of the test material,
delivering oil samples and sharing the analytical cost. A special
thanks to the FEDIOL secretariat for co-ordinating these support
activities. The authors also wish to thank Rob van den Brugghen
(Unilever R&D Vlaardingen) for his help in organizing the
shipment of the samples and their analysis.
The authors have declared no conflict of interest.
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