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chemical engineering research and design 8 9 ( 2 0 1 1 ) 2199–2206

Contents lists available at ScienceDirect

Chemical Engineering Research and Design

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

Design and control of reactive distillation for hydrolysis of


methyl lactate

Liu Mo, Jiang Shao-Tong ∗ , Pan Li-Jun, Zheng Zhi, Luo Shui-Zhong
School of Biotechnology and Food Engineering, The Key Laboratory for Agricultural Products Processing of Anhui Province, Hefei
University of Technology, Hefei 230009, China

a b s t r a c t

Esterification of raw lactic acid from fermentation broth and then hydrolysis of lactate ester in reactive distillation
column is an effective process for purification of lactic acid. Reactive distillation for hydrolysis of methyl lactate is
studied. First, the thermodynamic properties and reaction kinetics are analyzed; then the reactive distillation column
is designed based on the objective function total annual cost. The effects of tray number of rectifying section, tray
number of reactive section, and feed location on the total annual cost are investigated. And a dual-temperature
control structure is proposed for the optimal reactive distillation column, and the results show that it works quite
well for this hydrolysis system.
© 2011 The Institution of Chemical Engineers. Published by Elsevier B.V. All rights reserved.

Keywords: Methyl lactate; Hydrolysis; Reactive distillation; Process design

1. Introduction ried out esterification and hydrolysis reactions to recover lactic


acid in batch mode (Kim et al., 2002; Seo et al., 1999). Choi
Lactic acid (LA), CH3 CHOHCOOH, is an important naturally and Hong studied a batch reactive distillation (RD) process for
occurring organic acid that has many applications in food, the recovery of lactic acid through two reactors and one dis-
chemical, and pharmaceutical industries (Datta and Henry, tillation column (Choi and Hong, 1999; Kumar et al., 2006a),
2006). Recently, it was widely reported that lactic acid has based on this research a continuous process for the recovery
the potential to become a large volume commodity chemical of lactic acid by reactive distillation was proposed (Asthana
by the use of polylactic acid (PLA) for biodegradable poly- et al., 2005; Ma et al., 2005). Through esterification-hydrolysis
mers and controlled-release drugs and pesticides (Gupta et al., process, all of the undesired impurities such as unfermented
2007). LA can be produced by fermentation or chemical syn- sugars, other high boiling organic acids (succinic acid) are
thesis, fermentative production is more attractive because of expected to remain in the esterification reactor and a relatively
the availability of cheap raw material and the selective pro- pure lactic acid is recovered from the hydrolysis reactor.
duction of an optically active form (Zhang et al., 2007). Several RD offers some advantages over conventional processes
processes for LA recovery from fermentation broth have been where reaction and purification are carried separately. Some
reported, reactive extraction (Uslu, 2008; Wasewar et al., 2004), of them are the reduction of capital and operating costs,
ion-exchange (Gonzalez et al., 2006), and electro dialysis (Yi high selectivity, reduced energy consumptions, etc. (Harmsen,
et al., 2008). However, it is difficult to get highly pure and heat 2007; Zhang et al., 2010). Applications of RD are limited to sys-
stable LA due to its strong affinity to water, its low volatility, tems in which the reaction rates are fairly high and there
and its tendency to self-polymerize (Joglekar et al., 2006). is no mismatch of temperatures favorable for reaction and
Esterification of LA with a suitable alcohol and subsequent separation (Sundmacher and Kienle, 2003). A number of chem-
hydrolysis of the purified ester is an alternative technique for ical systems have been studied in the literature using RD
LA purification with high purity and efficiency (Gao et al., 2007; columns, most common applications are etherification and
Kim et al., 2000; Kumar et al., 2006b; Zhao et al., 2009). Seo et al. esterification. In recent years, there are many papers inves-
developed an apparatus with two distillation columns and car- tigating model, design and control aspects of RD columns


Corresponding author. Tel.: +86 0551 2901505/8224; fax: +86 0551 2901507.
E-mail addresses: liumo1985@gmail.com (L. Mo), jiangshotong@yahoo.com.cn (J. Shao-Tong).
Received 27 September 2010; Received in revised form 23 February 2011; Accepted 1 March 2011
0263-8762/$ – see front matter © 2011 The Institution of Chemical Engineers. Published by Elsevier B.V. All rights reserved.
doi:10.1016/j.cherd.2011.03.001
2200 chemical engineering research and design 8 9 ( 2 0 1 1 ) 2199–2206

a 1.0 b 1.0
Nomenclature
0.8

Molefrac lactic acid


0.8

Molefrac lactic acid


Ci concentration of component i in mixture,
0.6 0.6
mol L−1
E activation energy, kJ mol−1 0.4 0.4
Ke reaction equilibrium constant
0.2 0.2
k0 use in Eq. (2), mol−1 L s−1
kw use in Eq. (2), g−1 mol−1 L2 min−1 0.0 0.0
0.0 0.2 0.4 0.6 0.8 1.0 0.0 0.2 0.4 0.6 0.8 1.0
R gas constant, kJ mol−1 K−1
Molefrac water Molefrac methanol
r reaction rate, mol L−1 min−1
T temperature, K water / lactic acid / methanol methanol / lactic acid / methyl lactate
TAC total annual cost, ¥(×10,000) c
1.0 d 1.0
W catalyst loading, g L−1
xi mass fraction of component i in mixture 0.8 0.8

Molefrac lactic acid

Molefrac water
Subscripts 0.6 0.6

B bottom 0.4 0.4


cap capital
D distillate 0.2 0.2

HL lactic acid 0.0 0.0


H2 O water 0.0 0.2 0.4 0.6 0.8 1.0 0.0 0.2 0.4 0.6 0.8 1.0

MeOH methanol Molefrac water Molefrac methanol


ML methyl lactate water / lactic acid / methyl lactate methanol / water / methyl lactate
ope operating
Fig. 1 – Residue curve for methyl lactate hydrolysis
(P = 1 atm).

(Arpornwichanop et al., 2009; Cheng et al., 2009; Luyben and


are the lowest and highest boilers. To account for the nonideal
Yu, 2008; Taylor and Krishna, 2000; Ung and Doherty, 1995),
vapor–liquid equilibrium, the UNIFAC model is used for activ-
however, unlike conventional distillation columns, there are
ity coefficients. Because of the almost atmospheric pressure,
much more design variables, e.g., number of separation trays,
the vapor phase nonideality considered is the dimerization
number of reactive trays, feed tray location. The design of RD
of carboxylic acid as described by the Hayden–O’Connell sec-
columns becomes a combinatorial optimization problem with
ond virial coefficient model (Dong et al., 2006). The Aspen Plus
the objective function total annual cost (TAC) (Luyben and
built-in association parameters are used to compute fugacity
Yu, 2008). For accurate design of RD for LA recovery, kinetic
coefficients.
studies for LA esterification and LA ester hydrolysis have been
The phase equilibrium results reveal that this system
reported; however, relatively few researches were focused on
has only one minimum boiling binary azeotrope and has no
the design of RD column for LA purification.
ternary azeotrope, as shown in Fig. 1. The models predict that
Hydrolysis of methyl lactate is one important step for LA
methyl lactate and water form a homogeneous minimum-
recovery in esterification-hydrolysis method (Joglekar et al.,
boiling azeotrope with a composition of 97.0 mol% water at
2006). In this work, the steady-state economic optimum
1 atm and 99.87 ◦ C. This azeotrope has little effect on the sepa-
design of a RD column system for the hydrolysis of methyl
ration because it exists in the middle section of the RD column
lactate is presented. First, the thermodynamic properties
and the methyl lactate hydrolyzes to LA and methanol con-
of the quaternary system are investigated. Next, qualita-
tinuously. Fig. 1(c) shows the water–lactic acid–methyl lactate
tively, possible process flow sheet is generated based on the
three components residue curve map (RCM) which can be used
vapor–liquid-equilibrium (VLE) behavior. Then, design pro-
toward the bottom of the RD column where methanol is negli-
cedure is proposed to determine, quantitatively, the tray
gible. Fig. 1(d) shows the methanol–water–methyl lactate three
numbers in each section and feed tray location, the design
components RCM which can be used toward the top of the RD
is optimized based on the TAC. Finally, plant wide dynamic
column where lactic acid is negligible.
control structure is developed and tested. The commercial
simulation products Aspen Plus and Aspen Dynamics in
2.2. Reaction kinetics
ASPEN V7.0 are used in this study.

The liquid-phase reversible reaction considered is


2. Phase equilibrium and reaction kinetics
Methyllactate + Water ↔ Methanol + Lacticacid
2.1. Vapor–liquid equilibrium
The reaction is catalyzed by acidic cation-exchange resin
(D001 from Anhui Sanxing Resin Technology Co., Ltd.). From
For the methyl lactate hydrolysis process, the normal boiling
the experimental data of our previous work, the reaction rate
points are ranked, in ascending order, as follows:
can be expressed according to a pseudo-homogeneous model
CH3 OH < H2 O < CH3 CHOHCOOCH3 < CH3 CHOHCOOH
(Jiang et al., 2010)
64.53 ◦ C 100.02 ◦ C 144.81 ◦ C 122 ◦ C (2 kPa)
The two reactants, methyl lactate and water, are interme- 1291.4
ln Ke = − + 2.5543 (1)
diate boilers, whereas the products, methanol and lactic acid, T
chemical engineering research and design 8 9 ( 2 0 1 1 ) 2199–2206 2201

tion temperature will result in a small increase in the


equilibrium conversion. The catalyst loading in this
research was assumed to be 50% (W/V) of the liquid
Methanol
holdup.

Rectifying
Methyl lactate, 3. Process flow sheet and steady-state
section design
water,
methanol, 3.1. Process flow sheet
lactic acid Reactive
Several previous researches focused on continuous process
section for the recovery of lactic acid by reaction distillation have
been reported, a two-phase CSTR and RD column was involved
in this process. The stream containing LA and methanol is
Lactic acid,
continuously fed into the CSTR for esterification, the high
water boiling-point impurities in the broth are separated as a purge
through the bottom stream of the CSTR. The vapor stream of
Fig. 2 – Schematic drawing for methyl lactate hydrolysis the CSTR that contains methyl lactate, water and methanol is
using reactive distillation. fed into the RD column and methyl lactate is hydrolyzed to LA
and methanol in the presence of catalyst in the reactive zone
of the column. The distillate consists of volatile components
 E
  CHL · CMeOH

r = (k0 + kw · w) · exp − · CML · CH2 O − (2) (methanol and water) and the bottom product contains LA as
RT Ke aqueous solution.
However, in this process, the volatile components (lactate
ester, alcohol, and water) are evaporated under atmospheric
E = 45.84 kJ mol−1
pressure, these make the energy consumption huge; the
k0 = 600.52 mol−1 L min−1 hydrolysis of lactate ester is a slow reaction and it needs
kw = 44.34 g−1 mol−1 L2 min−1 long reaction zone for complete hydrolysis, this reduces col-
umn efficiency; in the purge stream, large amounts of LA and
where r is the reaction rate (mol L−1 min−1 ), C represents the
methyl lactate exist that need further recovery treatment to
mole concentration of the corresponding component (mol L−1 )
improve the process economics. So, we intend to propose a
and W is the catalyst loading (g L−1 ).
new process based on catalysis in fixed bed, vacuum distilla-
From the kinetics, it is observed that this is a slightly
tion and reactive distillation. (1) Esterification of lactic acid
endothermic reaction with an almost negligible heat
with methanol catalyzed by fixed bed; (2) vacuum distilla-
effect. This indicates that an increase in the reac-
tion of esterification products, and the residue is collected
and esterified with methanol again; (3) hydrolysis of methyl
Table 1 – Results of steady state design of reactive lactate catalyzed by fixed bed; and (4) the hydrolysis prod-
distillation for hydrolysis of methyl lactate. ucts are fed into reactive distillation column to hydrolyze
Item Results completely.
The schematic drawing of the methyl lactate hydrolysis in
Total number of trays 44
Number of trays in rectifying section 4
RD column is showed as Fig. 2, a prereactor (plug flow reactor)
Number of trays in reactive section 40 that handles a substantial part of the reaction duty is used
Reactive section 5–44 upstream of the RD column that consists of a rectifier and a
Feed tray 8 reactive section. The optimization of a RD column has a large
Catalyst in each tray/sum (kg) 12.15/473.85 number of design variables, in order to reduce the number
Catalyst in reboiler (kg) 50
of design optimization variables, the following specification
Mass reflux ratio 4.65
and assumption are made: (1) the feed flowrate is fixed at
Condenser duty (W) −784265.4
Reboiler duty (W) 733806.9 1 kg s−1 and it contains 90% water and 10% methyl lactate in
Column diameter (m) 0.59 mole fraction; (2) the product purity of the distillate stream
Column height (m) 21.12 is xD,MeOH = 0.95 (W/W); (3) the product purity of the bottom
Condenser heat transfer area (m2 ) 36.91 stream is xB,ML = 0.001 (W/W); (4) 70% conversion is obtained
Reboiler heat transfer area (m2 ) 20.67 after the prereactor; (5) the liquid that feed into the RD column
Distillate flow rate (kg/h) 427.1
is at saturation state.
Bottom product flow rate (kg/h) 3172.9
Mass fraction of the distillate product
Water 0.0539 3.2. Design procedure
Methanol 0.9461
Methyl lactate 6.3567e−07
Based on this flowsheet, a procedure is used to achieve an
Lactic acid 4.8067e−16
Mass fraction of the bottom product
improved design to reduce the TAC. The design variables
Water 0.6401 are: number of trays of the rectifying section (Nrec ), num-
Lactic acid 0.3587 ber of trays of the reactive section (Nrea ), feed tray location
Methanol 0.0002 in the reactive zone. Two manipulating variables consid-
Methyl lactate 0.0010 ered here including reflux ratio of RD column and reboiler
TAC (¥10,000/year) 234.8
duty.
2202 chemical engineering research and design 8 9 ( 2 0 1 1 ) 2199–2206

Fig. 3 – The effects of stages on the TAC. Nrec : number of trays in rectifying section; Nrea : number of trays in reactive section;
(a) feed on the first stage of reactive section, Nrec = 6; (b) feed on the first stage of reactive section; (c) feed on the second stage
of reactive section; (d) feed on the third stage of reactive section; (e) feed on the fourth stage of reactive section; and (f) feed
on the fifth stage of reactive section.

In this research, all simulations are carried out using RAD- the payback period is assumed to be 3 years and the catalyst
FRAC of Aspen Plus, the steps as follows are adopted to life is 3 months.
obtain a near optimal design: (1) place the reactants feed The details for the TAC computing are the same as Cheng
on the top of the reactive zone; (2) fix the number of reac- et al. (2009) with some changes as follows: M&S index of 1446.5
tive trays (Nrea ); (3) guess the tray numbers in the rectifying (2009, 4th Q) is applied in the calculation; the energy cost for
section (Nrec ); (4) change the reflux flow (R) and reboiler steam is ¥32.00/106 kJ; the price for cooling water is ¥2.00/cum;
heat duty until the products specification is met; (5) go back the price for resin is ¥25.00/kg.
to (3) and change Nrec until the TAC is minimized; (6) go For a RD column, one important issue is the tray holdup in
back to (2) and vary Nrea until the TAC is minimized; (7) go the reactive section, which is calculated by the column diame-
back to (1) and change the feed location until the TAC is ter, the active area of the bubble cap tray, and the liquid depth
minimized. on the tray. The active area of the bubble cap tray is usually
The estimation of the equipment follows the procedure 90% of the total cross-sectional area. The liquid depth is lim-
of Douglas (1988) and specific equation of Elliott and Luyben ited to about 0.1 m by the hydraulic limitation. The diameter of
(1996), Chiang et al. (2002) and Seider et al. (2003) were used. the column is unknown initially because it depends on vapor
The TAC is defined as: velocity that is not known until the column is converged to
the given specifications. So column sizing in RD column is
TACcap
TAC = TACope + (3) an iterative procedure, a diameter is estimated, tray holdups
3
calculated, and the column is converged, then the diameter
where the operating cost (TACope ) includes the costs of steam, calculated in “Tray Sizing” is compared with the estimated
cooling water, and catalyst, and the capital cost (TACcap ) covers diameter and the calculations repeated until the error can be
the cost of column, trays, and heat exchangers. In this work ignored.
chemical engineering research and design 8 9 ( 2 0 1 1 ) 2199–2206 2203

1.0 0.40 0.10 a 0.4


X (mass frac of water, methanol)

Reboiler duty +0.01%

X (mass frac of methyl lactate)


0.3

X (mass frac of lactic acid)


0.8 0.32 0.08 Reboiler duty -0.01%
0.2
0.6

ΔT/ΔQR (%/%)
0.24 0.06
lactic acid 0.1
water
0.4 methanol 0.16 0.04 0
methyl lactate
-0.1
0.2 0.08 0.02
-0.2

0.0 0.00 0.00 -0.3


10 20 30 40
Stage -0.4
0 10 20 30 40
405.0

Stage
b
390.0

0.3
Temperature K

Reflux ratio +0.01%


360.0 375.0

0.2
Reflux ratio -0.01%

ΔT/ΔRR (%/%)
0.1

0
345.0

-0.1
1.0 5.0 9.0 13.0 17.0 21.0 25.0 29.0 33.0 37.0 41.0 45.0
Stage -0.2

Fig. 4 – Composition and temperature profiles of RD column -0.3


for hydrolysis of methyl lactate. 0 10 20 30 40
Stage

Fig. 5 – Sensitivity analysis of reactive distillation column


for methyl lactate hydrolysis. (a) reboiler heat duty ±0.01%;
3.3. Design results
(b) reflux ratio ±0.01%.

From Fig. 3, it is found that the number of trays of the reac-


tive section (Nrea ) is an important design variable. Having too
few reactive trays results in high operating cost because the toward the top of the column, there is negligible lactic acid
reactants concentrations in the reactive zone must be large, composition, thus RCM of water–methanol–methyl lactate can
and this requires large vapor rate to keep the reactants from be used, at the bottom of the column, the methanol composi-
leaving the reactive sections. Adding more reactive trays can tion is negligible, thus RCM of water–lactic acid–methyl lactate
reduce the reboiler heat duty because reactant concentrations can be used. These agree with the earlier assumptions of using
in the reactive section decrease, but the capital cost increases. Fig. 1 for the conceptual design of this reactive distillation col-
The number of trays of the rectifying section is also impor- umn system. Even though 70% of reactions take place in the
tant on the TAC. More rectifying trays can lessen the reflux previous plug flow reactor, the remaining 30% reactions that
ratio so that the operating cost decreases. It is also observed take place in the reactive section cannot be neglected. With-
that the feed location is a very important variable. It turns out out this remaining 30% of reaction in the reactive section, the
that feeding on the fourth stage of the reactive section is most conversion of methyl lactate will not be high enough to meet
advantageous. its specification.
The results of design of this RD column and steady-state
operating conditions are given in Table 1. Fig. 4 shows the liq- 4. Temperature control
uid concentration and temperature profiles throughout the RD
column. In the table and the figure, the stages are counting For a distillation process, the ideal control structure would
from top down with condenser as stage 1 and reboiler as stage measure the compositions of the products and manipu-
44. late the operating variables (reflux flowrate, reboiler heat
From Table 1, one observes the optimal RD column contains duty, etc.) to keep the compositions of the products sat-
44 trays in total included condenser and reboiler, four trays in isfying the specification. However, composition analyzer is
rectifying section, forty trays in reactive section; It feeds on usually expensive to purchase and costly to maintain, and
eighth tray; the TAC is ¥2,348,000 per year; the aqueous prod- its reliability is sometimes inadequate for online continuous
uct stream from the condenser contains 94.61 wt% methanol control. Temperature control is widely used to provide infer-
and 5.39 wt% water, the aqueous product stream from the bot- ential control of composition. Temperature sensor is cheap,
tom contains 35.87 wt% lactic acid and 0.1 wt% methyl lactate, reliable and introduces only small lag time in the control
the methyl lactate is nearly completely hydrolyzed in the RD loop.
column.
From Fig. 4, it observes that the feed tray (eighth tray) 4.1. Selection of temperature control tray
exhibits the most methyl lactate liquid concentration inside
the column, the lactic acid liquid compositions inside the col- Sensitivity analyses are performed on this hydrolysis RD pro-
umn are quite flat between feed stage to the 43th stage due cess (Fig. 5). In order to find the steady-state gains of tray
to its high boiling point. Also from Fig. 4, one observes that temperature in the linear region, very small changes (±0.1%
2204 chemical engineering research and design 8 9 ( 2 0 1 1 ) 2199–2206

reflux flow rate and the temperature of the nineteenth tray is


chosen to be controlled by the reboiler heat duty.

4.2. Control structure

The control structure is presented in Fig. 6. Proportional con-


trollers are used for reflux drum level and reboiler level.
Proportional–integral (PI) controllers are used for feed flow
rate, pressure, and temperature of the fourth and nineteenth
tray. Dead time of 1 min is inserted in the two temperature con-
trollers. The relay-feedback tests are used to find the ultimate
gains and the ultimate periods of the two temperature con-
trollers followed by the Tyreus–Luyben PI tuning rule (Luyben,
Fig. 6 – Structure diagram for single temperature control.
2006).

of the design value) are made in the reboiler heat duty and 4.3. Control performance
the reflux ration. Dividing the change of the tray temperature
by the change of the manipulated variable gives the openloop The disturbances of feed flow rate changes (flow rate ±20%)
steady-state gain between temperature on that tray and each and feed composition variations (mass fraction of methyl lac-
manipulated variable. The tray temperatures of the RD col- tate ±5%, mass fraction of methanol ∓5 %) are used to evaluate
umn increase with the reboiler heat duty and an increase of the control performance of this hydrolysis RD system. The
the reflux ration leads to a decrease of the tray temperatures dual temperature control actually works very well for this sys-
of the column. For the disturbance of reboiler heat duty, there tem as shown in Figs. 7 and 8. For these two disturbances, the
are two peaks of temperature change on the fourth and nine- responses are quite symmetrical, the product compositions
teenth tray; for the disturbance of the reflux ratio, there is only settle in less than 5 h, and the steady state offsets are rather
one peak of the temperature change on the fourth tray. So, the small, 1 wt% for methanol in the distillate stream and 0.1 wt%
temperature of fourth tray is chosen to be controlled by the for methyl lactate in the bottom stream.

Fig. 7 – Test results for disturbances of feed flowrate under single temperature control — feed flowrate +20%; . . .. . . feed
flowrate −20%. (a) Temperature of the forth tray; (b) temperature of the nineteenth tray; (c) mass fraction of methanol in the
distillate; (d) mass fraction of methyl lactate in the reboiler; (e) actual duty of condenser; and (f) heat duty of reboiler.
chemical engineering research and design 8 9 ( 2 0 1 1 ) 2199–2206 2205

Fig. 8 – Test results for disturbances of feed composition under single temperature control — mass fraction of methyl lactate
+5%; . . .. . . mass fraction of methyl lactate −5%. (a) Temperature of the forth tray; (b) temperature of the nineteenth tray; (c)
mass fraction of methanol in the distillate; (d) mass fraction of methyl lactate in the reboiler; (e) actual duty of condenser;
and (f) heat duty of reboiler.

5. Conclusion Asthana, N., Kolah, A., Vu, D.T., Lira, C.T., Miller, D.J., 2005. A
continuous reactive separation process for ethyl lactate
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steady-state design of reactive distillation processes using
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annual cost; last, a dual-temperature control structure for this reactor/column and reactive distillation. Ind. Eng. Chem. Res.
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