Article pubs.acs.org/jced
Solubilities of Succinic Acid in Acetic Acid + Water Mixtures and Acetic Acid + Cyclohexane Mixtures Fuqiong Lei,† Qinbo Wang,*,† Xing Gong,† Binwei Shen,‡ Wenming Zhang,‡ and Qing Han‡ †
Department of Chemical Engineering, Hunan University, Changsha, 410082 Hunan, P. R. China Zhejiang Shuyang Chemical Co. Ltd., Quzhou, 324002 Zhejiang, P. R. China
‡
ABSTRACT: The solubilities of succinic acid in acetic acid + water solvent mixtures at (303.2 to 333.2) K and acetic acid + cyclohexane solvent mixtures at (303.2 to 343.2) K were determined. It was found that the solubility of succinic acid in acetic acid + cyclohexane mixtures increases with increasing mass fraction of acetic acid at constant temperature. However, for the system of acetic acid + water solvent mixtures, acetic acid with the mass fraction of 0.20 shows the best dissolving capacity for succinic acid. The experimental data were wellcorrelated with universal quasi-chemical (UNIQUAC) equations, and the solubilities calculated by the model were in good agreement with experimental data.
1. INTRODUCTION Adipic acid is widely used in the manufacturing of Nylon-66, polyesters, resins, plasticizers, and the like.1 Commercially, it is manufactured by the two-step oxidation of cyclohexane. The first step involves oxidizing cyclohexane with oxygen to a mixture of cyclohexanol and cyclohexanone (KA oil). The second step involves using nitric acid as a milder oxidant for the subsequent oxidation of the KA oil to adipic acid. Thus, the second step leads to a substantial amount of undesirable NOx, which shows a global warming effect 300 times higher than that of carbon dioxide. The direct oxidation of cyclohexane to adipic acid is a process which has been paid special attention for a long time.1,2 In particular, the process has the obvious advantages that it would convert cyclohexane into adipic acid in a single stage and without using nitric acid as the oxidant. During the oxidation process, usually the solvent is acetic acid and the oxidant is oxygen. Water and adipic acid are the main products. The byproducts formed contain glutaric acid and succinic acid. To obtain pure adipic acid, the crude adipic acid must be purified. Usually, crystallization is used to obtain products with a high purity.3 The solubility data of adipic acid (AA), glutaric acid (GA), and succinic acid (SA) in acetic acid + water solvent mixtures and acetic acid + cyclohexane solvent mixtures are essential for the proper design of the process and for controlling operation conditions in order to improve the purification of adipic acid. Also, solubility is an important basic property of solid−liquid equilibrium (SLE) in the chemical industry. Such data are required for the proper design and optimization of various processes. In our recent work, the solubility of AA in acetic acid + water mixtures and acetic acid + cyclohexane mixtures were reported.4 For the solubility of SA and GA, some data in pure water5−10 and pure acetic acid11 could be found, but no © 2014 American Chemical Society
reports in cyclohexane are available. For GA, it has an odd number of carbon atoms. The properties such as solubility and melting point are much more different from that of SA and AA, which have an even number of carbon atoms. These differences will be measured and discussed in detail in our later work. In this work, we focused on the solubility of succinic acid in acetic acid + water mixtures and acetic acid + cyclohexane mixtures. The experimental work was carried out at (303.2 to 343.2) K. The experimental data were correlated by the UNIQUAC12 equation and the model parameters were regressed. The obtained interaction parameters might be used in the calculation of solubility of succinic acid in acetic acid + water mixtures and cyclohexane + acetic acid mixtures as well as for the design and optimization of the related purification process.
2. EXPERIMENTAL SECTION 2.1. Materials. Succinic acid, pimelic acid, acetic acid, and cyclohexane were obtained from Aladdin Chemistry Co., and had a declared purity of 0.990 in mass fraction. The mass fraction purities of succinic acid and pimelic acid were checked by high-performance liquid chromatography (HPLC). The mass fraction purities of acetic acid and cyclohexane were checked by gas chromatography (GC). Purified water manufactured by Hangzhou Wahaha Group Co. was obtained from the supermarket (596 mL each bottle). All the chemicals were used in the experiment without further purification. The description of the chemical agents used in this work is given in Table 1. Received: March 10, 2014 Accepted: April 3, 2014 Published: April 10, 2014 1714
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the experimental apparatus had been verified in our recent work.4 2.3. Analysis. In each measurement, a 5 mL syringe was used to withdraw about 2 mL of the clear upper portion of the solution each time. Before sampling, a 25 mL sampling bottle was charged with about 5 mL of methanol. The total weight of the syringe and the sampling bottle with the preadded methanol was measured, which might be defined as m1. After sampling, the sample was immediately discharged into the sampling bottle, and the total weight of the syringe and the sampling bottle at this moment was measured again, which might be defined as m2. The difference between m2 and m1 is the amount of sampled solution. To collect the possibly crystallized solute in the syringe, the syringe was washed with methanol at least 10 times. The amount of SA in the solution was measured using a Shimadzu-15C high-performance liquid chromatography (HPLC) with an Inertsil ODS-3 (250 mm·4.6 mm, 5 μm) chromatographic column. The internal standard method was used and pimelic acid was the internal standard substance. The similar analytic procedure is described in detail elsewhere.4 Briefly, the mobile phase consists of two eluents (i.e., acetonitrile + water), and the following two-component elution program was adopted: from (0 to 10) min, 16 mass % acetonitrile, and 84 mass % water. Similar to that reported in our previous work, the estimated associated uncertainty of the measured solubility values based on error analysis and repeated observations was within 4 %.
Table 1. Suppliers and Mass Fraction Purity of the Materials component sucinic acid pimlic acid cyclohexane acetic acid a
suppliers Aladdin Aladdin Aladdin Aladdin
mass fraction
Chemistry Chemistry Chemistry Chemistry
Co. Co. Co. Co.
> > > >
0.990 0.990 0.995 0.990
analysis method HPLCa HPLCa GCb GCb
High-performance liquid chromatography. bGas chromatography.
2.2. Apparatus and Procedures. The experimental apparatus and sampling methods used in this work were described in detail by Wang and Shen.4,13 Briefly, in each experiment, an excess mass of SA was added to a known mass of the solvent in a 100 mL glass bottle, sealed by a rubber stopper to prevent the evaporation of solvent. The bottle was put in a thermostatic water bath and heated to the desired temperature with the uncertainty of ± 0.1 K. The mixture was mechanically stirred to accelerate the dissolution of solute SA. After at least 3 h, the mixture was allowed to settle down in the ensuing several hours before sampling. Different dissolution times were tested to determine a suitable equilibrium time. It was found that 2 h after stirring was stopped was enough time for solute SA in solvent to reach equilibrium, because repetitive measurements during the following several hours indicated the results were reproducible within ± 3 %. At each temperature, the mixture was kept isothermal and undisturbed for at least 12 h to ensure the solution had been saturated. The reliability of
Table 2. Solubilities of Succinic Acid (cr,1) in Acetic Acid (2) + Water (3) Solvent Mixtures at Temperature (303.2 to 333.2) K and Pressure p = 101.3 kPaa T/K
S/(g·(100g)−1)
Sc/(g·(100g)−1)
T/K
RD/%
S/(g·(100g)−1)
w2 = 1.0 303.2 313.2 323.2 333.2
2.97 4.17 5.67 7.72
303.2 313.2 323.2 333.2
4.73 6.59 8.72 11.21
303.2 313.2 323.2 333.2
6.68 9.47 12.04 16.46
303.2 313.2 323.2 333.2
8.46 11.84 15.97 21.02
303.2 313.2 323.2 333.2
9.85 14.61 18.35 26.15
303.2 313.2 323.2 333.2
11.34 15.79 21.14 28.96
Sc/(g·(100g)−1)
RD/%
w2 = 0.4 2.94 4.10 5.67 7.78
−0.97 −1.49 0.00 0.85
303.2 313.2 323.2 333.2
11.96 17.41 23.92 32.33
4.72 6.40 8.48 11.06
0.31 −2.90 −2.74 −1.41
303.2 313.2 323.2 333.2
12.23 17.97 24.63 35.47
6.98 9.46 12.63 16.45
4.53 −0.09 4.93 −0.01
303.2 313.2 323.2 333.2
12.32 18.31 25.85 35.75
8.89 12.15 16.28 21.40
5.17 2.63 1.90 1.80
303.2 313.2 323.2 333.2
11.94 17.62 25.06 35.34
10.36 14.26 19.35 25.55
5.23 −2.42 5.46 −2.31
303.2 313.2 323.2 333.2
10.47 16.55 24.44 34.12
11.36 15.85 21.68 29.05
0.17 0.44 2.57 0.31
w2 = 0.9
11.97 16.89 23.38 31.77
0.01 −2.97 −2.26 −1.76
12.20 17.46 24.48 33.83
−0.20 −2.83 −0.60 −4.62
12.15 17.62 25.08 35.13
−1.32 −3.79 −2.96 −1.73
11.87 17.38 25.07 35.69
−0.54 −1.33 0.04 1.00
11.34 16.84 24.66 35.54
8.28 1.77 0.93 4.15
w2 = 0.3
w2 = 0.8
w2 = 0.2
w2 = 0.7
w2 = 0.1
w2 = 0.6
w2 = 0.0
w2 = 0.5
a Standard uncertainties u are u(T) = 0.1 K, ur(p) = 0.05, ur(S) = 0.04. w2 is the mass fraction of acetic acid in binary acetic acid + water solvent mixtures. S and Sc are the experimental and calculated data, respectively. The solubility is defined as the mass of solute (g) in 100 g of solvent
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3. RESULTS AND DISCUSSION 3.1. Experimental Results. Solubility of SA in Acetic Acid + Water Mixtures. The solubility data of SA in acetic acid + water mixtures are summarized in Table 2, where w2 was defined as the mass fraction of acetic acid in binary acetic acid + water solvent mixtures. To verify the reliability of the experimental apparatus, comparisons have been made between experimental solubility of succinic acid in pure water5,11 and pure acetic acid11 with solubility data reported in literature. Figure 1 shows the comparison of the solubility of the SA in
Figure 3. Solubilities of succinic acid (1) in acetic acid (2) + water (3) solvent mixtures: ■, 303.2 K; ●, 313.2 K; ▲, 323.2 K; ▼, 333.2 K; w2 is the mass fraction of acetic acid in binary acetic acid + water solvent mixtures.
Wang et al. for the solubility of phthalic acid in the mixture of acetic acid + water,13 Chen and Ma for the solubility of terephthalic acid in the mixture of acetic acid + water,14 and Shen et al. for the solubility of adipic acid in the mixture of acetic acid + water.4 Solubility of SA in Acetic Acid + Cyclohexane Mixtures. The solubility data of SA in acetic acid + cyclohexane mixtures are summarized in Table 3, where w2 was defined as the mass fraction of acetic acid in binary acetic acid + cyclohexane solvent mixtures. From Table 3 and Figure 4, it can be seen that within the temperature range of the measurements, the solubility of SA in all of the mixtures shows an increasing trend as the temperature increases. The solubility of SA in the mixed acetic acid + cyclohexane increases with increasing mass fraction of acetic acid at constant temperature. 3.2. Correlation of Experimental Data. The models used to describe solid−liquid equilibrium are based on the activity coefficients and the expression is given by eq 1 that involves the properties of pure solute, such as enthalpy of fusion, melting point, and so forth.13−15
Figure 1. Comparisons between experimental solubility of succinic acid in water with solubility data reported in literature: ■, this work (w2 = 1.0); □, literature data from Apelblat;5 ○, literature data from Yu.11
ln(γ1x1) = −
ΔfusH ⎛ 1 1 ⎞ ΔtrsH ⎛ 1 1 ⎞ ⎜ − ⎟− ⎜ − ⎟ R ⎝T Tfus ⎠ R ⎝T Ttrs ⎠ (1)
For the system of SA + acetic acid + water and SA + acetic acid + cyclohexane, the solid−solid phase transition does not occur, and the last term in eq 1 can be neglected. Therefore, eq 1 can be simplified as
Figure 2. Comparisons between experimental solubility of succinic acid in acetic acid with solubility data reported in literature: ■, this work (w2 = 0.0); □, literature data from Yu.11
water. Figure 2 shows the comparison of the solubility of the SA in acetic acid.11 It can be seen that there is a fairly good agreement between the data from Apelblat,5 Yu,11 and those measured in this work, which indicates that the experimental solubility data are convincing and acceptable. From Table 2 and Figure 3, it can be seen that at each measured temperature, acetic acid with a mass fraction of 0.20 had the best dissolving capacity for SA within the solvent composition range of measurements. When the mass fraction of acetic acid was greater than 0.20, the solubility of SA decreased with the increasing mass fraction of acetic acid. Meanwhile, when the mass fraction of acetic acid was less than 0.20, the solubility of SA increased with the increasing mass fraction of acetic acid. This maximum-solubility effect was also noted by
ln(γ1x1) = −
ΔfusH ⎛ 1 1 ⎞ ⎟ ⎜ − R ⎝T Tfus ⎠
(2)
In eqs 1 and 2, ΔfusH is the molar fusion enthalpy of solute, Tfus is the fusion temperature, ΔtrsH is the molar enthalpy of solid− solid phase transition, Ttrs is the transition temperature, T is the absolute temperature, R is the universal gas constant, γ1 is the activity coefficient of solute, and x1 is the real mole fraction of solute in solution. The fusion temperature Tfus and molar enthalpy of fusion of solute ΔfusH are 458.15 K and 32950 J/ mol respectively, which are obtained from the literature.16 In this study, the UNIQUAC equation was used to calculate the activity coefficient γ1 for the ternary system. The activity coefficient of the UNIQUAC equation is given by 1716
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Table 3. Solubilities of Succinic Acid (cr,1) in Acetic Acid (2) + Cyclohexane (3) Solvent Mixtures at Temperature (303.2 to 343.2) K and Pressure p = 101.3 kPaa S/(g·(100g)−1)
T/K
Sc/(g·(100g)−1)
S/(g·(100g)−1)
T/K
RD/%
w2 = 1.0 303.2 313.2 323.2 333.2 343.2
2.97 4.17 5.67 7.72 11.56
2.77 3.89 5.40 7.41 10.17
−6.75 −6.61 −4.89 −3.96 −11.99
2.40 3.37 4.67 6.41 8.77
−3.74 −3.81 −3.24 0.22 −3.56
2.02 2.84 3.94 5.41 7.40
−0.52 −1.32 −2.86 1.39 −2.44
1.66 2.33 3.22 4.41 6.02
1.29 −0.85 −3.05 4.95 0.52
1.31 1.83 2.52 3.45 4.71
1.23 −1.40 1.42 6.64 0.96
0.97 1.36
4.82 4.33
2.49 3.50 4.83 6.39 9.09 2.03 2.88 4.06 5.33 7.58 1.64 2.35 3.33 4.20 5.99 1.29 1.86 2.49 3.24 4.66
303.2 313.2
0.93 1.31
303.2 313.2 323.2 333.2 343.2
0.63 0.90 1.23 1.60 2.36
303.2 313.2 323.2 333.2 343.2
0.39 0.57 0.73 1.01 1.55
303.2 313.2 323.2 333.2 343.2
0.22 0.30 0.44 0.53 0.76
303.2 313.2 323.2 333.2 343.2
0.09 0.12 0.16 0.20 0.26
3
∑ xjlj j=1
3
θτ j ij 3 j = 1 ∑k = 1 θkτkj
j=1
0.42 0.58 0.79 1.06 1.43
6.25 2.48 8.13 5.89 −7.45
0.22 030 0.41 0.54 0.72
0.04 0.58 −6.70 1.58 −6.36
0.08 0.11 0.15 0.20 0.26
−3.30 6.72 3.42 −2.23 1.77
⎛z⎞ ⎜ ⎟(r − q ) − (r − 1) j j ⎝2⎠ j
xiri 3 ∑i = 1 xiri
, θi =
xiqi 3 ∑i = 1 xiqi
(4)
⎛ bij ⎞ , τij = exp⎜aij + ⎟ T⎠ ⎝
(5)
where z is the number of close interacting molecules around a central molecule and set equal to 10; ri and qi are the structure parameters of pure component i; aij and bij are adjustable parameters unrelated to both composition and temperature needed to be regressed. The structural parameters for molecular volume and surface, ri and qi used for water + acetic acid + cyclohexane in the UNIQUAC equation were reported in the previous literature. The parameters r and q for succinic acid were not found in literature, which can be calculated from the procedure described earlier.17 The values of r and q for the pure compounds are listed in Table 4. The experimental solubility data were correlated by the UNIQUAC equation and the model parameters were regressed by the Nelder−Mead Simplex approach,18 which had been introduced in detail in the work of Wang et al.13 Function f minsearch in the optimization toolbox of Matlab (Mathwork, MA) uses the Nelder−Mead Simplex approach and can be employed for the minimization of the objective function, which
Figure 4. Solubilities of succinic acid (1) in acetic acid (2) + cyclohexane (4) solvent mixtures: ■, 303.2 K; ●, 313.2 K; ▲, 323.2 K; ▼, 333.2 K; ▶, 343.2 K; w2 is the mass fraction of acetic acid in binary acetic acid + water solvent mixtures.
− qi ln(∑ θτ j ji) + qi − qi ∑
6.72 3.63 4.39 8.76 −0.04
Standard uncertainties u are u(T) = 0.1 K, ur(p) = 0.05, ur(S) = 0.04. w2 is the mass fraction of acetic acid in binary acetic acid + cyclohexane solvent mixtures. S and Sc are the experimental and calculated data, respectively. The solubility is defined as the mass of solute (g) in 100 g of solvent
ψi =
3
0.67 0.94 1.29 1.74 2.36
a
lj =
ψ θ z + qi ln i + li − i ln γi = ln xi xi 2 ψi
0.07 8.33 −1.80
w2 = 0.1
w2 = 0.5
ψi
1.88 2.55 3.47
w2 = 0.2
w2 = 0.6 303.2 313.2 323.2 333.2 343.2
1.88 2.36 3.54
w2 = 0.3
w2 = 0.7 303.2 313.2 323.2 333.2 343.2
323.2 333.2 343.2
w2 = 0.4
w2 = 0.8 303.2 313.2 323.2 333.2 343.2
RD/%
w2 = 0.5
w2 = 0.9 303.2 313.2 323.2 333.2 343.2
Sc/(g·(100g)−1)
(3)
where 1717
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Table 4. r and q Values of the Used Pure Compounds for UNIQUAC component
r
q
succinic acid acetic acid water cyclohexane
3.8932 1.9000 0.9200 4.0475
3.5280 1.8000 1.4000 3.2400
Funding
The project was granted financial support from Key S&T Special Project of Zhejiang Province (2012C13007-2) and the Fundamental Research Funds for the Central Universities. Notes
The authors declare no competing financial interest.
■
is the average relative deviation (ARD) between the experimental and calculated mole fractions defined as ARD =
1 n
n
∑ abs(RDi),
RDi =
i=1
Sci − Si 100 Si
(8)
where n is the total number of experimental points, Sci and Si are the calculated and experimental solubility in mole fractions, and the subscripts i denote component. To obtain a unique set of parameters valid for all the range of temperatures studied, a simultaneous regression of all experimental SLE data of this system was carried out. The regressed UNIQUAC temperature-independent binary interaction parameters are listed in Table 5. As shown in Table 5, Table 5. Optimized Temperature-Independent Binary Interaction Parameters for the UNIQUAC Model for the SA (1) + Acetic Acid (2) + Water (3) and SA (1) + Acetic Acid (2) + Cyclohexane (4) i−j 1−2 1−3 1−4 2−3 2−4
αij
aji
bij
1.606 4.439 0.274 −0.476 −6.613
−0.263 0.626 −2.801 10.569 −0.151
−1.042·10 −2.651·103 −4.788·101 5.545·101 7.166·102
bji 3
ARD/% 2
3.232·10 2.233·102 4.555·102 −2.936·103 −7.741·101
2.95
the ARD value was 2.95 %. It shows that the UNIQUAC model equation can be used to correlate the solubility of SA in acetic acid + water mixtures and acetic acid + cyclohexane mixtures.
4. CONCLUSIONS In this work, the solubility of succinic acid in acetic acid + water solvent mixtures at (303.2 to 333.2) K and acetic acid + cyclohexane solvent mixtures at (303.2 to 343.2) K under atmospheric pressure were measured. The following conclusions might be reached: (1) The measured solubility of succinic acid in acetic acid + cylohexane mixtures increases with increasing mass fraction of acetic acid at constant temperature. (2) For the system of acetic acid + water solvent mixtures, acetic acid with a mass fraction of 0.20 has the largest dissolving capacity for succinic acid. (3) The experimental data were wellcorrelated by the UNIQUAC equation and the model parameters were regressed. (4) The obtained interaction parameters might be used in the calculation of the solubility of succinic acid in acetic acid + water mixtures and cyclohexane + acetic acid mixtures as well as for the design and optimization of the related purification process.
■
REFERENCES
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AUTHOR INFORMATION
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