Fuel 90 (2011) 16181623

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Fuel
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Conventional and in situ transesterication of castor seed oil

for biodiesel production
Gina Hincapi, Fanor Mondragn, Diana Lpez
Institute of Chemistry, University of Antioquia, A.A. 1226, Medelln, Colombia

a r t i c l e

i n f o

Article history:
Received 24 July 2010
Received in revised form 14 January 2011
Accepted 18 January 2011
Available online 2 February 2011
Keywords:
Castor oil
Transesterication
Biodiesel
In situ transesterication
Nuclear magnetic resonance

a b s t r a c t
In the present study, biodiesel production from Ricinus communis L. red and BRS-149 nordestina varieties
seed oil is reported. Reactions were made through conventional and in situ processes using ethanol and
evaluating the addition of n-hexane as co-solvent. The content of ethyl esters was quantied by 1H NMR.
The highest conversions were obtained from crude oil (conventional reaction) after pre-esterication,
using ethanol and a molar ratio of alcohol to oil of 60; furthermore, the addition of n-hexane was not signicant on yield. Under these conditions, best conversion was around 95% for both varieties.
2011 Elsevier Ltd. All rights reserved.

1. Introduction
The use of vegetable oils derivatives as alternative fuels has increased due to the diminishing oil reserves and the environmental
consequences of exhaust gases from petroleum-fueled engines [1].
Biodiesel is an alternative fuel produced by transesterication of
oils. This reaction consists of transforming triglycerides into fatty
acid alkyl esters in the presence of an alcohol, such as methanol
or ethanol, and a catalyst, with glycerol as co-product (Fig. 1)
[2,3]. The use of methanol is more common than ethanol because
its low cost, but several researches have started to investigate biodiesel production or optimization using ethanol derived from sugarcane [4,5]. Some advantages of biodiesel compared with
petrodiesel are that it is biodegradable, non-toxic; it is produced
from renewable sources and contains insignicant amounts of sulfur. Nevertheless, cold ow properties, NOx emissions and high
costs are features that have to be overcome [6].
Edible oils like soybean, rapeseed, sunower and palm oil are
being used for the production of biodiesel. However, in the last
few years, there has been a major concern about the use of these
oils for transportation purposes [1]. To overcome this problem,
there are several non-edible oil seed species which could be used
as a source for biodiesel production, among those, Ricinus communis L. and Jatropha curcas have considerable potential [79]. Castor
oil, extracted from the seeds of R. communis L. plant (also known as
castor bean, castor oil plant, higuerilla, mamona), is a viscous, pale
Corresponding author. Tel.: +57 4 2196613; fax: +57 4 2196565.
E-mail address: [email protected] (D. Lpez).
0016-2361/$ - see front matter 2011 Elsevier Ltd. All rights reserved.
doi:10.1016/j.fuel.2011.01.027

yellow, non-volatile and non-drying oil. Opposed to other vegetable oils it is characterized for its indigestibility, partial solubility
in alcohol, high hygroscopicity and high viscosity [10,11]. Like
other vegetable oils, castor oil is constituted mainly by tryglicerides which consist of three fatty acids and one molecule of glycerol. The fatty acids of this oil consist of approximately 8090%
of ricinoleic acid (12-hydroxy-cis-octadec-9-enoic acid), 36% linoleic acid, 24% oleic acid and 15% saturated fatty acids. Due to this
particular chemical composition, castor oil is a raw material in
great demand by the pharmaceutical and chemical industry [12].
Its use as fuel for internal combustion engines, however, can become complicated because of its extremely high viscosity and high
water content; biodiesel derived from castor oil exhibit much higher viscosities than those of more conventional biodiesels, and it can
be used in current diesel engines in admixture with fossil diesel or
with less viscous biodiesels [1315]. Nevertheless, the presence of
ricinoleic acid, which is a fatty acid that contains both a double
bond and a hydroxyl group, can afford an increase in lubricity as
compared to normal vegetable oils and becomes a prime candidate
as additive for diesel fuel [13,16,17].
Crude castor oil quality deteriorates gradually due to improper
handling and storage conditions. An improper handling would
cause the water content increase, and exposition to air and light
for long time would increase the concentration of free fatty acids
(FFA). A high FFA content (>1% w/w) will generate soap formation
and the separation of products will be very difcult, and as a result,
a low yield will be obtained. The acid-catalyzed esterication of
the oil is an alternative, but is much slower than the base-catalyzed
transesterication reaction [1,18]. Therefore, an alternative process

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G. Hincapi et al. / Fuel 90 (2011) 16181623

Fig. 1. Scheme of the transesterication reaction between one triacylglycerol (TAG) molecule and three ethanol (EtOH) molecules to form three molecules of ethyl esters
(biodiesel) and one glycerol (GLY) molecule.

such as a two-step process has been investigated for feedstocks

with a high FFA content, the rst step of the process is the acid-catalyzed esterication for reducing the FFA content of the oil and the
second step is the base-catalyzed transesterication [1820].
In situ transesterication differs from the conventional reaction
in that the oil-bearing material contacts with acidied or alkalized
alcohol directly instead of reacting with pre-extracted oil and alcohol. That is, extraction and transesterication takes place simultaneously, the alcohol acts as an extraction solvent and an
esterication reagent [21]. This route could eliminate the expense
associated with solvent extraction and oil cleanup, and simplied
the steps in ester production. This could result in a decrease in
the cost of the product [22]. In the paper of Harrington and
DArcy-Evans [23], under reux conditions sunower seeds were
transesteried with an excess of methanol relative to the number
of moles of triacylglycerols (TAG) present using sulfuric acid as catalyst, these authors observed ester production with yields up to
20% greater in the in situ than in the transesterication of pre-extracted oil. They attributed this behavior to an effect of the water
content of the seeds, to an increased extractability of some seed
lipids under acidic conditions, and to the transesterication of
seed-hull lipids.
Qian et al. [24], reported the in situ alkaline-catalyzed transesterication of cottonseed oil for biodiesel production and non-toxic
cottonseed meal, they studied the moisture content and catalyst
concentration over the conversion of TAG to biodiesel. It was found
that when moisture content decreases from 8.7% to 1.9% the conversion to methyl ester was increased from 80% to 98% and when
the alkaline catalyst concentration increases from 0.05 to
0.1 mol/L the conversion to methyl ester was increased from 33%
to 98%.
Georgogianni et al. [21] applied in situ alkaline-catalyzed
transesterication to sunower seeds, using methanol and ethanol
as reactants and NaOH as catalyst. The mixture was reuxed and
stirred either using the mechanical stirrer or the low frequency
ultrasonicator. They reported ester yield as high as 96% using
methanol and 90% using ethanol. They showed that ultrasonication
in most cases led to similar yields of alkyl esters as compared to
mechanical stirring.
Several authors [13,25,26] have discussed the problem of the
mass transfer limitations in transesterication reactions due to
low oil solubility in alcohol phase; this problem slows down the
reaction resulting in low ester yield. An alternative to solve this
problem is the use of a co-solvent that accelerates the reaction.
To perform the reaction in a single phase and increase the miscibility of oil in alcohol, co-solvents like tetrahydrofuran (THF), 1,4dioxane and n-hexane have been tested [13,25].
Gas chromatography (GC) and NMR spectroscopy are the most
used analytical methods on biodiesel analyses. In fact, GC has been
the most used technique due to its high accuracy for the quantication of minor components. However, baseline drift, overlapping
signals, and aging of standards and samples can affect the GC accuracy. Moreover, GC analyses frequently require sample derivatization, mainly to obtain trimethylsilyl derivatives of the hydroxyl
groups. Although this procedure improves chromatographic separation, it also increases the analysis time. NMR spectroscopic anal-

yses are most employed for monitoring the transesterication

reaction and for the determination of blending ratio [27]. NMR
spectroscopy can be used for quantitative analysis based on the
fact that the amplitude of a proton nuclear magnetic resonance
(1H NMR) signal is proportional to the number of hydrogen nuclei
contained in the molecule [28]. Although NMR spectroscopy does
not present the detection limit accuracy for the quantication of
minor components as chromatographic methods do, it is a suitable
method to monitor a chemical reaction, since small amounts are
required to obtain a quantitative spectrum with signicant information related to the substances of interest in the reaction media
[29].
This paper presents the production of biodiesel from crude castor
seed oil having a high content of FFA, by conventional and in situ
transesterication reactions. Furthermore, co-solvent (n-hexane)
effects on ethyl esters formation during the transesterication were
analyzed and the content of these esters were quantied by different
approximations of 1H NMR spectroscopy developed by several
author [2931].
2. Experimental
2.1. Reagents and materials
Analytical grade isopropyl alcohol (99.8%), n-hexane (96%), KOH
(P85%), anhydrous Na2SO4 (P99%) and H2SO4 (97%) from Merck
and anhydrous ethanol from Mallinckrodt Chemicals were used
without further purication. Castor seeds were donated by Corpoica (red variety) and Colombiana de Biocombustibles S.A (BRS-149
Nordestina variety).
2.2. Procedures
2.2.1. Oil extraction
Castor seeds were macerated, placed in a Soxhlet thimble and
extracted with isopropyl alcohol for various periods of time. Solvent was removed from the extracted oil using a vacuum rotary
evaporator at 75 C. The fatty acid composition of the oil was determined by gas chromatography using a DB5-HT column and is
shown in Table 1.
2.2.2. Conventional oil transesterication
Castor seed oil (red or nordestina variety, 10 g) extracted as described above was poured in a 100 mL rounded-bottomed ask
equipped with a reux condenser. The reaction ask was im-

Table 1
Fatty acid composition of castor oil.
Fatty acid

Composition (%)

Ricinoleic acid
Linoleic acid
Oleic acid
Palmitic acid
Estearic acid
Linolenic acid

89
5
3
1
1
1

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G. Hincapi et al. / Fuel 90 (2011) 16181623

Fig. 2. Full 1H NMR spectra of (a) crude castor oil (nordestina variety) and (b) biodiesel produced by conventional transesterication of castor seeds (nordestina variety).

Fig. 3. 1H NMR spectra of (a) crude castor oil (doublet of doublets), (b) a castor oil/ethyl ester mixture and (c) pure ethyl ester (quartet) from and 4.154.50 ppm.

G. Hincapi et al. / Fuel 90 (2011) 16181623

1621

Notebook program. The integration of the spectra was carried out

manually, ten times each one and the results were averaged to reduce the uncertainty (less than 5%) generated by the manual
adjustment.

3. Results and discussion

The oil from red variety had an initial acid value of 3.3 mg KOH/
g and the oil from nordestina variety had an initial acid value of
1.2 mg KOH/g corresponding to a FFA level of 1.65% and 0.6%
respectively. Despite these values are not far from the 1% limit
for satisfactory transesterication reaction using alkaline catalyst,
the oil used in the present work was crude and its acid value changed during storage and use. Therefore, FFAs were rst converted to
esters in a two-step pretreatment process using H2SO4 as catalyst.
3.1. 1H NMR results

Fig. 4. 1H NMR spectra at 2.202.35 ppm region from (a) pure ethyl ester and (b)
castor oil/ethyl ester mixture (partial conversion).

mersed in a mineral oil bath placed on the plate of a magnetic stirrer (300 rpm). The oil was heated to reaction temperature (60 C)
and then the solution of concentrated H2SO4 (1.0% based on the
oil weight) in ethanol or ethanolhexane (hexane 20% v/v based
on the oil volume) was added to the ask. This pre-esterication
was carried out for 1 h, the molar ratio of ethanol to oil for this step
was 40. Over this pretreated oil and by the same reaction conditions, transesterication step was conducted, a solution of KOH
(1.0% based on the oil weight to transesterication and an excess
to neutralize the sulfuric acid) in ethanol was added to the ask,
the molar ratio of ethanol to oil for this step was 20, the transesterication was carried out for 1 h. Finally, the reaction was stopped;
the excess of solvent was separated using a rotary evaporator. The
products were separated by centrifugation (3600 rpm), upper layer
(biodiesel) was puried by washings with hot distilled water and
dried over anhydrous sodium sulfate.
2.2.3. In situ oil transesterication
Castor seeds (red or nordestina variety, 20 g) were macerated
and transferred to the previously described reaction ask. In the
same way that above, the seeds were heated to reaction temperature and under mechanical stirring (300 rpm) a solution of H2SO4
(1.0%) in ethanol or ethanolhexane was added for pre-esterication. After 1 h, a solution of KOH (1.0%) in ethanol was added
and the reaction was carried out for 1 h. Finally, the reaction mixture was ltered, washed as described above and dried over anhydrous sodium sulfate.
2.3. Analytical methods
2.3.1. Acid value
The acid value of the oil was determined by the acidbase titration technique (ASTM, 2006) using a standard solution of KOH
0.5 N.
2.3.2. 1H NMR measurements
All 1H NMR analyses were performed on a Bruker AMX 300
apparatus, at 300 K using a 5 mm probe head and CDCl3 as solvent.
For each analysis, 40 mg of sample were dissolved in the solvent
which also served as internal reference (shift value of residual proton at 7.24 ppm). Before starting the analysis, the obtained spectra
were treated for phase and baseline corrections using the NMR

In the quantication of the ethyl esters using 1H NMR spectroscopy, there is a superimposition of glyceril methylenic hydrogens
of the crude oil and the OCH2 from ethyl ester in biodiesel (Figs.
2 and 3). Fig. 2 shows the full 1H NMR spectra of crude castor oil
(nordestina variety) and biodiesel produced by conventional
transesterication of castor seeds (nordestina variety). Fig. 3 shows
the 1H NMR spectra of crude castor oil (doublet of doublets), pure
ethyl ester (quartet) and a castor oil/ethyl ester mixture from 4.15
to 4.50 ppm.
Quantication of biodiesel using NMR can be done using several
equations that have been reported in the literature; three of them
will be described and used in the present work for the quantication of ethyl esters. The notation used to describe the methods corresponds to that reported by Ghesti et al., [29] (see Figs. 2 and 3 for
further clarication): (i) ITAG corresponds to integration of glyceril
methylenic hydrogens of TAG molecule at 4.334.45 ppm; (ii) ITAG+EE corresponds to integration of glyceril methylenic hydrogens
and OCH2 of ethoxy hydrogens superimposed at 4.164.28 ppm;
and (iii) IaCH2 corresponds to integration of a-acyl methylenic
hydrogens in castor oil and ethyl esters at 2.202.35 ppm (see
Fig. 4 for further clarication). Also, for describing the third method
it is necessary to introduce the term IE which corresponds to integration of signal at 4.164.18 ppm, this is exclusive to ethoxy
hydrogens (see Fig. 3b and c).
The equation proposed by Silva [30] and presented below (Eq.
(1)) was applied to determine castor oil conversion into biodiesel
(CEE). The notation used in his paper was adapted to the one followed in this research:



ITAGEE  ITAG
%C EE 100
IaCH2

Due to intermediary compounds such as monoglycerides (MAG)

and diglycerides (DAG) formed during transesterication that remain in the nal product, and considering that the hydroxyl group
(OH) of this species overlap with the a-CH2 signal at 2.20
2.35 ppm (Fig. 4), Ghesti et al. [29] proposed another equation
(Eq. (2)) where a-acyl methylenic hydrogens are not considered:



4ITAGEE  ITAG
%C EE 100
4ITAGEE  ITAG 62ITAG

The numbers 4 and 6 in Eq. (2) are related to four glyceryl

methylenic hydrogens present in TAG molecules and to six ethoxy
hydrogens (OCH2) formed in three ethyl ester products
respectively.
Finally, the equation reported by da Fonseca et al. [31] in their
study of transesterication of soybean oil with ethanol, was ap-

1622

G. Hincapi et al. / Fuel 90 (2011) 16181623

Table 2
Conversion into ethyl esters.
Red

Nordestina

Conventional (%)

Eq. (1)
Eq. (2)
Eq. (3)

In situ (%)

4IE
3
E

ITAG
2

In situ (%)

Ethanolhexane (EH)

EH

EH

EH

89.1
95.1
95.3

92.0
95.4
95.6

41.5
47.6
51.2

51.0
65.9
65.6

92.8
97.6
98.0

91.3
97.3
97.4

44.7
53.5
57.3

38.8
42.7
45.0

plied to the present research (Eq. (3)). The notation used in their
paper was adapted to the one followed in this research:

%C EE 4I

Conventional (%)

Ethanol (E)

The intention to acquire the conversion from the three previous

equations was to analyze the differences between them and how
these inuenced the value of the total conversion. Conversion results from nordestina and red varieties, through conventional
and in situ processes, using ethanol and ethanolhexane mixture
are reported in Table 2.
It is possible to observe in Table 2 that results from Eqs. (2) and
(3) do not present signicant differences, indicating that biodiesel
quantication considering TAG and ethyl esters signals at 4.15 and
4.45 ppm is appropriate since TAG signal decreases in intensity as
the reaction proceeds and the signal of ethyl esters progressively
increase. It is also possible to appreciate that larger differences occur with Eq. (1), this is probably due to the overlapping of hydrogen from a-CH2 group and hydroxyl group (OH) of the MAG and
DAG bringing as a result that the divider in Eq. (1) is greater and
therefore the conversion result is slightly lower than expected.
It is important to note that conversions obtained from conventional reactions are signicantly high considering that we worked
with low-quality crude oil whose only treatment or purication
step was pre-esterication. These results are promising and show
that if reaction conditions are improved, biodiesel production
could be carried out without the steps of oil rening, only transforming FFA in esters from the beginning of the reaction. It was
also observed in these reactions that n-hexane addition does not
produce a signicant effect on the conversion when ethanol is used
as solvent.
For in situ reactions, it is possible to observe that conversions
were low compared with some reports existing in the literatures
[21,24] for other vegetable species as cotton or sunower, in which
the conversions exceed 98%. This behavior may be due to the alcoholoil molar ratio that was used in the present study (60:1) which
is low compared with those used in the literature that reaches
226:1 [22]. The effect of the n-hexane is more evident in the
in situ process than in conventional one. During in situ reaction,
red seed produces higher conversion using ethanolhexane mixture that only ethanol; this shows that this co-solvent could improve the reaction probably facilitating the diffusion of the
ethanol through the particles of the seed. But this phenomenon
does not occur with nordestina seed, where the conversion with
ethanol is higher than using the solvent mixture; this may be
due a higher concentration of ricin that is a polar compound, avoiding the diffusion of the mixture through the particles; but this
hypothesis should be conrmed with another experiments.
It is important to emphasize that previous studies about the use
of castor seeds for in situ transesterication have not been found.
Therefore, this study gives an insight of this possibility indicating
that if the reaction conditions are enhanced there will be an
improvement in conversions.

4. Conclusions
Production of biodiesel from castor seeds is feasible by conventional and in situ processes. However, conversions obtained by conventional method are considerably higher than by in situ process.
The conventional results are promising considering that we work
with low-quality oils. To our knowledge these are the rst in situ
transesterication results of castor oil, however, more work should
be done to improve conversions. The use of hexane as co-solvent
does not have a marked effect except for reaction made over red
seeds. NMR spectroscopy is a useful technique to quantify TAG
conversions to ethyl esters.
Acknowledgments
The authors are grateful to Colciencias for nancing the Project
1115-452-21119. To Universidad de Antioquia for the nancial
support through Programa Sostenibilidad 20092010. To Corpoica
and Colombiana de Biocombustibles S.A. for the donation of the
seeds. G.H. wishes to thank to Colciencias for her Ph.D. scholarship.
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