Separation and Purification Technology 257 (2021) 117907

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Separation and Purification Technology

journal homepage: www.elsevier.com/locate/seppur

Superstructure modeling and stochastic optimization of side-stream

extractive distillation processes for the industrial separation of benzene/
cyclohexane/cyclohexene
Hao Lyu a, Shihan Li b, Chengtian Cui a, c, Xingong Yu b, Jinsheng Sun a, *
a
School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, PR China
b
Henan Shouheng New Material Co. LTD, No.1 Industrial Area of Circular Economy, Xiangcheng, Xuchang 461700, PR China
c
Institute of Intelligent Manufacturing, Nanjing Tech University, Nanjing 211816, PR China

A R T I C L E I N F O A B S T R A C T

Keywords:
Benzene/cyclohexane/cyclohexene separation
Adaptive selection of feasible flowsheets
Superstructure-differential evolution
optimization
Non-sharp side-stream extractive distillation
The non-sharp side-stream extractive distillation (SSED) differs from the sharp one in that it partially, instead of
entirely, collects intermediate components through the side stream. Compared to the sharp one, the non-sharp
SSED is preferred in some extractive distillation (ED) systems with high boiling-point solvents. However, the
number of candidate configurations increases sharply when a design considers both the sharp and non-sharp
SSEDs. Correspondingly, it results in a challenge to optimization, particularly in systems with multiple side-
stream options. In this study, we propose an adaptive superstructure-differential evolution (DE) method which
optimizes the sequences and parameters simultaneously. As a case study, the industrial benzene/cyclohexane/
cyclohexene separation is optimized, which has two extractive distillation columns and 30 feasible configura­
tions with different SSED options. Compared to the conventional superstructure-DE approach, the improved
method, which selects the feasible flowsheet instead of predetermining a random one, performs better in the
optimization. The less computational cost and better solutions demonstrate its superiority. Moreover, the opti­
mized 3-column and 4-column SSED configurations apply non-sharp side-stream options, which proves that the
non-sharp SSED options are more competitive for this ternary system. In summary, this study highlights the
significance to consider both the sharp and non-sharp SSED configurations and provides a systematic approach to
find high-quality configurations from an increased number of candidates.

operable alternative to reduce the remixing effect in ED systems [15].

1. Introduction
Extractive distillation (ED) is an extensively used alternative to
conventional distillation columns to separate mixtures with low relative
volatilities or azeotropes. It is usually more economical than other
methods such as pressure-swing distillation and azeotropic distillation
[1–4]. However, its energy efficiency is still low, due to the continuous
solvent regeneration and the remixing effect of intermediate
components.
The fully coupled configurations [5–7] are effective methods to
reduce the remixing effect. They were recommended for ED systems and
found to be economical in some cases [8,9]. However, their superiority
was not widely accepted due to manufacturing and control difficulties
[10–12]. Agrawal and Fidkowski [13,14] and Agrawal [6] proposed the
liquid-only side-stream column, which could be a simpler and more
Salvador et al. [16] found that the side-stream extractive distillation
(SSED) configuration, compared to the conventional extractive distilla­
tion (CED), could save 13.45%, 12.9%, and 12.45% of the TAC for
ethanol dehydration, heptane/toluene separation with aniline as the
solvent, and acetone/methanol separation with water as the solvent,
respectively. Wang et al. [17] demonstrated that the SSED configura­
tion, compared to the CED configuration, could save 28.67% of the TAC
for the separation of acetonitrile/benzene/methanol with chloroben­
zene as the solvent.
However, these works only considered the sharp SSED which entirely
collects intermediate components through the side stream. It usually
requires a higher reflux ratio or more theoretical stages of the extractive
distillation column (EDC), which leads to an increased cost. Besides,
without intermediate components, the elevated bottom temperature of
the EDC also increases the cost, in particular when the more expensive

* Corresponding author.
E-mail address: jssun2006@vip.163.com (J. Sun).

https://doi.org/10.1016/j.seppur.2020.117907
Received 19 February 2020; Received in revised form 11 September 2020; Accepted 16 October 2020
Available online 22 October 2020
1383-5866/© 2020 Elsevier B.V. All rights reserved.
H. Lyu et al.
Abbreviations
ANE cyclohexane
BEN benzene
CED conventional extractive distillation
DE differential evolution
DMAC dimethylacetamide
ED extractive distillation
EDC extractive distillation column
ENE cyclohexene
GA genetic algorithm
LMTD logarithmic mean temperature difference
LP low pressure
MP middle pressure
MTD minimum temperature difference
steam is required. Therefore, the sharp SSED will be less economical
when the reduced cost of the solvent recovery column (SRC) could not
compensate for the increased cost of the EDC. Brito et al. [9] reported
similar phenomena in the thermally coupled distillation configurations,
which indicated that it is not economical to obtain the pure solvent from
the bottom of EDC in the cases. Consequently, the non-sharp SSED, in
which the side stream partially collects intermediate components and
the bottom stream still feeds the next column, could be an alternative.
Since it considers both sharp and non-sharp SSEDs, the number of
feasible candidate flowsheets increases rapidly, which leads to a higher
computational cost for optimization. Only one distillation sequence is
feasible in binary systems unless an intermediate solvent is used [18],
while both direct and indirect distillation sequences become feasible in
ternary ED systems [19,20]. The different sequences lead to an increase
in the number of candidate configurations. Particularly, when the
ternary ED systems have two EDCs, such as benzene/cyclohexane/
toluene [21], tetrahydrofuran/ethanol/water [22], and acetonitrile/
benzene/methanol [17], the number of feasible candidates increases to
several times larger than that of a binary system, which makes it a great
challenge to obtain the optimal design. Moreover, since the performance
of heat integration options is system-specific for ED systems [23–26], it
requires to compare the configurations with different heat integration
options, which will further increase the number of candidates.
Apart from comparing a large number of candidate configurations, it
is also a hard task to optimize the structural and operating parameters of
each configuration. Since the number of decision variables of a SSED
configuration is large and the influence of them is usually not monotonic
or independent [27–29], it becomes necessary to optimize the decision
variables simultaneously, which is beyond the capability of heuristic
methods based on the rule of thumb. Both stochastic and deterministic
algorithms can be used to solve the optimization problem [30].
Compared to the deterministic methods, the stochastic ones have better
performance in dealing with integer variables and nonconvex objective
functions with many local optimal solutions. Moreover, the stochastic
methods are easier to be initialized and more robust against convergence
failures, which is more difficult for deterministic methods due to the
calculation of derivatives. Therefore, the stochastic algorithms, such as
genetic algorithm (GA), differential evolution (DE), particle swarm
optimization, and their variants [31–35], are gradually accepted in
recent years, despite the disadvantageous slow descent in the neigh­
borhood of an optimum and the expensive computational cost.
When it requires to optimize dozens of candidates separately, the
computational cost of the stochastic optimization becomes unaccept­
able. Consequently, Lashkajani et al. [36] proposed a method, which
combines stochastic algorithms and superstructure optimization, to
optimize operating parameters, structural parameters, and sequences
simultaneously. However, the hybrid approach will be less efficient for
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Separation and Purification Technology 257 (2021) 117907
PSO particle swarming optimization
SRC solvent recovery column
SSED Side-stream extractive distillation
Nomenclature and units
AOC annualized operating cost, US$/a
BPB payback period, year
CAP capital investment, US$
F feed flow rate, kg/h
NT number of theoretical stages
P pressure, kPa
RR reflux ratio
S solvent flowrate, kg/h
T temperature, ◦ C
TAC total annualized cost, US$/a
SSED configurations. Since a side-stream column has more design
specifications and fewer degrees of freedom than a CED configuration,
the probability of finding a feasible individual that matches the pre­
determined flowsheets by stochastic approaches is relatively low.
Therefore, a large part of the population is a convergence failure or an
infeasible solution, which does no contribution to evolution but requires
intensive computational cost. In this study, an adaptive superstructure-
DE approach is proposed, which automatically selects the feasible
flowsheet from all possible candidates to design multi-component SSED
configurations efficiently. As a case study, the industrial benzene/
cyclohexane/cyclohexane (BEN/ANE/ENE) separation, a ternary ED
process with two continuous EDCs and several potential heat integration
options, is optimized. The result could prove the superior performance
of the optimization framework and the necessity to consider the non-
sharp SSED option as well as the sharp one.
In adipic acid and caprolactam plants, the BEN/ANE/ENE separation
accounts for ~70% of the overall hot utility consumption and produces
quite a lot of waste heat. Since the total adipic acid capacity has reached
2,655,000 t/a in China by January 2020 (Supplementary Material S1),
the consumed steam for the separation reaches 8,750,000 t/a, although
some primary heat integration measures are already in use. According to
Modla and Lang [37], the consumed hot steam will lead to ~880,000 t/a
CO2 emission. Although the data emphasized the great significance for
further improvement on the separation, it attracted little attention in the
previous works. Moreover, the number of feasible configurations for this
process is quite large, when the direct and indirect distillation se­
quences, the sharp and non-sharp SSEDs, as well as the corresponding
heat integration options are all taken into consideration. The challenge
of this optimization problem is enough to prove the superior perfor­
mance of the improved superstructure-DE method.
This paper is organized as follows: Section 2 introduces the con­
ventional industrial process and the design basis. Section 3 provides
information about the benchmark and some other CED configurations.
Section 4 takes a glance into the various SSED configurations and in­
troduces the fundamentals of the improved superstructure-DE method.
The Comparison of the adaptive superstructure-DE method with some
other known approaches demonstrates its superior performance. With
the improved method to optimize the various SSED configurations
simultaneously, it obtains the 3-column and 4-column optimal designs.
The results could help to demonstrate the necessity to consider both non-
sharp and sharp SSEDs and provide a systematic approach to design
multi-component SSED configurations with enormous different variants
efficiently. Finally, Section 5 draws the conclusion.
H. Lyu et al. Separation and Purification Technology 257 (2021) 117907

Fig. 1. The residual curve maps and x-y diagrams of the ternary systems (in mole). (a) residual curves map (b) x-y diagrams for the binary mixtures without DMAC.
(c) x-y diagrams for each binary mixture with equivalent molar DMAC.

2. Process and problem description
2.1. Physical properties of BEN/ENE/ANE ternary system
BEN, ANE, and ENE are all C6s with similar molecular structures,
molecular weights, and very close boiling points. The boiling points of
BEN, ENE and ANE at 1 atm are 80.1 ◦ C, 83.0 ◦ C and 80.7 ◦ C, respec­
tively. Their residual curve maps represent two azeotropic points and a
distillation boundary (Fig. 1a), which excludes conventional distillation
from candidate separations. Besides, the x-y diagrams of the binary

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Fig. 2. The 4-column ED process for BEN/ANE/ENE separation.

Table 1
The design specifications for BEN/ANE/ENE separation.
Specifications Values

minimum temperature reboilers and 15 ◦ C

difference condensers
pressure drop condensers 5 kPa
theoretical stage 0.3 kPa
design specifications (in BEN separating column top: BEN/ENE ≤ 0.001
mass fraction) (C1) bottom: ENE/
BEN ≤ 0.005
ANE column (C3) top: ENE ≤ 0.007
DMAC ≤ 20 ppm
bottom: ANE/
ENE ≤ 0.00125
solvent regeneration top: trace DMAC
(C2 & C4) bottom:
DMAC ≥ 0.9999

systems show that they are pressure-insensitive with very low relative
volatilities, which means that pressure-swing distillation is infeasible
(Fig. 1b). In industrial practice, ED is used to separate the ternary
mixture with dimethylacetamide (DMAC, CH3CON(CH3)2) as the sol­
vent, of which the boiling point at 1 atm is 166.1 ◦ C. After the equivalent
molar DMAC is added, the relative volatility of each binary system is
enlarged (Fig. 1c), which indicates that ED is feasible to separate the
mixture.
Fig. 3. The architecture of the DE algorithm combined with Aspen Plus.
2.2. The industrial 4-column process
to estimate the missing parameters, due to the lack of available phase
In adipic acid/caprolactam plants, the BEN/ANE/ENE separation equilibrium data between some pairs within the range of the operating
serves as the downstream treatment of the benzene hydrogenation unit. pressure (Supplementary Material S2). The design specifications are
The 4-column ED process uses DMAC as the solvent to collect ENE for shown in Table 1. The minimum temperature difference (MTD), as well
further procedures, remove ANE, and recycle BEN back to the hydro­ as the pressure drop for heat exchangers and trays, are defined as con­
genator (Fig. 2). Due to the large temperature difference along the col­ stant for simplifications. The light ends are mainly methylcyclopentane
umns, it is difficult for the reboilers of the process to reuse the waste heat (the boiling point is 71.8 ◦ C at 1 atm), with trace water, nitrogen, and
from the overhead vapors and the hot solvent. Consequently, the hot light hydrocarbon. In this study, the light ends are treated as methyl­
solvent from the bottom of the solvent recovery columns (SRC) is first cyclopentane for simplification. The temperatures of the inlet and outlet
transferred to the downstream unit to heat a reboiler, of which the streams of the reboiler in the downstream unit, which is integrated to
temperature is within the range of 75 to 85 ◦ C, and cooled by cooling recover the waste heat, are 66.8 and 76.6 ◦ C, respectively, according to
water before recycled to the EDCs. the simulation results in Supplementary Material S3.

2.3. Design specifications 2.4. Economic evaluation

The process simulation in this study adopts NRTL thermodynamic TAC is used to evaluate the economic performance of the candidates.
model. The binary parameters are obtained from the Aspen built-in or The calculation is mainly based on Luyben [38,39], with the details in
the corresponding literature. UNIFAC group contribution method is used Supplementary Material S4. Since the separation of the ternary system is

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H. Lyu et al. Separation and Purification Technology 257 (2021) 117907

Fig. 4. The 4-column CED configuration (benchmark).

variables are dependent and calculated by Aspen Plus based on the

Table 2
design specifications.
Cost analysis for the CED configurations.
4-column 3-column 3. The benchmark and conventional alternatives
configuration configuration

column shells and internals/(×106 US$) 6.07 7.40 3.1. The industrial 4-column process (Benchmark)
heat exchangers/(×106 3.88 3.63
US$) The original 4-column CED configuration, which is designed by the
exhausting operation 0.06 0.11 rule of thumb, is far from an economical solution. For a fair comparison,
(×106 US$/a) it is optimized by the DE algorithm and selected as the benchmark
heat utility requirement/ LP steam 31.9 34.5 (Fig. 4). The composition data of the streams in the flowsheets in Fig. 4
103 kW MP steam 17.2 16.9
and the other figures are all in mass fraction. The regenerated hot sol­
cold utility requirement/ cooling 34.4 37.3
vent is partially heat integrated with the downstream process to recover
103 kW water
the waste heat. Since this option reduces the total hot utility require­
annualized operating cost/(×106 US 11.57 12.12
$/a)
ment, the reduced costs will be accounted for in the economic evalua­
cost reduction by heat integration/ − 4.01 − 3.58
tion. In detail, the TAC is calculated by subtracting the reduced costs
(×106 US$/a) from the sum of the annualized operating and capital cost. The cost of
total annualized cost/ 10.93 12.31 the benchmark is listed in Table 2.
(×106 US$/a)
3.2. The 3-column CED configurations
*Detailed data could be found in the supplementary material S7.
In this ternary ED system with heavy solvent, there is another
integrated with its downstream unit to reuse the waste heat, the profit feasible distillation sequence, which separates ANE in the first EDC,
from the waste heat recovery will be taken into account. collects ENE in the second EDC, and recovers DMAC from BEN in the last
column (Fig. 5). This direct sequence only requires 3 columns, which
2.5. Simultaneous optimization seems to be more attractive in most ternary ED systems at first glance.
The 3-column CED configuration is optimized by the DE algorithm, and
It is difficult for heuristic methods to optimize more than 20 inde­ the results are shown in Table 2. The TAC of the 3-column scheme is
pendent variables simultaneously. Consequently, the differential evo­ 12.6% higher than the 4-column CED configuration. This means that the
lution (DE), a competitive stochastic algorithm, is used in this study. The direct distillation sequence is not always the better choice where it re­
optimization is implemented by combining an optimizer (Matlab, Py­ quires a much higher reflux ratio or capital cost to separate the lightest
thon, VBA, GPROMs, etc.) with Aspen Plus through a win32.com component from the other components.
interface (Fig. 3). The control factors of DE are determined by a self-
adaptive strategy [34]. The pseudo-code and the declaration of vari­
ables are provided in Supplementary Material S5 & S6. The other

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H. Lyu et al. Separation and Purification Technology 257 (2021) 117907

Fig. 5. The 3-column CED configuration.

Fig. 6. The 4-column CED configuration (solvent feeds C1 top stage).

3.3. 4-Column CED configuration with heat integration options
Besides the benchmark, the DE algorithm can also find a 4-column
CED configuration that feeds the solvent to the C1 top (Fig. 6). In this
configuration, there is no section in C1 to remove DMAC. As a result, C1
top feeds C3 with significantly higher DMAC content. Although no sig­
nificant TAC reduction is observed with this configuration, the boiling
point of the C1 top product increases, which indicates that the latent
heat of the overhead vapor could be recovered. When the C1 top is
operated at elevated pressure, it could be integrated with the down­
stream process to recover the latent heat of the overhead vapor (Fig. 7).
Since this integration requires a much larger heat exchange area than
cooling the overhead vapor by water directly, a 6.1% increase in the
corresponding capital cost is observed (Table 3). In return, it recovers
~50% more waste heat for the downstream process than other 4-column
CED configurations. The TAC of this configuration is 8.75 million US$/a,
which is 19.9% less than the 4-column CED configuration. This result
indicates that the heat integration option should be considered in further

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Fig. 7. The 4-column heat-integrated CED configuration.

considered to be a reason for the low energy efficiency. In the EDCs, the
Table 3 content of intermediate components in the liquid phase increases stage
Cost analysis for 4-column CED configuration with the solvent feeding C1 top by stage from the feed location towards the bottom. It reaches a peak
stage. value in the middle of the stripping sections, where the lighter compo­
Without heat Heat nents are nearly completely separated. While below the peak stage, it
integration integrated begins to decrease, resulting in a lower content at the bottom. Then the
column shells and internals/(×106 US$) 5.81 6.14 bottom product is fed to the following column for regeneration or sep­
heat exchangers/(×106 US 3.93 4.19 aration, and the content of intermediate components increases from the
$) feed location to the top. In this path, the non-monotonically change in
exhausting operation (×106 0.06 0.05 the content of intermediate components should be considered as a
US$/a) remixing effect.
heat utility requirement/ LP steam 31.9 34.4 To reduce the remixing effect, SSED configurations are applied.
103 kW MP steam 17.9 14.8
However, being much more complex than a binary system, the SSED has
cold utility requirement/ cooling 34.4 24.2 several different schemes. In 3-column configurations, since the top
103 kW water
products do not contain the solvent and have low dew points, the heat
annualized operating cost/(×106 US$/a) 11.74 11.47
integration option is not feasible. The possible configurations can be
cost reduction by heat integration/(×106 − 3.97 − 6.18 distinguished based on their different side-stream connection ways and
US$/a)
coded by a vector [SC1, SC2] as shown in Fig. 9. The value of SC1 can be
total annualized cost/(×106 11.07 8.75
selected from [0, 1, 2, 3]: 0 represents the case that C1 has no side
US$/a)
stream, 1, 2 and 3 represent the cases that the bottom of the side-stream
*Detailed data could be found in the supplementary material S7. column C1 feeds C2, C3 and the solvent cooler, respectively. The value
of SC2 could be selected from [0, 1, 2]: 0 represents the case that C2 has
optimization. no side stream, 1 and 2 represent the cases that the bottom of the side-
stream column C2 feeds C3 and the solvent cooler, respectively. In this
4. The SSED configurations and the superstructure-DE way, 12 (4 × 3) different 3-column configurations are found.
optimization Similarly, 9 (3 × 3) different configurations are feasible for 4-column
flowsheets (Fig. 10). A vector [SC1, SC3] codes and distinguishes the
4.1. The remixing effect and SSED configurations different configurations based on their different side-stream connection
ways. The value of SC1 can be selected from [0, 1, 2]: 0 represents the
According to the liquid composition profiles along the columns, the case that C1 has no side stream, 1 and 2 represent the cases that the
remixing effect of the intermediate components in EDCs is observed in bottom of the side-stream column C1 feeds C2 and solvent cooler,
both the direct and indirect distillation sequences (Fig. 8), which is respectively. The value of SC3 can be selected from [0, 1, 2]: 0 represents
the case that C3 has no side stream, 1 and 2 represent the cases that the

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H. Lyu et al. Separation and Purification Technology 257 (2021) 117907

Fig. 8. Liquid composition profiles for CED configurations. 4-column CED configuration (b) 3-column CED configuration.

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H. Lyu et al. Separation and Purification Technology 257 (2021) 117907

Fig. 9. The possible 3-column configurations.

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Fig. 10. The possible 4-column configurations.

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H. Lyu et al.
Fig. 11. The superstructure for 3-column and 4-column flowsheets.
bottom of the side-stream column C3 feeds C4 and the solvent cooler,
respectively. Moreover, heat integration options are available in 4-col­
umn configurations. The configurations that fully couple the overhead
vapor of the first EDC with the downstream unit are still the same as the
basic ones. However, the boiling point of the overhead vapor is not al­
ways high enough to ensure that it can be cooled to liquid after heat
exchanging with the downstream unit. Consequently, it will require an
extra condenser to cool and liquefy the top product, which is a partially
heat integrated design. Since the fully and partially heat integrated
designs are both considered, each configuration has two extended
structures. For example, the configuration [0,1,0] and [0,1,1], where the
third element of the vector could be 0 or 1, corresponding to the original
configuration and the partially heat integrated one, respectively.
Therefore, the number of 4-column candidates increases to 18
(3 × 3 × 2).
4.2. Improved superstructure-DE optimization for SSED configurations
It is inefficient to optimize the enormous number of candidates
separately. Consequently, the superstructure optimization is used to
help optimize the different candidates, together with their structural and
operating parameters simultaneously [36]. Since the dozens of SSED
configurations with the direct distillation sequence are similar in their
main structures, except for a slight difference in the connection way of
the specific streams, these configurations can be integrated as a corre­
sponding superstructure with two splitters (Fig. 11). Similarly, the
configurations with the indirect distillation sequence can be merged into
a superstructure. All the possible configurations could be obtained by a
corresponding vector [SC1, SC2], where SCi is the parameters of the ith
splitter. Based on the vector, it connects the side streams to corre­
sponding destinations and can calculate various configurations in a su­
perstructure simulation.
However, the conventional superstructure-DE, which predefines the
schemes, is not efficient to deal with the SSED configurations. In the
conventional superstructure-DE optimization, the vector of independent
variables is defined as [SC, X], where SC is the superstructure code and X
is the operating and structural parameters. Since the side-stream EDC
needs to match more constraints than the conventional EDC, the feasible
solution space is smaller, resulting in a lower probability of finding
convergent and feasible results by the stochastic search. The tentative
solution X will be excluded unless the appropriate SC is selected,
although sometimes the excluded X can be a high-quality solution if the
appropriate SC is matched. A large number of nonconvergent or infea­
sible results could not promote the evolution of the population but
consume intensive computational resources.
Since many infeasible solutions [SC, X] will be feasible solutions
when a different SC is matched, the optimization will be more efficient if
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Separation and Purification Technology 257 (2021) 117907
it can adaptively choose the appropriate schemes. In a sharp SSED col­
umn, a feasible solution vector X should match 3 design specifications
DS1, DS2, and DS3, where DS1, DS2, and DS3 are the purity requirements
of the top, side-stream, and bottom product, respectively. The multiple
constraints lead to a very small feasible solution space V and make many
tentative solutions X to be infeasible. If the vector X only matches 2
design specifications, for example, DS1 and DS2, the X could be a feasible
solution of the non-sharp SSED column. Similarly, the vector X that
matches DS1 and DS3 may be a feasible solution of the CED column. If the
optimization approach matches the feasible structure SC to the vector X,
fewer solution vectors X will be excluded due to the mismatch. In this
way, the optimization will be more efficient and robust.
By adding the calculation rules for structure selection, we proposed
an adaptive superstructure-DE method, of which the computing archi­
tecture is shown in Fig. 12. During the sequential solving process, it
selects the feasible scheme based on the results of the front modules.
Both the outer code and the embedded Fortran code in Aspen Plus can
implement the scheme selection. The latter one is superior because of
the higher computational speed, and Supplementary Material S5 pro­
vides the pseudo-code. In this way, the optimization of the superstruc­
ture becomes simpler, which does not need to deal with the
superstructure code for scheme selection.
To demonstrate the superior performance of the improved
superstructure-DE framework, we optimize the 3-column configurations
by different optimization methods and compare the results (Table.4). All
computational tasks are run on an Intel Core i7-9700 CPU (3.00 GHz,
16.0 GB RAM). The adaptive superstructure-DE approach performs best
among the different methods. Although it takes a little more time to find
a high-quality solution than optimizing a single configuration ([1,1] in
Fig. 9), notably, the latter one will require ~300 h (25 h × 12 candi­
dates) to optimize all feasible configurations separately. Besides, the
adaptive superstructure-DE approach can find significantly better solu­
tions than the conventional superstructure-DE approach within the close
calculation time. In summary, the comparison demonstrates the superior
performance of the adaptive superstructure-DE method, which can be an
improvement of the conventional approach. Therefore, the 4-column
SSED configurations are also optimized by the improved approach,
and the result is shown in Fig. 14 and Table 5.
The optimized 3-column SSED configuration (Fig. 13) has two non-
sharp side streams, which saves 12.6% of the TAC compared to the 3-col­
umn CED configuration. The reduced remixing effect is the main reason
for the reduced cost. As shown in Fig. 15, the remixing effect from the
side stream of C1 to the upper feed location of C2 and that from the side
stream of C2 to the upper feed location of C3 are very small, because the
side streams and corresponding feed locations have equivalent inter­
mediate component contents. When drawing the side streams from C1
and C2, the flow rates of their bottom streams are reduced, which lowers
H. Lyu et al. Separation and Purification Technology 257 (2021) 117907

Fig. 12. The adaptive superstructure-DE framework to solve the 3-column and 4-column superstructures. (a) 3-column SSED (b) 4-column SSED.

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H. Lyu et al. Separation and Purification Technology 257 (2021) 117907

Table 4 Table 5
The performance for different optimization approaches. Cost analysis for the SSED configurations.
Optimization approach Trial number of computational results 3-column 4-column
iterations time configuration configuration

DE optimizes the [1,1] 1 500 26.4 h 11.10 column shells and internals/(×106 US$) 6.97 6.05
configuration heat exchangers/(×106 3.10 4.02
2 500 24.2 h 10.84 US$)
3 500 24.0 h 11.26
exhausting operation 0.09 0.05
DE optimizes the [3,2] 1 500 23.5 h 12.79
configuration (×106 US$/a)
2 500 25.4 h 12.13 heat utility requirement/ LP steam 0.0 18.0
3 500 25.9 h 12.36 103 kW MP steam 41.5 27.8
conventional 1 500 26.9 h 11.96 cold utility requirement/ cooling 31.1 22.6
superstructure-DE 103 kW water
2 500 28.6 h 12.19
annualized operating cost/(×106 US 10.14 10.84
3 500 27.5 h 11.70
$/a)
adaptive superstructure- 1 500 26.6 h 11.12
DE cost reduction by heat integration/ − 2.82 − 5.72
2 500 30.1 h 11.00 (×106 US$/a)
3 500 28.8 h 10.76 total annualized cost/ 10.76 8.53
(×106 US$/a)
*The detailed values of the variables of each trial is in Supplementary Material
S8. *Detailed data could be found in the supplementary material S7.

Fig. 13. The 3-column SSED configuration.

the remixing effect. Especially for C2, since most BEN is collected
through the side stream, the remixing effect is almost eliminated.
Meanwhile, when drawing the side stream, the temperature of the C1
bottom increases. If more intermediate components are collected
through the side stream, the elevated bottom temperature will require
more expensive hot utility. Since the heat duty of the C1 reboiler is much
larger than others, the usage of the higher-quality hot utility will cause a
great increase in its operating cost, which could not be covered by the
reduced cost of C2. Therefore, the sharp SSED is not economical in this
case. Different from C1, most of the intermediate component in C2 is
collected through the side stream, resulting in the great increase of the
temperature of the C2 bottom. However, since the reboiler duty is much
lower than those of C1 and C3, the increase of its operating cost will not
be so high when MP steam is used instead of LP steam. On the other
hand, the heat duty of the C3 reboiler, which always uses MP steam,
decreases rapidly when the remixing effect is almost eliminated. The
reduced cost of C3 is much higher than the increased cost of C2 to draw
the side stream, and it shows an economical performance to draw the
side stream at a very high flow rate. However, since it requires a much
higher reflux ratio and more stages to collect pure DMAC from C2 bot­
tom, it is still more economical for C2 to apply a non-sharp side-stream
configuration instead of a sharp one.
Different from the 3-column SSED configuration, the optimized 4-
column one has only one side stream (Fig. 14). When C1 draws a
sharp side stream, the increase in solvent content at the bottom will lead
to an elevated reboiler temperature, which means that more expensive
hot utilities are required. Since the reboiler duty of C1 is much larger
than that of C2, the sharply increased cost of C1 could not be covered by

13
H. Lyu et al.
Fig. 14. The 4-column SSED configuration.
the reduced cost of C2, making the sharp SSED less competitive. Simi­
larly, the sharp SSED is not economical for C3. Moreover, since the
temperature of the C3 reboiler is close to that of the feed location in C4
and the use temperature of LP steam and the temperature, even a slight
temperature increase will significantly increase the cost. As a result, C3
does not draw the side stream and the 4-column SSED configuration has
only one side stream. In this configuration, the side stream only collects
a small portion of intermediate components, and there is still a signifi­
cant remixing effect, which leads to the TAC of the 4-column SSED
configuration close to the heat integrated 4-column CED configuration.
5. Conclusion
In this paper, the sharp and non-sharp SSED configurations are both
considered as the alternatives to the CED ones for the industrial BEN/
ANE/ENE separation with DMAC as the solvent. The optimization
problem involves 30 different configurations, which have different
distillation sequences, side-stream column connection ways, and heat
integration options, together with more than 20 independent variables
that need to be optimized simultaneously. To solve the complex opti­
mization efficiently, we propose an improved superstructure-DE
method, which can adaptively select the feasible configuration for
different structural and operating parameters. The adaptive
superstructure-DE method and the conventional superstructure-DE one
are used to optimize the 3-column configuration, and the results
demonstrate the superior performance of the adaptive method. It can
obtain high-quality solutions from all possible candidates within the
equivalent computational time required for the DE algorithm to
14
Separation and Purification Technology 257 (2021) 117907
optimize a single configuration, and the results are much better than
those obtained by the conventional superstructure-DE method.
Using the adaptive superstructure-DE method, the 3-column and 4-
column SSED configurations are optimized, with 12 and 18 different
feasible candidates being considered, respectively. The optimized re­
sults do not apply any sharp side-stream options. The 3-column
configuration has two non-sharp side-stream options, while the 4-col­
umn configuration has only one non-sharp side-stream option, of
which the second EDC does not draw a side stream. This result shows the
necessity of considering different SSED options and highlights the sig­
nificance of an efficient optimization tool. Although the optimization
efficiency has been improved greatly, the adaptive superstructure-DE
approach still takes more than 1 day to obtain the result, due to the
inefficient random searching. Better searching and solving strategies
have to be developed in further work.
Declaration of Competing Interest
The authors declare that they have no known competing financial
interests or personal relationships that could have appeared to influence
the work reported in this paper.
Acknowledgment
The authors appreciate Benbin Li, Yongfeng Xu, Guoyao Jing in the
China Pingmei Shenma Group Nylon Technology Co., Ltd. for providing
basic feedstock composition information of this research. This research
did not receive any specific grant from funding agencies in the public,
H. Lyu et al. Separation and Purification Technology 257 (2021) 117907

Fig. 15. Liquid composition profiles for SSED configurations. (a) 3-column SSED configuration (b) 4-column SSED configuration.

commercial, or not-for-profit sectors. The authors also appreciate References

Dongxiao Zhang, for providing help for code debug.
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org/10.1016/j.seppur.2020.117907.
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