Eur. J. Lipid Sci. Technol.

2011, 113, 387–392 387

Research Article
Removal of 3-MCPD esters and related substances after
refining by adsorbent material

Ulf Strijowski, Volker Heinz and Knut Franke

German Institute of Food Technologies, Quakenbrueck, Germany

Possibilities of a removal of 3-chloro-1,2-propanediol fatty acid esters (3-MCPD esters) and related
substances from palm oil were investigated using different adsorption materials. Some of them are
already applied for the improvement of frying oils with respect to reducing polar components. For this
purpose nine different commercially available inorganic adsorbent materials were chosen and screened
with respect to their ability to reduce the contents of 3-MCPD esters and related substances in a refined
palm oil. Two of the materials, a calcinated zeolite and a synthetic magnesium silicate, were found to be
able to reduce the contents of these substances in a range of up to 40%. Further investigations revealed
that the ‘related substances’ which had been identified mainly as glycidyl esters, were removed but not the
3-MCPD esters. Especially the zeolite was able to lower the concentration of these substances relatively
fast in a broad range of treatment temperatures. No adverse effects were detected for this material with
respect to sensory properties and oxidative stability of the palm oil after the treatment.

Practical applications: The successful removal of the health relevant 3-MCPD esters and related
substances may open additional possibilities for the manufacturing of palm oils containing these
substances, for example for infant foods. The advantage of such an approach is that these procedures
may be easily implemented in a short time frame. In contrast, influencing of precursor contents and
formation pathways, like changes in culture and harvesting of palm fruits or modifications of refining
processes, requires more fundamental research and may have several impacts on the manufacturing
procedures.

Keywords: Adsorbents / Adsorption / Glycidyl ester / Palm oil / 3-MCPD

Received: July 6, 2010 / Revised: September 17, 2010 / Accepted: September 28, 2010
DOI: 10.1002/ejlt.201000323

1 Introduction
Free 3-chloro-1,2-propanediol (3-MCPD) has been known to
exhibit genotoxic effects in in vitro tests. Therefore, Joint FAO/
WHO Expert Committee on Food Additives (JECFA) recom-
mended a maximum tolerable daily intake of 2 mg/kg BW [1].
Since 2004, occurrence of 3-MCPD bound in 3-MCPD fatty
acid esters (3-MCPD esters) and related substances has been
Correspondence: Dr. Knut Franke, German Institute of Food
Technologies, Prof.-von-Klitzing-Strasse 7, D-49610 Quakenbrueck,
Germany
E-mail: k.franke@dil-ev.de
Fax: þ49 5431 183 114
Abbreviations: AMS, amorphous magnesium silicate; DGF, Deutsche
Gesellschaft für Fettforschung e.V.; SAS, sodium aluminium silicate; SCS,
synthetic calcium silicate; SMS, synthetic magnesium silicate; SO, silicon
oxide; Z, zeolite; 3-MCPD, 3-chloro-1,2-propanediol
reported for refined fats and oils by several groups [2–4].
Especially refined fruit oils like palm oil seem to be very
susceptible to formation of these substances [5, 6].
Meanwhile, it has been demonstrated that also substances
forming 3-MCPD during sample preparation are measured
by the method of Weißhaar [4, 7]. Therefore, substances
determined by this method have been named as the sum
of 3-MCPD esters and 3-MCPD ester forming substances
or in short ‘3-MCPD esters and related substances’. By now,
analytical methods are available to distinguish between
3-MCPD esters and the related substances [6, 8].
Weißhaar and Perz [6] showed that glycidyl esters are the
predominant part of these ‘related’ substances. However,
glycidyl esters are considered to be of health relevance, too
[9]. Therefore, reduction of the amounts of both 3-MCPD
esters and related substances in edible oils, especially palm
oil, remains a challenge for the oil manufacturer.
Regarding formation of these substances, it was found
that the main part was generated during refining process,

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388 U. Strijowski et al. Eur. J. Lipid Sci. Technol. 2011, 113, 387–392

especially deodorisation of the oil. There are indications Table 1. Overview of the adsorbent materials tested in the study
that higher temperatures and longer treatments during deo-
dorisation may contribute to increasing concentrations of Identifier Type Remarks (according to supplier)
these substances in the refined oil [10]. On the other hand, AMS1 Amorphous magnesium >97% magnesium silicate
deodorisation of palm oil has a large influence on oil quality silicate
with respect to sensory properties, colour (heat bleaching) AMS2 Amorphous magnesium >70% magnesium silicate
and contaminants [11]. Considering this, a modification in silicate
palm oil deodorisation process for reducing formation of AMS3 Amorphous magnesium >40% magnesium silicate
undesired substances may have an impact on the resulting silicate
overall quality of the palm oil and requires many tests to reach Z1 Zeolite <20% water (dried)
the desired product quality. Z2 Zeolite <1% water (calcinated)
Therefore, alternative ways for lowering the contents of SO Silicon oxide >99.9% silicon oxide
SAS Sodium aluminium Perlite with citric acid
3-MCPD esters and related substances should be considered.
silicate added
One opportunity is the use of adsorption materials which are
SCS Synthetic calcium 47% silicon oxide,
already applied for the removal of polar components from silicate 28% calcium oxide
frying oils. These compounds results from degradation reac- SMS Synthetic magnesium 65% silicon oxide,
tions in the oils due to the high temperatures during frying silicate 15% magnesium oxide
[12–14]. Such treatments can contribute to a prolonged
use of the oils for daily frying operations, for example in
restaurants.
It can be assumed that the 3-MCPD esters and related 6008C. Silicon oxide (SO) is sold as an additive for
substances differ in their polarity compared to those of pure bleaching of edible oils and sodium aluminium silicate
triacylglycerides, because their structures are closer to (SAS) and synthetic calcium silicate (SCS) are also
those of mono- and diacylglycerides than to those of triacyl- marketed as improvers for frying oils. The last one synthetic
glycerides. Mono- and diacylglycerides form a main part of magnesium silicate (SMS) is an adsorbent widely used
the polar compounds in edible oils [15]. for water treatment.
Therefore, it may be a promising way to bind the All chemicals used for analysis were of HPLC-grade
3-MCPD esters and related substances on solid adsorbent quality.
surfaces in the refined palm oil and remove them with the
adsorbents. The use of solid adsorbents to eliminate chlorine 2.2 Treatment of the palm oil
containing compounds was already described for plastics by
Uddin et al. [16]. For the screening tests of all adsorbent materials 180 g of
In the frame of this study several inorganic adsorbent palm oil were heated in a beaker to 808C by using a heated
materials, some of them already used for frying oils, were magnetic stirrer and stirred to obtain a uniform temperature
tested for the removal of 3-MCPD esters and related sub- distribution. After reaching this temperature 20 g of the
stances as well as for other polar components, for example adsorbent material were added and suspended by the stirrer.
mono- and diacylglycerides, from a refined palm oil. After the treatment time of 30 min adsorbent material was
separated by centrifugation (15 min, 2500 g). The separated
2 Materials and methods oil was used for the analytics. All treatments were carried out
in duplicate.
2.1 Materials Additionally to these standard conditions, a broader range
of treatment procedure settings with respect to temperature
About 50 kg of refined palm oil with a relatively high content (60–1208C), treatment time (5–120 min) and portion of
of 3-MCPD esters and related substances were supplied by adsorbent material in the oil (1–10%, w/w) was applied for
German oil mills via the Association of the German Oil Seed those materials showing a distinct removal in the screening
Processing Industry (OVID). For shipping, the total amount tests.
of oil was provided in ten containers.
Adsorbent materials listed in Table 1 were provided 2.3 Analytical procedures
by different suppliers. The adsorbents AMS1 to AMS3
are commercially available powders for a daily treatment Contents of 3-MCPD esters and related substances as sum
of used frying oils. Z1 and Z2 are zeolite powders parameter were measured using the Deutsche Gesellschaft
supplied as molecular sieves for adsorption of gases. für Fettforschung e.V. (DGF) method C-III 18 (09) part A
They differ in their final manufacturing step. Z1 was [7] and the contents of 3-MCPD esters were detected
dried at temperatures below 1008C, whereas Z2 was according to the DGF method C-III 18 (09) part B.
subjected to a calcination process with temperatures above Content of polar compounds was analysed gravimetrically

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Eur. J. Lipid Sci. Technol. 2011, 113, 387–392
according to the micro method published by Schulte [17].
Mono- and diacylglycerides as well as acid value were deter-
mined according to DGF methods C-III 3c (02), C-V 2
and D-IV 2a, respectively. Differences between the oils
regarding contents of 3-MCPD and related substances were
statistically tested using Mircrosoft1 Excel functions with
p < 0.05.
2.4 Quality evaluation of the treated oils
Additional blind tests of the untreated oil and selected
samples of treated palm oil by a trained sensory panel of
the edible oil industry were carried out. For these purpose,
four different oils, one of them the untreated sample, were
numbered randomly and sent to the panel. The oils were
evaluated with respect to their overall sensory quality using a
scale between 1 and 10 with 10 for best quality. Furthermore,
oxidation stability of the oils was tested by an external labora-
tory using the rancimat method (DIN EN 14122) at a
temperature of 1108C.
3 Results and discussion
3.1 Screening tests of the adsorbent materials
Data of the untreated palm oil as mean values and SDs
resulting from sampling of different containers of the palm
oil shipment are shown in Table 2. The acid value was low
indicating a well refined palm oil. Contents of polar com-
pounds were high compared to the values found by Goh and
Timms [18] and Lin and Yoo [19]. They reported levels up to
8% for palm oil, although levels up to 10% were also men-
tioned for palm oil [20]. Most of the polar compounds in such
a palm oil are formed by mono- und diacylglycerides as could
be observed from Table 2. Contents of 3-MCPD esters and
related substances were at a high but not fully unusual level
for an industrially refined palm oil [5, 6]. Approximately
60% of these substances were 3-MCPD esters as could be
approved by the modified DGF-method without incorpora-
tion of chloride in sample preparation.
The separation procedure of the adsorption material from
the oil as described in the M þ M section leaded to a removal
of a part of the oil adhering at the solids surfaces. Depending
on the type of solids between 2.8 and 36.7% of the oil stuck to
the adsorbent material in our experiments. However, it has to
Table 2. Composition of the untreated palm oil
Parameter Value
Acid value 0.12
0.01
Mono- and diacylglycerides 8.85
0.05
Total polar compounds 9.41
0.22
3-MCPD esters and related substances 6.59
0.19
3-MCPD esters 4.38
0.36
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Removal of 3-MCPD esters and related substances 389
be mentioned that the focus of the investigations was directed
to the ability of the materials reducing the contents of
3-MCPD and related substances. Therefore, a distinct
reduction of these amounts can be expected by an optimised
separation procedure.
The contents of total polar compounds as well as mono-
and diacylglycerides in palm oil before and after ‘standard’
treatment with the different adsorbent materials are pre-
sented in Fig. 1. As can be observed from this diagram, only
few of these materials contributed to a distinct reduction of
the polar compounds in the palm oil. Especially, one of the
commercial powders for frying fat improving, AMS2, and the
calcinated zeolite Z2 reduced the amounts of these substan-
ces for approximately 25%. On the other hand, it should be
mentioned that other commercially available powders mar-
keted as frying oil improvers, like SAS, had only a negligible
effect on polar components in the palm oil. As shown in
Table 2, the main part of polar compounds of refined palm
oil originated from mono- und diacylglycerides. Therefore,
the effects of the adsorbent materials with respect to mono-
and diacylglycerides were comparable to the effects concern-
ing polar compounds. However, most of the materials
seemed to reduce other polar compounds besides the mono-
and diacylglycerides in a slightly higher extent. Therefore,
the differences after treatment between the contents of polar
components and mono- and diacylglycerides for the oil
treated in the same way were lower compared to the differ-
ence in the untreated oil. A slightly higher content of mono-
and diacylglycerides compared to the total polar compounds
was measured for the oil treated with SMS. This can be
explained by the measurement accuracies of both methods.
The reduction potential of the adsorbent materials with
respect to contents of 3-MCPD esters and related substances
as well as contents of 3-MCPD esters is presented in Fig. 2.
Considering the total column height, only two adsorbent
mg KOH/g fat
g/100 g
g/100 g Figure 1. Concentrations of polar compounds (dark grey filled col-
ppm umns) and mono- and diacylglycerides (white columns) in a refined
ppm palm oil before and after treatment with different adsorbent materi-
als (abbreviations see Table 1).
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390 U. Strijowski et al. Eur. J. Lipid Sci. Technol. 2011, 113, 387–392

compounds. On the other hand, AMS2 which had similar

good reduction properties concerning polar compounds
had no effect on 3-MCPD esters and related substances.
Vice versa, SMS showed a reliable reduction of 3-MCPD
esters and related substances but had only low influence
on polar compounds. This means that it is not possible to
derive the reduction potential of adsorbent materials for
3-MCPD esters and related substances from their effects
on polar components. It can be concluded, that there are
different mechanisms responsible for the reduction these
classes of substances in a refined palm oil.

3.2 Influence of treatment conditions on reduction of

Figure 2. Concentrations of 3-MPCD (grey column sections) and 3-MCPD esters and related substances
3-MCPD esters and related substances (total column heights) in a
refined palm oil before and after treatment with different adsorbent Further tests with varying palm oil treatment conditions were
materials (abbreviations see Table 1), different capital and lower carried out using the two most promising materials, Z2 and
case characters indicates significant differences in concentrations SMS, and, additionally, AMS3 as the negative control. The
of 3-MCPD and 3-MCPD and related substances, respectively influence of temperature in the range between 60 and 1208C
( p < 0.05). on the reduction of 3-MCPD esters and related substances in
the palm oil is shown in Fig. 3. The other treatment con-
materials, the calcinated zeolite Z2 and the silicon calcium ditions, duration of 30 min and 10% portion of adsorbent
silicate SMS, were able to decrease the amounts of 3-MCPD material in the oil, remained constant. As could be observed
esters and related substances in the palm oil for the applied in this Figure, temperature influence on reduction efficiency
treatment conditions. Both materials reduced the amount by was different for the adsorbent materials investigated. For the
up to 40% compared to the initial concentration. All other calcinated zeolite (Z2) and the amorphous magnesium
adsorbent materials had either a negligible effect (SO, SAS) silicate (AMS3) the effect of temperature increase in the
or increased (AMS1-3, Z1, SCS) the contents of these sub- range between 60 and 1208C could be ignored. Especially,
stances. Especially, the behaviour of the zeolites is of interest. the good reduction properties of the zeolite seemed to be
The materials, Z1 and Z2, varying in their pre-treatment independent on temperature, whereas the second suitable
possess different water contents according to the specifica- material (SMS) required higher temperatures of 808C and
tions of the manufacturer. Due to their special microstructure more for a distinct reduction of 3-MCPD esters and related
zeolites have very good water binding abilities. Therefore, a substances.
drying step as applied for Z1 resulting in a water content of The influence of adsorbent material concentration on
approximately 20% delivers a material which was ineffective contents of 3-MCPD esters and related substances is
for reduction of 3-MCPD esters and related substances in
palm oil. Otherwise, a calcination step which had lowered
water content of the zeolite below 1% resulted in a material
showing the very positive effect regarding removal of these
substances.
A deeper look into the results obtained for different
adsorbent materials revealed that not the 3-MCPD esters
themselves but substances designated as ‘3-MCPD ester
forming substances’ mainly glycidyl esters [6] were influ-
enced. This effect could be observed for all adsorption
materials except Z2 and SAS both for a decrease and an
increase of these substances after the treatment. Z2 and
SAS significantly decrease the amounts of 3-MCPD esters
but the effect is very small compared to the effects of adsorb-
ent materials on ‘3-MCPD ester forming substances’.
A comparison of the effects of adsorbent materials on
3-MCPD esters and related substances and their influence Figure 3. Concentrations of 3-MPCD esters and related sub-
on concentration of polar components (Fig. 1) revealed that stances in palm oil treated at varying temperatures with the adsor-
there was no direct correlation between these two effects bent materials AMS2 (squares), Z2 (diamonds) and SMS (triangles),
except for the zeolite Z2 which reduced both types of grey bar reflects the initial content in the oil before treatment.

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Eur. J. Lipid Sci. Technol. 2011, 113, 387–392
Figure 4. Concentrations of 3-MPCD esters and related sub-
stances in palm oil treated with varying portions of adsorbent mate-
rials AMS2 (squares), Z2 (diamonds) and SMS (triangles), grey bar
reflects the initial content in the oil before treatment.
presented in Fig. 4. No concentration effects were found for
the negative sample AMS2. Therefore, the higher level of
‘3-MCPD ester forming substances’ observed in the oil
treated with this material did not depend on the amount of
adsorbent in the oil. The other two materials with positive
reduction ability behaved in a similar way showing a strong
dependency on concentration. Both materials had very low
effect at the lowest concentration (1%, w/w). Amounts of 5%
and more were required to realise the distinct reduction of
3-MCPD esters and related substances.
Time dependencies of reduction effects are shown in
Fig. 5. In the case of Z2 additional tests were carried out
for shorter times. The final reduction value was achieved
already after 5 min for this material and longer treatments
up to 60 min did not significantly affect the contents of
Figure 5. Concentrations of 3-MPCD esters and related sub-
stances in palm oil treated for varying durations with the adsorbent
materials AMS2 (squares), Z2 (diamonds) and SMS (triangles), grey
bar reflects the initial content in the oil before treatment.
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Removal of 3-MCPD esters and related substances 391
Table 3. Results of sensory tests and oxidation stability
investigations (rancimat) of palm oil before and after treatment with
SMS and different amounts of zeolite Z2
Adsorption Sensory points Induction
material Portion (10 – best quality) period (h)
Without 4.8
0.84 18.0
SMS 10% 7.2
0.45 37.4
Z2 10% 7.0
0.00 19.6
Z2 5% 2.2
1.10 18.2
3-MCPD esters and related substances in the palm oil.
Whereas, a distinct influence of treatment time on reduction
results was found for the other promising material, SMS. In
this case treatment times of 30 min and more were required
to obtain the reduction in 3-MCPD esters and related sub-
stances. Time effects on the resulting contents were not
observed for the control material (AMS3).
3.3 Quality aspects of the oil treatment
Because the treatment is designated to be carried out after the
oil refining process, quality of the treated oil is of interest for
the further use of such oils for food applications. Therefore,
additional sensory and quality tests (oxidation stability) were
carried out with the untreated oil and selected oils after the
treatment (Table 3).
The results of the sensory tests indicated that there were
no adverse effects but even a slight improvement of the oil
quality after treatment with zeolithe Z2. However, a worse
effect on sensory oil quality was found for SMS. Oxidation
tests of the palm oil revealed comparable stability of the
palm oil after treatment with the zeolite. The induction times
of the oils treated with Z2 are in the same range with the
untreated sample. On the other hand, a longer induction time
indicating better oxidation stability was found for the oil
treated with the second material possessing good reduction
potential, SMS.
4 Conclusions
3-Chloro-1,2-propanediol fatty acid esters and related sub-
stances differ in their structure compared to triacylglycerides.
Due to these differences there should be an opportunity to
remove these substances from refined oil by suitable adsorb-
ent materials similar to removal of polar compounds from
frying oil after longer use for deep-fat frying. For this purpose,
several inorganic powders were tested with respect to the
ability of lowering the contents of polar compounds as well
as 3-MCPD fatty ester esters and related substances.
Although some powders were able to reduce the concen-
tration of polar compounds, only two were effective for
reducing the contents of 3-MCPD esters and related
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392 U. Strijowski et al.
substances. However, a prediction of this ability based on the
reduction efficiency for polar components was not possible
for these materials. It can be assumed that there are different
reduction mechanisms for both classes of compounds. The
analytical method according to Weißhaar and Perz [6] con-
firmed that only the substances which formed 3-MCPD
during sample preparation, mainly glycidyl esters, could be
lowered by the treatment with the adsorbent material,
whereas the contents of 3-MCPD fatty acid esters were
practically not influenced.
To obtain more information on the reduction mechan-
isms, further investigations are been currently performed.
First of all, concentration of these substances in the oil which
remained immobilised at the adsorption material after sep-
aration has to be measured. These results are necessary to
check whether the reduction is based on adsorption or on a
reaction taking place at the solid surface. A transformation of
peroxides at solid surfaces was described for the bleaching
process [21].
Additionally, potential adsorbent materials will be charac-
terised with respect to their surface properties to get more
information about the correlation between reduction activity
and material properties.
This research project was supported by the German Ministry of
Economics and Technology (via AiF) and the FEI
(Forschungskreis der Ernährungsindustrie e.V., Bonn). Project
AiF 16004N. The authors also wish to thank OVID (Verband der
ölsaatenverarbeitenden Industrie in Deutschland e.V.) for
supplying palm oil and support for sensory analyses of the oils.
The authors have declared no conflict of interest.
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