Renewable Energy 77 (2015) 521e526

Contents lists available at ScienceDirect

Renewable Energy
journal homepage: www.elsevier.com/locate/renene

Biodiesel production from waste cooking oil by acidic ionic liquid as a

catalyst
Zahoor Ullah*, Mohamad Azmi Bustam, Zakaria Man
PETRONAS Ionic Liquid Centre, Department of Chemical Engineering, Universiti Teknologi PETRONAS, Tronoh 31750, Malaysia

a r t i c l e i n f o a b s t r a c t

Article history: The production of biodiesel from waste palm cooking oil using acidic ionic liquid as a catalyst was
Received 23 April 2014 investigated. Generally, alkaline based catalysts are used to catalyze the transesterication reaction, but
Accepted 16 December 2014 for waste cooking oil where it contains high free fatty acids, direct usage is not possible due to separation
Available online
of layers and saponication problems. In this study, a two-step process i.e. esterication and trans-
esterication was performed. The ionic liquid butyl-methyl imidazolium hydrogensulfate (BMIMHSO4)
Keywords:
was found to be effective due to its longer side chain. The highest biodiesel Yield was obtained with
Waste cooking oil
5 wt.% BMIMHSO4, methanol:oil of 15:1, 60 min reaction time, at 160
C, and agitation speed of 600 rpm,
Biodiesel
Ionic liquids
reduced the waste cooking oil acid value lower than 1.0 mg KOH/g. The second step of transesterication
Esterication/transesterication catalyzed by KOH at 60
C, 1.0 wt.% and 60 min of reaction time. The nal yield was 95.65 wt.%. The
synthesized biodiesel was analysed by 1H NMR, FTIR TGA and GC, and its physiochemical properties were
determined by standard ASTM methods.
2014 Elsevier Ltd. All rights reserved.

1. Introduction
Rising concern for world energy crises and the effect on global
warming due to heavy consumption of fossil resources have
steered, researchers to focus on alternative fuel resources; and one
resource that has receive substantial attention is bio-based fuels
(ethanol and biodiesel). A recent study on biodiesel life cycle, in-
dicates a considerable reduction of greenhouse gas (GHG) when
bio-based fuels is used as a blending component with petroleum
diesel [1,2]. Biodiesel is an alternative upcoming clean-burning fuel
currently being produced from different sources like grease, vege-
table oils, or animal fats etc. The chemical structure of biodiesel
molecule is almost entirely of fatty acid alkyl esters [3,4]. It is used
as an alternative fuel to conventional petroleum diesel, mainly
because biodiesel has advantageous properties such as renewable
resources, biodegradable and environmentally pleasant emission
prole. Currently, the most common way to synthesize biodiesel is
from fats and oil by transesterication of triacyl glycerols with
methanol or ethanol in the presence of alkali or acid catalysts. In
this process, methanol is the most commonly used due to its
availability and low price; even though in the literature researchers
have developed other alcohol of choice according to their
* Corresponding author.
E-mail address: zahoor7979@yahoo.com (Z. Ullah).
processes. The main product of fatty acid methyl esters produced
are called biodiesel and the produced glycerine is the by-product. In
this process, diglycerides and monoglycerides are the in-
termediates [5,6]. The transesterication process occurs according
to the chemical equation as shown in Fig. 1.
Biodiesel has found favour for use as a mix constituent of petro-
diesel fuel due to its advantageous properties such as low sulphur
content, lack of aromatics, higher lubricity and very high cetane
values. Biodiesel can be used with petro-diesel as freely in all
proportions, and all the major automotive manufacturers have
approved its use. It can be used in existing conventional
compression ignition engines and does not require any special
modication to the engines [1,7].
However, in spite of its favourable properties economic reasons
have been one of the major obstacles to its commercialization.
Depending on the oil feedstock, it is reported that biodiesel is costly
and its price is a half times higher than that of petroleum diesel.
According to the literature, 70e95% of biodiesel price is due to the
cost of raw material, which is, either vegetable oil or animal fats.
Therefore, in an attempt to enhance the economic viability of bio-
diesel, feedstock of non-edible oil such as waste cooking oil (WCO)
has been considered because it is available at a reasonable price or
even free [5,8], which is an effective way to reduce the production
cost. The application of WCO as feedstock for biodiesel production
is perceived as one of the potential way of effectively reducing the

http://dx.doi.org/10.1016/j.renene.2014.12.040
0960-1481/ 2014 Elsevier Ltd. All rights reserved.
522 Z. Ullah et al. / Renewable Energy 77 (2015) 521e526
cost of producing biodiesel [10]. However, during frying the oil can
undergo various chemical reactions such as polymerization, hy-
drolysis and oxidation owing to their reaction to light, heat and
oxygen. Which as a result form different chemical compounds such
as dimer, polymer, oxidized triglycerides (by hydroperoxides in-
termediate to obtain aldehydes, ketones, etc.) diglyceride and fatty
acids [11]. In order to obtain a reasonable conversion to biodiesel,
when WCO is used as the raw material, the fatty acids of WCO
should be converted to FAME (biodiesel) by esterication with
methanol. Usually the esterication process is an acid catalysed
process, in which acids such as sulphuric acid, hydrochloric acid,
and sulfonic acid are usually selected as the traditional acid catalyst
[12]. However, the majority of acid catalysts are highly corrosive
and are not easy to recover for reuse [13]. Several methods have
been developed for the synthesis of biodiesel e.g., blending and
direct use of raw oil, micro-emulsication, pyrolysis [14e16], and
acid catalysed transesterication with alcohols like methanol or
ethanol, where the catalyst plays the vital role for biodiesel pro-
duction. The conventional production generally uses strong acid/
base catalysts and raw materials such as cotton seed oil, soybean
oil, waste cooking oil, rapeseed oil or sunower oil. However, due to
the undesirable properties of acids and bases, there is the need to
nd an alternative catalyst with high catalytic activity, while
avoiding the foregoing short comings. A new emerging type of
chemical that has shown some potential as catalyst for the process
is called ionic liquids (ILs) owing to their favourable properties such
as environmentally friendly, high thermal stability, negligible
vapour pressure, non-ammable, and has adjustable physical and
chemical properties [17]. Recently, for the esterication and
transesterication reactions, the use of ionic liquids (ILs) as the
alternative catalyst for biodiesel production has been considered.
As a clean and promising catalyst, ionic liquids have attracted more
interest over conventional catalysts. Even though there are many
types of ionic liquids possible, in the case of producing biodiesel by
transesterication process, only three ILs have shown the potential
of obtaining high yield. To search other possible applications for
acidic ILs for their catalytic action and to study the inuence of their
different functional groups on biodiesel production, it will be
highly interesting as they have tremendous properties [8,18e20].
In this study, an acidic (Brnsted) ionic liquid was prepared and
used as a catalyst to esterify the waste cooking oil for biodiesel
production. It was characterized by NMR, FTIR spectroscopy and
TGA. The effects of various process parameters on the production of
biodiesel were studied.
2. Experimental
2.1. Materials
The feedstock waste cooking oil (WCO) used in this work was
collected from a local cafeteria. The chemicals including 1-
methylimidazole, N-butylimidazole, 1-Butyl-3-methyl-imidazo-
lium chloride, sulphuric acid, diethyl ether, toluene, acetonitrile,
methanol, and potassium hydroxide were bought from Merck, all of
these chemicals were used without any further purication.
The WCO was collected and its different physiochemical prop-
erties such as acid value, peroxide value, saponication value,
caloric value, kinematic viscosity, density, specic gravity, ash
point and water content were determined by ASTM and EN
methods.
2.2. Ionic liquids preparation
All the ionic liquids were prepared by known methods reported
in the literature [21] with little modication.
Fig. 1. Biodiesel synthesis by transesterication process from vegetable oils with
methanol.
The starting material such as butyl-methyl-imidazolium chlo-
ride, N-butyl-imidazole, or N-methyl-imidazole was separately
dissolved in anhydrous acetonitrile in 250 mL ask tted with a
long condenser for reux, with vigorous stirring and under nitro-
gen purge. Then, still continuously stirring, under icy condition,
concentrated sulphuric acid was slowly added to the mixture. The
mixture was stirred continuously to ensure completion of reaction
and for immediate removal of HCl gas from the reaction phase, N2
gas was used to ush it. The Brnsted acidic IL was washed three
times with toluene and dried in vacuum for 8 h. The synthesized ILs
are BMIMHSO4, BIMHSO4, MIMHSO4.
2.3. Two step catalytic process
2.3.1. Esterication of WCO by ionic liquids (rst stage)
The aim of this step is to minimize the WCO acid value. Firstly
the WCO was preheated in an oven to evaporate any trace amount
of moisture, before starting the esterication process. A measured
amount of WCO was place in a reux condenser placed on a heating
plate. A calculated amount of ionic liquid and methanol solution
were prepared and charged to the oil with continuous stirring. The
reux condenser was assembled with cooled water chillier to
provide and circulate the cooled water to maintain the super
heated methanol during the conversion process. The reaction was
conducted at various conditions to study the effect of ionic liquid
type on the percentage of conversion of the esterication reaction.
The concentration range of ILs was 3e7.5 wt.%, the reaction tem-
perature range was 80e180
C, stirring speed was between 100 to
700 rpm, the methanol to WCO molar ratio range was from
3:1e18:1 and the reaction time was varied from 30 to 120 min.
These three catalysts (ILs) displayed different trends of FFA con-
version to esters. At the completion of every reaction, the mixture
was poured into a separating funnel and was left overnight to allow
the layers to completely separate. The ionic liquid was separated
and the treated oil was subjected to alkali catalyst for trans-
esterication reaction.
2.3.2. Transesterication of WCO by KOH (second stage)
In order to achieve successful result of treated WCO trans-
esterication by alkali catalyst, the feedstock is required to have
lower FFA content [22]. KOH has been suggested by many re-
searchers as an alkali catalyst for the transesterication of oil
having lower FFA [23e25]. A methanolic KOH solution was pre-
pared and added to the treated WCO in a round bottom three
necked ask. The reaction was performed at 60
C for 60 min with
constant stirring. Next, the mixture was transferred to a separating
funnel and allowed to settle at room temperature; the mixture
separated into three layers. The upper layer, which was biodiesel,
was separated and washed with deionized water and ethyl acetate
to remove any minor impurities, and dried under vacuum for
100
C for 5 h (Fig. 2).
 Z. Ullah et al. / Renewable Energy 77 (2015) 521e526 523

2.5. Ionic liquid recovery

The IL was recovered from the esterication (1st step). After

completion of the esterication step the methanol was distilled off
under vacuum, and cooled the mixture for a few moments and then
centrifuge for 30 min, separates the IL from the bottom phase of the
treated oil and then washed with hexane and ethyl acetate and then
dried in vacuum for 4 h to reuse.

3. Results and discussion

The different physio-chemical properties of WCO along with

unused cooking oil of the same type were determined by estab-
lished methods as shown in Table 1
There is limited information in the literature on the use of ILs as
a catalyst for biodiesel production from WCO. The acidic ionic liq-
uids used in this work were selected, synthesized and characterized
by 1HNMR. Before using, as a catalyst for biodiesel production from
WCO by the two step process. The experiments were conducted in a
small scale setup to determine the optimum values for different
reaction parameters. A possible reaction mechanism of triglyceride,
ionic liquid and methanol is proposed as shown in Fig. 3.

3.1. 1H NMR results of butyl-methyl-imidazolium hydrogensulfate

(BMIMHSO4)

1
Spectroscopic analysis: H NMR (500 MHz, DMSO):
d 0.84e0.87 (3H, t), 1.19e1.26 (2H, m), 1.71e1.77 (2H, m), 3.85
(3H, s), 4.15e4.18 (2H, t), 7.72 (1H, s), 7.79 (1H s), 9.19 (1H, s).

1
3.2. H NMR result of butylimidazolium hydrogensulfate (BIMHSO4)

Spectroscopic analysis: 1H NMR (500 MHz, DMSO):

Fig. 2. Schematic diagram of the process, which includes, pre-treatment of feedstock, d 0.85e0.88 (t, 3H), 1.17e1.25 (m, 2H), 1.72e1.78 (m, 2H),
catalyst preparation, esterication and transesterication reaction, methanol recovery, 4.17e4.20 (t, 2H), 5.74 (s, 1H), 7.60 (s, 1H), 7.75 (s, 1H), 9.03 (s, 1H).
catalyst removal, and biodiesel separation and purication.

2.4. Determination of yield 3.3. 1H NMR result of methylimidazolium hydrogensulfate

According to Leung and Guo, the yield of the product can be
calculated by using the following Eq. (1) [22,26]. After collection the
upper layer, the biodiesel yield was calculated by the following
equation. It is the product yield dened as the percentage weight of
the nal product relative to the oil weight at the start.
(MIMHSO4)
Spectroscopic analysis: 1HNMR (500 MHz, DMSO): d 3.86 (s,
3H), 5.72 (s, 1H), 7.59 (s, 1H), 7.66 (s, 1H), 8.98 (s, 1H).
3.4. Optimization study of different parameters

Weight of methyl ester produced 3.4.1. The inuence of catalyst concentration

Yield of BD  100 The catalyst amount is very important for the reaction. For the
weight of oil used in reaction
conducted esterication reaction, the catalyst concentration was
(1)
optimized by varying the concentration range between 3 and
7.5 wt.% while other parameters were xed at 160
C, 1 h, 600 rpm
and 15:1. The results of biodiesel yield with different amount of
Table 1 BMIMHSO4, BIMHSO4, MIMHSO4 catalysts are shown in Fig. 4. The
Physiochemical properties of used and unused cooking oil.
three catalysts show a different trend of conversion to esters, and
Properties Unused cooking Used cooking the amount of catalyst required to achieve the same conversion
oil values oil values varies. The utmost conversion was obtained at 5 wt.% and 5.5 wt.%
Acid value (mg KOH/g) 0.3 4.03 of the catalysts. As indicated in Fig. 4 the ionic liquids in terms of
Caloric value (J/g) e 39658 increasing percentage of conversion is in the order of
Saponication value (mg KOH/g) 194 177.97
BMIMHSO4 > BIMHSO4 > MIMHSO4. This result also indicates that
Peroxide value (meq/kg) <10 10
Density (gm/cm3) 0.898 0.9013 increasing the cation alkyl side chains enhances the effect of ILs on
Kinematic viscosity (mm2/s) 39.994 44.956 the conversion of WCO to biodiesel. A similar statements reported
Dynamic Viscosity (mpa.s) 35.920 40.519 and cited in literature [8,21,27e30]. Therefore, according to the
Flash point (
C) 161e164 222e224 result, BMIMHSO4 was selected as the best catalyst for the study of
Moisture content (wt%) 0.101 0.140
other parameters for biodiesel synthesis from WCO.
524 Z. Ullah et al. / Renewable Energy 77 (2015) 521e526
Fig. 3. Proposed reaction mechanism of triglycerides and methanol using the ionic
liquid [BMIM] HSO as a catalyst.
3.4.2. The inuence of reaction time
The effect of reaction time on yield was investigated. Fig. 5
shows the reaction time effect on biodiesel production within the
range of 30e120 min. The catalyst was efcient in the rst hour of
reaction with the yield reaching up to 95.65%. After that there was
no considerable change in the yield, therefore the reaction time of
1 h was identied as the optimum reaction time.
3.4.3. The inuence of reaction temperature
Temperature is one of the vital factors which inuence the re-
action and yield of FAME product. The effect of reaction tempera-
ture on the esterication of WCO with methanol in the presence of
ionic liquids was investigated in the temperature range of
80e180
C in steps of 20
C for 1 h. Fig. 6 shows the effects of re-
action temperature on the ester yield. The other variables were
xed as: BMIMHSO4 concentration 5 wt.%, methanol:oil ratio 15:1,
time 1 h and stirring rate 600 rpm. The biodiesel yield increased as
the temperature increased, which suggests that increasing the re-
action temperature will push the catalytic activity to a certain
Fig. 4. Effect of ILs type on yield at time 2 h, temperature 160
C, and methanol:oil ratio 15:1.
Fig. 5. The effect of reaction time on yield at BMIMHSO4 concentration of 5 wt.%,
methanol:oil ratio 15:1, and 160
C.
Fig. 6. Effect of reaction temperature on yield at BMIMHSO4 concentration 5 wt.%,
methanol:oil ratio of 15:1, and 1 h reaction time.
extent. The highest methyl ester yield was achieved at almost
160
C. Therefore, in the present study 160
C was decided as the
optimum reaction temperature.
3.4.4. The inuence of methanol:oil ratio
The methanol to oil ratio is also a very important factor that
affects the yield of biodiesel. In this study, the effect of methanol to
oil ratio was studied in the range of 3:1 to 18:1. Six experiments
were conducted and the results are shown in Fig. 7. The
gure shows that as the molar ratio increases, the yield also in-
creases; this is observed up to 15:1 ratio. For the 18:1 ratio, there is
almost no increase in yield. Thus it can be concluded that conver-
sion increases when the molar ratio is increased from 3:1 to 18:1.
Further increase in the molar ratio had little effect, probably as a
result of a dilution effect on the concentration of ionic liquid.
 Z. Ullah et al. / Renewable Energy 77 (2015) 521e526 525

Table 2
Characterization of biodiesel.

Property Unit ASTM D-6751 EN14214 Synthesized

biodiesel

Kinematic Mm2/s 1.9e6.0 3.50e5.00 5.24

viscosity at 40
C
Density at 15
C Kg/m3 860e894 860e900 879


Flash point C >120 >120 174
Moisture content % <0.05 <0.05 0.03
Acid value mgKOH/g 0.5 0.5 0.41
Cetane number e 48e60 >51 58.3
Caloric value J/g n.r. N.R 40,110

Fig. 7. Effect of methanol:oil ratio on yield at BMIMHSO4 concentration 5 wt.%, reac-

tion time 1 h, and temperature 160
C.
3.4.5. Inuence of agitation speed on the reaction
The effect of agitation speed on the esterication of WCO with
methanol using BMIMHSO4 as catalyst was also investigated.
Different experiments were conducted with different agitation
rates from 100 up to 700 rpm while other parameters were kept
constant at the optimum conditions. The conversion at the stirring
speed, of 500 rpm and 600 rpm was 93.2% and 95.6% yield
respectively, and due to the high yield 600 rpm was decided as the
optimum agitation speed (Fig. 8).
3.4.6. Catalyst recovery
One of the reasons that render ILs as green solvent is their
recycling ability. Experiments for BMIMHSO4 recycling were con-
ducted to study the efciency of recovery. After settling at room
temperature, the product mixture separated into three layers; the
upper one is of biodiesel, the middle one is of glycerol and the
bottom one is of IL, but most of the time the IL layer was invisible as
it is miscible in glycerol. After separating this mixture from the
biodiesel layer, it was then centrifuged to separate the layers. The
bottom layer, which was IL, was separated and washed with hexane
before reuse. The recycled IL was then charged with methanol
followed by WCO for biodiesel synthesis; the process was suc-
cessfully repeated for ve times after which a slight decrease was
observed as can be seen clearly from Fig. 9. After the sixth time of
reusing this catalyst, the yield decreased to 83%.

3.5. Physical properties of biodiesel from WCO oil

The results of fuel properties of the nal product are given in

Table 2. It can be seen that these fuel properties of biodiesel from
WCO catalysed by acidic ILs meets the ASTM D-6751 and EN14214
standards.

4. Conclusion

The conversion of waste palm cooking oil to biodiesel by the two

Fig. 8. Effect of agitation speed on yield at BMIMHSO4 concentration 5 wt.%, meth-
anol:oil ratio of 15:1 reaction time 1 h and temperature 160
C.
step process using ILs as a catalyst has been successful with the
yield upto 95%. The three Bronsted acidic ionic liquids were syn-
thesized, and it was discovered that different amounts are required
to convert the low feedstock into esters. The ionic liquid
BMIMHSO4, due to its longer chain length, has higher conversion
efciency as compared to the other two ILs; thus it was selected as a
better one. This nding agrees with other works described in the
literature where different alkyl chain lengths with increment of
even one or two carbon atoms in the chain had been observed to
give a similar effect. The optimized reaction conditions for the
process are concentration of catalyst is 5 wt.%, methanol:WCO is
15:1, reaction time is 60 min, temperature is 160
C, and agitation
speed is 600 rpm. At the optimum conditions, the biodiesel yield
was 95.65%. In comparison to conventional solvents, the ILs with
Bronsted acidity has the potential to produce low cost biodiesel
from low cost feedstocks in addition to being environmentally
friendly.

Acknowledgement

The author gratefully acknowledges the nancial assistance

provided by the Petronas Ionic Liquid center, Chemical Engineering
Fig. 9. Catalyst reusability versus yield (%) of biodiesel. Department, Universiti Teknologi PETRONAS (UTP) Malaysia.
526 Z. Ullah et al. / Renewable Energy 77 (2015) 521e526

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