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Laboratory Experiment

pubs.acs.org/jchemeduc

Synthesis and Determination of Biodiesel: An Experiment for High


School Chemistry Laboratory
Jun Yang,, Chunli Xu,*,, Baoxin Li,, Guijia Ren,, and Lu Wang,

Key Laboratory of Applied Surface and Colloid Chemistry, Shaanxi Normal University, Ministry of Education, Xian 710062, PR
China

School of Chemistry and Chemical Engineering, Shaanxi Normal University, Changan South Road 199, Xian 710062, PR China

Key Laboratory of Analytical Chemistry for Life Science of Shaanxi Province, Shaanxi Normal University, Xian, 710062, PR China
*
S Supporting Information

ABSTRACT: Biodiesel has gained attention in recent years as a renewable and


environmentally friendly fuel source. A laboratory experiment designed for high school
students is described to study biodiesel production. Under optimum conditions, the time of
running the reaction of biodiesel synthesis was less than a half-hour. Moreover, based on the
dierence in density and solubility of reactants and products in the transesterication, one
visualizing method of detection of biodiesel product was suggested. The results
demonstrated that the visualizing method was simple, quick, and eective in determining
whether biodiesel was produced. This proposed experiment is typically completed in less
than two one-hour laboratory periods, which makes it suitable for a high school chemistry
laboratory.

KEYWORDS: High School/Introductory Chemistry, Organic Chemistry, Laboratory Instruction, Hands-On Learning/Manipulatives,
Inquiry-Based/Discovery Learning, Biotechnology, Catalysis, Student-Centered Learning, Synthesis

T ransesterication is an important chemical reaction found


in high school textbooks.1 It is the process of exchanging
the organic group R of an ester with the organic group R of
Scheme 2. Production of Biodiesel through
Transesterication

an alcohol (Scheme 1). These reactions are often catalyzed by

Scheme 1. Transesterication between Alcohol and Ester

the addition of an acid or base catalyst. Catalysis, esters, such as combustion and viscosity of biodiesel.49 However, to
alcohols, and edible oils are also important topics found in high the best of our knowledge, there is not a laboratory experiment
school textbooks.2 A simple and interesting experiment is about biodiesel for high school students. In those published
helpful for high school students to understand this reaction. experiments, instruments, such as gas chromatography,7 IR
Biodiesel is a fashionable topic nowadays because it is spectroscopy,6 thin-layer chromatography,7 and 1H NMR
environmentally friendly and is made from renewable spectroscopy,5 were used to determine the yield of biodiesel.
resources.3 Biodiesel is a term applied to a fuel derived from Though these methods are accurate, these instruments are
the transesterication of vegetable oils or animal fats. In the expensive and are typically not available to high school
production of biodiesel, the triglycerides in the fats and oils students. Furthermore, the fundamentals of these instruments
react with methanol to make glycerine and methyl esters are also unknown to high school students. In addition, these
(biodiesel) in the presence of a catalyst (Scheme 2). We methods of detection are time-consuming. Therefore, these
describe a biodiesel synthesis that is suitable for high school methods of instrumental analysis are not suitable for a high
students to learn about transesterication, catalysis, esters, school chemistry laboratory. A simple and quick chemical
alcohols and edible oil. experiment is suitable for the education of high school
There have been several excellent experiments about students.10,11
biodiesel published for undergraduate students in recent years
that include new and used oil and determination of properties, Published: September 11, 2013
2013 American Chemical Society and
Division of Chemical Education, Inc. 1362 dx.doi.org/10.1021/ed400210r | J. Chem. Educ. 2013, 90, 13621364
Journal of Chemical Education Laboratory Experiment

In this work, a biodiesel synthesis utilizing transesterication spectra with the student to show the dierences between the
was designed for the high school chemistry laboratory. In the two layers. For this instrumental method, the reaction products
presence of an active catalyst NaOH, the reaction for biodiesel were analyzed using the following procedure: The biodiesel
synthesis could be completed in 30 min. Referring to the samples were separated from glycerol by centrifugation, with
reaction shown in Scheme 2, the density of reactant methanol the separation of glycerol being achieved because it was
(0.79 g cm3) was lower than that of reactant vegetable oil insoluble in the esters and had a much higher density. After
(0.9190.925 g cm3), whereas the density of byproduct removal of methanol residue in vacuo, the product was
glycerol (1.261 g cm3) was higher than that of product dissolved in chloroform-d and the methyl ester could be
biodiesel (0.850.90 g cm3). Based on the dierence in determined quantitatively from the NMR spectra using the
density and solubility of reactants and products in the method described by Gelbard et al.12
transesterication, a visualizing method of analysis of the Students worked in groups. The experiment could be divided
reaction product was used. As shown in Figure 1, methanol into two 50 min sessions. Students run reactions (with and
without catalyst) in the rst session. They repeated the
procedure to investigate dierent oils and the eect of the
catalyst in the second session.

HAZARDS
The vegetable oils purchased in markets are edible. Methanol is
ammable and poisonous so it must be handled with care.
Anhydrous sodium hydroxide is irritant and caustic. In this
work, 1H NMR spectroscopy was used to evaluate the
proposed visualizing method, but not incorporated into the
experiment for high school students. If evaluation of the
product by 1H NMR spectroscopy is incorporated, chloroform-
d is needed. Chloroform-d is poisonous and must by handled
Figure 1. Photograph of transesterifaction of vegetable oil and with care.


methanol for biodiesel synthesis: (A) before reaction and (B) after
reaction. RESULTS AND DISCUSSION
The yield of biodiesel was aected by reaction variables, such as
oated on triglyceride before reaction, whereas the byproduct the methanol/oil ratio, catalyst amount, or reaction time.13
glycerine was below the layer of product biodiesel after Under the reaction conditions of catalyst (0.31.0 wt %) and
reaction. Through the dierence in appearance of the reaction methanol to vegetable oil molar ratio (6:1), a clear interface
system before and after reaction, one can determine whether between biodiesel and glycerol was observed at 10 min of
biodiesel was produced. This method is simple and quick, and it running time (Figure 2). This indicated that reaction time of
is suitable for high school chemistry students.

transesterication could be reduced to 10 min.


EXPERIMENT
Chemicals
Vegetable oils are available in supermarkets: sesame oil,
soybean oil, canola oil, peanut oil, olive oil, and so forth.
Methanol and NaOH used were of analytical grade. All reagents
were used without further purication.
Procedure
The catalytic transesterication reaction was carried out under
vigorous magnetic stirring in a round-bottomed ask equipped
with a reux condenser. The reaction was heated by an
Figure 2. Eect of the catalyst amount (from left to right: 0, 0.3, 0.5,
electromagnetic heater. Typical reactions were performed with
0.6, 0.8, 1.0 wt %).
11.76 mL of vegetable oil and 2.78 mL of methanol (methanol
to vegetable oil molar ratio 6:1) using 1 wt % (catalyst to oil
weight ratio) of NaOH catalyst at methanol reux temperature
(65 C) for 10 min. After cooling, the solution was transferred The type of vegetable oil was also studied. The vegetable oils
to a transparent vial. After standing for 5 min, the interface tested were sesame oil, canola oil, and soybean oil. The
between biodiesel layer and glycerol layer was clearly observed. photographs show that biodiesel was produced in each case
As shown in Figure 1, formation of biodiesel was analyzed by a (Figure 3). One phenomenon observed was the color of the
visualizing method. The analysis of product was completed glycerol layer. Pure glycerol is colorless and transparent;
within 20 min. however, the glycerol layer in the biodiesel system was colored
To validate its viability, the visualizing method was checked and not transparent. The glycerol layer contained, besides the
by 1H NMR spectroscopy. 1H NMR spectroscopy provided the main components of glycerol, minor amounts of methanol
accurate yield. The NMR spectra of vegetable oil and biodiesel residue, NaOH residue, and sodium salt of fatty acid (soap).
are shown in Figure S4 (see the Supporting Information). The The sodium salt of fatty acid could accumulate colorful
instructors obtained the NMR of the products to conrm the components of oil, which resulted in the color of glycerol
presence of the biodiesel and glycerol. They did not share the layer.14
1363 dx.doi.org/10.1021/ed400210r | J. Chem. Educ. 2013, 90, 13621364
Journal of Chemical Education


Laboratory Experiment

REFERENCES
(1) Chemistry textbook for high school (II, a required course); Peoples
Education Press: Beijing, 2007; pp 7376.
(2) Chemistry textbook for high school (V, an elective course); Peoples
Education Press: Beijing, 2007; pp 4596.
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Figure 3. Photographs of reaction system using dierent vegetable oils experiment for the undergraduate organic chemistry laboratory. J.
as reactants: (A) sesame oil, (B) canola oil, and (C) soybean oil (left, Chem. Educ. 2011, 88, 201203.
before reaction; right, after reaction). (6) Ault, A. P.; Pomeroy, R. Quantitative investigations of biodiesel
fuel using infrared spectroscopy: An instrumental analysis experiment
for undergraduate chemistry students. J. Chem. Educ. 2012, 89, 243
The benets of the proposed experiment to students are as
247.
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To train the students in experimental techniques relating Duenas, J. A.; Serafino, J. O. A simple, safe method for preparation of
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apparatus. (8) Akers, S. M.; Conkle, J. L.; Thomas, S. N.; Rider, K. B.
To develop the students ability of applying chemical Determination of the heat of combustion of biodiesel using bomb
knowledge of transesterication. calorimetry. A multidisciplinary undergraduate chemistry experiment.
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To stimulate the students interest in chemical research.
(9) Clarke, N. R.; Casey, J. P.; Brown, E. D.; Oneyma, E.; Donaghy,
Through the proposed experiment, students learn a K. J. Preparation and viscosity of biodiesel from new and used
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1
alcohol and edible oil (ester) are used as both reactants H nuclear magnetic resonance determination of the yield of the
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(13) Ma, F. R.; Hanna, M. A. Biodiesel production: a review.
CONCLUSIONS Bioresour. Technol. 1999, 70, 115.
A simple and quick chemical experiment of biodiesel synthesis (14) Li, C.; Jiang, L.; Cheng, S. Biodiesel-Green Energy; Chemical
for high school students is described. This experiment is helpful Industry Press: Beijing, 2007; p 73.
for high school students to understand transesterication,
catalysis, esters, alcohols, and biodiesel. This experiment was
typically completed in less than two hours: a half-hour for
preparation, a half-hour for running the reaction of biodiesel
synthesis, and 20 min for analyzing the product. This
experiment is suitable for a high school chemistry laboratory.

*
ASSOCIATED CONTENT
S Supporting Information

Student handout; tables of the equipment and chemicals


needed; procedure and tips for the experiment; answers to
prelab questions. This material is available via the Internet at
http://pubs.acs.org.

AUTHOR INFORMATION
Corresponding Author
*E-mail: xuchunli@snnu.edu.cn.
Notes
The authors declare no competing nancial interest.

ACKNOWLEDGMENTS
We thank students (Hongyu Liang, Yan Guo, Lan Ma, Shufeng
Ji, Yahong Li, Xinrui Qin, Jiaoyan Xiang, Liming Tan, Xueqin
Zhao) for testing the experiment.
1364 dx.doi.org/10.1021/ed400210r | J. Chem. Educ. 2013, 90, 13621364