Article

pubs.acs.org/IECR

Solubility of Dimethyl Terephthalate and Monomethyl Terephthalate

in the Methanol Aqueous Solution and Its Application To Recycle
Monomethyl Terephthalate from Crude Dimethyl Terephthalate
Hui Zhang, Qing Xia,* Ying Yang, Feng-Bao Zhang, and Guo-Liang Zhang
School of Chemical Engineering and Technology, Tianjin University, Tianjin, 300072, P.R. China
*
S Supporting Information

ABSTRACT: The solubilities of dimethyl terephthalate (DMT) and monomethyl terephthalate (MMT) in methanol aqueous
solutions were determined in the temperature range of 280−336 K. The solute-free mass fractions of methanol extended from
0.3 to 1.0. Both the solubilities of DMT and MMT in aqueous methanol solution increase with the temperature and the addition
of methanol. The experimental data were correlated with the Wilson and the NRTL models. The root-mean-square deviations
for the system of (DMT + methanol + water) were 1.30 and 1.33 K calculated by the Wilson and the NRTL models, respectively,
while for the system of (MMT + methanol + water), the root-mean-square deviations were 0.55 and 0.82 K. The melting points
and the enthalpy of fusion of DMT and MMT were detected by the differential scanning calorimetry (DSC). A simple
purification and recycling process was designed to separate MMT from the esterification reaction product according to the
solubility difference between DMT and MMT.

1. INTRODUCTION
DMT (CAS No.120-61-6) was mainly used to produce
polyethylene terephthalate (PET) prior to 1965.1 The
industrial process of producing DMT from p-xylene was first
developed by Chemische Werke Witten, modified by Hercules
and Dynamit-Nobel. Hüls Troidorf licensed the process with Figure 1. Chemical reaction process for producing CHDM by
further modifications.2 It contained two oxidation steps and reduction of DMT.
two esterification steps.3 Since the purification process for
terephthalic acid (PTA) developed by Amoco Chemical was a
success, DMT has been substituted gradually by the PTA which
could be directly condensed with ethylene glycol to form PET.
However, almost 30% of PET production is still based on
DMT. A great effort has been devoted to the modification of
PET by copolymerization to improve some of its properties. An
example is the commercial amorphous polyester named PETG, Figure 2. Chemical reaction process from PTA to DMT.
in which almost 30% mole fraction of ethylene glycol units of
PET are replaced by 1,4-cyclohexanedimethanol (CHDM)
units, which could be used to produce tough and high-
resistance materials, while low-level CHDM (<5% mole including trying to separate and recycle MMT in the crude
fraction) incorporation into PET is important in the develop- DMT product. It is necessary to know the solubility difference
ment of PET for container applications.4 As one of the of DMT and MMT. However, limited information is available
important modifiers in the polymer industry,5 CHDM6−8 is in the literature. Efremova14 reported the solubility of DMT in
mainly prepared by reduction of DMT in the two-step process, the methanol over the temperature range from 333.15 to
just as shown in Figure 1. First, DMT is reduced to dimethyl 413.15 K. Pryanikova and Efremova 15 researched the
1,4-cyclohexanedicarboxylate (DMCD), and second, DMCD is solubilities of DMT in (water + methanol) over the
reduced to CHDM under the catalytic action of copper temperature range from 323.15 to 413.15 K, with the mass
chromite.4 fractions of methanol of 0.259, 0.396, 0.48, 0.525, and 0.746.
DMT can be obtained from esterification PTA with However, no literature information about the solubility of
methanol.1,9 MMT is the intermediate product, and it is a MMT in methanol aqueous solution and that of DMT over the
reversible reaction from MMT to form DMT (the process is temperature range from 283.15 to 323.15 K could be found.
shown in Figure 2).10 Therefore, MMT is the main impurity in
the final product. Vacuum distillation or recrystallization in Received: February 4, 2013
methanol solvent has been used to purify DMT industri- Revised: March 15, 2013
ally.11−13 We have been working on the research and Accepted: March 18, 2013
development of the process of esterification PTA to DMT, Published: March 18, 2013

© 2013 American Chemical Society 5230 dx.doi.org/10.1021/ie400421e | Ind. Eng. Chem. Res. 2013, 52, 5230−5234
Industrial & Engineering Chemistry Research
In this work, the solubilities of DMT and MMT in the
aqueous methanol solutions will be determined by a dynamic
method at the temperature range from 280 to 336 K. The
Wilson and the NRTL models, which have been successfully
used to predict the solid−liquid equilibrium in several
systems,16−20 will be applied to correlate the experimental
data. The interaction parameters of the models are obtained.
According to the determined solubility data, a simple separation
and recycling MMT method will be designed.
2. EXPERIMENTAL SECTION
2.1. Materials. DMT was purchased from Aladdin
Chemical Co., Ltd., Shanghai, China, with a purity of 0.99
mass fraction, and was dried in vacuum to constant weight at
the temperature 303.15 K (DMT will sublimate when the
temperature is higher than 318.15 K) before using. The sample
of MMT was supplied by Meryer Chemical Co., Ltd., Shanghai,
China, with a purity of 0.99 mass fraction, and was dried to
constant weight at the temperature 353.15 K. Methanol was
obtained from Guangfu Chemical Reagents Co., Tianjin, China,
with a purity greater than 0.99 mass fraction. Deionized water
was purchased from Nankai Chemical Reagents Co., Tianjin,
China. Methanol and deionized water were used without
further purification.
2.2. Apparatus and Procedure. The solubilities of DMT
and MMT were determined by a dynamic method, which has
been described in detail previously.21,22 Briefly, predetermined
sample (weighed by the analytical balance, Gibertini,
Crystal200, Italy, with an accuracy of ±0.0001 g) was heated
slowly at a defined rate (0.2 K·h−1). A refrigerated/heating
circulator (Julabo FP45-HE, Germany, temperature stability
±0.01 K) was used to control the temperature of the sample,
and the temperature was measured by a platinum resistance
thermometer (PT-100), which was calibrated with an accuracy
of ±0.01 K. When the last crystal in the sample disappeared,
the temperature was taken as the equilibrium dissolution
temperature. The uncertainty of the temperature measurement
was ±0.3 K.
The melting point and the molar enthalpy of fusion for the
DMT and MMT have been measured in triplicate by the DSC
(Perkin-Elmer Pyris Diamond) at 5 K·min−1.
3. RESULTS AND DISCUSSION
3.1. Experimental Solubility Data of DMT and MMT.
Solid−liquid equilibrium experimental data for the systems of
(DMT + methanol + water) and (MMT + methanol + water)
are summarized in Tables S1 and S2 (Supporting Information),
respectively, where Texp is the measured absolute temperature,
x1 is the mole fraction solubility of DMT in the methanol
aqueous solution;, x2 is the mole fraction solubility of MMT in
the methanol aqueous solution, and ω03 is the mass fraction of
methanol in the solute-free solution. From Figure 3 it can be
seen that both the solubilities of DMT and MMT increase with
the temperature and decrease with addition of water. The
solubility of MMT is larger than that of DMT in the same
solvent mixture, which exhibits the feasibility of separating
MMT and DMT according to their solubility difference.
3.2. Correlation of Solid−Liquid Equilibrium. The
solid−liquid equilibrium behavior can be calculated by the
following equation:
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Figure 3. Difference of mole fraction (x) solubilities of MMT and
DMT in methanol aqueous solutions. Mass fractions of methanol on
the solute-free basis are (▲, Δ) ω03 = 0.3; (★, ☆) ω03 = 0.5; (■, □) ω03
= 0.7; (●, ○) ω03 = 0.9; (▼, ▽) ω03 = 1.0; solid symbols (▲, ★, ■, ●,
▼) express mole fraction solubilities of DMT; hollow symbols (Δ, ☆,
□, ○, ▽) express mole fraction solubilities of MMT.
ΔHt ⎛ Ttp ⎞ ΔCp ⎛ Ttp ⎞ ΔCp
−ln(γixi) = ⎜ − 1⎟ − ⎜ − 1⎟ +
RTtp ⎝ T ⎠ R ⎝T ⎠ R
⎛ Ttp ⎞
ln⎜ ⎟
⎝T ⎠ (1)
where γi denotes the activity coefficient of solute, xi denotes the
mole fraction of solute in the liquid phase, ΔHt is the molar
enthalpy of fusion of the solute, Ttp is the triple-point
temperature, and ΔCp is the difference in solute heat capacity
between the solid and the liquid at the melting point. Usually,
ΔHt and Ttp can be substituted by the enthalpy of fusion at the
melting point, and the melting point and the contribution of
heat capacity (the last two terms of eq1) are small and can be
neglected. Thus the eq1 can be simplified into the following
style:
ΔHf ⎛ Tf ⎞
−ln(xiγi) = ⎜ − 1⎟
RTf ⎝ T ⎠ (2)
where ΔHf is the enthalpy of fusion at the normal melting point
of Tf. The melting points of DMT and MMT measured by
DSC are 414.25 ± 0.10 K and 493.70 ± 0.15 K, respectively.
They have a good agreement with the data reported by
Datoussaid et al. (414.15−415.15 K for DMT),23 Dozen et al.
(415.15 K for DMT),24 and Zhang et al. (493.15−494.15 K for
MMT).25 And the molar enthalpies of fusion of DMT and
MMT measured by DSC are 34.87 ± 0.30 kJ·mol−1 and 39.73
± 0.38 kJ·mol−1, respectively. These data are close to the values
reported by Elliot and Chris (31.65 kJ·mol−1 for DMT),26
Dozen et al. (32.9 kJ·mol−1 for DMT),24 and Monte and Sousa
(37.68 kJ·mol−1 for MMT).27
The activity coefficient in eq 2 is calculated by the Wilson
model and the NRTL model separately.
The Wilson model28is described in eq 3
dx.doi.org/10.1021/ie400421e | Ind. Eng. Chem. Res. 2013, 52, 5230−5234
Industrial & Engineering Chemistry Research Article

Table 1. Parameters of the Wilson Model for the Systems of (DMT + Methanol + Water) and (MMT + Methanol + Water)
i j aij bij (K) aji bji (K)
DMT methanol 79.787 8248.4 −1.7739 −1273.0
DMT water 4.2981 −2405.9 −21.476 3451.5
MMT methanol 1.8960 22.549 −2.8340 1222.1
MMT water 15.413 −3155.5 −2.3692 −1487.1
methanol water 2.2568 −590.44 7.7015 −1535.0

Table 2. Parameters of the NRTL Model for the Systems of (DMT + Methanol + Water) and (MMT + Methanol + Water)
i j cij dij (K) cji dji (K)
DMT methanol 0.96458 −951.75 −3.2866 3063.4
DMT water −62.076 18562 1.3766 1963.6
MMT methanol 3.579 −1489.4 −4.7522 1786
MMT water −48.35 13891 −32.064 11863
methanol water −48.546 12804 19.365 −5238.9

n n
Aki xk Table 3. Root-Mean-Square Deviations (RMSD) Described
ln γi = 1 − ln(∑ Aij xj) − ∑ n by the Wilson and the NRTL Models
j k
∑ j Akj xj (3)
Wilson NRTL
where xi represents the mole fraction solubility of component i
RMSDDMT RMSDMMT RMSDDMT RMSDMMT
and the binary interaction parameter Aij is defined as a function solvent system (K) (K) (K) (K)
of temperature: water + 0.51 0.45 0.81 0.52
bij 30% methanol
Aij = aij + water + 1.93 0.49 1.97 0.91
T (4) 50% methanol
water + 1.94 0.85 1.87 1.19
where aij and bij are constants. 70% methanol
The NRTL model29 employed in this study is described in water + 0.90 0.70 0.76 0.81
eq5 90% methanol
pure methanol 0.65 0.23 0.87 0.70
n
∑ j xjτjiGji n xjGij ⎛ ∑m xmτmjGmj ⎞
n
ln γi = + ∑ ⎜ τ − ⎟ average RMSD 1.30 0.55 1.33 0.82
∑k xkGkj ⎜⎝ ∑k xkGkj ⎟⎠ value
n n ij n
∑k xkGki j
(5)
where xi represents the mole fraction of component i, and the systems, respectively. The curves of calculated results are
binary interaction parameter Gij = exp(−αijτij), with τij defined presented in Figures 4 and 5, together with the experimental
as a function of temperature in eq 6 data points. The average RMSD values for the system of (DMT
dij
τij = cij +
T (6)
where τij ≠ τji, τii = 0, and cij and dij are constants; no-random
parameter αij = αji is taken as 0.3, which is recommended by
Renon and Prausntz.29
The parameters aij, bij, cij, and dij are determined using the
Nelder-Mead Simplex Method. The root-mean-square devia-
tion between the experimental equilibrium absolute temper-
ature and the calculated equilibrium absolute temperature,
RMSD, is chosen as the objective function, which is defined as
follows:
N
∑i = 1 (Tiexp − Tical)2
RMSD =
(N − 1) (7)
where N is number of experimental data points; Texp i is the
experimental equilibrium absolute temperatures which are
summarized in Tables S1 and S2 (Supporting Information);
and Tcal
i is the calculated equilibrium absolute temperature.
The parameters for the activity coefficient models are shown Figure 4. Mole fraction (x1) solubilities of DMT in methanol aqueous
in Tables 1 and 2 . RMSD values calculated by the Wilson solutions. Mass fractions of methanol on the solute-free basis are (▲)
model and the NRTL model are listed in Table 3, and ω03 = 0.3; (★) ω03 = 0.5; (■) ω03 = 0.7; (●) ω03 = 0.9; (▼) ω03 = 1.0; 
subscripts DMT and MMT expresses the RMSD values for the calculated from the NRTL model; --- calculated from the Wilson
(DMT + methanol + water) and (MMT + methanol + water) model.

5232 dx.doi.org/10.1021/ie400421e | Ind. Eng. Chem. Res. 2013, 52, 5230−5234

Industrial & Engineering Chemistry Research
Figure 5. Mole fraction (x2) solubilities of MMT in methanol aqueous
solutions. Mass fractions of methanol on the solute-free basis are (▲)
ω03 = 0.3; (★) ω03 = 0.5; (■) ω03 = 0.7; (●) ω03 = 0.9; (▼) ω03 = 1.0; 
calculated from the NRTL model; --- calculated from the Wilson
model.
+ methanol + water) are 1.30 K for the Wilson model and 1.33
K for the NRTL model, while for the system of (MMT +
methanol + water), the average RMSD values are 0.55 and 0.82
K for the Wilson model and the NRTL model, respectively.
The average RMSD values of NRTL model are higher than
those of the Wilson model. It is therefore considered that the
NRTL model is less accurate than the Wilson model in
correlating the solid−liquid phase equilibria of the studied
systems.
3.3. Application of the Solubility Difference To Design
a Simple Purification and Recycling Process. We have
been working on improving the process of esterification PTA
with methanol. The solubility difference of DMT and MMT
presents a reference for designing a process to separate MMT
from the esterification reaction product. Because of low
solubility and difficult melting of PTA, excess methanol needs
to be used in the esterification reaction. Usually the mass ratio
of methanol to PTA (denoted as n) is 3 to 10. The excess
methanol should be recovered in order to reduce the
production cost. Here we determine optimum value of n
according to the solubility difference of MMT and DMT and
design a process to separate MMT from the crude products and
reuse excess methanol.
If the yield of DMT is 0.95 in the esterification of PTA with
methanol, the solid−liquid mixture of reaction residue may
contain excessive methanol, DMT, water, a little MMT, and
trace PTA. It is reasonable to neglect trace PTA because the
estetrificaiton rate of the first carboxyl group in PTA is faster
than that of the second one.10 If using n = 4.3, after the
esterification reaction the solute-free mass fraction of methanol
will be 0.95, and the mole fraction of MMT equals 2.45 × 10−3.
According to the determined solubility data, it can be calculated
that the solubility of DMT in the 0.9 solute-free mass fraction
methanol aqueous solution is 1.02 × 10−3 at the temperature of
298.36 K, while for that of the MMT is 2.45 × 10−3. It means
that all of MMT existing in the mixture of the crude product is
dissolved, while the DMT dissolved in the solution will be no
more than 1% of the produced DMT. Filtrating the mixture of
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the reaction residue at room temperature, the cake which
contains DMT and trace PTA can be washed by dilute alkali
solution to remove trace PTA, and the filtrate which contains
methanol, a little MMT, and water can be reused as shown in
Figure 6. Of course, some MMT will still stay in the cake after
Figure 6. Simple process for separation MMT and DMT and recycling
methanol.
filtration because some filtrate will stay in the pores of the cake.
Operation conditions of the filtration will affect the amount of
filtrate in the pores of the cake. But anyway, designing the
optimum value of n according to the solubility data, the
intermediate MMT can be recycled as much as possible.
Therefore, solubility data presented in this work can be useful
in optimizing the esterification process.
4. CONCLUSION
The solubilites of DMT and MMT in the methanol aqueous
solution have been investigated. Both of them increase with the
temperature and the addition of methanol in the solvent
mixtures. The solubility of MMT is larger than that of DMT in
the same composition solvent. The experimental solubility data
have been correlated with the Wilson and the NRTL models.
The average RMSD values for the DMT systems are 1.30 and
1.33 K for the Wilson and the NRTL models, respectively,
while for the MMT systems, the values are 0.55 and 0.82 K.
The melting points of DMT and MMT measured by DSC are
414.25 ± 0.10 K and 493.70 ± 0.15 K, and the molar enthalpies
of fusion of DMT and MMT measured by DSC are 34.87 ±
0.30 kJ·mol−1 and 39.73 ± 0.38 kJ·mol−1, respectively. A simple
process has been designed to separate MMT from the crude
product of esterification reaction according to the solubility
difference between DMT and MMT. The excess methanol and
intermediate MMT can be recycled.
■
ASSOCIATED CONTENT
*
S Supporting Information
Tables of the experimental solubilities and solute-free mass
fractions of methanol. This material is available free of charge
via the Internet at http://pubs.acs.org.
■
AUTHOR INFORMATION
Corresponding Author
*Tel.: +86-22-27400292. Fax: +86-22-27408778. E-mail:
xiaqing@tju.edu.cn.
Notes
The authors declare no competing financial interest.
■ ACKNOWLEDGMENTS
The authors thank the support by the Program of Introducing
Talents of Discipline to Universities, China, No. B06006.
dx.doi.org/10.1021/ie400421e | Ind. Eng. Chem. Res. 2013, 52, 5230−5234
Industrial & Engineering Chemistry Research

■
Article

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