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Article history:
Received 30 March 2015
Received in revised form 3 July 2015
Accepted 30 July 2015
Available online 3 August 2015
An assessment of different intensied processes for ethyl acetate production by direct esterication was
performed. After the selection and validation of the adequate thermodynamic and kinetic models, a
comparison among different reported processing technologies (i.e., conventional, reactive distillation,
reactive distillation with pressure swing, dividing wall column with reactive reboiler), and a novel
proposed conguration using a reactive dividing wall column was carried out. Specications of raw
materials and products used as constrains during simulations were dened according with market
requirements. To perform a fair assessment among different alternatives, each process was optimized
using a mixed strategy of sensitivity analysis coupled with sequential quadratic programming algorithm.
Total annual cost was selected as the optimization variable. Conversion, productivity, mass intensity,
mass productivity, Sheldons Factor (E-Factor), water-free Sheldons factor (EW-Factor), and energy
intensity were used as sustainability indicators. According with results, the novel reactive dividing wall
column conguration proposed in this work ends up being the more energy efcient and cost effective
(46% energy and 26% cost savings compared with the traditional process) and also it is characterized by
the best sustainability indicators.
2015 Elsevier B.V. All rights reserved.
Keywords:
Reactive distillation
Dividing wall column
Ethyl acetate
Esterication
Sustainability
1. Introduction
Over the last decades, there has been an increasing interest in
products and processes that meet sustainable development
criteria. After the broad denition of sustainability accounting
for the triple bottom line dimensions (environmental, social and
economic), different attempts have been done to transform such a
concept into basic green engineering principles, and furthermore
into sustainability indicators to measure how green processes or
products can be. Despite the sustainability indicators can be used
to evaluate existing processes, its major value can be encountered
when applied in the analysis of new processes that need to be more
cost-effective and environmentally friendly than existing ones; for
example, when developing processes that switch from fossil to biobased feedstock. Due to the increase use of biomass as a feedstock,
and taking into account its higher costs compared with fossil
feedstock, it is necessary to develop more efcient technologies to
reach cleaner, safer, and more cost-effective production of biobased derivatives [1].
* Corresponding author.
E-mail address: aorjuelal@unal.edu.co (A. Orjuela).
http://dx.doi.org/10.1016/j.cep.2015.07.027
0255-2701/ 2015 Elsevier B.V. All rights reserved.
Nomenclature
BRD
C
Ea
EtAc
EtOH
H2O
H2SO4
HAc
k
Kc
PS
RD
RDWC
Wcat
x
y
TAC
these routes despite the fact both have high atom economy and
that hydrogen co-produced in the second route could be of interest.
Comparatively, direct esterication (route 1) has the lowest atom
economy from all three reactions; however it has the lower value
of the safety indicator being the most benign chemical route
according with metrics described by Srinivasan et al. [2].
Additionally, in a recent study it was found that among the
chemical routes of Table 1, direct esterication of bio-based acetic
acid and ethanol appears to be the more cost-effective alternative
as well as the one with the lower global warming potential [3].
Despite Fisher esterication to EtAc is a classic example used in
the academia to introduce basic concepts on chemical reaction
engineering and thermochemistry, this system is still under active
investigation. In recent years, different processing technologies
applied to EtAc production have been reported, most of which
focus on a process intensication (PI) approach. Notwithstanding
the proposed technologies have claimed to be cost-effective and
environmentally friendly, no sustainability assessment of such
technologies has been carried out. Furthermore, as there is room
for future processes development by introducing more complexity
during PI (for instance by implementing heat-integrated reactive
separations), there is need for including also the sustainability
evaluation in the early stages of the process synthesis.
Benets of PI are associated with the enhanced safety, space and
waste reductions, energy savings, higher efciency and productivity, and consequently better economic and environmental performance. As an effort to classify most PI attempts reported in the
literature, Van Gerven and Stankiewick [4] described four
approaches commonly used according with the studied domain:
thermodynamic, functional, spatial, and temporal.
From a general point of view, the thermodynamic approach for PI
consists of energy integration of streams, stages or operations, to
replace the required amount of heating and/or cooling provided with
Table 1
Industrial chemical routes for ethyl acetate production and some sustainability indicators.
Chemical route
Reaction
Safety indicatora
1
2
3
83,0
100
95,6
1.7
2.6
2.2
Calculated as a cumulative index of the four chemical safety parameters (Toxicity, Reactivity, Explosiveness and ammability) as mentioned in [2].
market for EtAc is around 3 million tons per year, and large plants
have a capacity for manufacturing around 100.000 t per year [7],
this was selected as the base case production capacity. For the xed
costs calculation, the methodology proposed by Douglas [8] was
used (Eqs. (1)(4). To calculate the variable costs, updated
averaged raw material and utility prices were consulted. Natural
gas was used as fuel and 85% efciency was assumed for heating
loop.
TAC Fixed Costs Variable Costs
Fixed Costs
Installed Cost
3yr
(1)
(2)
(3)
EnergyCosts
yr
h
Heat duty kW
Natural gas price USD
8160 yr
h
m3
(4)
0; 85 Natural gas energy kW
m3
After the preliminary economic evaluation of the base cases,
optimization of each conguration was performed by running a
sensitivity analysis over the discrete variables, coupled with a
sequential quadratic programing (SQP) algorithm for the continuous variables to minimize TAC. Thereafter, sustainability indicators
were calculated to complement the economical comparison. First,
traditional indicators such as conversion, recovery and productivity were calculated according to Eqs. (5) and (7). These indicators
contribute to evaluate the inherent safety and therefore the
sustainability of a given process since conversion and recovery, and
hence productivity and yield, are also directly related to the
inventory of reactants and recycle streams ow rates.[2]
ConversionX
RecoveryRc
ProductivityP X Rc
moles of EtAc in product Stream
(5)
(6)
(7)
Energy usedW
mass of product kg
EW
(8)
mass IntesityMI
Mass productivityMP
1
100
MI
(11)
(12)
(9)
Table 2
Kinetic expressions reported for acetic acidethanol esterication with different catalyst.
Catalyst
Rate
Parameters
H2SO41
H2SO42
HCl
rA
dC AcA
p
q
k1 C nAcA C m
EtA k2 C EtAc C H2 O
dt
r k1 c1 c2 k2 c3 c4
C A C B CEKCW
2:6 1014 e 104129
RT
dC
rA A
dt
C B 3:7C W
Amberlyst
152
Ea;3
xEtAc xH2 O
r3 wcat rsol ka;3 exp
xAcAc xEtOH
RT
K a;3
Amberlyst
153
dC
k
A kC A C B
CE CW
Ke
dt
Amberlyst
35 wet
Amberlyst
36
Amberlyst
70
Purolite1
CT179
Auto cat.
1
Auto cat.
2
6500:1
k1 4:195C k 0:08815exp
T
kc 7:558 0:012T
310
k1 4:86 104 0:496exp
0:205C 0:85
T
220
k2 3::715 104 0:01572exp
0:09785C 0:85
T
n = m = 0.5, p = q = 1
k1 = 4.76 104
k2 = 1.63 104
T = 100 C
keq 4:0 0:2
Ka,3 = 1320
Ka,3 = 4550
Ka,3 = 2.71
K = 0.0026
Ke = 3.2
T = 343K (70 C)
Wcat = 100gcat/L
6105:6
k1 1:24 109 exp
T
5692:1
k1 1:34 108 exp
T
57960
k 131137exp
RT
Ea;3
xEtAc xH2 O
ka,3 = 12,500 200
r3 wcat rsol ka;3 exp
xAcAc xEtOH
RT
K a;3
Ea,3 = 56,700 200
Ka,3 = 3.0 0.1
r k1 xEtOH xm
m = 1.5
AcOH k2 xEtOAc xH2 O
r k1 c1 c2 k2 c3 c4
CE CW
E
r A1 e RT C A C B
Ke
60550
k 81389exp
RT
48300
k1 4:24 106 exp
RT
66200
k2 4:55 108 exp
RT
59774
k1 0:485exp
RT
59774
k2 0:123exp
RT
A1 = 4.85 102
E = 14,300 cal/mole
Ke = 4
Ref
Units
Comments
Modications
C:Sulphuric acid
conc (wt%)
rA:kmol/m3min
Ci:kmol/m3
[21]
C:mol/L
r:gmol/(Lmin)
k:L/(mingmol)
[22] Ci:mol/dm3
Time :min
Cinetic factor
(m3)2kmol2
s1
kmol
1
[24]
ka;3 :
kgcat
s
Ea,3:kJ/kmol
[20] k:L/(molmin)
[14]
m:gcat
r:mol/min
[13]
R: Jmol/K
C: mol/L
r:mol/Lgmin
k:L/molming
wcat:g
kmol
1
[17]
ka;3 :
kgcat
s
Ea,3:kJ/kmol
[25] k1,k2:mol/kgcats
R: J/mol
[26]
A1 :
1
mole:s
C:mol/L
r:mol/Ls
Amberlyst
15 1
k1
r 1 k1 C 1 C 2 C 3 C 4
Kc
HAc Conversion
0.8
0.7
Amb15-1
0.6
Amb15-2
Amb35
0.5
Amb36
0.4
Amb70
Purolite CT179
0.3
H2SO4 -1
0.2
H2SO4 -2
0.1
0
Auto cat -1
0
200
400
600
800
1000
Auto cat -2
Time (min)
Fig. 1. Effect of catalysts on conversion of acetic acid (HAc) during esterication with ethanol (EtOH) at 80 C and molar ratio 1:1.
Table 3
Reports on intensied processes involving reactive distillation for ethyl acetate production.
Technology
Catalyst
Thermodynamic
model
Ref.
RD
RD + pressure swing
RD
RD
BRD
RD
RD + coproduction of butanol
Heat integrated RD
RDWC
RD
R and RD
H2SO4
H2SO4
H2SO4
Purolite
Potassium Butanolate
H2SO4
Equilibrium
H2SO4
Purolite
UNIFAC:IDEAL
WILSON:IDEAL
WILSON:IDEAL
KOMATSU
Constant a
UNIQUAC-HOC
NRTL:IDEAL
NRTL:IDEAL
NRTL:IDEAL
NRTL:IDEAL
NRTL:IDEAL
82,2a
99,5
98,6c
83,3a
82,4a
99,7a
99,7a
82,6a
80,4a
92,8
[27]
[16]
[30]
[23]
[18]
[31]
[32]
[28]
[33]
[34]
[35]
BRD
RDWC
RD
SBRD
RD
RD
RD
RD
RD
RD + coproduction of butyl acetate
RD
Equilibrium
Non-cat
Purolite
H2SO4
H2SO4 and Purolite
H2SO4 and Purolite
Amberlyst 15 and Purolite
H2SO4
Amberlyst 15
Amberlyst 35
NRTL:IDEAL
NRTL:IDEA
NRTL:IDEAL
NRTL:IDEAL
NRTL:PR:IDEAL
NRTL:HOC
NRTL:HOC
NRTL:HOC
NRTL:HOC
NRTL:HOC
NRTL:HOC
97,3b
83,4a
73,0a
63,3b
99,6a
99,5a
99,5a
99,5a
99,5
99,5
99,95
[36]
[37]
[38]
[39]
[40]
[12]
[41]
[42]
[5]
[13]
[14]
RD
Purolite
NRTL:HOC
99,5a
[43]
RD
RDWC
H2SO4
H2SO4 (at equilibrium)
NRTL:HOC
NRTL:RK
Pure
Pure
Pure
HAc:95,2 mol EtOH:82,2 mol
Pure
Pure
Pure
Pure
Pure
HAc:glacial 100wt
EtOH: p.a. grade 96 vol
Pure
Pure
HAc:49,63 mol EtOH48,08 mol H2O:2,29 mol
Pure
EtOH:88,17 mol HAc:100 mol
EtOH:87 mol HAc 95 mol
EtOH:87 mol HAc:95 mol
Pure
ETOH:95,2 mol HAc:82,2 mol
Pure
EtOH:86,98 wt
HAc:96,75 wt
EtOH:87 mol
HAc:95 mol
EtOH:82,2 mol HAc:95,2 mol
Pure
99,5
99,5
[29]
[6]
D: distillation, RD: reactive distillation, BRD: batch reactive distillation, SBRD: semi batch reactive distillation, RDWC:reactive distillation dividing wall, a; relative volatility.
a
Calculated from reported molar composition.
b
Calculated from molar purity assuming EtOH as other compound.
c
Calculated from transformed molar coordinate.
H2O
RC
HAC
DC
ETOH
H2O
Rx
ETAC
H2O
AD
Fig. 2. Conventional production processadapted from Kirk-Othmer [44] and completed (dotted line) with water-acid azeotropic distillation column for acid recovery and
recycle.
Fig. 3. Reactive distillation processadapted from Tang et al. [5] (shaded region
corresponds to catalytic section).
of raw materials within the product, the side stream from the main
column also contained large amount of HAc, which cannot be
recycled before water removal (difcult separation as mentioned
in Section 3.3.1).
To perform a fair comparison with other technologies, the
original DWC scheme [33] was coupled to a side stripper (RC) in
order to obtain the required high purity EtAc, as presented in Fig. 5.
As in the original report, the catalyzed reaction is assumed to take
place in the reboiler only. The distillate from the DWC is directed to
a decanter where water is added to induce phase splitting. A
fraction of the organic phase is reuxed to the DWC and the
remaining fraction is directed into a side stripper for purication.
Maintaining the original concept, a side stream is withdrawn from
the main column containing over 75% wt water.
3.3.5. novel proposalreactive dividing wall column
Taking into account the improvements reported for the
intensied schemes presented above, a novel process was
conceptually constructed. Analyzing the RD conguration presented by Tang et al. [5] and the DWC presented by Barroso-Muoz
et al. [6], it was expected that a conguration of a reactive dividing
wall column (RDWC) like the presented in Fig. 6a, would have
resulted in higher conversions and energy savings. This was
expected because the continuous removal of water would help
reducing the remixing effect into the reactive section. This kind of
technology is far from new, and one of the rst descriptions of a
RDWC was reported by Keibel in 1984 [49].
After a preliminary evaluation of a proposed RDWC scheme
described in Fig. 6a, large losses of EtAc were observed within the
aqueous stream leaving the overhead decanter (7% w/w). An
attempt to improve EtAc recovery led to the modied conguration
presented in Fig. 6b with water removal as a side stream. According
with a preliminary analysis of this design, EtAc losses were
minimized dramatically. However, there was either some HAc
losses in the side stream or an internal water recycle to the reboiler
and to the reactive stages, all resulting in lower conversions.
Finally, a new RDWC conguration presented in Fig. 6c was
proposed and the preliminary analysis indicated improved
performance compared with the previous ones. This RDWC
conguration was evaluated in further detail in this work, and it
consists of a reactive dividing wall column that uses two reboilers.
In a basic sense, the proposed scheme represents a main RD
column with a side stripper, both located inside the same shell. The
Fig. 6. Different proposed RDWC congurations. (a) Side stream to remove water.
Organic phase used as reux. (b) Side stream to remove water. Both organic
(partially) and aqueous (totally) phases reuxed back to the column. (c) Additional
reboiler (right) and additional bottoms stream (right) to remove water. Both organic
(partially) and aqueous (totally) phases reuxed back to the column.
dividing wall goes from the last stage up to the rectifying section of
the main column. As in the other schemes, this new conguration
also requires a decanter and an additional recovery column. This
scheme can be modeled as a thermally coupled reactive distillation
sequence with side stripper, so an additional reboiler was required.
In this case the catalyst is fed and contained within the main
reactive column where the appropriate catalytic kinetics was used.
In the other side of the wall, self-catalytic reaction can occur, and
the corresponding kinetic model was included. The organic phase
withdrawn from the decanter was partially reuxed to the dividing
wall column and the remaining fraction is sent to the recovery
column (RC) for further purication. The aqueous phase from the
decanter was directed to the non-reactive section of the dividing
wall column in order to remove pure water from the bottom
Base Case
Base Case
Simulaon
Modify
Design
No
Yes
M=Mo-Ones
i=1
j=-1
M(i)=Mo(i)+j
Minimize: TAC
Method: SQP
Constrains: Purity>99.5wt%
j>1?
No
j=j+1
Yes
i>Nvars?
No
i=i+1
Yes
End
Fig. 7. Design-optimization procedure for each case study.
10
Table 4
Design specications values and ranges for each conguration.
Design specication
(intervals*)
Column
RD
Conventional
DC
AD
0,01-4
Reux Ratio
Reboiler Duty (kW)
Reboiler Duty right side (kW)
Material
SS
Pressure (bar)
1
Bubble
Tray type
cap
1416
Number stages
Feed stage for reactive
1315
mixture
Feed stage for ethanol stream
Residence time (min)
2
D/F
0,60,8
B (kmol/h)
B Ratio
RD + PS
DWC
RDWC
RC
RD
RC
RD
RC
DWC
0,01-4
0,001-10**
N/A
0,001-10
0-10
0,5-1**
RC
RDWC
RC
0,001-4
N/A
05000
SS
1
Bubble
cap
1921
1416
CS
1
Bubble
cap
911
4
SS
1
Bubble
cap
2830
911
CS
1
Bubble
cap
810
1
SS
1
Bubble
cap
2224
57
CS
3,5
Bubble
cap
1517
79
SS
1
Bubble
cap
3941
Reb
CS
1
Bubble
cap
10
1
40220
SS
1
Bubble
cap
2830
911
CS
1
Bubble
cap
9
1
2
0,30,9
2
0,60,8
2628
2
0,91
2
0,60,7
1517
2
0,10,85
2
0,010,85
Reb
2
1
2729
2
2002000
050
4,374
810
1012
1921
100200
170200
350380
13
0
6080
Table 5
Main characteristics of the optimized reactive distillation processes.
Process
EtOH
stream
(kg/h)
HAC
stream
(kg/h)
Heating
duty
(kW)
Cooling
duty
(kW)
Number of
stages main
column
Number of
reactive
stages
Reux ratio
Reux ratio
main column recovery
column
Fresh water
inlet (kg/h)
D (m)
main
column
D (m)
recovery
column
Conventional
RD
RD+PS
DWC
RDWC
10219
7465
7397
1357
6989
10079
8680
8601
15936
8541
26582
29213
19302
16217
14098
26664
29704
19203
16565
14155
15
29
24
40
29
1
18
18
1
19
0.93
5,14a
0.25
0,78
0,03
19309
1247
29575
1516
4,3
7,4
4,1
4,3
4,5
3,1
2,7
3,4
3,1
2,4
0.67
1,87
1.5
1.75
2,08
11
Table 6
Fixed, variable and total annual costs.
Process
TAC MM.USD/yr
Conventional
RD
RD + PS
DWC
RDWC
6,5
7,1
4,7
3,9
3,4
123,5
97,3
96,5
177,5
93,4
130
104,4
101,1
181,4
96,8
2,3
0,8
0,5
0,6
0,5
132,3
105,2
101,6
182
97,3
Table 7
Sustainability indicators of optimized reactive distillation processes for EtAc production.
Conventional
RD
RD + PS
DWC
RDWC
Conversion
Recovery
Productivity
MI
EW
MP
EI
0.98
1
0.98
0.71
0.99
0.86
0.97
1
0.75
1
0.84
0.97
0.98
0.53
0.99
1.58
1.26
1.25
2.3
1.21
2.23
0.42
0.31
3.82
0.39
0.34
0.05
0.04
1.02
0.01
0.63
0.79
0.8
0.44
0.83
2.17
2.38
1.69
1.32
1.15
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
Catalytic stages
Mole Fraction
the column. In Fig. 9, the composition proles of the most costeffective conguration (RDWC) are presented. While the most of
the HAc is maintained in the reactive side, EtOH is separated from
water in the side column and sent to the reactive stages assuring
complete conversion. Almost pure water is removed from bottoms
of the side stripper and the azeotrope is send to EtAc purication
column. In the modeling specications, it was established that
both the reactive and side columns had the same number of stages.
However, as observed in the composition proles of Fig. 9, the side
stripper is oversized. In this case, the use of different column
internals or a lower number of trays in the side column might
decrease even more the capital costs of the RDWC. It is interesting
to notice how the intensied congurations (RD, RD + PS and
RDWC) have similar conversion to that of the conventional scheme
but different productivity. The overall high conversion from the
conventional process is achieved by recycling almost all of the
limiting reagent of the process, which is the HAc from the AD
column. However, the low recovery capacity of the decanters in the
conventional scheme, where a large amount of fresh water is
needed to trigger phase separation explain the low productivity.
On the other hand, the productivity of DWC scheme is very low
Stage Number
Stage Number
the reactive zone of the column, some acid is pulled to the top and
lost within the distillate. To avoid such losses, and similarly to the
AD column of the conventional conguration (Fig. 2), a high reux
ratio of the organic phase is needed. With this, the EtAc rich stream
acts as an extracting agent that helps pushing the acid back to the
reactive zone improving conversion. This large reux explains why
RD presents the worst performance according with the EI indicator,
being even 10% more energy intensive than the conventional
process. Comparatively, and despite the fact that a higher pressure
is required, the RD+PS conguration requires a lower reux ratio
than the RD process (i.e., less energy), since the recycle stream
from the high pressure column helps keeping the acid content low
in the condenser from the reactive column. The herein proposed
RDWC conguration offers the lowest energy intensity and the
higher savings from all intensied processes since it avoids
remixing during multicomponent distillation, and also allows
selective product separation during esterication inside the same
unit. In this case, the low organic phase reux ow rate (see
Table 5) is possible due to the recycle of the aqueous stream from
the decanter back to the column, since it lowers the top stage
temperature and increases the actual amount of liquid reuxed to
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
0
Mole Fraction
Fig. 9. Liquid phase composition proles in a reactive dividing wall column conguration for ethyl acetate production using sulfuric acid as catalyst. Leftmain reactive
column, rightside stripper. () HAc, (--) EtOH, () EtAc, ( . . . ) H2O.
12
13
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