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How Does The Number of Times Oil Is Reheated Affect Its Iodine Value?
How Does The Number of Times Oil Is Reheated Affect Its Iodine Value?
Essay
Words: 3678
Extended Essay
Abstract
This report is investigating How does the number of times oil is reheated
affect its iodine value? This was researched in order to determine which oil is best
suited for deep fat frying. The experiment carried out involves iodine (a halogen) in
the form of iodine monochloride reacting with the monounsaturated fatty acids
(contain only 1 carbon-carbon double bond) and polyunsaturated fatty acids (contain
more than 1 carbon-carbon double bond) found in the olive, sunflower and linseed
oils. This creates a saturated di-halogenated single bond with the carbons in the
carbon chain of the fatty acids. After this reaction has been completed, the amount of
iodine that has reacted with the carbon is determined by adding a potassium iodide
solution. This reaction causes the remaining iodine monochloride, which has not yet
reacted to form iodine. The iodine is then titrated with a standard solution of sodium
The conclusions found vary for each oil. The iodine value decreases as the oil
is reheated for both olive oil and sunflower oil. There was not much change present in
the iodine value when reheating linseed oil. It was evaluated that this is due to an
issue within the method. The main issue found was the opening of the bottle of
linseed oil weeks before it was used for the experiment, allowing it to oxidize before
the experiment was started. As linseed oil contains more polyunsaturated fatty acids
than olive oil and sunflower oil, it is more susceptible to oxidation, thus being
saturated before the experiment and therefore displaying no change in iodine value.
It was concluded that whilst the data was limited, sunflower oil was the best
oil to use when deep fat frying, as it was more stable, thus less prone to oxidation and
going rancid.
(300 words)
Extended Essay
Table of Contents
Abstract 2
Research Question 1
Introduction on the Structure of Oils 1
Hypothesis 9
Aparatus & Chemicals 11
Safety 11
Variables 12
Method 13
Results Table 1 14
Results Table 2 15
Sample Calculations 16
Graph 1: Iodine Value when heating Olive Oil 16
Graph 2: Iodine Value when heating Sunflower Oil 17
Graph 3: Iodine Value when heating Linseed Oil 17
Conclusion & Evaluation 18
Bibliography 22
Appendix 1: Detailed Method 24
Extended Essay
Research Question
How does the number of times oil is reheated affect its iodine value?
Fats and oils are a mixture of triglycerides. Triglycerides are made up of three
fatty acids (see diagram 1) linked to glycerol (see diagram 2) by fatty acyl esters (see
diagram 3). Fatty acids are long chain hydrocarbons with carboxyl groups (COOH
Ester bond
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unsaturated based on how many carbon-carbon double bonds are present within the
fatty acid. A saturated substance is one in which the atoms are linked by carbon-
considered to be unsaturated. (Helmenstine) The less unsaturated the fatty acid is, the
the carbon chain. There are 2 types of unsaturated fatty acids, monounsaturated and
bond, with the rest of the carbon-carbon bonds in the chain being single bonds. A
polyunsaturated fatty acid contains more than 1 carbon-carbon double bond (see
diagram 4) Carbon carbon double bonds will cause the carbon chain to create a “kink”
(see diagram 5). The carbon-carbon double bonds occurring in unsaturated fatty acids
can be found in both the Trans and the Cis form (see diagram 6). The majority of
unsaturated oils contain fatty acids with bonds in the Cis form.
Fig. 4. The source. “Monounsaturated fatty acid displaying 1 carbon-carbon double bond and polyunsaturated fatty
acid displaying 2 carbon-carbon double bonds”. Food science Academy, 15.06.2013,
foodscienceacademy.org/2013/06/15/fats-explained/. 2016
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Fig. 5. “Carbon-carbon double bond causing carbon chain to bend”. University of Washington,
courses.washington.edu/conj/membrane/fattyacids.htm, 2016
Fig. 6. The source. “Structure of molecules with Cis carbon-carbon double bonds compared with the structure of
molecules with Trans carbon-carbon double bonds”. Food science Academy, 15.06.2013,
foodscienceacademy.org/2013/06/15/fats-explained/. 2016
hydrogenation. The unsaturated fatty acids can combine with oxygen or halogens to
form saturated fatty acids. The degree to which this happens, depends on how
unsaturated the fatty acid is. The more unsaturated a fatty acid is, the less stable it is.
This means that it is more prone to undergoing oxidation and thus going rancid. This
is why it is important to know how unsaturated they are, in order to determine their
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stability and therefore if they are prone to going rancid faster than other oils. This can
be useful information for use with deep fat fryers. Oils are subjected to high
temperatures and the oil is often reused several times. If the oil were more prone to
going rancid, then it would not be favored, as the flavor changes once the oil is rancid.
For this reason, it would be preferred to use oil, which is more stable and thus can be
used to fry with more times before going rancid. There are many methods for
determining the degree of unsaturation of a fatty acid, one of which is determining the
100 grams of the substance. (“Iodine Number”) This unsaturation is in the form of
double bonds, which react with iodine compounds. The higher the iodine value, the
more carbon-carbon double bonds are present in the fatty acid portion of the oil and
therefore the more unsaturated the oil is. The iodine value varies per oil, as can be
seen in table 1. Oil with a lower iodine value is less prone to rancidity. This is due to
oil with a lower iodine value being more stable, as it is more saturated, thus having
less carbon-carbon double bonds. For this reason, oil with a lower iodine value is
favored, as it will not go rancid as fast as oil with a higher iodine value.
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Source: Zambotto, Tagliaro. “Iodine values for different types of oils”. Google Patents, 26.03.2004,
www.google.com/patents/EP1622446A1?cl=en, 2016
For the experiment, which will be undertaken, 3 different oils will be used.
These are Olive oil, Sunflower oil and Linseed oil. These oils have been chosen due
to their range in stated literature values. The literature iodine values for these oils can
be found in table 2.
Table 2: Literature iodine values for the oils being used in the
experiment
Olive 79-90
Sunflower 125-140
Linseed 170-180
Source: “Literature iodine values for the oils being used in the experiment”. Chempro, www.chempro.in/fattyacid.htm, 2016.
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Each of these oils has a different composition to one another. This is due to
them having different fatty acid chains in their molecules. The predominant fatty
acids in olive oil are oleic, palmitic and linoleic. The predominant fatty acids in
sunflower oil are linoleic and oleic. The predominant fatty acids in linseed oil are
linolenic, linoleic and oleic. The composition of the oils also varies within the same
oil. This is because each oil contains a small percentage of other fatty acids. These in
turn make up a certain percentage of the oil. This percentage can vary, based on many
different factors, for example where the plant was grown, thus how much sunlight it
received etc. This means the amount of each fatty acids differ within 2 different
samples of the oil. This is why the literature iodine value is a range and not a
specified value.
The most common fatty acid found in olive oil is oleic acid (see diagram 7). It
is monounsaturated and makes up 55-83% of olive oil. The second most common
fatty acid is palmitic acid (see diagram 8), which is saturated and makes up 7-20% of
olive oil. The third most common is linoleic acid (see diagram 9), which is
polyunsaturated and makes up 3-21% of olive oil. As a large amount of olive oil
contains saturated and monounsaturated fatty acids, the iodine value is expected to not
Sunflower oil is mostly made out of the fatty acid linoleic acid (see diagram
9). It is a polyunsaturated fatty acid and makes up 44-75% of the oil. The second most
common fatty acid is oleic acid (see diagram 7), which is monounsaturated and makes
up 14-35% of the oil. As both of the fatty acids found within sunflower oil are
Linseed oil is composed of the fatty acids of linolenic acid 35-60% (see
diagram 10), linoleic acid 17-24% (see diagram 9) and oleic acid 12-34% (see
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diagram 7). As all of these fatty acids are unsaturated, 2 of which are polyunsaturated,
unsaturated-fats.html, 2016
Fig. 9. May, Paul. “Polyunsaturated Linoleic Acid”. Bristol University, 05. 2006,
www.chm.bris.ac.uk/motm/linoleic/linv.htm, 2016
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detail-linolenic%20acid.php, 2016
The method being used to determine the iodine value is the Wijs method. The
theory behind the method is that the carbon-carbon double bonds in the fatty acids
portion of the oil react with halogens, in this case iodine, resulting in the addition of
the halogen at the carbon-carbon double bond. In this reaction, a known amount of
iodine monochloride reacts with the unsaturated carbon-carbon double bonds found in
the fatty acid to produce a di-halogenated carbon-carbon single bond, of which one
H H
C=C + ICl C C
Cl I
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After this reaction has been completed, the amount of iodine that has reacted
solution. This isolates the remaining iodine that did not react with the fatty acid from
the iodine monochlordide solution, as the chlorine is more reactive than the iodine,
ICl + KI à KCl + I2
This reaction causes the remaining ICl, which has not yet reacted with the
carbon-carbon double bonds in the fatty acid, to form iodine. The resulting iodine is
then titrated with a standard solution of 0.1N Sodium Thiosulfate, to determine how
much of the iodine monchloride reacted with the unsaturated carbon-carbon double
Hypothesis
The prediction for this experiment is that the more times the oil gets heated,
the smaller the iodine value will become. This prediction is based on oxidation.
process of losing an electron. When the oil is heated, carbon-carbon double bonds in
the hydrocarbon chain start splitting. This leads to the formation of free radicals. A
free radical is a molecule, which contains at least one unpaired electron. Free radicals
are very unstable and react quickly with other compounds, as they now have unpaired
electrons. The free radicals formed by the oxidation of the fatty acids come in the
form of volatile aldehydes and ketones (see diagram 12). These free radicals are then
able to bond with the oxygen in the air, as they have free electrons available.
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Temperature is a catalyst for oxidation. The more the oil is heated, the more it
is subjected to oxidation. The more the oil is oxidized, the more free radicals become
available to bond with oxygen. If the free radicals have bonded with the oxygen in the
air, they are no longer able to bond with the iodine from the iodine monochloride,
which is added in the experiment. How much iodine monochloride the fatty acid
bonds with, determines the iodine value. As the free radicals, which contained the
unsaturated carbon-carbon double bonds, have already bonded with oxygen sourced
from the air, the fatty acid becomes saturated. This means that the molecule can no
longer bond with the iodine monochloride. This would therefore lead to a decrease in
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Apparatus
• Balance • Funnel
• 50cm3 Burette
Chemicals
• Iodine monochloride
• Trichloromethane
Safety
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trichloromethane
5. Warn people in the vicinity that you will be working with trichloromethane
Variables
Control:
• Time allowed for the oil, trichloromethane and iodine monochloride to react
(30min),
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Method
The method used for this experiment was the wijs method.
For this method 0.5g of olive oil was weighed into a conical flask and mixed with
10cm3 trichloromethane and 25cm3 iodine monochloride and left to sit in a dark
The contents of the conical flask are titrated against 0.1N sodium thiosulfate.
This process is repeated 2 further times with a different sample of olive oil.
The main source of olive oil (from the bottle) is then heated to 120°C and cooled
down.
0.5 g of this heated olive oil was mixed with trichloromethane, iodine monochloride
This heating process was repeated twice more (The oil is heated 2 more times, each
A blank titration is also done by adding 10cm3 trichloromethane and 25cm3 iodine
monochloride into a conical flask, adding potassium iodine and then titrating it
against 0.1N sodium thiosulfate. For a full detailed method, consult appendix 1.
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titration
120°C
*The data that has been highlighted red is data, which has not been used for calculations. The first data
point of 2.9cm3 is not being used, as the wrong concentration of sodium thiosulfate was present in the
burette, thus the result is not controlled. The second data point of 3.8cm3 is not being used as it used a
combination of old and new iodine monochloride, thus not being comparable to the other data points,
The blue signifies values, which are not concordant. Where it is possible, only concordant values have
been taken into account. Concordant values are successive values within 0.1cm3 of one another.
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Olive 0 86.0
Olive 1 87.4
Olive 2 84.6
Olive 3 83.6
Sunflower 0 97.2
Sunflower 1 96.3
Sunflower 2 95.7
Sunflower 3 95.4
Linseed 0 97.3
Linseed 1 109.9
Linseed 2 109.3
Linseed 3 109.8
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Sample Calculations
11 + 11.1 + 11.1
= 11.07
3
Average of Sodium Thiosulfate used for linseed oil after heating 1 time:
1.7 + 1.6
= 1.65
2
(44.95 − 6.65)×1.269
= 97.2
0.5
88
87.5
87
86.5
86
85.5
85
84.5
84
83.5
83
0 0.5 1 1.5 2 2.5 3 3.5
Times Oil was heated to 120° C
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97.4
97.2
97
96.8
96.6
96.4
96.2
96
95.8
95.6
95.4
95.2
0 0.5 1 1.5 2 2.5 3 3.5
Times Oil was heated to 120° C
112
110
108
106
104
102
100
98
96
0 0.5 1 1.5 2 2.5 3 3.5
Times Oil was heated to 120° C
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iodine value, however this is not true for the second data point as it presents an
increase in iodine value. This could come down to the inaccuracy of the data for this
specific point, as the three values gathered where 2.9cm3, 10cm3 and 11cm3 (heating
olive oil the first time). Due to this large spread it is difficult to calculate an accurate
result. Overall the trend presented in this graph does support the overall theory that
the more times an oil is heated, the lower the iodine value becomes when applied to
olive oil. This also means that the more olive oil is heated, the less unsaturated it
becomes, which would be expected due to the carbon-carbon double bonds present in
both the oleic fatty acid and linoleic fatty acid found in olive oil.
Graph 2 displays a decreasing trend. The relationship between the iodine value
and the number of times the oil was heated, is inversely proportional. One would
expect this to happen, because as the carbon-carbon double bonds become saturated,
there are fewer carbon-carbon double bonds left which are still unsaturated and can
therefore be subjected to oxidation. Each time the oil is heated, fewer carbon-carbon
Graph 3 does not display a clear trend like the other 2 graphs. All the data
points of the linseed oil once it has been heated are all relatively close together, thus
displaying a plateau. This could be due to a number of reasons. Linseed oil has the
highest literature iodine value out of all of the oils that were used. This means that it
is the most susceptible to oxidation. The linseed oil could have therefore had a chance
to oxidise before it was used for the experiment. Another issue could be found with
the chemicals. The bottle of iodine monochloride finished, thus a new one had to be
ordered. The results that were gathered using the new iodine monochloride were for
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heating the linseed oil. There is a clear difference between the non-heated oil and the
heated oil, which is not displayed in the other oils. As the iodine value changed from
97.3 to 109.9 after heating the oil once, it is clear that the control variables are no
longer controlled, otherwise the jump would not have been as significant. The last
issue could be waiting for the iodine monochloride to be acquired. Whilst waiting for
the iodine monochloride the bottle of linseed oil was open. This could also lead to
unfair and imprecise results, as the other bottles of oil were opened and the
experiment was completed the same day, whereas the linseed oil was opened and then
used some weeks later. This could have given it the opportunity to oxidise more than
the others, and hence the values are not what are expected.
When looking at the iodine values of the oils before heating and comparing
them with literature values, one can see that only the result for olive oil is precise, as
the results for sunflower oil and linseed oil are not that close to their literature values.
The literature value for olive oil is between 79-90 (“Fatty Acid Composition Of Some
Major Oils”) and the value, which was recorded from the experiment, was 86.0,
which is within the literature range. The literature value for sunflower oil is 125-140
(“Fatty Acid Composition Of Some Major Oils”), however with a value of 97.5, the
experimental value is not precise. This is also the case for linseed oil. The
experimental value, which was obtained for linseed oil, was 97.3, which is not within
the literature range of 170-180. As both the sunflower oil and the linseed oil started
with an imprecise value, it is harder to trust the data, which they provide.
that the more the oil is heated, the lower the iodine value becomes, and therefore the
less unsaturated the oil will be. However the trend is not strong enough to be able to
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When doing further research into the reheating of oils, the recommendation
would be to make sure that the oil is kept sealed in a cool dark place, to limit the
oxidation process. One could also make sure when acquiring the oil that the
manufacture dates are checked in order to have the freshest oil possible and therefore
The experimental method should be altered. Instead of heating the oil until it
gets to a certain temperature, one should wait until the oil reaches a specific
temperature and then keep it at that temperature for a specified length of time. This
would then be able to model a deep fat fryer better than the method used for this
investigation. When heating the oil, one should also make sure that the same amount
of heat is transferred each time, so that the oils can reach a specified temperature
within a specific amount of time. As it was difficult to determine a clear trend from
the limited points on the graph, another recommendation for the method would be to
heat the oil up at least 2 more times, to allow for a clearer trend to form.
Another source of error could also come from the waiting time of the reaction
between the oil, trichloromethane and iodine monochloride. When multiple samples
were prepared at the same time, some had a longer reaction time whilst titrations were
being done. If time allows, prepare each solution separately and allow for 15 minutes
between preparations, which will allow enough time for titration. If the improvements
were made to the method, then the results would become more reliable and precise,
Even though the results of the experiment are limiting, one can still conclude
that the iodine value decreases when the oils are heated. It is possible to conclude this,
as this trend was displayed by 2 of the 3 oils. One can also conclude that from the
results received, sunflower oil was the most stable under heating, as the iodine value
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only dropped by 1.9%, as opposed to the 2.8% drop of the olive oil. From this
investigation, it would then make it the best oil to use in a deep fat fryer.
The recommendation for further investigation would be to use the same oils,
however heat them at a higher temperature, in order for more oxidation to occur, and
thus also allow for a more realistic simulation of a deep fat fryer. It would also be best
to keep the oil at the specified temperature for a longer duration of time. This way it
also mimics the cooking process of a deep fat fryer. With further regards to cooking,
it would also be interesting to investigate what happens to the oil if it is an open bottle
left on the side for a couple of months. This way one can also see what is happening
to the oils that we use when cooking day to day, whilst they stand open in a kitchen.
reheating of the oils and the iodine value was not as strong as expected. It was
concluded that from the tests done, sunflower oil is the best oil to use in a deep fat
fryer in relation to olive oil and linseed oil. Some errors have been addressed in order
investigate the question of reheating oils and how it affects their iodine values.
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Bibliography
Alirezera, S., C.P. Tan, Max Hamed, and Y.B. Che Man. "Effect of
<http://www.ifrj.upm.edu.my/17%20(02)%202010/IFRJ-2010-295-
302_Tan_Malaysia_OK%5B1%5D.pdf>.
Summer 2016.
<http://www.oilsfats.org.nz/documents/Oxidation%20101.pdf>.
<http://vlab.amrita.edu/?sub=3&brch=63&sim=1111&cnt=1>.
<http://www.chempro.in/fattyacid.htm>.
<http://link.springer.com/article/10.1007%2Fs00897000438a#page-1>.
<chemistry.about.com/od/chemistryglossary/a/saturateddef.htm>.
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webster.com/dictionary/iodine%20number>.
content/uploads/2009/12/H-32.pdf>.
2016.
<https://www.utdallas.edu/~scortes/ochem/OChem1_Lecture/Class_Materials/
17_redox_states_carbon.pdf+>.
<https://www.classle.net/#!/classle/book/estimation-iodine-value-oil/>.
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1. Place a 150cm3 conical flask on the balance and tare the balance
4. Using a 10cm3 glass pipette, pipette 10cm3 of trichloromethane and add to the
conical flask with oil. Do this for each of the 3 conical flasks. After the
trichloromethane has been added to the conical flask, place on the stopper
5. Using a 25cm3 glass pipette, pipette 25cm3 of iodine monochloride and add to
the conical flask with oil. Do this for each of the 3 conical flasks. Place the
stoppers back on
6. Swirl each conical flask for a minute and place in dark cupboard. Set a timer
for 30 minutes
8. Rinse the burette through with 0.1N Sodium thiosulfate, making sure there is a
9. Using the funnel if needed, fill the burette with 0.1N Sodium thiosulfate until
full
10. By slowly opening the tap, make sure the top of the meniscus is on the 50cm3
11. In the 10cm3 measuring cylinder, pipette out 10cm3 of 30% potassium iodide
solution
12. Once the 30 minutes is over, remove a conical flask containing the oil,
13. Add the 10cm3 of potassium iodide solution and immediately place the stopper
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15. Place the conical flask under the tap of the burette
16. Slowly open the tap and add the sodium thiosulfate. The colour will change
17. Once the colour of the solution in the conical flask is a vibrant orange, close
18. Add 5-7 drops of 1% starch indicator into the conical flask and swirl. The
19. Drop by drop, add more sodium thiosulfate until the solution in the conical
flask goes a milky white. When the solution is a milky white turn the tap off
20. The titration is finished. Record the volume of sodium thiosulfate used in a
results table.
21. Repeat the titration (steps 11-20) for the other 2 conical flasks
22. Using the hot plate and pan, heat up 50g of olive oil
23. Place the thermometer into the pan, making sure that it doesn’t touch the pan
24. Once the oil gets to 120°C, take the pan off the heat and allowed the pan and
oil to cool back to room temperature (22°C). This can be sped up by placing
25. Using the oil from the pan repeat the experiment (steps 1-21)
26. Repeat the whole experiment, making sure that you have heated up the oil a
27. The whole experiment (steps 1-26) should be repeated using 2 other oils
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28. Blank tests also need to be done. Using a 10cm3 glass pipette, pipette 10cm3 of
trichloromethane and add to a conical flask. Repeat with another conical flask.
29. Using a 25cm3 glass pipette, pipette 25cm3 of iodine monochloride and add to
the conical flask with trichloromethane. Do this for both of the conical flasks.
30. Swirl each conical flask for a minute and place in dark cupboard. Set a timer
for 30 minutes
31. In the 10cm3 measuring cylinder, pipette out 10cm3 of 30% potassium iodide
solution
32. Once the 30 minutes is over, remove a conical flask containing the
33. Add the 10cm3 of potassium iodide solution and immediately place the stopper
35. Place the conical flask under the tap of the burette
36. Slowly open the tap and add the sodium thiosulfate. The colour will change
37. Once the colour of the solution in the conical flask is a vibrant orange, close
38. Add 5-7 drops of 1% starch indicator into the conical flask and swirl. The
39. Drop by drop, add more sodium thiosulfate until the solution in the conical
flask goes a milky white. When the solution is a milky white turn the tap off
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40. The titration is finished. Record the volume of sodium thiosulfate used in a
results table.
41. Repeat the titration (steps 31-40) for the other conical flask
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