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Chemical Engineering and Processing 73 (2013) 8186

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Chemical Engineering and Processing:

Process Intensication
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A novel intensied reactive distillation process to produce pure ethyl

acetate in one columnPart I: Parametric study
Yadollah Tavan a, , Reza Mosayebi Behbahani a , Seyyed Hossein Hosseini b
Gas Engineering Department, Petroleum University of Technology, 63431 Ahwaz, Iran
Chemical Engineering Department, Faculty of Engineering, University of Ilam, 69315-516 Ilam, Iran

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

Article history: Production of pure ethyl acetate (EtAc) is a difcult and heavy energy consuming process. In this work,
Received 9 March 2013 a novel reactive distillation (RD) process for EtAc production intensied by the hydration of ethylene
Received in revised form 15 May 2013 oxide (EO), as an auxiliary reaction, is proposed for removing the EtAc/water azeotrope. Impacts of three
Accepted 22 May 2013
important parameters, i.e., ethanol (EtOH) ow rate, EO ow rate and reux ratio on temperature and
Available online 5 June 2013
component compositions along the RD column are investigated to achieve an optimal process design.
The proposed RD process predicts the pure EtAc and ethylene glycol (EG) with low energy requirements.
The results show that the proper feed rates of EtOH, EO and acetic acid are 0.45 mol/s, 0.45 mol/s and
Reactive distillation 0.42 mol/s, respectively, when the reux ratio is 3.5.
Ethyl acetate 2013 Elsevier B.V. All rights reserved.
Ethylene glycol
Process intensication

1. Introduction and mass transfer, the RD behavior tends to be quite complex and
high sensitive to operating variables. Hence special consideration
Reactive distillation (RD) has become an interesting alternative should be given to the design of the RD columns.
for some conventional processes, especially the equilibrium- Ethyl acetate (EtAc) is an important organic solvent which is
limited reactions such as esterications, etherications and ester widely used in production of varnishes, ink, synthetic resins, and
hydrolysis reaction [1]. The RD combines reaction and distillation adhesive agents [810]. In addition, the mixtures containing EtAc
in a single column, in which reactants are converted to prod- are commonly used in chromatography columns and extractions
ucts with simultaneous separation of the products and of unused in laboratory and retail scales. EtAc is normally produced by the
reactants [25]. This simultaneous reaction and separation allows reversible reaction of acetic acid (HAc) with ethanol (EtOH) as
crossing of azeotropic concentrations and distillation boundaries,
hence facilitating product purication. The equilibrium yield can CH3 CH2 OH + CH3 COOH  CH3 COOCH2 CH3 + H2 O (1)
be signicantly increased far beyond equilibrium limitations by
The mixture of HAc and EtOH converts to the ester by about 65%
continuous product removal from the reaction mixture [1,6]. This
yield at room temperature. One major drawback of this reversible
process also brings some important advantages such as reduction
reaction is the relatively low conversion of the mixture to the
in energy, solvent consumption, the number of equipment unit
desired product (EtAc). The reaction can be accelerated by the
and avoidance of hot spots by simultaneous liquid evaporation [3].
homogeneous acid catalyst and the equilibrium shifts to the right
These advantages lead to the reduction in capital and operating
by removal of water. Therefore, RD process can be used to improve
costs. However, the application of RD is somewhat limited by con-
the reaction yield of this reaction. In the previous work [1], it was
straints such as operating conditions (temperature and pressure)
found that the maximum obtainable mole fraction of EtAc in the RD
for distillation and reaction and difculties in providing proper res-
column is about 0.67 and a single RD column is not able to produce
idence time characteristics [2]. In other words, application of RD is
the adequate purity of EtAc. Accordingly, subsidiary units were pro-
limited to systems that the reaction rates are fairly high and there
posed to increase the purity of EtAc [1]. Moreover, to produce EtAc
is no mismatch of favorable temperatures for reaction and separa-
in the traditional RD column, excess water is added to the system to
tion [7]. Due to strong interactions of chemical reaction and heat
ensure the liquid-liquid separation and the residue water from this
section is sent back to the process. It is noteworthy that presence
of water in the reaction zone retards the esterication reaction and
Corresponding author. Tel.: +98 611 5550868; fax: +98 611 5550868. leads to formation of the water/EtAc azeotrope that limits further
E-mail address: (Y. Tavan). purication in distillation column. Therefore, the excess water is

0255-2701/$ see front matter 2013 Elsevier B.V. All rights reserved.
82 Y. Tavan et al. / Chemical Engineering and Processing 73 (2013) 8186

Table 1
Investigations to nd the azeotropes at atmospheric pressure.

Component ID Component name Normal boiling

point ( C)


ETHAN-01 or EtOH ETHANOL 78.31
ACETI-01 or HAc ACETIC-ACID 118.01

Fig. 1. Intensication mechanism of the auxiliary reaction. Number of Components Mole Temperature ( C) Type
azeotrope fraction
1 EtAc 0.6734 71.39 Heterogeneous
not avoided in the system and high energy consumption is needed Water 0.3266
to entrain water from the RD column. 2 EtAc 0.5533 71.78 Homogeneous
In the present study, to eliminate residue water in the system EtOH 0.4467
3 Water 0.1048 78.15 Homogeneous
and to overcome the drawback of energy-intensive related to the
EtOH 0.8952
RD column, the reaction of ethylene oxide (EO) hydration (C2 H4 O) 4 EtAc 0.5370 70.33 Homogeneous
is activated as an auxiliary reaction to intensify the EtAc production Water 0.2819
unit. With this intensication, the EtAc/water azeotrope is removed EtOH 0.1811
and leads to water-free EtAc in the top stream of the RD column. In
the proposed RD column, both the esterication and the hydration
reactions are activated and EtOH and HAc react reversibly with each steady state design of the RD process using HYSYS, based on a
other to produce pure EtAc. Further, pure ethylene glycol (EG) is novel process. The sensitivity analysis for three important param-
produced in bottom of the RD column by the EO hydration reaction. eters, which have major effects on the process duty, is conducted
Therefore, the purication of EtAc more than that of the heteroge- to achieve a nearly optimal design of the proposed process. The
neous azeotrope of EtAc/water with low energy consumption and implemented process can simplify the whole process, decreasing
direct transformation of EO to EG (C2 H6 O2 ) can be expected when the number of columns, and increasing the purity of the products,
the hydration of EO is introduced to the RD column due to remov- EtAc and EG, without entering any excess water.
ing the produced water in the second reaction. It is worthwhile that
EG is an industrially relevant product used mainly as antifreeze 2. Base simulation
in coolers, e.g., in motor vehicles and a precursor to polymers. It
is interesting to note that only a few works are published in the 2.1. Phase equilibrium and kinetic models
literature on the subject of EG production through RD technique
[1116]. However, the addressed researches are mainly focused on The process of EtAc production includes four components (EtAc,
the control process of RD column based on the same conguration. water, HAc, EtOH) and four azeotropes mixtures that the charac-
It should be noted that the relevant process intensication and also teristics of the azeotropes are listed in Table 1. It is evident that
the application of RD to break the azeotrope have not been inves- the reactants, HAc and EtOH, have highest and intermediate boil-
tigated in the literature yet. Therefore, the main advantages of this ing points, respectively. The lowest temperature in the system is
novel process can be listed as follows related to the azeotrope No. 4 (ternary azeotrope) with the value
of 70.33 C and then azeotropes Nos. 1 and 2, respectively. It is
1) From Fig. 1 that shows the intensication mechanism of the noteworthy that the products of EtAc reaction, EtAc and water are
auxiliary reaction, the produced water by the esterication reac- neither the lightest nor the heaviest components in the system,
tion is removed and in situ is used in the EO hydration reaction which this matter causes further complexity to the system. Fig. 2
that promotes the EtAc conversion. In this gure, water is an
inner-cycling component and the reaction is self-feeding. Thus,
no additional water is required for EtAc production and water is
transformed to EG in situ. As a result, this intensication can
save a huge amount of energy that previously consumed for
entraining water.
2) Such an arrangement provides more prots in comparison with
the single RD column to produce EtAc due to co-production of
3) The EtAc and EG production systems can be down in an inte-
grated process with high efciencies and the proposed system
performs its role for both targets simultaneously due to integra-
tion process.
4) The azeotrope between EtAc and water is broken and no
decanter is required to separate liquid and vapor phases in the
RD column. Also, no additional units are required to purify EtAc.

The main contribution of the present work is investigation of

the feasibility of EtAc unit intensication that leads to signicant
energy saving. The other part of this study is optimization of the
process and discovering the inuence of operating and design vari-
ables on energy demand of the process. Therefore, to examine the
feasibility of using the EO hydration reaction to intensify the EtAc
production unit, two rate equations are taken into account in the Fig. 2. Ternary diagram of the EtAc production unit.
Y. Tavan et al. / Chemical Engineering and Processing 73 (2013) 8186 83

shows the ternary map of the components at atmospheric pres-

sure. As can be seen in Fig. 2, the singular points show the location
(composition and temperature) of the four azeotropes and map the
distillation boundaries for the system. Fig. 2 also shows a signicant
liquid-liquid envelope where the azeotrope No. 4 lies closely to the
boundary of this envelope. In addition, the tie lines slope toward
pure water node and, consequently, relatively pure water can be
recovered from the process. The kinetic model for the exothermic
and reversible reaction (heat of reaction = 1.5 104 kJ/kg mol) of
EtAc production that takes place in the liquid phase, in the presence
of sulfuric acid as homogenous catalyst is adapted as follows
E1 E1
rHAc = 2.8 107 exp CHAc CEtOH 7.1 106 exp CEtAc CWater
kJ kgmol kg mol
E1 = 41868 ,R , T (K), C , Liq Phase
kg mol m3 .K m3 Fig. 3. Conguration of the RD process to co-production of pure EtAc and EG.

of 0.4 mol/s is introduced at the 5th stage of the RD column. The run
In order to eliminate the produced water from esterication specications for the RD column are reux ratio that is assumed to
reaction, EG production, which usually takes place via the EO hydra- be 3 and the EO concentration in the bottom stream (0.0001 mol%).
tion, is used (Eq. (3)). The kinetic model of uncatalyzed EG formation It is noted that the RD system is prone to exhibit multiple steady
based on the reactant (water) can be shown as follows [16,17] state and nonlinear behavior. Consequently, the integrated design
and control of the system is of utmost importance. Nevertheless,
EO + Water  EG, (heat of reaction = 80 103 kJ/kg mol) (3)
these undesired phenomena can be avoided if the RD inlets are set
to ow control or self-regulation as described by Kiss et al. [19].
r(mol cm3 s1 ) = 3.15 109 exp[9547/T ]xEO xWater (4)
In addition, the other researchers have studied the control cong-
EO can react further with EG to produce the unwanted urations of the RD processes regarding EG and EtAc [3,4,6]. They
by-product diethylene glycol (C4 H10 O3 , DEG). Though, both reac- have classied these multiplicities and suggested proper control
tions (EG and DEG production reactions) are highly exothermic, congurations for the mentioned processes.
reversible and occur at moderate temperatures. The rate of the side The input data and simulation results of the system are listed
reaction is much lower than that of the main reaction and con- in Table 2. The main products of this conguration are pure EtAc
sequently, the effect of this side reaction on the column proles and EG with concentrations of 95 mol% for both products from the
is neglected. The system can operate at the atmospheric pressure top and the bottom of the RD column. It is worthwhile that the pro-
or even at higher pressures. Although a higher operating pressure posed system is not in its optimized state yet. Consequently, the RD
favors the acceleration of the reaction rate, the additional expendi- system should be optimized in the next section in order to make
tures are essential on the xed investment and operating costs [11]. a fair comparison with the conventional scheme [1]. The effects of
Accordingly, the system is simulated at atmospheric pressure. three parameters, i.e., EO rate, EtOH rate and reux ratio, which
It is worthwhile that the reaction of EtAc production is cat- have important inuences on the column duties, are examined in
alyzed by the sulfuric acid homogenously and the concentration the process. The method of examination is manipulating only one
of the catalyst is assumed to be 0.4 vol% [10,18]. Since the concen- variable at the time, by keeping any other variables constant. There-
tration of catalyst is quite low, it is neglected in the calculation of fore, it does not guarantee the global optimal design of the process
vaporliquid equilibrium. Moreover, the EG reaction uncatalyzed and nearly optimal design of the RD column can be achieved by
takes place in the RD column. Therefore, no catalyst arrangement this method. The problem can be tackled only with the coupling
and recovery is required for the proposed RD column, in the indus- of an external sub-routine/software for optimization with process
trial point of view. simulators, which is out of the scope of this research. Further opti-
mization of the process is needed to have a better understanding
2.2. Simulation of the process of the process which will be reported in the next work (part II).
Furthermore, it is tried to keep the nal product streams at the
In order to simulate the process, the rate equations (Eqs. (2) industrial conditions (EtAc > 95 mol% and EG > 95 mol% in the prod-
and (4)) are implemented into HYSYS process software and the uct streams) when sensitivity analysis is conducted.
owchart of the system is shown in Fig. 3. It is worth mentioning
that the system exhibits non-ideal phase behavior and in order to 3. Results and discussions
represent the phase equilibrium of the system accurately, the selec-
tion of the thermodynamic model is essential. As shown in Fig. 2, to 3.1. The effect of EO rate
account the non-ideal vaporliquid equilibrium (VLE) and possible
vaporliquidliquid equilibrium (VLLE) for this system, the NRTL The inuence of the EO rate is investigated by xing the stage
(non-random-two-liquid) activity coefcient model is adopted. It number of the RD column, reux ratio and the other feed rates. Fig. 4
should be noted that the accuracy of the present model has been shows the inuence of EO rate on the total energy requirement,
examined and conrmed, previously [1]. The tower that operates summation of all duties of the reboiler and condenser, component
at atmospheric pressure includes 28 ideal stages and all trays are compositions and the temperature prole along the RD column. It
considered for the reactions. Notice that the number of trays used is found that the EO rate in the RD column is an important param-
in the current simulations is chosen based on the previous work [1]. eter and should be optimized. As can be seen in Fig. 4a, when the
In this system, the mixture of EtOH and HAc are fed to the RD col- EO rate in the RD column is increased from 0.2 mol/s to 0.7 mol/s,
umn at 4th stage from the top of RD column. The EO stream with the the total duty signicantly diminishes from 27,000 kJ/h to the mini-
operating conditions of 20 C and atmospheric pressure by the rate mum value of 16,500 kJ/h. Increasing the EO rate leads to a decrease
84 Y. Tavan et al. / Chemical Engineering and Processing 73 (2013) 8186

Table 2
Input data and simulation results of the proposed system.

Property/stream EO HAc EtOH EtAc EG RD results

Flow rate (mol/s) 0.45 0.42 0.45 0.41 0.47

Pressure (kPa) 101.3 101.3 101.3 101.3 101.3
Temperature ( C) 20 25 25 78.76 193
EO 100 0 0 0 0
HAC 0 100 0 3.12 3.7
EtOH 0 0 98 0.92 0
EtAc 0 0 0 95.71 0.47
EG 0 0 0 0 95.83
Water 0 0 2 0.25 0
RD column properties
Condenser duty (kJ/h) 184115.8
Reboiler duty (kJ/h) 24963.86
Reux ratio 3.5
Condenser temperature ( C) 78.7
Reboiler temperature ( C) 193

in total duty till the ow rate of 0.4 mol/s; with further increase desired purication of EO in the product stream of the RD column,
of the EO ow rate, energy demand increases due to the pres- energy demand increases and this fact is illustrated in Fig. 4a and
ence of more EO in the column, implying that the degradation of b. Moreover, Fig. 4b shows that with an increase in the EO rate, the
system performance occurs (see Fig. 4b). Therefore, to attain the mole fraction of water in the top product of RD column decreases
and conrms that water is removed by the hydration reaction. As
a result, the both reactions are favored in the RD column. How-
ever, when the EO rate reaches to 0.45 mol/s, there is no water
in the distillate stream and the rate of the hydration reaction is
then decreased. So, excess EO in the feed plays a key role in con-
sumption of all produced water by the esterication reaction and
to meet the stringent product specications. Fig. 4b indicates that,
increase of the EO rate more than 0.45 mol/s causes a decrease in
purity of the products and consequently, has a negative effect on
the product purities. Hence, the optimum EO rate for the RD col-
umn is 0.45 mol/s while product specication is concerned. It is
noticed that the optimum EO rate lies closely to the point of min-
imum energy demand. Moreover, Fig. 4c depicts the effect of EO
rate on the temperature prole of the RD column. It is revealed
that both reactions are exothermic and reduction in column tem-
perature implies decreasing the reaction rates. Fig. 4c shows that
by increasing the rate of EO, the temperature of upper trays in
the RD column increases, mostly attributed to the progress of both
reactions. However, further increase of the EO rate decreases the
column temperature because of consumption of all water in the
hydration reaction. Therefore, it is essential to keep the EO rate
near to the stoichiometric ratio.

3.2. The effect of EtOH rate

The inuence of the EtOH ow rate on the total energy demand

of the RD system is illustrated in Fig. 5 using the xed stage
number of the column, reux ratio and EO ow rate (0.45 mol/s).
Fig. 5a shows that as the rate of EtOH increases from 0.22 mol/s to
0.6 mol/s, the column duties increase which attributed to enhance
in the column stream rates. So, there is no economic balance for
the additional EtOH in the RD column when energy consumption
is concerned. Fig. 5b shows that an increase in the EtOH rate leads
to increase of the esterication reaction, resulting in the enhance-
ment of the purity of EtAc in the RD column. At the same time,
more water is produced through the esterication reaction. So, the
amount of EO is consequently decreased in the column and the con-
centration of EG increases along the column as shown in Fig. 5b.
Also, more heat is produced through the both reactions and tem-
perature of the column is consequently increased as is shown in
Fig. 5c. However, with further increase in EtOH rate (more than of
0.45 mol/s), the concentrations of EG and EtAc decrease gradually
Fig. 4. The effect of EO rate on (a) column duty, (b) composition prole and (c) due to the absence of EO in the column and more water is accumu-
temperature prole. lated in the distillate stream which alters the desired specications
Y. Tavan et al. / Chemical Engineering and Processing 73 (2013) 8186 85

Fig. 5. The effect of EtOH rate on (a) column duty, (b) composition prole and (c)
temperature prole.

and reduces the esterication reaction rate. Therefore, to obtain

pure EG and EtAc, the optimum rate of EtOH is 0.45 mol/s and in
this case, the inlet rate ratio of HAc/EtOH is nearly equal to the stoi-
chiometric one (1.07). The stoichiometric ratio of the reactants in Fig. 6. The effect of column reux ratio on (a) column duty, (b) composition prole
and (c) temperature prole.
the EtAc production unit has been previously reported in the lit-
erature [1]. Also, it can be concluded that when all inlet streams
are stoichiometry introduced to the RD column, produced water shows that by raising the reux ratio, the mole fraction of EtAc
in the esterication reaction matches the consumed water in the rstly increases due to enhance in the system performance and
hydration reaction and it can be said that whole process is mostly then decreases. In this case, the rates of all feeds are constant in
restricted by the esterication reaction. the column, so with an increase in the reux ratio, the amount
of the distillate stream decreases and more EtAc produces in the
3.3. The effect of reux ratio column which retards the esterication reaction. Therefore, water
and EO can not sufciently encounter in the reaction zone and
Fig. 6 shows the inuence of reux ratio on the total energy further increase in the reux ratio leads to decrease in the concen-
requirement, component compositions and temperature proles trations of EG and EtAc in the nal product stream. The high reux
along the RD system. It is observed that the reux ratio has a critical ratio normally means long resistance time to reach physical and
impact on the process duty and column specications; therefore, chemical equilibrium. However, with an increase in reux ratio the
the reux ratio is an important parameter in the design of the RD amount of EO increases in the column which implies no advance
system that needs to be optimized. As can be seen in Fig. 6a, an in the hydration reaction consequently and the column temper-
increase in reux ratio leads to a steadily increase of the total duty ature decreases as shown in Fig. 6c. Based on these results, it is
in order to attain the desired purication in the column. Fig. 6b observed that the reux ratio exhibits an advantage (enhance in the
86 Y. Tavan et al. / Chemical Engineering and Processing 73 (2013) 8186

phase, an extreme point for the composition of EO is also seen for

both phases. The simulation results show that both pure EG and
EtAc are produced through the RD column. So, with this congura-
tion the EtAc purication and EG production can be achieved in an
integrated process with high efciencies and the proposed system
performs its role for both targets simultaneously (production of EG
and breaking the EtAc/water azeotrope) due to the intensication

4. Conclusions

The concept of intensifying EtAc production by the auxiliary

reaction of EO hydration was proposed and simulated in this study.
The simulation results revealed that the RD with the auxiliary reac-
tion is highly prospective with valuable product streams. High
esterication conversion and pure products were reached and
the equipment costs and energy requirements were signicantly
reduced with the help of new proposed process.


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