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Bioresource Technology 99 (2008) 17161721

Biodiesel production from crude Jatropha curcas L. seed oil with a

high content of free fatty acids
Hanny Johanes Berchmans a, Shizuko Hirata
b

b,*

a
Energy Technology Center, Agency for Assessment and Application of Technology, Kawasan Puspiptek, Serpong, Tangerang 15314, Indonesia
Biomass Technology Research Center, Advanced Industrial Science and Technology, Chugoku, 2-2-2 Hirosuehiro, Kure, Hiroshima 737-0197, Japan

Received 27 January 2007; received in revised form 30 March 2007; accepted 30 March 2007
Available online 24 May 2007

Abstract
A technique to produce biodiesel from crude Jatropha curcas seed oil (CJCO) having high free fatty acids (15%FFA) has been developed. The high FFA level of JCJO was reduced to less than 1% by a two-step pretreatment process. The rst step was carried out with
0.60 w/w methanol-to-oil ratio in the presence of 1% w/w H2SO4 as an acid catalyst in 1-h reaction at 50 C. After the reaction, the mixture was allowed to settle for 2 h and the methanolwater mixture separated at the top layer was removed. The second step was transesteried using 0.24 w/w methanol to oil and 1.4% w/w NaOH to oil as alkaline catalyst to produce biodiesel at 65 C. The nal yield for
methyl esters of fatty acids was achieved ca. 90% in 2 h.
 2007 Elsevier Ltd. All rights reserved.
Keywords: Biodiesel; Jatropha curcas; Transesterication; Free fatty acids

1. Introduction
Biodiesel as an alternative fuel for diesel engines is
becoming increasingly important due to diminishing petroleum reserves and the environmental consequences of
exhaust gases from petroleum-fuelled engines. Biodiesel,
which is made from renewable sources, consists of the simple alkyl esters of fatty acids. As a future prospective fuel,
biodiesel has to compete economically with petroleum diesel fuels. One way of reducing the biodiesel production
costs is to use the less expensive feedstock containing fatty
acids such as inedible oils, animal fats, waste food oil and
byproducts of the rening vegetables oils (Veljkovic et al.,
2006). The availability and sustainability of sucient
supplies of less expensive feedstock will be a crucial determinant delivering a competitive biodiesel to the commercials lling stations. Fortunately, inedible vegetable oils,
mostly produced by seed-bearing trees and shrubs can provide an alternative. With no competing food uses, this
*

Corresponding author. Tel.: +81 823 72 1931; fax: +81 823 72 1990.
E-mail address: s-hirata@aist.go.jp (S. Hirata).

0960-8524/$ - see front matter  2007 Elsevier Ltd. All rights reserved.
doi:10.1016/j.biortech.2007.03.051

characteristic turns attention to Jatropha curcas, which

grows in tropical and subtropical climates across the developing world (Openshaw, 2000).
Oil contents, physicochemical properties, fatty acid
composition and energy values of Jatropha species were
investigated (Banerji et al., 1985; Kandpal and Madan,
1995; Kumar et al., 2003; Pramanik, 2003; Akintayo,
2004; Shah et al., 2004). While, it is considered that Jatropha has toxic substance (Hirota et al., 1988; Gandhi et al.,
1995; Makkar et al., 1998; Haas and Mittelbach, 2000;
Abdel Gadir et al., 2003).
In many cases CJCO quality deteriorate gradually due
to improper handling and inappropriate storage condition.
It was known that improper handling of CJCO would
cause the water content increase. In addition, exposing
the oil to open air and sunlight for long time would aect
the concentration of FFA increase signicantly to high
level of FFA above 1%. The FFA amount of CJCO will
vary and depend on the quality of feedstock.
The FFA and moisture contents have signicant eects
on the transesterication of glycerides with alcohol using
catalyst (Goodrum, 2002). The high FFA content (>1%

H.J. Berchmans, S. Hirata / Bioresource Technology 99 (2008) 17161721

w/w) will happen soap formation and the separation of

products will be exceedingly dicult, and as a result, it
has low yield of biodiesel product. The acid-catalyzed
esterication of the oil is an alternative (Crabbe et al.,
2001), but it is much slower than the base-catalyzed transesterication reaction. Therefore, an alternative process
such as a two-step process was investigated for feedstock
having the high FFA content (Ghadge and Raheman,
2005; Veljkovic et al., 2006).
This paper presents the development of two-step process
for the production of biodiesel from the CJCO having the
high FFA. The special attention was focused to optimize
the rst step of the process for reducing the FFA content
of CJCO to below 2%. The second attention was focused
to optimize the reaction condition for weight ratio of catalyst to oil and weight ratio of methanol to oil at 65 C.
2. Methods
2.1. Materials
The CJCO used in this study was supplied by Chemical
Engineering Department Laboratory, Bandung Institute of
Technology, Bandung, Indonesia. Fatty acid composition
of CJCO is given in Table 1. While the Crude Palm oil
(CPO) and Net Coconut oil (NCO) used in this study were
supplied by Lion Oleo Chemical Company, Japan. Certied methanol of 99.8% purity was obtained from Sigma
Aldrich, Tokyo, Japan. The catalyst was pure sodium
hydroxide from Wako Chemicals, Tokyo, Japan. Concentric sulphuric acid of 98% purity was purchased from
Wako Chemicals, Tokyo Japan.
2.2. Equipments
Experiments were conducted in a 15 cm3 special reaction
glass tube, of which thickness was 2 mm and was sealed
tightly with a silicon rubber cap that retained any vaporized mixture. The reaction glass tube was immersed in a
glass water bath placed on the plate of magnetic stirrer
Table 1
Fatty acid composition of crude Jatropha curcas oila
Fatty acid

Formula

Systemic name

Structureb

wt%

Myristic
Palmitic

C14H28O2
C16H32O2

Tetradecanoic
Hexadecanoic

14:0
16:0

Palmitoleic
Stearic
Oleic

C16H30O2
C18H36O2
C18H34O2

cis-9-Hexadecenoic
Octadecanoic
cis-9-Octadecenoic

16:1
18:0
18:1

Linoleic

C18H32O2

18:2

Linolenic

C18H30O2

18:3

Arachidic
Behenic

C20H40O2
C22H44O2

cis-9,cis-12Octadecedianoic
cis-6,cis-9,cis-12Octadecatrienoic
Eicosanoic
Docosanoic

00.1
14.1
15.3
01.3
3.79.8
34.3
45.8
29.0
44.2
00.3

20:0
22:0

00.3
00.2

a
b

Adapted from Gubitz et al. (1999).

xx:y indicates xx carbons in the fatty acid chain with y double bonds.

1717

of 400 rpm. Inside the glass water bath, there was a

100 V, 500 W electric water heater and a shielded K type
thermocouple probe. A voltage regulator controls temperature level and heat supply.
2.3. Experimental procedure
2.3.1. One-step alkali base catalyzed transesterication
One-step alkali base catalyzed transesterication was
carried out for methyl ester production process from
CPO, NCO, and CJCO. It was established that transesterication depends on several basic variables, namely, catalyst
type, alcohol type, catalyst-to-oil ratio, alcohol-to-oil ratio,
reaction temperature, reaction time, agitation rate, FFA,
and water content of oils (Ma and Hanna, 1999). In this
work, extensive preliminary experimentation with vegetable oils samples indicated that it was most ecient to x
reaction temperature at 65 C, agitation rate 400 rpm,
and reaction time for 2 h.
Firstly, in the transesterication process, dierent catalyst NaOH-to-oil ratios (0.5%, 1.0%, 1.5%, 2.0%, 2.5%
and 3.0% w/w) and dierent methanol-to-oil ratios (10%,
15%, 20%, 25%, 30% and 40% w/w) were used to investigate their inuence on the methyl ester yields of the oils.
All the reactions were carried out in the reaction glass
tubes, which were immersed in a glass water bath placed
on the plate of magnetic stirrer of 400 rpm. The temperature and the reaction time for all process were maintained
at 65.0 0.5 C and for 2 h, respectively. After the reaction, the mixture was allowed to settle for 2 h to overnight
before separating the glycerol layer and the top layer
including methyl ester fraction was removed in a separated
bottles, weight and analyzed by GC. In practically, the separated methyl esters must be conducted to remove impurities by washing with hot water until washing water was
neutral. However, due to small amount of the oil samples
used in the glass reaction tubes, the renement stage on this
experiment was omitted.
2.3.2. A two-step acidbase catalyzed transesterication
Therefore, a two step process, acid-catalyzed esterication process and followed by base-catalyzed transesterication process, were selected for converting CJCO to methyl
esters of fatty acids. The rst step was acid esterication
and pretreatment for removing FFA in the oil, which is
mainly a pretreatment process, which could reduce the
FFA. It was reported that to get complete FFA esterication in some vegetable oils, could be done in the reaction
temperature 50 C. The process was intended to convert
FFA to esters using an acid catalyst (H2SO4 1% w/w) to
reduce the FFA concentration of CJCO below 2%. Second
step was alkali base catalyzed transesterication.
2.3.2.1. Acid pretreatment. On this step, the CJCO was
poured into the reaction glass tubes and heated. The solution of concentration H2SO4 acid (1.0% based on the oil
weight) in methanol was heated at 50 C and then added

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H.J. Berchmans, S. Hirata / Bioresource Technology 99 (2008) 17161721

into the reaction glass tubes. Dierent methanol to oil

ratios by weight were used, namely at 0.10, 0.15, 0.20,
0.25, 0.30, 0.40, 0.50, 0.60 and 0.70 to investigate their
inuence on the acid value of CJCO. The acid values of
the reaction mixtures were measured, while the compositions of the reaction mixtures were investigated by high
performance liquid chromatography (HPLC) and by gas
chromatography (GC). After one hour of reaction, the
mixture was allowed to settle for 2 h and the methanol
water fraction at the top layer was removed. The optimum
condition having the lowest acid value was used for the
main transesterication reaction.
2.3.2.2. Base catalyzed transesterication. In the second
step, optimum condition for NaOH to oil ratio and methanol to oil ratio were investigated. Firstly, the oil product
that has been pretreated from the rst step was poured into
the reaction glass tubes and heated at 50 C. The solution
of NaOH in methanol at 0.5%, 1.0%, 1.5%, 2.0% and
3.0% w/w of the oil were heated to 50 C prior to addition
and then added to the heated oil. The reaction mixture was
heated and stirred again at 65.0 0.5 C and 400 rpm for
2 h. The mixture was allowed to settle 2 h or overnight
before separate the glycerol layer to get the methyl ester
layer of fatty acids on the top. Then the produced methyl
esters were determined by GC. The same procedure was
conducted for the investigation of optimum methanol to
oil ratio. The investigation was carried out by using optimum NaOH amount in various methanols to oil ratio by
weight at 0.1, 0.2, 0.35, 0.5, and 0.6.

6890 series that equipped with a ame ionization detector

and a capillary column of acidied polyethylene glycol
(HP-624, 30 m 25 lm 0.25 lm). The GC oven was kept
at 80 C for 5 min, heated at 10 C/min up to 310 C, where
it was kept for 1 min, and a total analytical time was
29 min. The carrier gas was helium (0.7 ml/min). The analysis of a sample by GC was carried out by injecting 1 ll of
the sample solution into the GC. The formed methyl ester
was identied by comparing its retention time to the retention time of standard methyl ester of fatty acid. Quantitative analysis of the weight percentage of the produced
methyl esters/biodiesel was determined by decane internal
standard method (Nguyen et al., 2005). Free fatty acids
in the oils were transestericated using boron triuoride
methanol solution and measured by GC (Yamaoka, 1978).
2.4.3. LC method
Fatty acids in the methanol extracts from the oils were
then analyzed by using high performance liquid chromatography (HPLC) (Shimadzu, LC-10AT) which consisted
of the column (Capcell Pak C18, 25 cm in length 4.6 mm
in inner diameter, 5 lm, Shiseido Finechemicals. Co.) and
ultraviolet detector at 220 nm (Tosoh, UV-8024) operated
at 30 C with 0.7 ml/min ow rate of 80% acetonitrile solution containing 20% of 0.1% H3PO4 as a carrier solvent.
The sample volume was 20 ll and a peak identication
was made by comparing the reaction time between the sample and the standard compound.
3. Result and discussion

2.4. Analytical methods

3.1. One-step alkali base catalyzed transesterication

2.4.1. Acid value

The acid value of the reaction mixture in the rst stage
was determined by the acid base titration technique
(ASTM, 2003). A standard solution of one mol potassium
hydroxide solution was used.

Alkali base catalyzed transesterication result of CPO,

NCO, and CJCO were investigated by changing catalyst
NaOH to oil ratios (% w/w) and catalyst to oil ratios (%
w/w) as shown in Fig. 1a and b. The high conversion
was obtained with 1.0% of catalyst NaOH to oil ratio
and 28% of methanol to oil ratio, and under these condition, the FAME yield was 80% for CPO and 85% for
NCO. The results of CJCO were shown in Fig. 2. Fig. 2
indicated that the optimum condition of alkali base cata-

2.4.2. GC method
The composition of biodiesel products were analyzed
using a Gas Chromatography of Hewlett Packard Plus

Fig. 1. FAME yields of alkali base catalyzed transesterication of CPO and NCO: (a) eect of NaOH-to-oil-ratio and (b) eect of methanol-to-oil-ratio.

H.J. Berchmans, S. Hirata / Bioresource Technology 99 (2008) 17161721

1719

Table 2
The analytical result of FFA for CJCO, CPO and NCO by GC

Fig. 2. FAME yields of alkali base catalyzed transesterication of CJCO.

lyzed transesterication for CJCO required more catalyst

and methanol. The optimum NaOH to oil ratio and the
optimum methanol to oil ratio were 3.3% w/w and 70%
w/w for CJCO. The reason of higher consumption catalyst
NaOH and methanol in the transesterication process of
CJCO is considered to be FFA. A high FFA in the oil
deactivates the catalyst NaOH, and the addition of excess
amount of NaOH as compensation gave rise to the formation of emulsion, which increased viscosity, lead to the formation of gels and the problem associated with glycerin
separation and loss in ester yield. Although it is shown that
the maximum FAME yields of CPO and NCO were 85%
and 87%, respectively as shown in Fig. 1b, the methyl ester
yield of CJCO was only 55% as shown in Fig. 2.
Since one of reasons for low yield of base catalyst
transesterication of CJCO is considered to be due to coexistence of FFA in the oil, FFA in the oil were investigated
by HPLC, GC and acid titration method.
3.2. Contents of FFA in CJCO
In Jatropha curcas seed oil extraction, CJCO is stored at
long time prior to utilization. Without proper handling and
storage, the process causes various chemical reactions such
as hydrolysis, polymerization, and oxidation. Therefore,
the physical and chemical properties of the CJCO changes
during handling and storage. Many researches have been
conducted to characterize these physical and chemical
changes in the other vegetable oils (Monyem and Van Gerpen, 2001; Leung et al., 2006; Oversen et al., 1998). The
percentage of FFA has been found to increase due to the
hydrolysis of triglycerides in the presence of moisture and
oxidations. Degradation of the CJCO results higher concentration of FFA. Comparing to CPO and NCO, CJCO
contains higher concentration of unsaturated fatty acids,
which are mainly linoleic acid (18:2) and oleic acid (18:1),
as shown Table 1. The oxidation of the unsaturated fatty
acids component in the CJCO might occur easily and it

Oil

FFA
(%)

Myristic
(%)

Palmitic
(%)

Linoleic
(%)

Oleic
(%)

Stearic
(%)

Crude Jatropha
curcas oil
(CJCO)
Crude palm oil
(CPO)
Net coconut oil
(NCO)

14.9

0.0

2.4

6.9

5.4

0.2

6.1

0.2

2.6

2.5

0.5

0.3

1.2

0.3

0.2

0.2

0.3

0.2

could lead to degradation of the oil (Canakci, 2007). The

reason for auto oxidation is due to the presence of double
bounds in the chains of unsaturated fatty acids
compounds.
The free fatty acids in the extracts with methanol from
the oils were analyzed by HPLC. Oleic acid and linoleic
acid were detected in the FFA extract from CJCO, and
their concentrations were much higher than FFA in the
methanol extracts from CPO and NCO. The precise contents of FFA in the oils were analyzed by GC, and the total
concentrations of FFA in the oils were 14.9% w/w for
JCJO, 7.2% w/w for CPO and 1.8% w/w for NCO, respectively (see Table 2).
3.3. A two-step acidbase transesterication of CJCO
The problem with processing of CJCO that had high
content FFA was that FFA could not be converted to
FAME using an alkaline catalyst due to formation of fatty
acid salts (soap). The soap could prevent separation of the
methyl ester layer from the glycerin fraction. An alternative
method is to use acid catalysis, which are able to esterify
FFA. While, the esterication reaction stop in many cases
due to the eect of the water produced when the FFA react
with methanol to form esters (Canakci and Van Greppen,
1999). Therefore, the two steps process, acid-catalyzed
esterication process and followed by base-catalyzed
transesterication process, were selected for converting
CJCO to methyl esters of fatty acids.
3.3.1. Acid pretreatment
The objective of this stage was to reduce the acid value
or FFA contents of CJCO. Important variable aecting the
acid value in the esterication process was the methanol to
oil ratio, the acid to oil ratio, reaction temperature, and
reaction time. It was reported that to get completely FFA
esterication in some vegetable oils, could be done in the
reaction temperature 50 C, the reaction time one hour,
and the acid H2SO4 to oil ratio 1% w/w (Ghadge and
Raheman, 2005; Veljkovic et al., 2006). Therefore, these
conditions were selected to investigate the eect of methanol to oil ratios in the acid values of CJCO. The eect of
methanol amount on acid values and FFA of the mixtures
after one hour reaction is shown in Fig. 3. The gure
indicates that the acid value or FFA concentration was

1720

H.J. Berchmans, S. Hirata / Bioresource Technology 99 (2008) 17161721

Fig. 3. Inuence of methanol quantity on acid value and FFA of crude

Jatropha curcas oil in the acid catalyst esterication stage.

inuenced by the quantity of methanol. The FFA concentration reduced sharply to 3% at 10% w/w of methanol to
oil ratio and then decreased gradually to 1% at 70% w/w of
methanol to oil ratio. Increasing the methanol amount was
no signicant eect to acid value or FFA concentration
reduction. It was due to the eect of water produced during
the esterication of FFA. In practically, the esterication
process might be improved by water removal in the mixture
continuously. Therefore, there was an optimum quantity of
methanol required to complete the esterication process of
all FFA in CJCO. The optimum methanol to oil ratio was
selected 60% w/w at the FFA concentration less than 1%,
acid value of 2 mg KOH/g-oil. The rst stage process
was pretreatment process for removing FFA in the oil
and the second stage process.
3.3.2. Base catalyzed transesterication
Successful alkali base catalyzed transesterication process requires lower FFA content in CJCO, which is less
than 2%. However, Table 2 indicates higher FFA content
in CJCO sample, which is about 15%. Although Fig. 2
shows the result of direct transesterication of CJCO using
basic catalyst, by direct transesterication, methyl ester
yield of CJCO was only 55%, which was very low yield
comparing to methyl ester yield of CPO and NCO. Thus,
it is clear that high FFA content in the oil aected the
methyl ester yield.
The two-stage transesterication process of CJCO
showed higher methyl ester yield than single stage or direct
transesterication process. After acid pretreatment/acid
catalyst esterication, FFA in the oil moved into methanol
phase. The cleaned oil was brought to the second stage,
base catalyzed transesterication with only NaOH to oil
ratio at 1% w/w. In the second stage, the low level of
remained FFA from the rst stage clearly aected the
transesterication process. Therefore, investigation of optimum catalyst to oil ratio and optimum methanol to oil
ratio was required. Fig. 4 shows that the optimum catalyst
to oil ratio was 1.4% w/w and optimum methanol to oil
ratio was 24% w/w. At this optimum condition, the methyl
ester yield was 90%, which was higher than the methyl ester
yield of direct transesterication.

Fig. 4. FAME yields of CJCO after a two step acid/base transesterication process.

Table 3
The analytical result of components of FAME for CPO, NCO and CJCO
Methyl ester

CPO (%)

NCO (%)

CJCO (%)

Methyl
Methyl
Methyl
Methyl
Methyl
Methyl
Methyl

0.41
1.24
42.42
0.28
3.30
47.04
5.32

54.39
21.40
10.58
0.24
1.69
6.41
5.29

0.06
0.10
14.96
1.10
3.85
32.49
47.43

laurate
myristate
palmitate
palmitoleate
stearate
oleate
linoleate

Qualitative and quantitative analysis result of methyl

ester components in CJCO, CPO, and NCO transesterication product are presented in Table 3. The table indicates
that the FAME from CJCO contained mainly methyl linoleate (47.4%) and methyl oleate (32.4%), which are comparable to fatty acid composition in CJCO feedstock. The
other hand, the methyl esters from CPO contained mainly
methyl palmitate (42.4%) and methyl oleate (47.0%), and
the methyl esters from NCO contained mainly methyl laurate (54.4%), methyl myristate (21.4%), and methyl Palmitate (10.6%).
4. Conclusion
Biodiesel production from CJCO with a high content of
FFA has been investigated. In alkali base catalyzed transesterication process, the presence of high concentration of
FFA reduced the yield of methyl esters of fatty acids significantly. A two-stage transesterication process was selected
to improve the methyl ester yield. The rst stage was acid
pretreatment process, which could reduced the FFA level
of CJCO to less than 1%. The second stage, alkali base catalyzed transesterication process gave 90% methyl ester
yield.
Acknowledgements
This work was done in Biomass Technology Research
Center AIST Chugoku, Kure-Hiroshima and was supported by Japanese International Centre Agency (JICA),
Japan under the project Research on Standard, Material

H.J. Berchmans, S. Hirata / Bioresource Technology 99 (2008) 17161721

Reference, and Evaluation Technology for the year 2006.

We are very grateful and express our gratitude to Dr. Tomoaki Minowa, Dr. Kinya Sakanishi and Mrs. Takemi
Nishikiori in Biomass Technology Research Center Laboratory for their technical support in this research.
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