Extended Essay Chemistry (HL) - A Comparison of Oil Content on Candlenut Seed, Coriander Seed, Peanut, Sesame Seed and Soybean with Free Fatty Acid Content and Iodine Value Tested as Potential Biodiesel Feedstock

Extended Essay
Chemistry
Higher Level
A Comparison of Oil Content on Candlenut Seed, Coriander

Seed, Peanut, Sesame Seed and Soybean with Free Fatty Acid
Content and Iodine Value Tested as Potential Biodiesel Feedstock
In candlenut seed, coriander seed, peanut, sesame seed and soybean, how does the amount
of oil extracted vary with the number of extractions using n-hexane and how does the total
amount of oil extracted, free fatty acid content and iodine value of the extracted oil compare
among the samples?
Candidate Name: Sadha Satya Lotan
Candidate Number: 002115 0019
School Name: Cita Hati Christian High School
Supervisor Name: David Lesmana
Session: May 2016
Abstract Word Count: 299
Essay Word Count: 3,999

Sadha Satya Lotan/002115-0019
Extended Essay Chemistry Higher Level
Abstract
Biodiesel can solve energy issues, but not all samples can become its feedstock,
inspiring the research question, In candlenut seed, coriander seed, peanut, sesame seed and
soybean, how does the amount of oil extracted vary with the number of extractions using n-
hexane and how does the total amount of oil extracted, free fatty acid content and iodine
value of the extracted oil compare among the samples?
Oil is extracted from the grounded dried samples using n-hexane as solvent and then
heated to separate the oil from n-hexane. It was repeated five times with the mass recorded
after each extraction. FFA content was measured by performing titration on the oil using
NaOH. Iodine value was measured through reverse-back titration using Na2SO3 on the oil
reacted with excess iodine in a dark place. This was repeated again but without the oil
sample.
After more extraction, more oil was extracted. The amount of oil extracted decreased
as more extraction was done because less oil was present in the sample. Not all of the oil
could be extracted from the sample even after five times because of the oil equilibrium
between the solvent and the sample. The oil content of the sample from lowest to highest is
coriander (8.13%), soybean (18.43%), peanut (39.15%), sesame (48.59%) and candlenut
(59.71%). The FFA content of the sample from lowest to highest is sesame (0.9%), soybean
(1.1%), peanut (1.4%), candlenut (4.1%) and coriander (4.7%). The iodine value of the
sample from lowest to highest is coriander (82 g/g), peanut (93 g/g), sesame (100 g/g),
soybean (100 g/g) and candlenut (110 g/g). Overall, candlenut seed has greatest potential as
biodiesel feedstock because it has highest oil content, but it will need esterification as a pre-
treatment to reduce FFA content and directly used because of its high iodine value.
Word Count: 299
1
Table of Contents
Section Title Page
Abstract 1
1 Introduction 3
2 Research Question 4
3 Background Information 4
3.1 Oil 4
3.2 Free Fatty Acid (FFA) 5
3.3 Iodine Value (IV) 8
4 Methodology 12
4.1 Sample Preparation 12
4.2 Oil Extraction 12
4.3 Preparing Solutions 12
4.4 FFA Test 13
4.5 IV Test 13
5 Result and Analysis 14

5.1 Oil Extraction 14
5.2 FFA Content 16
5.3 Iodine Value (IV) 18
6 Conclusion 20
7 Evaluation and Improvement 21
8 Further Research 22
9 Bibliography 23
10 Appendix 26
10.1 Appendix 1 Raw Data and Data Processing 26
10.2 Appendix 2 Molar Mass of the Fatty Acid of Oil 35
10.3 Appendix 3 Variables, Materials and Apparatus 37
10.4 Appendix 4 Documentation of the Investigation 42
2
1. Introduction
Many aspects of our daily lives highly require energy, such as transportation and
industry. Some energy sources are not renewable, (e.g. fossil fuel), and their supply will run
out. This energy issue is problematic because it is a fundamental necessity in our lives,
especially when living in Indonesia, a developing country with many residents. Energy is
always needed everywhere. Therefore, we need a renewable energy supply which usually
comes from living organisms, such as oil from plants. The samples used for this investigation
will be candlenut seed, coriander seed, peanut, sesame seed and soybean. In Indonesia, they
are all easy to find and usually used as food resources.
In industrial processes, oil can be used to make biodiesel, an alternative energy that
has great fuel efficiency and durability1. Having high oil content is necessary for a plant to be
utilized for efficient biodiesel production. The first focus of this investigation is to compare
the oil content of the aforementioned seeds. Solvent extraction method can be used to extract
oil from the samples but it can leave a considerable amount of oil residue on the sample if
extracted only once. The second focus will be to investigate the relationship between the
number of extractions and the amount of oil extracted.
FFA (Free Fatty Acid) is one of the important characteristics of oil to be considered in
making biodiesel. The third focus is to compare the FFA content of the extracted oil. Iodine
value (IV) is another significant characteristic of biodiesel stability which is notable for
storage and influenced by the IV of oil. The last focus will be to compare the IV of the
extracted oil.
1
CarsDirect,. (2012, March 19). Diesel Truck Prices vs Gasoline Trucks. Retrieved 27 September 2015, from
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3
2. Research Question
In candlenut seed, coriander seed, peanut, sesame seed and soybean, how does the amount
of oil extracted vary with the number of extractions using n-hexane and how does the total
amount of oil extracted, free fatty acid content and iodine value of the extracted oil compare
among the samples?
3. Background Information
3.1. Oil
Most of the carbons in fatty acids are reduced and covalently linked to light hydrogen,
allowing the oil to have high energy content2. In our body, oil is used as energy storage,
thermal insulator to prevent heat loss and preserve body temperature, as a solvent for several
vitamins and many other functions.
There are several methods to extract oil from the samples, such as mechanical
pressing and solvent extraction. Mechanical pressing will leave a residual oil of around 6-
14% while solvent extraction will only leave around 0.5-0.7%3. Being more effective, the
solvent extraction method will be used in this investigation.
Being a non-polar molecule, oil can be extracted using other non-polar molecules
such as n-hexane. N-hexane can easily extract oil from the samples and leave out the protein
and sugar4. After extracting oil, separation of extracted oil from the n-hexane needs to be
2
Brandt, M. (2000). Introduction to Lipid Metabolism (1st ed., p. 1). Terre Haute: Rose-Hulman Institute of
Technology. Retrieved from https://www.rose-hulman.edu/~brandt/Chem330/Lipid_metab.pdf
3
Srsbiodiesel.com,. Solvent Extraction. Retrieved 8 April 2015, from
http://www.srsbiodiesel.com/technologies/solvent-extraction
4
Anderson, G. (2011, December 8). Solvent Extraction - AOCS Lipid Library. Lipidlibrary.aocs.org. Retrieved
27 September 2015, from http://lipidlibrary.aocs.org/OilsFats/content.cfm?ItemNumber=40337
4
done by heating them, because n-hexane has a high volatility and a low boiling point (69oC)5,
while oil has relatively high boiling point because of its longer hydrocarbon chain.
The extraction is done five times for each sample. The mass is recorded after each
extraction. Oil content is found through the mass ratio of the total extracted oil to the sample.
3.2. Free Fatty Acid (FFA)
Oil can be used to make biodiesel, an alkyl ester produced from transesterification of
triglyceride of oil with alcohol, usually in the presence of base catalyst which is more
preferred than acid catalyst due to higher yield in shorter time 6. Transesterification will
produce glycerol as side product7. The general equation, mechanism of alkaline and acid
catalyzed transesterification is shown respectively in Fig. 3.2.1, Fig. 3.2.2 and Fig. 3.2.3 8.
Fig. 3.2.1. General equation of transesterification between triglyceride in vegetable oil

and alcohol to produce alkyl ester (biodiesel) and glycerol as side product
5
Rsc.org,. The Merck Index Online. Retrieved 10 August 2015, from https://www.rsc.org/Merck-Index/
6
Predojevi, Z. (2008). The production of biodiesel from waste frying oils: A comparison of different
purification steps. Fuel, 87(17-18), 3522-3528. http://dx.doi.org/10.1016/j.fuel.2008.07.003
7
Lucena, I., Silva, G., & Fernandes, F. (2008). Biodiesel Production by Esterification of Oleic Acid with
Methanol Using a Water Adsorption Apparatus. Industrial & Engineering Chemistry Research, 47(18), 6885-
6889. http://dx.doi.org/10.1021/ie800547h
8
Schuchardt, U., Sercheli, R., & Vargas, R. (1998). Transesterification of vegetable oils: a review. Journal of
the Brazilian Chemical Society, 9(3). http://dx.doi.org/10.1590/s0103-50531998000300002
5
1. Alcohol reacts with base producing
alkoxide and protonated catalyst.
2. Alkoxide does nucleophilic attack to
carbonyl group of triglyceride, forming
a tetrahedral intermediate.
3. The tetrahedral intermediate dissociates
into its conjugate anion and alkyl ester.
4. The conjugate anion deprotonates the
catalyst and regenerate the active
Fig. 3.2.2. Mechanism of alkaline catalyzed transesterification species.
Carbonyl group in ester is protonated
forming carbocation II.
Alcohol does nucleophilic attack
on carbocation II, forming
tetrahedral intermediate III,
which later forms new ester IV
by removing glycerol, and H+
catalyst is regenerated.
Fig. 3.2.3. Mechanism of acid catalyzed esterification
Triglyceride could experience hydrolysis forming FFA (free fatty acid), fatty acid that
is no longer attached to glycerol. With fewer bonds present, FFA is reactive and could react
with the alkaline catalyst during transesterification causing saponification reaction, producing
carboxylate anion (soap) that hinders the separation of biodiesel and glycerol and decrease
6
the yield of biodiesel. The overall reaction and its mechanism are respectively shown in Fig.
3.2.4 and Fig. 3.2.59.
Fig. 3.2.4. Overall reaction of saponification
1. OH- ion does nucleophilic attack
on ester forming ether.
2. Ether is removed to form
carboxylic acid.
3. Ether deprotonates the carboxylic
acid, forming carboxylate anion
and alcohol.
Fig. 3.2.5. Mechanism of saponification reaction
FFA content could be reduced through esterification reaction (Fig. 3.2.3) as pre-
treatment in the presence of acid catalyst to produce biodiesel, but its yield depends on the
amount of FFA in oil which is few and ineffective to produce biodiesel. In transesterification
using alkaline catalyst, it is recommended by Freedman et al. for the oil to have less than 1%
of FFA content10.
9
Farmer, S. (2013). Saponification - Chemwiki. Chemwiki.ucdavis.edu. Retrieved 9 December 2015, from
http://chemwiki.ucdavis.edu/Organic_Chemistry/Esters/Reactivity_of_Esters/Saponification
10
Freedman, B., Pryde, E., & Mounts, T. (1984). Variables affecting the yields of fatty esters from
transesterified vegetable oils. Journal of the American Oil Chemist Society, 61(10), 1638-1643.
http://dx.doi.org/10.1007/bf02541649
7
In this investigation, the FFA content is measured by titrating FFA in oil with NaOH
(sodium hydroxide) of known normality to have saponification reaction (Fig 3.2.2) using
phenolphthalein as pH indicator that turns pink from colorless around the titration equivalent
point.
Knowing that:
FFA content is mass ratio of FFA to oil.
Mass of FFA is obtained by multiplying mol FFA and molar mass of fatty acid.
Mol FFA is obtained by multiplying V.NaOH and its normality.
The formula to find FFA content can be written as:
. () . ()
(%) = 100%
. ()
Equation 3.2.1. Formula to find FFA Content
Molar mass of the fatty acid of each oil sample will be obtained through a calculation
from the fatty acid composition of the oil from literature which will be shown in Appendix
2.
3.3. Iodine Value (IV)
Some fatty acid may have bond in double or triple bond. It becomes unsaturated and
the oil becomes less stable. To prevent unwanted issues, the biodiesel should have low
unsaturation degree, and so the oil used to produce biodiesel should also have low
unsaturation degree. Unsaturation degree is usually measured in the quantity iodine value
(IV), the mass of iodine needed to react with the double bond present in 100 g of sample.
Iodine is the least reactive halogens. When iodine collides with organic compound,
two possible reactions may happen; an addition reaction when iodine reacts with the double
8
bond of unsaturated compound, or a substitution reaction when iodine reacts with the single
bond of unsaturated or saturated compound. However, substitution reaction can only occur in
the presence of ultraviolet catalyst, therefore putting the oil and iodine mixture in a dark place
will allow the addition reaction to occur while preventing the substitution reaction. The
addition of unsaturated compound by halogen can be seen in Fig 3.2.6 and its mechanism in
Fig 3.2.711 using bromine as example of halogen.
1. The bond in bromine is polarized triggering
heterolytic cleavage. Bromine cation forms
intermediate cycle with the double bond of the
unsaturated molecule.
2. Bromide anion attacks any carbon of the
bridged bromonium ion from the back side of
the cycle, causing it to open and attach two
Fig. 3.3.2. Mechanism of addition reaction by bromine halogens in the position anti.
The substitution reaction can be seen in Fig 3.2.8 and its mechanism in Fig 3.2.9 12
using bromine and methane as reactants.
Fig. 3.3.3. Substitution of halogen on saturated compound
11
Chemwiki.ucdavis.edu,. (2013). Electrophilic Addition of Halogens to Alkenes - Chemwiki. Retrieved 10
December 2015, from
http://chemwiki.ucdavis.edu/Organic_Chemistry/Hydrocarbons/Alkenes/Reactivity_of_Alkenes/Electrophilic_
Addition_of_Halogens_to_Alkenes
12
Mhhe.com,. Radical Substitution Reactions. Retrieved 10 December 2015, from
http://www.mhhe.com/physsci/chemistry/carey/student/olc/ch04radical.html
9
1. Initiation, bromine undergoes hemolytic cleavage
caused by heat or ultraviolet, forming two bromine
radicals.
2. Propagation, bromine radical attracts hydrogen of
methane forming hydrogen bromide and radical
methyl. Radical methyl attracts bromine from another
molecule forming methyl bromide and another bromine
radical, creating a repeatable cycle.
3. Termination, reaction among radical molecules to end
the cycle.
Fig. 3.3.4. Mechanism of substitution

reaction by bromine and methane
In this investigation, IV is measured through reverse-back titration. Double bond in
oil is reacted with excess iodine of constant amount (Fig 3.3.1) in dark place to prevent
substitution reaction (Fig 3.3.3). The remaining iodine is titrated with Na 2S2O3 (sodium
thiosulfate) of known normality. This is repeated but without the presence of oil (blank
sample). The overall reaction is shown in Fig 3.3.5 13 and all the steps involved in the reaction
are shown in Fig 3.3.6.
Fig. 3.3.5. Overall reaction of iodine and sodium thiosulfate
13
Meritnation.com,. (2010). How is O3 estimated quantitatively. Retrieved 10 December 2015, from
http://www.meritnation.com/ask-answer/question/how-is-o3-estimated-quantitatively/the-p-block-
elements/6303229
10
Na2S2O3 dissociates into ion S2O3- and Na+.
S2O3- is oxidized by iodine forming tetrathionate anion
and iodide ion.
Na+ is reduced by iodide ion forming sodium iodide and
by tetrathionate anion forming sodium tetrathionate.
Fig. 3.3.6. Steps of reaction between iodine and

sodium thiosulfate
When iodine is given starch, iodine-starch complex with blue-black color is formed.
Therefore, when blue-black color turns colorless in the presence of starch, it will indicate the
absence of iodine as it has completely reacted with Na 2S2O3.
Knowing that:
The difference in V.Na2S2O3 of sample and blank is V.Na2S2O3 that reacts with
iodine.
Mol Na2S2O3 is obtained by multiplying V.Na2S2O3 and its normality.
One molecule of iodine reacts with two molecules of Na 2S2O3.
Mass of iodine is obtained by multiplying mol iodine and its molar mass.
IV is mass of iodine needed to react with double bonds in 100 g of oil.
The formula to find IV can be written as:
1
(. 2 2 3 () . 2 2 3 ()) . 2 2 3 () 2 253.8 100
=
. ()
Equation 3.3.1. Formula to find Iodine Value
Literature data that was used as reference to find molar mass of fatty acid will not be
used for the IV because the literature data will not exactly be the same with the composition
of the samples.
11
4. Methodology
Variables, Materials and Apparatus list are in the Appendix 3.
4.1. Sample Preparation
Candlenut seed was cut into small pieces using scissors. The skin of peanuts was
peeled manually. Candlenut seed, coriander seed, peanut and sesame seed were separately
blended continued by grinding using mortar and pestle until become powder and then
heated using oven at temperature 90oC for two hours.
Soybean was soaked in distilled water for two hours. The skin was peeled manually. It
was blended and heated using oven at temperature 90 oC for 16 hours. They were grinded into
small pieces using mortar and pestle continued by blending until become powder.
4.2. Oil Extraction
50.00 g of prepared samples were put in a beaker 500 ml. 100 ml of n-hexane was
poured into it, and then stirred. The beaker was covered using aluminum foil and left for 24
hours. The solution of oil and n-hexane was filtered using filter funnel and filter paper into a
weighed conical flask 250 ml and then heated at temperature 65-75oC until no more bubble of
gas was observed. The mass of conical flask and its content was recorded. These were
repeated until 5 times using the same conical flask and the same type of sample from the
same beaker. It was done three times for each sample.
4.3. Preparing Solutions
The required solid was weighed according to Table 4.3.1 in a tared beaker 100 ml.
The beaker was filled with distilled water and stirred until all solid dissolved. The solution
was poured into a volumetric flask 250 ml. The beaker 100 ml was filled again with distilled
12
water and poured again into the volumetric flask. It was repeated until the line 250 ml is
reached. The solution was then shaken.
Table 4.3.1 Mass of the required solids

No. Solid Desired Normality (N) Mass (g) 0.01
1. NaOH 0.0200 (0.0010) 0.20
2. Na2S2O3 0.1000 (0.0003) 3.95
The calculation to determine the required mass is shown in Appendix 1.
Starch solution 1% was prepared by weighing 3.00 g of starch in a tared 500 ml
beaker, and then distilled water was added until the reading of balance is 300.00 g.
4.4. FFA Test
Burette 50 ml was filled with the prepared NaOH 0.0200 N. 0.50 g of oil sample was
taken into a conical flask 250 ml. 10 ml of ethanol was taken using a 10 ml volumetric pipette
and added into the conical flask. Three drops of phenolphthalein were pipetted into the
conical flask. Drops of NaOH solution from the burette 50 ml were added to the conical flask
and shaken after each drop until pink color appeared and remained for 30 seconds. The
volume of NaOH solution was recorded. It was repeated until three trials for each oil sample.
4.5. IV Test
0.20 g of oil sample was taken into a conical flask 250 ml. 10.0 ml of chloroform was
taken using a 10.0 ml volumetric pipette and added into the conical flask. The flask was
shaken until the oil dissolve completely in chloroform. 3.0 ml of iodine 10% was measured
using a 5.0 measuring cylinder and added into the flask. The opening of the flask was covered
using aluminum foil. It was shaken vigorously and put in a dark place, left for one hour. After
one hour of waiting, the flask was rinsed using 100 ml of distilled water. A burette 50 ml was
filled with the prepared Na2S2O3 0.1000 N. Magnetic bars was added into the flask. The flask
was put on a hotplate stirrer and stirred. While stirring, drops of Na 2S2O3 were added to the
13
flask until the color turned pale yellow. 5.0 ml of starch 1% was added to the flask using a 5.0
measuring cylinder. The titration was continued until the color turned colorless. The volume
of Na2S2O3 was recorded. It was repeated until three times for each sample replicate and
repeated without having the oil sample for three times.
5. Result and Analysis
Raw Data and Data Processing are in Appendix 1
5.1. Oil Extraction
70
60
50
Oil Yield (%)
Candlenut
40
Seed
Coriander
30 Seed
Peanut
20
Sesame
10 Seed
Soybean
0
0 1 2 3 4 5 6
Number of Extractions
Graph 5.1.1. Oil Yield Measured by Mass in Different Number of Extractions in Several Samples
14
A chart to compare the oil yield in several samples is made based the amount of oil
obtained after five times of extractions.
70
59.71
60
48.59
50
Total Oil Yield (%)
39.15
40
30
18.43
20
8.13
10
0
Candlenut Coriander Peanut Sesame Soybean
Seed Seed Seed
Samples
Chart 5.1.1. Comparison of Total Oil Yield by Mass
From Graph 5.1.1, it could be deduced that not all oil could be extracted from the
sample after several extractions, because the equilibrium between the extracted oil in n-
hexane and in sample, leaving few oil residual in sample. Replacing n-hexane and its oil from
the beaker with new n-hexane would allow extraction of oil residual to proceed by shifting
the equilibrium to extracting more oil from sample.
There was a decline in the increase of extracted oil as more extraction was done,
because in the sample there was now less oil to be extracted where equilibrium was still
present. In candlenut seed, it was observed that the amount of oil extracted in the first time
only slightly differed to the second time. This was because the used 100 ml of n-hexane had
been saturated and could not extract any more oil. In other samples, this was also the cause of
many residual oil in sample after one extraction.
From Chart 5.1.1, the sample with oil yield from greatest to lowest one in order are
respectively candlenut seed (59.71%), sesame seed (48.59%), peanut (39.15%), soybean
(18.43%) and coriander seed (8.13%). The small error bar indicated the data was precise.
15
Candlenut seed has the highest oil content, so it has the greatest potential and is most
suitable for biodiesel feedstock. On the contrary, coriander seed has lowest oil content
making it the least suitable as biodiesel feedstock. The difference in oil content could be
caused by the difference in the necessity of each sample in their environment as the result of
adaptation.
When blending sample, some of the oil might get extracted out of the sample because
some external force causing oil to get extracted just like in mechanical pressing. This was
found out from the blender knife that became oily where this happened mostly in candlenut
seed. This caused the amount of oil extracted when doing solvent extraction to be less than
the actual value. Blending aimed to optimize the oil extraction by increasing the surface area
to provide more contact between oil and solvent. Blending would also open more oil gland to
boost the rate of extraction.
5.2. FFA Content
6
4.7
5
FFA Content (%)
4.1
4
3
2 1.4
0.9 1.1
1
0
Candlenut Coriander Peanut Sesame Seed Soybean
Seed Seed
Samples
Chart 5.2.1. Comparison of Free Fatty Acid Content of the Extracted Oil
Fatty acid is a weak acid. It does not dissociate completely into H+ ion when it
dissolves. FFA content was tested by reacting it with strong alkaline. After it had completely
reacted, the pH would slightly be greater than 7 because of the salt hydrolysis where the
16
anion from FFA would react back into FFA and this did not occur for cation of strong
alkaline NaOH, so OH- ion was more than H+ ion. Phenolphthalein was chosen because it
could turn into pink from colorless in a slightly basic condition (pH around 8.3) which fit the
nature of the produced solution. Pink color needed to be observed for minimum 30 seconds to
ensure all FFA had dissociated into H+ ion and reacted with OH- ion from NaOH.
Based on the investigation, the FFA content of oil extracted from candlenut seed,
coriander seed, peanut, sesame seed, and soybean are respectively 4.1%, 4.7%, 1.4%, 0.9%
and 1.1%. Only sesame seed oil has FFA content lower than 1%, indicating no pre-treatment
is needed according to Freedman et al. The other four samples have FFA content greater than
1%. Therefore, these oils will need pre-treatment esterification to reduce FFA content before
transesterification with alkaline catalyst since high FFA content will donate more H + ion to
react with alkaline in faster rate to produce soap which hinders separation of polar glycerin
and non-polar biodiesel, decreasing the biodiesel yield.
The FFA content of each sample was affected by the hydrolysis occurring on the oil.
Several factors may affect this, such as the presence of lipase enzyme, triggering the
triglyceride hydrolysis by lowering the activation energy. Lipase could come from the sample
or the plant, or produced by bacteria around them. The heating during separating the oil from
the solvent could also affect the hydrolysis.
To ensure that each replicate of a sample had similar FFA content to another,
Analysis of Variance F-Ratio Test14 (ANOVA F-Test) was conducted (Appendix 1). Each
sample had F-Ratio lower than the critical value 5.14 with confidence level 95% except for
sesame seed with F-ratio 17.33 (Table 10.1.5). Replicate of sesame seed had significant
difference among them and could be caused by the difference heating time during separation
14
Longstreet, D. (2012). How To Calculate and Understand Analysis of Variance (ANOVA) F Test.. Retrieved
from https://www.youtube.com/watch?v=-yQb_ZJnFXw
17
of oil and solvent or because of its low FFA content and slight deviation would have greater
impact.
5.3. Iodine Value (IV)
120 110
100 100
100 93
Iodine Value (g/g)
82
80
60
40
20
0
Candlenut Coriander Peanut Sesame Seed Soybean
Seed Seed
Samples
Chart 5.3.1. Comparison of Iodine Value of the Extracted Oil
Based on the results of this investigation, the IV in g/g of candlenut seed, coriander
seed, peanut, sesame seed, and soybean are respectively 110, 82, 93, 100 and 100. Candlenut
seed has the highest IV while coriander seed has the lowest IV. The difference in IV was
caused by the chemical structure or composition of the oil, which could be the result of the
plants adaptation to fulfill certain conditions such as environmental change. A study
suggested that high degree of unsaturated fatty acid (higher iodine value) is commonly found
in the mitochondria of chilling-resistant plants than in chill-sensitive plants15.
If biodiesel is made from oil of high IV, the biodiesel will also have IV value as the
chemical structure does not change much, just change from carboxylic acid functional group
into alkyl ester. Having high IV means a lot of bonds in double or triple bond causing fewer
15
Peoples, T., Koch, D., & Smith, S. (1978). Relationship between Chloroplast Membrane Fatty Acid
Composition and Photosynthetic Response to a Chilling Temperature in Four Alfalfa Cultivars. Plant
Physiology, 61(3), 472-473. http://dx.doi.org/10.1104/pp.61.3.472
18
CH bonds. Although the CC bond is becoming C=C or CC bond which is stronger, but
two bonds of CH are absent because the two carbon atoms are bonded to each other and not
to hydrogen, causing overall bonds in oil molecule become weaker. This can be justified
through the following example:
Table 5.3.1 Average bond enthalpies at 298 K16:

Bond Enthalpy (kJ/mol)
CC 346
CH 414
C=C 614
In saturated compound such as ethane:
= 2 12 + 6 1 = 30 g/mol
= 1 (C C) + 6 (C H) = 1 346 + 6 414 =
2,830 kJ/mol
2,830
= = 94.3 kJ/g
30
Fig 5.3.1 Chemical structure
of ethane
In unsaturated compound such as ethene:
= 2 12 + 4 1 = 28 g/mol.
= 1 (C = C) + 4 (C H) = 1 614 + 4 414 =
2,270 kJ/mol.
2,270
= = 81.1 kJ/g.
28
Fig 5.3.2 Chemical structure

of ethene
The overall bonds in unsaturated compound is weaker than in saturated compound
due to the presence of double bond, lessening the activation energy and causing the oil to
16
Aylward, G., & Findlay, T. (2008). SI Chemical Data (5th ed.). Queensland: John Wiley and Sons.
19
become unstable and could react easily. So it is not suitable for long term storage as it may
cause issue or form deposit in the engine.
Again, to ensure similar IV of the replicate, ANOVA F-Test was conducted. All
samples had F-Ratio lower than the critical value 5.14 with confidence level 95% except for
soybean with F-Ratio 7.68 (Table 10.1.9). So soybean replicate was statistically different
from another and could be caused by the difference in exposure of the replicate to the
ultraviolet light which may trigger the substitution reaction by forming the radical molecules.
6. Conclusion
The research question In candlenut seed, coriander seed, peanut, sesame seed and
soybean, how does the amount of oil extracted vary with the number of extractions using n-
hexane and how does the total amount of oil extracted, free fatty acid content and iodine
value of the extracted oil compare among the samples? can now be answered.
Using n-hexane as the solvent, most of the oil could be obtained from the first
extraction. The amount of oil extracted gradually decreased as less oil was present in the
sample, and not all of the oil could be extracted completely even after five extractions
possibly caused by the equilibrium between sample and solvent.
Different samples exhibit different oil content, FFA content and IV. The oil content of
the samples in the order from lowest to highest is coriander seed (8.13%), soybean (18.43%),
peanut (39.15%), sesame seed (48.59%), and candlenut seed (59.71%) with a quite
significant difference among them. The FFA content of the samples from highest to lowest is
sesame seed (0.9%), soybean (1.1%), peanut (1.4%), candlenut seed (4.1%) and coriander
20
seed (4.7%). The IV of the samples from lowest to highest is coriander (82 g/g), peanut (93
g/g), sesame (100 g/g), soybean (100 g/g) and candlenut (110 g/g).
From the five tested samples, the usage of coriander seed for oil supply should be
avoided because it has very low oil content and high FFA content. Candlenut seed is most
suitable because of its high oil content; however it will need esterification as pre-treatment
before doing transesterification and may have some small issues with long term storage,
therefore it is recommended to be directly used.
7. Evaluation and Improvement
In this investigation, the obtained data might not be accurate due to several factors or
experimental error. There might be residual oil in the sample which required further
extractions. Number of extractions or amount of solvent could be increased. Using soxhlet
instrument and distillation to recover the solvent is recommended to get more oil efficiently.
These were not done due to limitation of solvent and unavailability of the instruments and
condenser for distillation.
The concentration of NaOH or Na2S2O3 solution might not be accurate enough as it
was calculated only from the ratio of mass of solid and volume of solution. This could be
solved by standardizing those solutions using stable substance like stable oxalic acid where
this was not done because of the absence of required stable substance.
In the calculation to find the average molar mass which was used for calculating FFA
content, the used literature data chemical composition of the oil might slightly differ from the
obtained oil because of different environmental conditions (e.g. weather, temperature)
causing the calculated value and FFA content to be inaccurate. In addition, some non-oil
21
substances could have been extracted during oil extraction from the samples, increasing the
calculated oil content compared to its actual oil content while also affecting the FFA and IV
test. The chemical composition of oil and its purity could be found for greater accuracy by
using Gas Chromatography Mass Spectrometer which was not available.
During the IV test, after adding iodine to the oil, the mixture usually got exposed to
sunlight for a while, triggering the single bond of fatty acid to react with iodine, causing the
experimental IV to be greater than the actual value. This could be prevented by using
polarizer and analyzer at angle 90o to prevent light passing through, preventing the
substitution reaction.
8. Further Research
Several aspects of this investigation were not investigated. The samples used in this
investigation are all edible ones because it was hard to find inedible samples. It would be
interesting to compare the results with oil from inedible samples.
To optimize the oil extraction, relationship between amount of solvent and oil
extracted could be investigated. If soxhlet instrument is used, investigating the effect of
number of soxhlet cycles or time with the amount of oil extracted would also be beneficial to
optimize the oil extraction.
Investigating the FFA content of the esterified oil would be recommended to know
the efficiency of the esterification process. Investigating the IV of the biodiesel from the
extracted oil will have a direct test to see whether the sample is suitable for the oil supply for
biodiesel or not.
22
9. Bibliography
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Sons.
Brandt, M. (2000). Introduction to Lipid Metabolism (1st ed., p. 1). Terre Haute: Rose-
Hulman Institute of Technology. Retrieved from https://www.rose-
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Alkenes/Electrophilic_Addition_of_Halogens_to_Alkenes
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toxicological aspects: A review. Plant Foods for Human Nutrition, 57(3/4), 319-341.
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http://dx.doi.org/10.1002/047084289x
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2015, from
http://chemwiki.ucdavis.edu/Organic_Chemistry/Esters/Reactivity_of_Esters/Saponificat
ion
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Freedman, B., Pryde, E., & Mounts, T. (1984). Variables affecting the yields of fatty esters
from transesterified vegetable oils. Journal of the American Oil Chemist Society, 61(10),
1638-1643. http://dx.doi.org/10.1007/bf02541649
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Acid with Methanol Using a Water Adsorption Apparatus. Industrial & Engineering
Chemistry Research,47(18), 6885-6889. http://dx.doi.org/10.1021/ie800547h
Longstreet, D. (2012). How To Calculate and Understand Analysis of Variance (ANOVA) F

Test. Retrieved from https://www.youtube.com/watch?v=-yQb_ZJnFXw
Meritnation.com,. (2010). How is O3 estimated quantitatively. Retrieved 10 December 2015,

from http://www.meritnation.com/ask-answer/question/how-is-o3-estimated-
quantitatively/the-p-block-elements/6303229
Mhhe.com,. Radical Substitution Reactions. Retrieved 10 December 2015, from

http://www.mhhe.com/physsci/chemistry/carey/student/olc/ch04radical.html
Pamata, N. (2008). Sintesis Metil Ester (Biodiesel) dari Minyak Biji Kemiri (Aleurites
moluccana) Hasil Ekstraksi melalui Metode Ultrasonokimia [Synthesis of Methyl Ester
(Biodiesel) from Candlenut Seed Oil (Aleurites moluccana) Extracted through
Ultrasonic Chemical Method]. Depok: Universitas Indonesia.
Peoples, T., Koch, D., & Smith, S. (1978). Relationship between Chloroplast Membrane Fatty Acid
Composition and Photosynthetic Response to a Chilling Temperature in Four Alfalfa Cultivars.
Plant Physiology, 61(3), 472-473. http://dx.doi.org/10.1104/pp.61.3.472
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different purification steps. Fuel, 87(17-18), 3522-3528.
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http://www.srsbiodiesel.com/technologies/solvent-extraction
Schuchardt, U., Sercheli, R., & Vargas, R. (1998). Transesterification of vegetable oils: a
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50531998000300002
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of the seed in the world collection of sesame introductions. Journal of the American Oil
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25
10. Appendix
10.1. Appendix 1 Raw Data and Data Processing
Here the raw data and the data processing will be presented. There will be numbers in the
brackets that represent there is a repetition done in collecting the data.
Before presenting the data, there are several formulas that are going to be used throughout all
of the data and therefore will be shown here in the beginning:
=1 1 + 2 + 3 + +
( ) = =

( ) =
2
The symbol represents uncertainty.
For example, if there is data: 9.34, 8.39 and 7.91 (Mass of oil in candlenut 1st extraction),
9.34 + 8.39 + 7.91

( ) = = 8.54667 8.55
3
9.34 7.91 1.43

( ) = = = 0.715 0.72
2 2
There will also be some data obtained by adding or subtracting a data by another data, the
uncertainty of the new data is obtained by adding the absolute uncertainty of both data:
( + ) ( ) = +
For example to find the mass of oil in candlenut (1) at 1 st extraction:
. = . . = 114.81 105.47 = 9.34
. = . + . = 0.01 + 0.01 = 0.02
26
Table 10.1.1. The Amount of Extracted Oil in Several Samples (Mass of Sample = 50.00 g)
1st Extraction 2nd Extraction
Mass of
Mass of Mass of
conical Mass of Mass of
No Sample conical flask conical flask
flask (g) oil (g) oil (g)
and oil (g) and oil (g)
0.01 0.02 0.02
0.01 0.01
1. Candlenut (1) 105.47 114.81 9.34 124.02 18.55
2. Candlenut (2) 112.94 121.33 8.39 129.87 16.94
3. Candlenut (3) 107.58 115.49 7.91 125.38 17.80
4. Coriander (1) 112.53 113.79 1.26 114.74 2.21
5. Coriander (2) 110.09 111.14 1.05 112.25 2.16
6. Coriander (3) 102.92 104.54 1.62 105.39 2.47
7. Peanut (1) 116.57 125.60 9.03 132.37 15.80
8. Peanut (2) 111.12 121.88 10.76 127.15 16.03
9. Peanut (3) 197.17 118.35 10.18 124.62 16.45
10. Sesame (1) 111.84 122.92 11.08 127.34 15.50
11. Sesame (2) 110.60 121.82 11.22 126.76 16.16
12. Sesame (3) 110.53 123.71 13.18 127.03 16.50
13. Soybean (1) 112.83 117.96 5.13 119.52 6.69
14. Soybean (2) 109.32 113.96 4.64 116.57 7.25
15. Soybean (3) 115.45 120.27 4.82 122.05 6.60
3rd Extraction 4th Extraction 5th Extraction
Mass of Mass of Mass of
Mass of Mass of Mass of
No Sample conical flask conical flask conical flask
oil (g) oil (g) oil (g)
and oil (g) and oil (g) and oil (g)
0.02 0.02 0.02
0.01 0.01 0.01
1. Candlenut (1) 132.45 26.98 135.53 30.06 135.58 30.11
2. Candlenut (2) 139.36 26.42 143.13 30.19 143.20 30.26
3. Candlenut (3) 133.24 25.66 135.79 28.21 136.78 29.20
4. Coriander (1) 115.68 3.15 116.30 3.77 116.75 4.22
5. Coriander (2) 113.22 3.13 113.76 3.67 114.13 4.04
6. Coriander (3) 105.89 2.97 106.53 3.61 106.85 3.93
7. Peanut (1) 134.12 17.55 134.91 18.34 135.89 19.32
8. Peanut (2) 129.66 18.54 130.40 19.28 131.06 19.94
9. Peanut (3) 126.20 18.03 127.08 18.91 127.63 19.46
10. Sesame (1) 132.35 20.51 134.92 23.08 135.23 23.39
11. Sesame (2) 131.43 20.83 134.12 23.52 134.72 24.12
12. Sesame (3) 132.24 21.71 135.61 25.08 135.91 25.38
13. Soybean (1) 120.42 7.59 121.35 8.52 121.77 8.94
14. Soybean (2) 117.05 7.73 117.51 8.19 118.13 8.81
15. Soybean (3) 123.18 7.78 125.13 9.73 125.30 9.90
27
Table 10.1.2. Oil Yield and Its Average in Several Samples (Mass of Sample = 50.00 g)
1st Extraction 2nd Extraction
Mass of Average Average oil Mass of Average Average oil
No Sample
oil (g) mass of yield based oil (g) mass of yield based
0.02 oil (g) on mass (%) 0.02 oil (g) on mass (%)
1. Candlenut (1) 9.34 18.55
8.55 17.10 17.76
2. Candlenut (2) 8.39 16.94 35.53 (1.62)
(0.72) (1.43) (0.81)
3. Candlenut (3) 7.91 17.80
4. Coriander (1) 1.26 2.21
1.31 2.28
5. Coriander (2) 1.05 2.62 (0.57) 2.16 4.56 (0.31)
(0.29) (0.16)
6. Coriander (3) 1.62 2.47
7. Peanut (1) 9.03 15.80
9.99 19.98 16.09
8. Peanut (2) 10.76 16.03 32.19 (0.66)
(0.87) (1.73) (0.33)
9. Peanut (3) 10.18 16.45
10. Sesame (1) 11.08 15.50
11.83 23.65 16.05
11. Sesame (2) 11.22 16.16 32.11 (1.00)
(1.05) (2.10) (0.50)
12. Sesame (3) 13.18 16.50
13. Soybean (1) 5.13 6.69
4.86 6.85
14. Soybean (2) 4.64 9.73 (0.49) 7.25 13.69 (0.65)
(0.25) (0.33)
15. Soybean (3) 4.82 6.60
3rd Extraction 4th Extraction
Mass of Average Average oil Mass of Average Average oil
No Sample
oil (g) mass of yield based oil (g) mass of yield based
0.02 oil (g) on mass (%) 0.02 oil (g) on mass (%)
1. Candlenut (1) 26.98 30.06
26.35 52.71 29.49
2. Candlenut (2) 26.42 30.19 58.97 (1.99)
(0.66) (1.33) (0.99)
3. Candlenut (3) 25.66 28.21
4. Coriander (1) 3.15 3.77
3.08 3.68
5. Coriander (2) 3.13 6.17 (0.18) 3.67 7.37 (0.16)
(0.09) (0.08)
6. Coriander (3) 2.97 3.61
7. Peanut (1) 17.55 18.34
18.04 18.84
8. Peanut (2) 18.54 36.08 (1.00) 19.28 37.69 (0.95)
(0.50) (0.47)
9. Peanut (3) 18.03 18.91
10. Sesame (1) 20.51 23.08
21.02 42.03 23.89
11. Sesame (2) 20.83 23.52 47.79 (2.01)
(0.60) (1.21) (1.00)
12. Sesame (3) 21.71 25.08
13. Soybean (1) 7.59 8.52
7.70 15.40 8.81
14. Soybean (2) 7.73 8.19 17.63 (1.54)
(0.10) (0.19) (0.77)
15. Soybean (3) 7.78 9.73
th
5 Extraction
Mass of Average Average oil
No Sample
oil (g) mass of yield based
0.02 oil (g) on mass (%)
1. Candlenut (1) 30.11
29.86 59.71
(0.53) (1.07)
4. Coriander (1) 4.22
4.06
5. Coriander (2) 4.04 8.13 (0.29)
(0.15)
6. Coriander (3) 3.93
28
7. Peanut (1) 19.32

19.57 39.15
8. Peanut (2) 19.94
(0.31) (0.63)
9. Peanut (3) 19.46
10. Sesame (1) 23.39
24.30 48.59
11. Sesame (2) 24.12
(1.00) (2.00)
12. Sesame (3) 25.38
13. Soybean (1) 8.94
9.22 18.43
14. Soybean (2) 8.81
(0.55) (1.09)
15. Soybean (3) 9.90

o = 100%

8.55
o In Candlenut for the 1st Extraction, = 50
100% = 17.1%
. .
o = +
. .
0.72 0.01
o In Candlenut for the 1st Extraction, = 8.55
+
50.00
17.1% 1.4%
Fig. 10.1.1. Formula and example of calculation to find average oil yield based on mass and their uncertainties
29
To compare the difference between each sample replicate and another (compare
between Coriander Seed (1), Coriander Seed (2) and Coriander Seed (3), and other samples),
statistical test Analysis of Variance F-Ratio Test17 will be done using coriander seed as the
example of calculation in both FFA Test and Iodine Value Test.
Table 10.1.3 Volume of NaOH used in FFA Test (mass of oil sample = 0.50 g)
V.NaOH 0.02 N V. NaOH 0.02 N
No Sample No Sample
(ml) 0.05 (ml) 0.05
1. Candlenut Seed (1) 3.8 25. Peanut (3) 1.3
4. Candlenut Seed (2) 3.6 28. Sesame Seed (1) 0.7
10. Coriander Seed (1) 4.4 34. Sesame Seed (3) 0.9
13. Coriander Seed (2) 4.2 37. Soybean (1) 1.0
19. Peanut (1) 1.2 43. Soybean (3) 1.0
20. Peanut (1) 1.1 44. Soybean (3) 1.1
21. Peanut (1) 1.2 45. Soybean (3) 1.2
22. Peanut (2) 1.2
23. Peanut (2) 1.3
24. Peanut (2) 1.2
o Molar Mass of NaOH = 40.00 g/mol
.().() 0.020.2540.00
o . () = = = 0.20 g
. 1
. . 0.01 0.15
o Uncertainty = ( . + ) = 0.0200 (0.20 + 250 ) = 0.0010
.
Fig. 10.1.2. Formula and the calculation to find the normality of NaOH solution and its uncertainty
17
Longstreet, D. (2012). How To Calculate and Understand Analysis of Variance (ANOVA) F Test.. Retrieved
from https://www.youtube.com/watch?v=-yQb_ZJnFXw
30
Table 10.1.4. Comparing difference between replicate of coriander seed in FFA Test
V.NaOH Sum of SS Total SS
Average Total
Sample 0.02 N Square Within Average Between
V. NaOH SS
(ml) 0.05 (SS) Group V. NaOH Group
Candlenut Seed (1) 3.8
Candlenut Seed (1) 3.6 3.7 0.027
Candlenut Seed (2) 3.6 3.6 0.0067 0.093 3.7 0.14 0.047
Candlenut Seed (3) 3.5 3.7 0.060
o () = =1( )2
o In Candlenut Seed (1), = (3.7 3.8)2 + (3.7 3.6)2 + (3.7 3.8)2 = 0.027
o = =1 = 1 + 2 + 3 = 0.027 + 0.0067 + 0.060 = 0.093
o Total Sum of Square is found using same formula as Sum of Square, but it uses all
data of Candlenut Seed (1), (2) and (3) and using the total average.
o = = 0.14 0.093 = 0.047
Fig. 10.1.3. Formula and the calculation to find SS Within Group and SS Between Group
Table 10.1.5. F-Ratio to get the significance level of difference in replicate of each sample in FFA Test
SS Between SS Within Degree of
Sample DFx DFy F-Ratio
Group Group Freedom (DF)
Candlenut Seed 0.047 0.093 1.50 (2,6)
Coriander Seed 0.167 0.016 0.28 Confidence Level
Peanut 0.016 2 0.020 6 2.33 95%
Sesame Seed 0.116 0.020 17.33 Critical Value
Soybean 0.062 0.087 2.15 5.14
o = 1 = 3 1 = 2
o = = 9 3 = 6

o =
0.0476
o In candlenut seed, = = 1.50
20.093
Fig. 10.1.4. Formula and the calculation to find F-Ratio
31
Table 10.1.6. Free Fatty Acid Content of Several Oil Samples (mass of oil sample = 0.50 g)
Molar Mass Total Average
No. Sample Average FFA (%)
(g/mol) FFA (%)
1. Candlenut Seed (1) 4.2 (0.1)
2. Candlenut Seed (2) 278 4.0 (0.1) 4.1 (0.2)
3. Candlenut Seed (3) 4.1 (0.2)
4. Coriander Seed (1) 4.7 (0.2)
5. Coriander Seed (2) 280 4.6 (0.2) 4.7 (0.3)
6. Coriander Seed (3) 4.7 (0.1)
7. Peanut (1) 1.3 (0.1)
8. Peanut (2) 281 1.4 (0.1) 1.4 (0.1)
9. Peanut (3) 1.4 (0.1)
10. Sesame Seed (1) 0.8 (0.1)
11. Sesame Seed (2) 278 0.7 (0.1) 0.9 (0.2)
12. Sesame Seed (3) 1.0 (0.1)
13. Soybean (1) 1.0 (0.1)
14. Soybean (2) 278 1.1 (0.2) 1.1 (0.2)
15. Soybean (3) 1.2 (0.1)
For molar mass of the fatty acid of each oil, please refer to the Appendix 2.
The average value was calculated from all of the data and then rounded to two significant figures.
.().() . 100%
o (%) = .()
3.8 1
o For candlenut seed (1) trial 1, = 1000 0.0200 278 100% 0.50 4.2%
Figure 10.1.5. Formula and example of calculation to find FFA content.
32
Table 10.1.7. Volume of Na2S2O3 used in Iodine Value (mass of oil sample = 0.20 g)
V. Na2S2O3 0.1 N V. Na2S2O3 0.1 N
No. Sample No. Sample
(ml) 0.05 (ml) 0.05
19. Peanut (1) 27.2 43. Soybean (3) 24.8
20. Peanut (1) 27.0 44. Soybean (3) 25.0
21. Peanut (1) 26.6 45. Soybean (3) 24.9
22. Peanut (2) 26.5
23. Peanut (2) 26.0
24. Peanut (2) 26.8
o Molar Mass of Na2S2O3 = 158.10 g/mol
.2 2 3 ().() 2 2 3 0.10.25158.10
o . 2 2 3() = .
=
1
= 3.95 g
. . 0.01 0.15
o = 0.100 ( . 2 2 3 + ) = 0.100 (3.95 + 250 ) = 0.0003
2 2 3 .
Figure 10.1.6. Formula and the calculation to find the normality of Na2S2O3 solution and its uncertainty
Table 10.1.8. Volume of Na2S2O3 in Iodine Value Test for Blank Sample
Trial Volume of Na2S2O3 0.1 N (ml) 0.05
1 40.8
2 41.2
3 41.4
Average 41.1 (0.3)
33
Table 10.1.9. F-Ratio to get the significance level of difference in replicate of each sample in Iodine Value Test
SS Between SS Within Degree of
Sample DFx DFy F-Ratio
Group Group Freedom (DF)
Candlenut Seed 0.249 0.233 3.20 (2,6)
Coriander Seed 1.936 1.340 4.33 Confidence Level
Peanut 1.056 2 0.693 6 4.57 95%
Sesame Seed 0.309 1.433 0.65 Critical Value
Soybean 0.376 0.147 7.68 5.14
Table 10.1.10. Iodine Value of Several Oil Samples (mass of oil sample = 0.20 g)
Average Iodine Total Average
No. Sample
Value (g/g) Iodine Value (g/g)
1. Candlenut Seed (1) 108 (1)
2. Candlenut Seed (2) 110 (1) 110 (3)
3. Candlenut Seed (3) 110 (2)
4. Coriander Seed (1) 80 (2)
5. Coriander Seed (2) 80 (4) 82 (6)
6. Coriander Seed (3) 86 (3)
7. Peanut (1) 90 (2)
8. Peanut (2) 93 (3) 93 (4)
9. Peanut (3) 95 (2)
10. Sesame Seed (1) 110 (3)
11. Sesame Seed (2) 110 (1) 100 (5)
12. Sesame Seed (3) 100 (4)
13. Soybean (1) 110 (1)
14. Soybean (2) 100 (1) 100 (3)
15. Soybean (3) 100 (1)
The average value is calculated from all of the data and then rounded to two significant figures.
1
(.2 2 3 ().2 2 3 ()).2 2 3 () 253.8100
2
o (/) = =
. ()
(0.0411.223 ()).2 2 3()12,690

. ()
1
o For candlenut seed (1) trial 1, = (0.0411 0.0242) 0.1 12,690 0.20 110g/g
Figure 10.1.7. Formula and example of calculation to find Iodine Value.
34
10.2. Appendix 2 Molar Mass of the Fatty Acid of Oil

Table 10.2.1. The Fatty Acid Composition of Tested Oil
Sesame
Molar Mass Candlenut Coriander Peanut Soybean
Fatty Acid Seed
(g/mol) Seed Oil18 Seed Oil19 Oil20 Oil22
Oil21
Caprylic (8:0)
144 0.01
C8H16O2
Pelargonic (9:0)
158
C9H18O2
Capric (10:0)
172 0.20 0.01
C10H20O2
Lauric (12:0)
200 0.28
C12H24O2
Myristic (14:0)
228 0.05 0.11 0.1
C14H28O2
Pentadecenoic
240
(15:1) C15H28O2
Palmitic (16:0)
256 6.32 4.02 8.23 9.5 11.0
C16H32O2
Palmitoleic (16:1)
254 0.28 0.11
C16H30O2
Margaric (17:0)
270 0.07
C17H34O2
Stearic (18:0)
284 2.31 1.02 2.46 4.4 4.0
C18H36O2
Petroselinic (18:1,
282 62.08
n-12) C18H34O2
Oleic (18:1, n-9)
282 26.93 13.29 58.69 39.6 23.4
C18H34O2
Vaccenic (18:1, n-
282 0.82
7) C18H34O2
Linoleic (18:2)
280 38.52 17.3 21.77 46.0 53.2
C18H32O2
Linolenic (18:3)
278 25.25 0.70 0.34 7.8
C18H30O2
Arachidic (20:0)
312 0.18 1.83
C20H40O2
Behenic (22:0)
340 0.07 3.89
C22H44O2
18
Pamata, N. (2008). Sintesis Metil Ester (Biodiesel) dari Minyak Biji Kemiri (Aleurites moluccana) Hasil
Ekstraksi melalui Metode Ultrasonokimia [Synthesis of Methyl Ester (Biodiesel) from Candlenut Seed Oil
(Aleurites moluccana) Extracted through Ultrasonic Chemical Method]. Depok: Universitas Indonesia.
19
EFSA NDA Panel (EFSA Panel on Dietetic Products, Nutrition and Allergies), 2013. Scientific Opinion on
the safety of coriander seed oil as a Novel Food ingredient. EFSA Journal 2013;11(10):3422, 20 pp.
doi:10.2903/j.efsa.2013.3422
20
Aluyor, E., Aluyor, P., & Ozigagu, C. (2009). Effect of refining on the quality and composition of groundnut
oil. African Journal Of Food Science, 3(8), 201-205.
21
Yermanos, D., Hemstreet, S., Saleeb, W., & Huszar, C. (1972). Oil content and composition of the seed in the
world collection of sesame introductions. Journal of the American Oil Chemist Society, 49(1), 20-23.
http://dx.doi.org/10.1007/bf02545131
22
Edem, D. (2002). Palm oil: Biochemical, physiological, nutritional, hematological and toxicological aspects:
A review. Plant Foods for Human Nutrition, 57(3/4), 319-341. http://dx.doi.org/10.1023/a:1021828132707
35
Petroselinic acid, oleic acid and vaccenic acid have the same chemical formula and
molar mass but they have different structures because they are isomer to each other.
Table 10.2.2. Molar Mass of Fatty Acid

Sample Molar Mass (g/mol)
Candlenut Seed Oil 278
Coriander Seed Oil 280
Peanut Oil 281
Sesame Seed Oil 278
Soybean Oil 278
Average Molar Mass

=1
=
=1 /
In soybean, the average molar mass:

0.20 + 6.32 + 2.31 + 26.93 + 38.52 + 25.25 99.53
= = = 277.52
0.20 6.32 2.31 26.93 38.52 25.25 0.357879
+ + + + +
172 256 284 282 280 278
278
Figure 10.2.1. Formula and example of calculation to find the average molar mass of fatty acid of oil
36
10.3. Appendix 3 Variables, Materials and Apparatus
Table 10.3.1. Variables in the Investigation

Variables Factors Observation and Measurement
Number of extractions The oil extraction done will not be only one, but
repeated until five times of extraction.
Samples used The samples used will be different and compared and
Independent
not mixed to each other. The samples used are
candlenut seed, coriander seed, peanut, sesame seed
and soybean.
Mass of extracted oil After each extraction of each sample, the mass of
extracted oil will be recorded by using digital
balance. And after the first extraction, the recorded
mass will be all of the extracted oil mass, not only
the increase.
Dependent Volume of NaOH The volume of NaOH solution will be responsible
solution for the free fatty acid test. It will be recorded through
titration using burette.
Volume of Na2S2O3 The volume of Na2S2O3 solution will be responsible
solution for the iodine value test. It will be recorded through
titration using burette.
Temperature of drying All of the samples will be dried by using oven at
using oven temperature 88-92oC.
Mass of sample for oil The mass for each trial of extraction of each sample
extraction will be kept constant, which is 50.00 g measured by
using a digital balance.
Amount of solvent The amount of solvent for each extraction of each
sample will be kept constant by using only 100 ml of
n-hexane as the solvent.
Time of oil extraction The time for each oil extraction of each sample is
kept constant by leaving it for 24 hours before
separating the oil from the solvent.
Total number of Each sample will be extracted for five times in total.
extractions
Temperature to The temperature for each separation will be kept to
Controlled separate n-hexane be ranging from 65-75oC by setting it in the hotplate
from the oil and ensured using thermometer to measure the
temperature.
Mass of oil sample in The mass of oil for each trial of each sample is kept
FFA and iodine value constant to be 0.50 g for iodine value and 0.20 g for
test FFA.
Normality of NaOH The normality of the solution will be kept constant
and Na2S2O3 solution by using the same solution for all of the trials. If the
solution is running out, it will be made again by
dissolving the same mass of the solid in the same
amount of solution.
The mass will be 0.20 g for NaOH solid and 3.95 g
for Na2S2O3 solid, while volume of each solution
will be 250 ml. The normality of NaOH solution is
0.02 N while for Na2S2O3 solution is 0.1 N.
37
Amount of ethanol The amount of ethanol and phenolphthalein indicator

and phenolphthalein in FFA test for all trials of each sample will be kept
indicator. constant by using 10.0 ml measured using a 10.0 ml
volumetric pipette for ethanol and 3 drops for
phenolphthalein indicator using drop pipette.
Amount of The amount of chloroform, iodine and distilled water
chloroform, iodine and in iodine value test for all trials of each sample will
distilled water and be kept constant by using 10.0 ml measured using a
starch indicator. 10.0 ml volumetric pipette for chloroform, 3.0 ml
measured using a 5.0 measuring cylinder for iodine
10%, 100 ml measured using a 100 ml measuring
cylinder for distilled water and 5.0 ml measured by
using a 5.0 ml measuring cylinder for the 1% starch
solution by mass.
Time of reaction The oil will be reacted with iodine in the same time
between oil and iodine interval, which is one hour measured by using
stopwatch.
Light intensity when The light intensity in testing iodine value will be
oil is reacted with kept constant by putting the mixture of reacting oil
iodine and iodine in the same dark place, which is inside a
closed shelf.
Materials and Apparatus
Table 10.3.2. Materials

Samples
No. Materials Quantity
1. Candlenut Seed 200 g
2. Coriander Seed 200 g
3. Peanut 200 g
4. Sesame Seed 200 g
5. Soybean 200 g
Oil Extraction
1. Filter paper 75 pcs
2. N-hexane 7,500 ml
FFA Test
1. Anhydrous NaOH solid 0.20 g
2. Distilled water 250 ml
3. Phenolphthalein Indicator 100 ml
Iodine Value Test
1. Anhydrous Na2S2O3 solid 23.70 g
2. Chloroform 480 ml
3. Distilled water 6,600 ml
4. Iodine solution 10% 144 ml
5. Starch 3.0 g
38
Table 10.3.3. Apparatus

Oil Extraction
No. Apparatus Quantity
1. Aluminum foil 1
2. Beaker 500 ml 15
3. Blender 1
4. Conical flask 15
5. Digital balance (0.01 g) 1
6. Filter funnel 15
7. Hotplate 5
8. Measuring cylinder 100 (1) ml 1
9. Mortar and Pestle 1
10. Oven 100oC (0.1oC) 1
11. Stirring rod 5
12. Thermometer (max. 110oC, 0.5oC) 5
13. Tray 1
FFA Test
1. Beaker 100 ml 1
2. Burette 50.0 (0.05) ml 1
3. Burette clamp 1
4. Conical flask 250 ml 48
6. Drop pipette 2
7. Filter funnel 1
8. Spatula 5
9. Volumetric flask 250.0 (0.15) ml 1
10. Volumetric pipette 10 (0.05) ml 1
Iodine Value Test
1. Beaker 100 ml 1
2. Beaker 500 ml 1
3. Burette 50.0 (0.05) ml 1
4. Burette clamp 1
5. Conical flask 250 ml 48
7. Drop pipette 3
8. Filter funnel 1
9. Hotplate 1
10. Magnetic bar 5
11. Measuring cylinder 5.0 (0.05) ml 2
12. Measuring cylinder 100 (1) ml 1
13. Spatula 5
14. Stirring Rod 1
15. Volumetric flask 250.0 (0.15) ml 6
16. Volumetric pipette 10.0 (0.05) ml 1
39
Information for Chemical Reagents23:
1. N-hexane
Molecular Formula: C6H14
Molar Mass: 86.18 g/mol
Melting Point: -95oC
Fig 10.3.1 Chemical structure of n-hexane
Boiling Point: 69oC
It is a colorless liquid with slightly disagreeable odor. It is highly volatile and
flammable. It is insoluble with water and miscible with alcohol, chloroform and ether.
2. Sodium hydroxide
Molecular Formula: NaOH
Molar Mass: 40.00 g/mol Fig 10.3.2 Chemical structure of sodium hydroxide
Melting Point: 318oC
Specific Gravity: 2.13
Physical State: White, deliquescent pellets or flakes
It is very soluble in water, alcohol, and glycerin.
It is highly corrosive and reactive, irritating to the skin, eyes and gastrointestinal tract.
3. Phenolphthalein
Molecular Formula: C20H14O4
It is insoluble in water but soluble in alcohol.
pKa = 9.6
pH range = 8.3 10.0
Acid: colorless; alkali: pink Fig 10.3.3 Chemical structure of phenolphthalein
4. Sodium thiosulfate
Molecular Formula: Na2O3S2
Melting Point: 43oC
Specific Gravity: 1.667 Fig 10.3.4 Chemical structure of sodium thiosulfate
Physical State: White crystal
Readily soluble in water
23
Encyclopedia of Reagents for Organic Synthesis. (2001). http://dx.doi.org/10.1002/047084289x
Chemicalland21.com,. (2013). Chemicalland21.com. Retrieved 10 August 2015, from
http://www.chemicalland21.com/
Rsc.org,. The Merck Index Online. Retrieved 10 August 2015, from https://www.rsc.org/Merck-Index/
40
5. Iodine
Molecular Formula: I2
Melting Point: 113.7oC
Fig 10.3.5 Chemical structure of iodine
Physical state: solid metallic grey
6. Chloroform
Molecular Formula: CHCl3
Melting Point: -63.5oC
Boiling Point: 61oC
Fig 10.3.6 Chemical structure of chloroform
Physical State: Clear volatile liquid.
It is slightly soluble in water and miscible with ethanol.
It can cause carcinogenic effects.
41
10.4. Appendix 4 Documentation of the Investigation
Image 10.4.1. Candlenut Seed Image 10.4.2. Candlenut Seed Image 10.4.3. Candlenut
Powder Seed Oil
Image 10.4.4. Coriander Seed Image 10.4.5. Coriander Seed Image 10.4.6. Coriander
Powder Seed Oil
Image 10.4.8. Peanut Image 10.4.9. Peanut Powder Image 10.4.10. Peanut Oil
Image 10.4.7. Peanut
Peeled Skin
42
Image 10.4.11. Sesame Seed Image 10.4.12. Sesame Seed Powder Image 10.4.13. Sesame Seed Oil
Image 10.4.14. Image 10.4.15. Soybean Image 10.4.16. Soybean

Soybean Soaked in Water Skin Peeled
Image 10.4.17. Soybean Powder Image 10.4.18. Soybean Oil

Image 10.4.19. Example
of Powder Soaked in N-
Hexane
43
Image 10.4.20. FFA Test Image 10.4.21. FFA Test Image 10.4.22. FFA Test
Oil Dissolved in Ethanol Reaction with NaOH Titration End Point
Image 10.4.23. Iodine Value Image 10.4.24. Iodine Value

Image 10.4.25. Iodine Value
Oil Dissolved in Chloroform After Adding Iodine
Rinsed with Distilled Water
Image 10.4.27. Iodine Value

Image 10.4.26. Iodine Value After Adding Starch Indicator Image 10.4.28. Iodine Value
Titration until Pale-Yellow Color Titration End Point
44

Extended Essay Chemistry (HL) - A Comparison of Oil Content on Candlenut Seed, Coriander Seed, Peanut, Sesame Seed and Soybean with Free Fatty Acid Content and Iodine Value Tested as Potential Biodiesel Feedstock

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Extended Essay Chemistry (HL) - A Comparison of Oil Content on Candlenut Seed, Coriander Seed, Peanut, Sesame Seed and Soybean with Free Fatty Acid Content and Iodine Value Tested as Potential Biodiesel Feedstock

Hochgeladen von

Copyright:

Extended Essay

A Comparison of Oil Content on Candlenut Seed, Coriander

among the samples?

Candidate Name: Sadha Satya Lotan

Candidate Number: 002115 0019

School Name: Cita Hati Christian High School

Supervisor Name: David Lesmana

Session: May 2016

Abstract Word Count: 299

Essay Word Count: 3,999

value of the extracted oil compare among the samples?

Word Count: 299

Section Title Page

5 Result and Analysis 14

7 Evaluation and Improvement 21

are all easy to find and usually used as food resources.

number of extractions and the amount of oil extracted.

among the samples?

vitamins and many other functions.

solvent extraction method will be used in this investigation.

3.2. Free Fatty Acid (FFA)

Fig. 3.2.1. General equation of transesterification between triglyceride in vegetable oil

1. Alcohol reacts with base producing

alkoxide and protonated catalyst.

2. Alkoxide does nucleophilic attack to

carbonyl group of triglyceride, forming

3. The tetrahedral intermediate dissociates

into its conjugate anion and alkyl ester.

4. The conjugate anion deprotonates the

catalyst and regenerate the active

Fig. 3.2.2. Mechanism of alkaline catalyzed transesterification species.

Carbonyl group in ester is protonated

forming carbocation II.

Alcohol does nucleophilic attack

on carbocation II, forming

tetrahedral intermediate III,

which later forms new ester IV

by removing glycerol, and H+

3.2.4 and Fig. 3.2.59.

Fig. 3.2.4. Overall reaction of saponification

1. OH- ion does nucleophilic attack

on ester forming ether.

2. Ether is removed to form

3. Ether deprotonates the carboxylic

acid, forming carboxylate anion

Fig. 3.2.5. Mechanism of saponification reaction

FFA content is mass ratio of FFA to oil.

Mol FFA is obtained by multiplying V.NaOH and its normality.

The formula to find FFA content can be written as:

Equation 3.2.1. Formula to find FFA Content

3.3. Iodine Value (IV)

Fig 3.2.711 using bromine as example of halogen.

1. The bond in bromine is polarized triggering

heterolytic cleavage. Bromine cation forms

intermediate cycle with the double bond of the

2. Bromide anion attacks any carbon of the

bridged bromonium ion from the back side of

the cycle, causing it to open and attach two

using bromine and methane as reactants.

Fig. 3.3.3. Substitution of halogen on saturated compound

1. Initiation, bromine undergoes hemolytic cleavage

caused by heat or ultraviolet, forming two bromine

2. Propagation, bromine radical attracts hydrogen of

methane forming hydrogen bromide and radical

methyl. Radical methyl attracts bromine from another

molecule forming methyl bromide and another bromine

radical, creating a repeatable cycle.