MATEC Web of Conferences 156, 06003 (2018)

https://doi.org/10.1051/matecconf/201815606003
RSCE 2017

Diethyl Ether Production as a Substitute for Gasoline

Riza Alviany1, Arifuddin Wahyudi1, Ignatius Gunardi1, Achmad Roesyadi1*, Firman Kurniawansyah1, Danawati Hari
Prajitno2

1
Chemical Engineering Department, Industrial Technology Faculty, Sepuluh Nopember Institute of Technology (ITS), Surabaya 60111,
Indonesia
2
Chemical Engineering Industry Departement, Vocation Faculty, Sepuluh Nopember Institute of Technology (ITS), Surabaya 60111,
Indonesia

Abstract. Diethyl ether is one of alternative fuel that could be used as a significant component of
a blend or as a complete replacement for transportation fuel. The aim of this research is to
produce diethyl ether through dehydration reaction of ethanol with fixed bed reactor using
nanocrystalline ɣ-Al2O3 catalyst. Nanocrystalline ɣ-Al2O3 catalyst was synthesized by
precipitation method using Al(NO3)3.9H2O as precursors and NH4OH as the precipitating agent.
Dehydration reaction was performed at temperature range of 125 to 225°C. The result shows
that synthesized ɣ-Al2O3 catalyst gave higher ethanol conversion and diethyl ether yield than that
of commercial Al2O3 catalyst. The use of synthesized ɣ-Al2O3 catalyst could reach ethanol
conversion as high as 94.71% and diethyl ether yield as high as 11,29%.

1 Introduction conventional gasoline [3], [5], [6]. Consequently,

ethanol-DEE mixtures are considered as excellent
Diethyl ether (DEE) is an important chemical for the gasoline alternatives which diethyl ether can be
laboratory and industry uses. It has been widely used as produced by dehydration of ethanol over acidic catalysts.
a solvent or extractant, reaction medium, fragrance, Diethyl ether is generally prepared by the
explosive materials, pharmaceutical chemical processes, dehydration process of ethanol (Barbet process) using
fuels and fuel additives [1]–[6]. As a fuel, DEE has been sulfuric acid catalyst (homogeneous catalyst). The
used as starting fluid in countries with cold climates downside of this process is the difficulty of catalyst
because of its high volatility and low flash point [6]. In separation and catalyst corrosiveness. Corrosive catalysts
addition, cetane and octane number, reasonable energy, make investments in equipment quite expensive. Thus,
high oxygen content, and high miscibility in diesel fuel homogeneous catalysts are replaced by heterogeneous
and bioethanol become DEE available advantage as catalysts. heterogeneous catalyst that has long been
blending material to improve the ignition [3]. DEE has a known for ethanol dehydration is Al2O3. One of the
potential as an alternative transportation fuel to replace phase types of Al2O3 is γ- Al2O3. γ- Al2O3 which is
an excessive use of fossil fuels as major energy sources. widely used as catalysts and catalyst supports. γ-Al2O3
The volumetric heating value and octane number are has been known for having a large surface area with
very important parameters for an alternative fuel of acidic and alkaline active sides. The active sides have
gasoline. The latent heat of ethanol is about 3.7 times resulted from the release of water molecules [7]. Primary
higher than that of gasoline, which causes lower alcohol dehydration reaction catalysis by using γ-Al2O3
temperatures during combustion in the engine. A catalyst can produce ether compounds and alkenes.
decrease in engine temperature also causes a formation While the reaction of the secondary alcohol with an acid
of less amount of NOx. Ethanol with an octane number catalyst can produce alkenes and base catalyst produces
of 113 and low Reid vapor pressure is considered as an ketones through dehydrogenation reaction [8]. To
excellent alternative to gasoline but it also causes some maximize the effectiveness of the catalyst, a study was
problems in cold-start of the engine. Fuel regulations carried out by varying technology of catalyst
mandate that motor vehicle fuels should have sufficient manufacturing.
vapor pressure to cold-start, as low as -30 °C [5]. Because of an excessive use of fossils fuel, it is
Combustion of alcohols and ethers produce much less important to produce desirable, higher value chemicals
unburned hydrocarbons and CO and CO2 than and fuels from clean, cheap, abundantly available feed to

*
Corresponding author: aroesyadi@yahoo.com
© The Authors, published by EDP Sciences. This is an open access article distributed under the terms of the Creative Commons Attribution
License 4.0 (http://creativecommons.org/licenses/by/4.0/).
MATEC Web of Conferences 156, 06003 (2018) https://doi.org/10.1051/matecconf/201815606003
RSCE 2017

contribute to the solution of the two major problems of The surface area, pore size distribution and pore
the next century, namely global warming and depletion volume were determined using a nitrogen adsorption-
of oil reserve. desorption method at Chemical Engineering
This research was carried out the synthesis of Departement, Sepuluh Nopember Institute of
nanocrystalline γ-alumina from Al(NO3)3.9H2O by Technology (ITS).
precipitation method. Then, to test the activity of
prepared γ-Al2O3, it was applied in 96% ethanol
2.4 DEE production
dehydration reaction into diethyl ether and compared its
activity with γ-Al2O3 commercial catalyst. DEE production process was performed by adsorption
process in adsorption column and followed by
dehydration of ethanol in a reactor. The dehydration of
2 Experimental
ethanol was carried out in a fixed-bed microreactor with
Some of the steps being taken in this study were γ-Al2O3 an inside diameter of 0.5 in. and length of 30 cm. In the
catalyst synthesis by precipitation method, γ-Al2O3 experiment, 10 gram of molecular sieve was loaded into
catalyst characterization, and DEE production. the adsorption column and 3 gram of catalyst was loaded
into the reactor. The liquid ethanol was vaporized in a
flowing of nitrogen at a flow rate 200 ml/min. the
2.1. Materials reaction was carried out at several temperatures (125,
The commercial Al2O3 used in this study was purchased 150, 175, 200, 225°C). The products condensed by a
from Merck Company. Aluminium nitrate nonahydrate condenser were analyzed by HP 6890 gas
(Merck), ammonium hydroxide (Sigma-Aldrich Co. chromatograph with FID using crosslinked methyl
LLC), distilled water (Sumber Ilmiah Persada), siloxane column. Helium (22.98 psi) was used as carrier
hydrochloric acid (37% from Sigma-Aldrich Co. LLC), gas in GC using the temperature detector at 250°C. The
molecular sieve, nitrogen gas (PT. Aneka Gas Industri) arrangement of equipment used for DEE production is
were also employed. shown in Fig. 1 below.

2.2 Catalyst Preparation

Synthesis of γ-Al2O3 was performed by precipitation

method. Firstly, aluminum nitrate nonahydrate with
different concentration (0.2, 0.3, 0.4, 0.5, and 1 M) was
dissolved in a solution of HCl (0.5 M) and distilled
water. Subsequently, the precipitation was carried out by
adding ammonium nitrate to the solution by stirring at
several temperatures (60, 70, 80, 90, 100oC) by careful
pH adjustment to 9. The precipitate was stirred for
different time (3, 4, 5, and 6 hours) and was maintained
at the same temperature just like in precipitation step.
Then, precipitate filtered and washed by distilled water
and ethanol and then dried at 75oC for 24 hours. The Fig. 1. DEE production equipment
solid precipitate was calcined at 600oC under air flow for
6 hours to obtain the synthesized γ-Al2O3 catalyst.
3 Result and discussion
2.3 Catalyst Characterization
3.1 Nano-crystallite Al2O3 preparation
The synthesized γ-Al2O3 catalyst were characterized
using X-ray diffraction (XRD) at Material and The synthesis/preparation of γ-Al2O3 was performed
Metallurgy Engineering Departement, Sepuluh using precipitation method in which aluminum nitrate
Nopember Institute of Technology (ITS) to determine nonahydrate (Al(NO3)3.9H2O) was used as an aluminum
the crystallinity and the crystal size of the catalyst. Size precursor, hydrochloric acid (HCl) and distilled water as
of the crystal was calculated by using Scherrer formula a solvent, and ammonium hydroxide (NH4OH) as a
based on the data of XRD analysis: precipitating agent. In this research, a variation of the
type of solvent used, the concentration of precursor
D = ĸ λ/βcosɵ (1) solution, stirring time and temperature of the solution
during the precipitation process, has been studied.
Where D is the diameter of the crystal, κ is the shape For the synthesis process of γ-Al2O3 includes several
factor with a value of 0.9-1.4 (generally used ~ 0.9), λ is stages, these are [9]:
the wavelength of X-ray (0.15406 nm), θ is the First stage
diffraction angle (radians), and β is the FWHM (Full The formation of aluminum hydroxide occurs when
Width Half Maximum) of the diffraction peak at half NH4OH added into the aluminum precursor solution.
maximum intensity (radians). Equations 2 and 3 are used for reactions using HCl

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solvents, whereas reaction 4 is used for reactions using 24

distilled water solvent. This stage is illustrated by the

Crystal diameter (nm)

22
reaction as follows: 20
18
Al(NO3)3 + 3HCl AlCl3 + 3HNO3 (2) 16
14
AlCl3 + 3NH4OH  Al(OH)3↓ + 3NH4Cl (3) 12
10
Al(NO3)3 + 3NH4OH  Al(OH)3↓ + 3NH4NO3 (4) 8
0,2 0,4 0,6 0,8 1
Second stage Concentration of precursor (M)
The solution containing precipitate of aluminum
hydroxide in the first stage transformed to boehmite Distilled Water HCl 0.5 M
crystal precipitate after stirring at a constant temperature
(aging with stirring). The reaction is as follows:
Fig. 2. Crystal diameter of γ-Al2O3 at different solvent type and
Al(OH)3 AlOOH↓ + H2O (5) precursor concentration

Third stage
3.1.2 Effect of stirring time in precipitation process
The precipitate of boehmite crystals from the second
stage then washed with water and ethanol sequentially to The operation was performed at the varied stirring time
remove impurities in the form of anions such as nitrate (3, 4, 5, 6 hours) while the concentration of precursor
and chloride ions [10]. After that, the boehmite crystal and precipitation temperature was kept constant at 1 M
precipitate filtered, dried and then calcined at 600°C for and 80°C respectively. The solvent used was 0.5 M HCl.
6 hours. The dried precipitate of boehmite crystal is
calcined to form γ-Al2O3. The following reactions occur: 22
Crystal Diameter (nm)

2AlOOH Al2O3 + H2O (6) 20

18
3.1.1 Effect of solvent in precipitation process 16
14
Two different types of solvents are used to determine the
effect of solvent on the diameter of the resulting Al2O3 12
crystals. The operation was performed at temperature 10
80°C with 5 hours stirring time. 3 4 5 6
The results in Fig. 2 show that in all precursor
Stirring Time (hours)
concentration variations, using 0.5 M HCl solvent
produces the smaller size of Al2O3 crystal than using
distilled water solvent. This occurred due to the reaction Fig. 3. Crystal diameter of γ-Al2O3 at different stirring time
between HCl and NH4OH will produce NH4Cl. The
presence of NH4Cl in the solution would increase the In Fig. 3 it has been shown that the stirring time on
viscosity of the solution, decreasing the molecular precipitation processes influence a crystal diameter of γ-
mobility and dielectric matrix constant of mother Al2O3 produced significantly. The longer the stirring
solution. It also increased the distance between particles time, the greater the diameter of the resulting crystals.
of aluminum hydroxide thus preventing aggregation of This happens because of the longer the stirring time the
aluminum hydroxide particles during the process of mobility of particles in the solution lasts longer Longer
nucleation and growth of particles [10]. duration of stirring time cause particle mobility and
Based on Fig. 2, it can be seen that the crystal size of collision intensity between the particles in solution
the resulting γ-Al2O3 is proportional to the amount of increased, so aggregation that occurs will be greater and
precursor used. The lower the concentration of precursor cause a growth of the crystal particle size of γ-Al2O3
used, the resulting crystal size is also smaller. A lower greater. The smallest particle size is produced by stirring
concentration of precursor make the distance between for 3 hours which is 11.85287 nm.
the particles of aluminum hydroxide higher where can
reduce the aggregation of particles of aluminum 3.1.3 Effect of temperature in precipitation process
hydroxide on the stage of nucleation and growth of
particles. The size of the smallest crystal produced at 0.2 The operation was performed at several operating
M concentration of precursor and 0.5 M HCl solvent. temperatures (60, 70, 80, 90, 100°C) while the
The crystal diameter is 8.62248 nm, while the size of the concentration of precursor and stirring time was kept
largest crystals produced at 1 M concentration of constant at 1 M and 3 hours respectively. The solvent
precursor with distilled water solvent which has diameter used was 0.5 M HCl.
23.6881 nm.

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MATEC Web of Conferences 156, 06003 (2018) https://doi.org/10.1051/matecconf/201815606003
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Fig. 5. XRD patterns of synthesized (PR-C) and commercial γ-

16
Al2O3 (REF-C)
Crystal diameter (nm)

15
14
13
12
11
10
60 70 80 90 100
Temperature of Precipitation (°C)

Fig. 4. Crystal diameter of γ-Al2O3 at different precipitation

temperature

Fig. 4 shows precipitation temperature is a parameter

that influences the size of crystals γ-Al2O3. Generally,
Fig. 6. XRD patterns of γ-Al2O3 from JCPDS
the size of γ-Al2O3 crystals produced increases with the
rising temperature of the precipitation process. An The crystallite sizes were calculated using Scherrer
increasing temperature at precipitation process decrease formula. Results of calculation are listed in Table 1.
the viscosity of the solution and increase the particle
movement so at higher temperature the aggregation of Table 1. Crystallite sizes of the catalyst
the particle bigger. The optimum condition was 70°C
KatalisCJJCatalyst D (nm)
which produce the smallest crystal size, i.e. 10.12907
nm. PR-C 10.1183
REF-C 80.3913
3.2 Catalyst characterization for catalytic test
3.2.2 N2 adsorption-desorption (BET) analysis
For the catalytic test, the catalyst which used was the
catalyst that prepared using 1 M precursor concentration Physical properties of catalyst (specific surface area,
and 0.5 M HCl as a solvent stirred for 3 hours at 70°C total pore volume, and average pore diameter) are
(PR-C) while commercial γ-Al2O3 catalyst as a presented in Table 2.
comparison. Those variables are the optimum variable
which produce high yield of γ-Al2O3 and γ-Al2O3 crystal Table 2. Physical properties of the catalyst
size is still in a nano size.
Catalyst Specific Surface Pore Pore
Area (m2/g) Diameter Volume
3.2.1 Phase analysis (nm) (cc/g)
PR-C 241.437 3.839 0.241
The XRD patterns of the synthesized and commercial γ-
REF-C 133.420 6.185 0.253
Al2O3 are shown in Fig. 5. In that figure, both of catalyst
has three peaks at 2θ = 38°, 2θ = 45.7° and 2θ = 66.7°, The result shows that synthesized γ-Al2O3 (PR-C)
this pattern is suitable with the data (JCPDS) Joint have a higher specific surface area and smaller pore
Committee on Powder Diffraction Standards in Fig. 6. diameter than commercial catalyst γ-Al2O3 (REF-C)
which may decrease higher hydrocarbon and byproducts
leading to increasing of main product selectivity and
ethanol conversion. In addition, the high surface area
would affect to the increased catalytic activity of ethanol
dehydration [11].
intensity (a.u)

Result at Table 1 and Table 2 show a correlation with

an assumption that solids in the form of particles, so the
PR-C surface area for a solid with a certain mass is greater if
REF-C the particle size is smaller. By defining the specific
surface area as the ratio of the total area of the solid
surface to the mass, the specific surface area is greater if
the particle size is smaller.
20 40 60
2ϴ (0) 3.3 DEE process production

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Diethyl ether production process in this research catalytic reactions. The catalytic test aimed to determine
combining two steps, they are adsorption process and the performance of γ-Al2O3 catalyst that was prepared in
the previous process. For this purpose, it will be chromatographic analysis of the liquid product reaction
compared the activity of γ-Al2O3 catalyst which prepared at a temperature of 175°C using PR-C catalyst (Fig. 7)
by precipitation method (PR-C) with γ-Al2O3 and REF-C catalyst (Fig. 8). From chromatogram,
commercial catalysts (REF-C). diethyl ether and residual ethanol compounds were
Adsorption process aimed to reduce the water content detected, while the water was not detected in the GC
in the ethanol feed. To determine the achievement of the chromatogram. Ethylene compounds might be formed in
adsorption process, an analysis of the ethanol feed before the gas phase products, but in this research,
entering the adsorption column and the output product of chromatographic analysis was not performed for gas
adsorption column was done. Ethanol was detected at a product. Diethyl ether was detected at a retention time of
retention time of 3.27 minutes and water was detected at 6.052 minutes, ethanol was detected at a retention time
a retention time of 3.82 minutes. Based on the results of of 5.3 minutes, and methanol was detected at a retention
the GC analysis, there is increasing of ethanol time of 4.5 minutes. Methanol formation process might
concentration from 95.3% (before entering the exist due to the reaction between methane with water
adsorption column) to 97.77% (after passing through the (Eq-7).
adsorption column). An increase in ethanol
concentration is happened because of some water in the CH4 + H2O CH3OH + H2 ∆G398.15 = 117,437.85 J
ethanol solution are adsorbed by molecular sieve. (7)
Basically, a molecular sieve adsorbent using in any
practice can adsorb sufficient water contained in ethanol Another process might happen as the effect of
[12], [13]. catalytic activity of alumina ie cracking, isomerization
In the ethanol conversion process, the reaction which and dehydration process [14]. The methanol formation
may occur is a dehydration reaction of ethanol might also occur through the reaction:
(formation
of diethyl ether compounds, and the formation of CO + 2H2 CH3OH ∆G398.15 = -2,347.41 J
ethylene compounds) [4]. Fig. 7 and 8 shows (8)

Fig.7. Chromatogram of reaction product using PR-C catalyst at 175°C of reaction temperature

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Fig.8. Chromatogram of reaction product using REF-C catalyst at 175°C of reaction temperature

Based on thermodynamics concept, the reaction can the reaction using catalyst PR-C and REF-C. The diethyl
be predicted using thermodynamic parameters. A ether yield is shown in the following figure.
chemical reaction can happen if the value of the Gibbs
96
energy change of a reaction at a specific operating
temperature is negative (ΔGreaction<0) [15]. Judging 94
Conversion (%)

from the value of ∆Gibbs energy, the possible reaction

for the formation of methanol compounds in the present 92
study is reaction (8). It can be seen at the operating
conditions (reaction temperature) in this research, the 90 PR-C
value of the Gibbs energy change in reaction (8) is REF-C
negative (ΔG398.15 <0), while the reaction (7) has positive 88
Gibbs energy change (ΔG398.15 >0).
To know the effectiveness of catalyst, calculation of 86
diethyl ether yield and ethanol conversion are necessary 125 150 175 200 225
as a reaction parameter. Reaction Temperature (°C )
Fig. 9 shows the result of the conversion of ethanol
dehydration reaction at various operating temperatures.
From the fig. 9, either with the use of γ-Al2O3 catalyst Fig.9. Ethanol coversion vs reaction temperature of ethanol
which was prepared by precipitation method (PR-C) or dehydration process using PR-C dan REF-C catalyst
with γ-Al2O3 commercial catalyst (REF-C) has
increasing conversion of ethanol as increasing of the 12
reaction temperature. Increased temperatures can 10
DEE Yield (%)

increase the conversion of ethanol according to the 8

Arrhenius equation. In this equation, the increase of
temperature will increase the reaction rate constants that 6
PR-C
will increase the rate of reaction [5]. 4
The uses of PR-C catalysts generally produced REF-C
2
ethanol conversion greater than using REF-C catalyst. 0
This happened because it has been known that the PR-C 125 150 175 200 225
catalyst has higher surface area than the REF-C catalyst.
Higher surface area will increase the conversion of Reaction Temperature (°C )
ethanol because it can increase the opportunity for the
occurrence of reaction (adsorption and conversion Fig.10. DEE yield vs reaction temperature of ethanol
process) [14]. dehydration process using PR-C and REF-C catalyst
In addition to the ethanol conversion, in this research
also calculated the diethyl ether yield which produced by From Fig. 10, we can see that using PR-C catalyst
has a greater yield of diethyl ether than using REF-C

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catalyst. That happens because PR-C catalyst has a Fig. 11 shows that the value of the Gibbs energy
higher surface area than REF-C catalyst. The greatest change (ΔGreaction) in diethyl ether formation reaction (Eq
DEE yield is 11.29% was produced by using PR-C 9) are more positive (go up) with the increase of reaction
catalyst while the REF-C catalyst produced DEE yield as temperature. It indicates that the reaction towards the
9.28%. formation of diethyl ether decreases with increasing
Fig. 10 also shows that the increasing of DEE yield is temperature, due to more minimum (more negative)
not linear to the increase of reaction temperature. This value of the Gibbs energy change (ΔGreaction) make the
suggests that the reaction occurs in the catalytic test is reaction easier take place [15]. Instead of gas-forming
not a single reaction but a multi-reaction where some reaction (Eq-10 and Eq-12) has the value of Gibbs
reactions occur other than diethyl ether formation energy change (ΔGreaction) are more negative (go down)
reaction of ethanol. Other reactions that might occur in with increasing reaction temperature. This shows that
the catalytic reaction process is dehydration reaction of with increasing temperature the reaction rate of the
ethanol to diethyl ether (Eq-9); dehydration reaction of reaction towards the formation of gas will be even
ethanol to ethylene (Eq-10); reaction of steam reforming greater.
(steam reforming) to produce carbon monoxide and
hydrogen (Eq-11); and decomposition of ethanol to
methane, carbon monoxide and hydrogen (Eq-12) [11]. 4 Conclusion

2C2H5OH C2H5OC2H5 + H2O ∆G398.15 = -57,822.3J (9) Based on this research, it may be concluded that: γ-
Al2O3 nanocrystallite can be produced by using
C2H5OH C2H4 + H2O ∆G398.15 = -4,363.3 J (10) precipitation method with Al(NO3)3.9H2O as an
aluminum precursor, NH4OH as precipitating agent and
C2H5OH + H2O 2CO + 4H2 ∆G398.15 = 77,331.5 J (11) 0.5 M HCl and distilled water as solvent. Concentration
of aluminum precursors, type of solvent, time of stirring,
C2H5OH CH4 + 2CO + 4H2 ∆G398.15 = -42,577.7 J (12) temperature of precipitation process influences the size
From some reactions above, theoretically (based on of γ-Al2O3 crystal produced. Generally, the catalyst
the value ΔGreaction) reactions which occured in this which prepared by precipitation method (PR-C) have a
catalytic reaction of ethanol is ethanol dehydration greater ethanol conversion and DEE yield than γ-Al2O3
reaction (Eq-9 and 10) and the decomposition of ethanol commercial catalysts because of its high surface area.
(Eq-12), while the steam reforming reaction (Eq-11) at The biggest conversion reaction is resulted by using PR-
the operating temperature of this research did not occur C catalyst at 225°C of reaction temperature as
which can be seen from the value of the Gibbs energy 94.8216%. The biggest DEE yield is resulted by using
changing has positive value. PR-C catalyst 175°C of reaction temperature as 11.04%.
Fig. 10 shows that the yield of diethyl ether The authors would like to thank Ministry of Research
decreased at high temperatures. This could happen Technology and Direktorat Riset dan Pengabdian Masyarakat –
because the catalytic test process at this research which Direktorat Jenderal Penguatan Riset dan Pengembangan –
operated at high temperature can trigger reactions to Kementerian Riset, Teknologi, dan Pendidikan Tinggi
produce a larger gas product and decreasing the rate of Republik Indonesia for financial support under grant PTUPT
the reaction towards the formation of diethyl ether. This Scheme for the year of 2017 granted through Institute for
can be explained by analyzing changes in the Gibbs Research and Community Services Sepuluh Nopember
energy of the reactions (Eq-9, Eq-10, and Eq-12) at each Institute of Technology.
reaction temperature. Value of Gibbs energy change for
each reaction is shown by the following picture. References

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