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BASE-CATALYZED TRANSESTERIFICATION OF
GUYABANO (ANNONA MURICATA) SEED OIL DERIVED
THROUGH SOLVENT EXTRACTION FOR THE
PRODUCTION OF FATTY ACID METHYL ESTER
Submitted by:
GROUP 3
BS ChE 3-1
Submitted to:
Date Submitted:
Project Study 1
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TABLE OF CONTENTS
I. Introduction
II. Statement of the Problem
III. Objectives
IV. Significance of the Study
V. Background of the Study
Review of Related Literature
Review of Related Studies
VI. Procedure
VII. Summary of Equivalent Unit Operations
VIII. Summary of Parameters
IX. Summary of Process Flow Diagram
X. Conclusion
XI. Recommendation
XII. References
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I. INTRODUCTION
Soursop continues flowering year around but the peak is May to June.
The fruits are harvested when fully developed and still green. They are
considered mature when their spines are set far apart and the shiny green
color turns dull-green or yellowish green. Selective harvesting is practiced
because the fruits on a tree do not mature at the same time.
Soursop seeds constitute 20% - 25% mass of the fruit and have potential
to produced 33.87% oil with nutritional and functional properties highly
similar to those of edible oils (Okoro, 2013).
TRANSESTERIFICATION PROCESS
The end products of the transesterification process are raw biodiesel and
raw glycerol. After a cleaning step biodiesel is produced. The purified glycerol
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can be used in the food and cosmetic industries, as well as in the oleochemical
industry (EBTP, 2011).
Fatty Acid Methyl Ester (FAME) is produced from vegetable oils, animal
fats or waste cooking oils by transesterification. Transesterification is a
reversible reaction and is carried out by mixing the reactants. A strong base or
a strong acid can be used as a catalyst.
Pure vegetable oils have been considered as alternatives for diesel fuel,
but the high viscosity at room temperature made them unsuitable for diesel
engines. However, fatty acid methyl esters (FAME) have lower viscosity than the
pure oils, and as such are promising alternatives. While the focus has been
mostly on oils like soybean, rapeseed, and sunflower (Lang et al., 2001), which
are essentially edible in nature, biodiesel has also been produced from non-
edible sources such as used frying oil and greases (Alcantara et al.,2000;
Canakci and Gerpen, 2001; Mittelbach et al., 1992).
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factories located at Cavite and Makati, were noted that the fruit juices or
concentrated of guanabana contain toxic material from the fruit seed
incorporated into the finished product during the manufacturing process.
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III. OBJECTIVES
A. General Objective
To produce fatty acid methyl ester used in the production of biodiesel
under the process of transesterification of guyabano seed oil which will
conform to the properties of the standard fatty acid methyl ester.
B. Specific Objectives
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The study utilizes guyabano seeds as its major raw material for the
production of fatty acid methyl ester. This will provide guyabano tree plantation
owners a potential market for fatty acid methyl ester rather than ending up the
guyabano seeds as waste.
Both the materials and procedure of this study could be utilized and
developed by other institutions and could be a reason for a local production of
fatty acid methyl ester from the raw material. Moreover, this study would help
create jobs for local citizens since fatty acid methyl esters are versatile products
covering a wide range or industry like agriculture, fuels, solvents, polymers,
and food industry.
This study may serve as an additional reference for related and similar
studies of fellow researchers. Chemical engineers could help in conducting
further research and study of the process involved in the production of fatty
acid methyl ester. With the help of this field, scientific and economic condition
in the country could be improved.
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A. RAW MATERIALS
Soursop (Guyabano)
The nature green fruits are used as a vegetable and for making sweet
meats, while the ripe one is eaten off hand or as dessert. Its juice is used for
flavoring ice cream, sherbets, canning and for preparation of refreshing drinks.
It may also be processed intro preserve, candies, jam and jelly. Guyabano also
possess some medicinal properties. (Agribusiness, 2017)
Guyabano SU Production
2010 6,922
2011 7,007
2012 7,305
2013 7,579
2014 7,150
2015 7,671
*SU Supply
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Based on BAS crop statistics of 2003; a total land area of 3,016 has.
were planted to guyabano with the following as the five leading producing
regions: Western Visayas (705 has.); Region IV-A (643 has.); Cagayan Valley
(400 has.); Central Visayas (169 has.); and Central Luzon (165 has.).
Guyabano seeds
For the dried seeds, they are tolerant of the moisture extraction, showing no
problems for long-term storage under reasonable
conditions.
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the guyabano processing plants. If teeth could tear a seed apart, the more the
heavy-duty machines can. (Foodrecap, 2013)
Figure 1 Compositional analyses of the seed of sour sop, Annona muricata L., as a potential
animal feed supplement (Fasakin, et.al. 2008)
B. PROCESS
Solvent Extraction
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C. PRODUCT
Fatty Acid Methyl Esters (FAME) are esters of fatty acids. The physical
characteristics of fatty acid esters are closer to those of fossil diesel fuels than
pure vegetable oils, but properties depend on the type of vegetable oil. A
mixture of different fatty acid methyl esters is commonly referred to as
biodiesel, which is a renewable alternative fuel. FAME has physical properties
similar to those of conventional diesel. It is also non-toxic and biodegradable.
(EBTP, 2011)
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FAME is produced from vegetable oils, animal fats or waste cooking oils
by transesterification. In the transesterification process a glyceride reacts with
an alcohol in the presence of a catalyst, forming a mixture of fatty acids esters
and an alcohol. Using triglycerides results in the production of glycerol. (EBTP,
2011)
Rapeseed, sunflower, soybean, palm oils, UCO and animal fat are the
most common raw materials being used for the production of biodiesel. Using
methanol in the transesterification process has the advantage that the
resulting glycerol can be separated simultaneously during the
transesterification process. When using ethanol during the process the ethanol
needs to be free of water and the oil needs to have a low water content as well
to achieve an easy glycerol separation. (EBTP, 2011)
The end products of the transesterification process are raw biodiesel and
raw glycerol. After a cleaning step biodiesel is produced. The purified glycerol
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can be used in the food and cosmetic industries, as well as in the oleochemical
industry. The glycerol can also be used as a substrate for anaerobic digestion.
(EBTP, 2011)
Uses of FAME
Fatty acid methyl esters are products that are produced by an alkali-
catalyzed reaction between fats or fatty acids and methanol. In biodiesel, fatty
acid methyl esters are the primary constituent, usually obtained from vegetable
oils by transesterification.
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A. PROCESS
And for the data gathered and the comparison for the standard and
commercially available properties of Biodiesel or FAME:
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In order to improve the yield of oil and the quality of remaining protein
various attempts have been made to alter the basic steps of cooking, pressing
and extracting the oil from oil bearing seeds and nuts. One approach is
disclosed in the patent to Drenning, U.S. Pat. No. 2,629,722 wherein it is
taught that if best results are to be achieved in oil production then the
moisture content of the cooked seeds must be closely controlled, evaporation
prevented, and the time and temperature of the cooking reduced. Thus, a
process is disclosed in which oil bearing seeds and nut meats are first flaked
and then treated prior to extraction of the oil by raising the moisture content of
the seeds to a value of between 12 and 20% by the addition of steam or water
and then cooking the seeds for a period of time between 7 and 20 minutes at a
temperature between 190 and 215 F under such conditions as to ensure that
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evaporation does not reduce the moisture in the seed nut meats below 12%.
The oil may then be extracted from the treated (cooked) seed by a combined
process involving mechanized presure followed by solvent extractions. This
process is said, among others, to produce a meal of high nutritional value
above that obtained from a standard high temperature processing and to
achieve higher oil yields.
Soursop seeds constitute 20% - 25% mass of the fruit and have potential
to produced 33.87% oil with nutritional and functional properties highly
similar to those of edible oils (Okoro, 2013). Previous researchers applied
solvent extraction technique for the extraction of oils from different plant
oilseeds due to it cost effectiveness, simplicity, remarkable reduction in solvent
volume and short time needed for the extraction (Tan et al., 2009; Betiku and
Adepoju, 2012; Bimakr et al., 2012; Adepoju et al., 2013).
The study showed that the Soursop seed is a good source rich in oil.
Also, this work demonstrated Response Surface Methodology is a good tool for
optimization in oil extraction processes. The maximum seed oil yield of 34.
6074% (w/w) was established at the optimal condition of extraction time, 38.10
min, sample weight, 30.0 g and solvent volume, 100 ml. The optimized
condition was validated with the actual seed oil yield of 33.593% (w/w). The
fatty acid profile of the seed oil showed it is highly unsaturated (73.42%).
Project Study 17
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And from the stated above study Solvent Extraction of Oil from Oil
Seeds by Ayres et al. (1997) a process is disclosed in which oil bearing seeds
and nut meats are first flaked and then treated prior to extraction of the oil by
raising the moisture content of the seeds to a value of between 12 and 20% by
the addition of steam or water and then cooking the seeds for a period of time
between 7 and 20 minutes at a temperature between 190 and 215 F under
such conditions as to insure that evaporation does not reduce the moisture in
the seed nut meats below 12%.
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being a hydrophilic this interferes in the reaction which leads to lesser yield if
the product. Among these solvents, methanol works best because it has the
least molecular weight. The molecular weight of methanol is 32.05g/gmol while
the molecular weight of ethanol and propanol are 46.08 and 60.11 g/gmol
respectively. Increasing the chain length of RO-(alcohol) group results in the
increase of reaction rate and causes steric hindrance which prolonged the
reaction.
B. PRODUCT
The main criterion of biodiesel quality is the inclusion of its physical and
chemical properties into the requirements of the adequate standard. Quality
standards for biodiesel are continuously updated, due to the evolution of
compression ignition engines, ever stricter emission standards, reevaluation of
the eligibility of feedstocks used to produce biodiesel, etc.
The biodiesel standards in Brazil and the U.S. are applicable for both
fatty acid methyl esters (FAME) and fatty acid ethyl esters (FAEE), whereas the
current European biodiesel standard is only applicable for fatty acid methyl
esters (FAME).
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And for the data gathered and the comparison for the standard and
commercially available properties of Biodiesel or FAME:
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In order to improve the yield of oil and the quality of remaining protein
various attempts have been made to alter the basic steps of cooking, pressing
and extracting the oil from oil bearing seeds and nuts. One approach is
disclosed in the patent to Drenning, U.S. Pat. No. 2,629,722 wherein it is
taught that if best results are to be achieved in oil production then the
moisture content of the cooked seeds must be closely controlled, evaporation
prevented, and the time and temperature of the cooking reduced. Thus, a
process is disclosed in which oil bearing seeds and nut meats are first flaked
and then treated prior to extraction of the oil by raising the moisture content of
the seeds to a value of between 12 and 20% by the addition of steam or water
and then cooking the seeds for a period of time between 7 and 20 minutes at a
temperature between 190 and 215 F under such conditions as to insure that
evaporation does not reduce the moisture in the seed nut meats below 12%.
The oil may then be extracted from the treated (cooked) seed by a combined
process involving mechanized pressure followed by solvent extractions. This
process is said, among others, to produce a meal of high nutritional value
above that obtained from a standard high temperature processing and to
achieve higher oil yields.
Soursop seeds constitute 20% - 25% mass of the fruit and have potential
to produced 33.87% oil with nutritional and functional properties highly
similar to those of edible oils (Okoro, 2013). Previous researchers applied
solvent extraction technique for the extraction of oils from different plant
oilseeds due to it cost effectiveness, simplicity, remarkable reduction in solvent
volume and short time needed for the extraction (Tan et al., 2009; Betiku and
Adepoju, 2012; Bimakr et al., 2012; Adepoju et al., 2013).
The study showed that the Soursop seed is a good source rich in oil.
Also, this work demonstrated Response Surface Methodology is a good tool for
optimization in oil extraction processes. The maximum seed oil yield of 34.
6074% (w/w) was established at the optimal condition of extraction time, 38.10
min, sample weight, 30.0 g and solvent volume, 100 ml. The optimized
Project Study 22
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condition was validated with the actual seed oil yield of 33.593% (w/w). The
fatty acid profile of the seed oil showed it is highly unsaturated (73.42%).
And from the stated above study Solvent Extraction of Oil from Oil
Seeds by Ayres et al. (1997) a process is disclosed in which oil bearing seeds
and nut meats are first flaked and then treated prior to extraction of the oil by
raising the moisture content of the seeds to a value of between 12 and 20% by
the addition of steam or water and then cooking the seeds for a period of time
between 7 and 20 minutes at a temperature between 190 and 215 F under
such conditions as to insure that evaporation does not reduce the moisture in
the seed nut meats below 12%.
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II. Reagent
Table 2 presents the reagents that were used for the experimental
method. They were purchased from local chemical supplier Tough Stone
Lab Enterprises, which is located at Bambang, Manila; and was used
without further purification.
Hexane
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Methanol
2.13
NaOH 39.997 1,388
g/cm3
Sodium Hydroxide
Potassium Hydroxide
2.21
Ca(OH)2 74.093 580
g/cm3
Calcium Hydroxide
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Oven Timer
1.2 Procedure
1. Weigh the initial moist soursop seeds.
2. Dry the seeds until a constant weight or negligible change in mass.
3. Place the first set over the oven tray.
4. Dry the soursop seed for 30 minutes.
5. After drying, weigh the dried soursop seeds.
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After drying the soursop seeds, the next process is size reduction. It is
necessary to reduce the size of the seeds to increase the rate of reaction for
the next process.
Blender
1.2 Procedure
1.From the drying process, place the dried seeds in the blender.
2. Grind the seeds for 3 minutes.
3. Weigh the ground soursop seeds.
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Fume hood
1.2 Procedure
2. Add the 100-mL of hexane to the flask and put a rubber stopper
to prevent the hexane from evaporating.
4. Distill the solution to separate the oil from the hexane (B.P. 60-
70 C) with its temperature varying from 55, 65, and 75C. Note:
Recover the solvent and water to recycle.
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MASS OF OIL
7.5
MASS OF GUYABANO OIL,
7
6.5
6
GRAMS
5.5
5
4.5
4
30 45 60
SETTLING TIME, MINUTES
Mass of Oil
1.4 Conclusion
The amount of oil that can be extracted from the seed varies with the
time it takes for the solvent to fully absorb the oil present in the seed. At
60-minute mark, 7.2 grams of oil are extracted from 25 g of sample
crushed soursop seeds
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DOCUMENTATION
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E. PREPARATION OF METHOXIDE
1.2 Procedure
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Best Catalyst
14
MASS OF OIL, GRAMS
13
12
11
10
Best Catalyst
9
8
7
NaOH KOH Ca(OH)2)
CATALYSTS
1.4 Conclusion
The amount of methyl ester that can be obtained from oil depends
on the catalyst used and its type. Among three basic catalyst used,
sodium hydroxide (NaOH) yields the highest amount of oil weighing
13.8 grams of Methyl Ester using only soursop seeds.
2.2 Procedure
1.Weigh 10 g of methanol and place it in a 100-mL beaker.
2. Cover the beaker with a watch glass.
3. Prepare three sets of NaOH with 0.10, 0.15 and 0.20 grams
separately.
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4. Weigh the first set of catalyst and add it on the methanol. Note:
This solution is toxic; use preventive measures to limit exposure.
5. Repeat procedure for the remaining two sets.
DETERMINATION OF AMOUNT OF
CATALYST
20
MASS OF OIL, GRAMS
19
18
17
16 DETERMINATION
15 OF AMOUNT OF
14 CATALYST
13
12
0.1 0.15 0.2
MASS OF CATALYST, GRAMS
2.4 Conclusion
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3.2 Procedure
1. Measure 10 g of Methanol and place it on a 100-mL beaker,
cover it with a watch glass.
2. Weigh 0.15 g of NaOH and add it on the Methanol. Take note
that this solution is toxic; use preventive measures to limit
exposure.
3. Weigh 30g of oil and place it on a 250 ml Erlenmeyer flask.
Preheat it to 60 C. Add the prepared Methanol-catalyst to the
preheated oil. Continue heating the oil with constant
temperature of 60 C with continuous stirring for 30 minutes.
4. Set the solution aside until warm to touch (about 25 30 C).
Transfer the solution to a separatory funnel to completely cool
and to settle the produced mixtures (soap and FAME).
5. Separate the solutions by discarding the formed soap and
keeping the produced Fatty Acid Methyl Ester.
6. Repeat steps 1-5 using 5 grams and 7.5 grams of Methanol.
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WEIGHT OF METHANOL
18
17.5
MASS OF OIL, GRAMS
17
16.5
16
15.5 WEIGHT OF
15 METHANOL
14.5
14
13.5
5 7.5 10
MASS OF METHANOL
3.4 Conclusion
The 7.5 grams of methanol yielded the highest weight of Methyl
Ester using 0.15 g of the Sodium Hydroxide (NaOH) catalyst.
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Thermometer Timer
1.2 Procedure
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TEMPERATURE
22.5
MASS OF OIL, GRAMS
22
21.5
21
20.5
20 TEMPERATURE
19.5
19
18.5
60 75 90
HEATING TEMPERATURE, DEGREE CELCIUS
1.4 Conclusion
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Thermometer Timer
2.2 Procedure
2. Preheat it to 60C.
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HEATING TIME
29
MASS OF METHYL ESTEER
27
25
23
21
HEATING TIME
19
17
15
30 60 90
HEATING TIME, MINUTES
2.3 Conclusion
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Documentation
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SUMMARY OF PARAMETERS
Type of Catalyst to
NaOH
be Used
Mixing (Methoxide
Preparation) Amount of Catalyst
0.15 grams
Used
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CONCLUSION
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RECOMMENDATION
1. For further efficiency of the final product, the researchers must use more
specific variations which do not rely only on numbers divisible by five
and ten.
2. The venue of the experiment must be fit for environment with standard
temperature and pressure so that in the manufacturing process for mass
production of this product is standardized.
3. As much as possible, the researchers must not rely on three to five
review of related literature and studies. This part must be plenty as
much as possible so that the best variation will be determined for the
experiment.
4. The researchers must determine and include the possible errors during
the experiment and make some assumptions on how it will be avoided.
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REFERENCES
Adepoju, T.F., Olatunji, E.M., Olawale, O., Okunola, A.A. 2014. Solvent
Extraction Of Oil From Soursop Oilseeds & Its Quality Characterization.
International Journal of Sustainable Energy and Environmental Research.
Retrieved from http://www.pakinsight.com/pdf-files/ene/13/IJSEER-2014-
3(2)-80-89.pdf
Ayres, J.L., Barr, D.R., Hunt, C.T., Steele, B.C. (1997) Solvent Extraction of Oil
from Oil Seeds. US4008210 A.
Barabas, I., Todorut, I.A. 2011. Biodiesel Quality, Standards and Properties.
Technical University of Cluj-Napoca Romania. Retrieved from
http://cdn.intechopen.com/pdfs/23666/InTech-
Biodiesel_quality_standards_and_properties.pdf
Comparison of Dietary Fats and Oils. (2010) Retrieved 2016 December 29 from
http://www.seniorscan.org/SeniorsCAN/Comparison_Fats_Oils.html
Desbois AP, Smith VJ. (2010) Antibacterial free fatty acids: activities,
mechanisms of action and biotechnological potential. Appl Microbiol
Biotechnol. 2010;85:16291642. doi: 10.1007/s00253-009-2355-3.
European Biofuel Technology Platform (EBTP). 2011. Fatty Acid Methyl Esters
(FAME): Biofuel Fact Sheet. Retrieved 2017 January 01 from
http://www.biofuelstp.eu/factsheets/fame-fact-sheet.pdf
Project Study 47
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Hebbal, O.D., Hotti, S.R. 2014 Biodiesel Production Process Optimization from
Sugar Apple Seed Oil (Annona squamosa) and Its Characterization. Department
of Automobile Engineering, PDA College of Engineering, Gulbarga Karnataka
585102, India
Project Study 48
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2010. (2009). Fatty acid methyl Ester, fatty acid, methyl esters exporters from
India. Retrieved February 23, 2017, from http://www.krishioils.com/fatty-
acid-methyl-ester.htm
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