Article pubs.acs.org/jced
Phase Equilibria of trans-1,3,3,3-Tetrafluoropropene with Three Imidazolium Ionic Liquids Xiaopo Wang,* Yao Zhang, Dongbo Wang, and Yanjun Sun Key Laboratory of Thermo-Fluid Science and Engineering, Ministry of Education, Xi’an Jiaotong University, Xi’an, 710049, China ABSTRACT: In recent years, trans-1,3,3,3-tetrafluoropropene (R1234ze(E)) was proposed as a possible replacement for hydrofluorocarbons. In this work, the vapor−liquid phase equilibrium of R1234ze(E) with three imidazolium ionic liquids (ILs) were measured from (283.15 to 343.15) K based on the isochoric method. The ILs include 1-ethyl-3-methylimidazolium tetrafluoroborate ([Emim][BF4]), 1-hexyl-3-methylimidazolium tetrafluoroborate ([Hmim][BF 4 ]), and 1-octyl-3-methylimidazolium tetrafluoroborate ([Omim][BF4]). The experimental results were correlated using the nonrandom two-liquid activity coefficients model. The deviations between experimental data and calculated values for pressure were 1.77%, 2.07%, and 2.32% for R1234ze(E) + [Emim][BF4], + [Hmim][BF4], and + [Omim][BF4] systems, respectively.
1. INTRODUCTION As we all know, the absorption refrigeration cycle is an effective technology to utilize low-quality waste heat. The traditional refrigerant-absorbent pairs, such as H2O−LiBr or NH3−H2O, have been widely used in industrial absorption refrigeration systems for many years.1,2 However, because of the drawbacks (for example, crystallization and corrosiveness for LiBr, flammability and toxicity for NH3) of these working fluids, ionic liquids (ILs) were considered as promising alternative absorbents in absorption refrigeration systems.3−5 The ILs usually have tunable properties and negligible vapor pressure, and are thermally stable. Moreover, an easy choice of the cation−anion pair for ILs can improve the performance of the refrigeration system. Hydrofluorocarbon (HFC) refrigerants with ILs as working pairs for the absorption cycle have been investigated extensively in the past few years.6−17 Recently, R1234ze(E) was proposed as a potential substitution for HFCs, especially for R134a.18 Hence, the possibility of R1234ze(E) + ILs pairs used in the absorption refrigeration systems deserves investigation. Phase behavior of R1234ze(E) with ILs is necessary for simulation and optimization of the refrigeration systems. However, to our best knowledge, only one published paper reported the experimental results of vapor−liquid equilibrium of R1234ze(E) with [Hmim][Tf2N].19 In this investigation, the phase equilibria of R1234ze(E) with three imidazolium ILs was measured based on the isochoric method. In addition, the comparisons of different anions or cations of ionic liquids on R1234ze(E) solubilities were performed.
tetrafluoroborate ([Omim][BF4]) were provided by Aladdin Chemistry. R1234ze(E) was purchased from Honeywell. The sample information used is given in Table 1. ILs were first filled to a borosilicate glass tube, and then dried under the vacuum condition and at about 348 K for 3 days. Water content of the purified ILs was measured by Karl Fischer Titrator (MKC710B, Kyoto Electronics Manufacturing Co., Ltd.), the results show that the mass fraction of water for the three ILs are lower than 3 × 10−5. 2.2. Apparatus and Procedure. The solubilities of R1234ze(E) with ILs were measured using the isochoric technique.20,21 The main parts of the apparatus were two cells which were made of stainless steel, as shown in Figure 1. The two cells were located in a Fluke 7008 bath. A thermometer (Fluke 5608, 100 Ω platinum resistance) was used to measure the temperature of the cell. Before the measurement, the thermometer was calibrated by NIM (National Institute of Metrology, China). The combined expanded uncertainty of temperature measurement was less than 0.03 K (0.95 level of confidence). The pressure of the system was measured by a Rosemount 3051S transducer with the combined expanded uncertainty of 2.0 kPa (k = 2). Prior to the measurements, the prepurified ILs were carefully filled into the equilibrium cell and heated to 345 K. A turbopump (Pfeiffer, model TM80) was used to further remove any trace amounts of water or other volatile impurities in ILs under a pressure of about 10−3 Pa for 24 h. At the same time, a magnetic stirrer was turned on to stir the ionic liquid and to accelerate the evacuation. The mass of ILs was determined by a Mettler Toledo balance (ME204), the uncertainty of mass was 0.002 g, and the
2. EXPERIMENTAL SECTION 2.1. Materials. 1-Ethyl-3-methylimidazolium tetrafluoroborate ([Emim][BF4]), 1-hexyl-3-methylimidazolium tetrafluoroborate ([Hmim][BF4]), and 1-octyl-3-methylimidazolium © XXXX American Chemical Society
Received: January 17, 2017 Accepted: May 3, 2017
A
DOI: 10.1021/acs.jced.7b00047 J. Chem. Eng. Data XXXX, XXX, XXX−XXX
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Table 1. Sample Used in the Measurements chemical name
source
CAS No.
mass fraction purity
purification method
water content (mass fraction)
CO2 R1234ze(E)a [Emim][BF4]b [Hmim][BF4]c [Omim][BF4]d
Pracair Inc. Honeywell Aladdin Aladdin Aladdin
124-38-9 29118-24-9 143314-16-3 244193-50-8 244193-52-0
0.99999 0.999 0.99 0.99 0.99
none none vacuum drying vacuum drying vacuum drying
3 × 10−5 2 × 10−5 2 × 10−5
a
R1234ze(E) = trans-1,3,3,3-tetrafluoropropene. b[Emim][BF4] = 1-ethyl-3-methylimidazolium tetrafluoroborate c[Hmim][BF4] = 1-hexyl-3methylimidazolium tetrafluoroborate d[Omim][BF4] = 1-octyl-3-methylimidazolium tetrafluoroborate
Figure 1. Schematic diagram of the solubility measurement system.
mass loss was not found during drying. After that, the solubilities can be investigated at different temperatures. R1234ze(E) was introduced into the cell and the pressure of the gas system cell was obtained. It should be pointed out that a molecular sieve trap was used in this work to remove any trace amounts of water from R1234ze(E). Then, gaseous R1234ze(E) entered the equilibrium cell, and the values of pressure were recorded when the equilibrium was obtained. The temperature of the bath was then changed to measure the next equilibrium point. After all measurements were completed, the water content of the studied ILs was reanalyzed by Karl Fischer titration, and the mass fraction was still less than 3 × 10−5. 2.3. Calculations. The solubilities (x) of gaseous R1234ze(E) in ILs can be expressed as
n1 x= n1 + n2
n11 =
n1 =
−
n11
Vcell − V2,cell υgas(Tequilib , pequilib )
Vabs,gas υgas(Tequilib , pequilib )
Vabs,gas = n1υabs,gas
(4)
(5)
where υabs,gas is the molar volume of the liquid R1234ze(E) in ILs.25 The relative expanded uncertainty of the solubilities was less than 3.0% (k = 2).
(1)
3. RESULTS AND DISCUSSION To check the reliability and accuracy of the apparatus, the solubilities of CO2 in [Emim][BF4] and [Hmim][BF4] at 298.15 K were measured and compared with that in the literature.26 Table 2 lists the results. The average relative deviation (ARD) between the experimental results and literatures is 1.26% and 0.88% for CO2/[Emim][BF4] and CO2/[Hmim][BF4], respectively. The maximum deviation (MD) is 2.83% and 2.79%. In addition, the relative deviation distributions are shown in Figure 2; good agreements are observed.
(2)
Vsys υgas(Tini , pini )
+
The subscript “ini” and “equilib” means the initial condition and equilibrium state of the system, respectively. Vsys and Vcell are gas system volume and equilibrium cell volume, respectively. The ILs volume (V2,cell in eq 4) is obtained from the charged mass and its density.23,24 The volume of R1234ze(E) absorbed in the solvent Vabs,gas is given by
where n01 and n11 are the initial mole number and the remaining moles in the system at the equilibrium condition. n01 and n11 are calculated by22 n10 =
υgas(Tequilib , pequilib ) −
where n2 is the ILs mole number, n1 is the mole number of R1234ze(E) absorbed in ILs and can be obtained as follows:
n10
Vsys
(3) B
DOI: 10.1021/acs.jced.7b00047 J. Chem. Eng. Data XXXX, XXX, XXX−XXX
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⎛ piexp − pical ⎜ MD/% = max⎜100 piexp ⎝
Table 2. Mole-Fraction Solubilities of CO2 in [Emim][BF4] and [Hmim][BF4] at 298.15 Ka [Emim][BF4]
[Hmim][BF4]
x1
p/MPa
x1
p/MPa
0.0262 0.0335 0.0455 0.0568 0.0700 0.0821 0.0935 0.1056
0.202 0.252 0.341 0.440 0.541 0.645 0.746 0.849
0.0424 0.0674 0.0858 0.1044 0.1197 0.1366 0.1523 0.1675
0.184 0.307 0.416 0.520 0.613 0.720 0.820 0.924
⎞ ⎟ ⎟ ⎠
(7)
The experimental data for R1234ze(E) in [Emim][BF4], [Hmim][BF4], and [Omim][BF4] are given in Tables 3−5. Figures 3−5 show the solubility in mole fraction of R1234ze(E). As expected, the solubilities decrease with temperature for each system, and at fixed temperature, the solubility increases with increasing pressure. 3.1. Data Correlation. Because of the very low vapor pressure of ILs, we can neglect ILs in the vapor phase (that is y1 = 1). The activity coefficient γ1 for R1234ze(E) therefore can be calculated by
a The combined expanded uncertainties U are U(T) = 0.03 K, U(p) = 2.0 kPa, and Ur(x1) = 0.03, with a 0.95 level of confidence (k = 2).
γ1 =
pΦ1 x1p1s
(8)
where ps1 is vapor pressure, x1 is R1234ze(E) liquid phase mole fraction, and Φ1 is a correction factor: ⎡ (B1 − V1̅ )(p − p s ) ⎤ 1 ⎥ Φ1 = exp⎢ RT ⎣ ⎦
(9)
where R is the gas constant (8.31445 J·K−1·mol−1). B1 and V1̅ are the second virial coefficient and the saturated molar liquid volume of R1234ze(E), respectively. In this work, ps1, B1, and V1̅ are obtained from REFPROP 9.1.25 Shiflett and Yokozeki6,7 correlated the phase equilibrium data of HFC/ILs based on the NRTL activity coefficients model, which can be expressed as, ⎡
Figure 2. Deviations between experimental data and literature26 for CO2 in [Emim][BF4] and [Hmim][BF4] at 298.15 K: ●, [Emim][BF4]; ■, [Hmim][BF4].
ln γ1 =
The average relative deviation (ARD) and maximum deviation (MD) were calculated using the following equations: 100 ARD/% = N
N
∑ i=1
piexp
⎢⎣
+
piexp − pical
⎞2 exp( −0.2τ21) ⎟ ⎝ x1 + x 2 exp( −0.2τ21) ⎠ ⎛
x 22⎢τ21⎜
⎤ ⎥ (x 2 + x1 exp( −0.2τ12))2 ⎥⎦ τ12 exp( −0.2τ12)
(10)
where the subscripts 1 and 2 are R1234ze(E) and ILs, respectively. τ12 and τ21 are the interaction parameters. Expressions
(6)
Table 3. Mole Fraction Solubilities of R1234ze(E) in [Emim][BF4]a x1 T/K = 283.15 0.0269 0.0501 0.0738 0.0980 0.1230 0.1511 0.1814 T/K = 323.15 0.0105 0.0187 0.0273 0.0358 0.0445 0.0540 0.0641 a
p/MPa 0.050 0.095 0.140 0.182 0.221 0.259 0.294 0.064 0.123 0.182 0.238 0.292 0.346 0.399
x1 T/K = 293.15 0.0213 0.0376 0.0555 0.0742 0.0923 0.1127 0.1338 T/K = 333.15 0.0082 0.0151 0.0220 0.0289 0.0363 0.0441 0.0525
p/MPa
x1 T/K = 303.15 0.0164 0.0294 0.0428 0.0569 0.0706 0.0859 0.1018 T/K = 343.15 0.0063 0.0120 0.0181 0.0235 0.0289 0.0350 0.0409
0.054 0.103 0.153 0.199 0.243 0.286 0.327 0.067 0.128 0.191 0.249 0.306 0.363 0.418
p/MPa 0.058 0.111 0.164 0.213 0.261 0.309 0.354
x1 T/K = 313.15 0.0133 0.0232 0.0339 0.0445 0.0553 0.0674 0.0797
p/MPa 0.061 0.117 0.173 0.226 0.277 0.328 0.378
0.070 0.134 0.198 0.260 0.319 0.379 0.438
The combined expanded uncertainties U are U(T) = 0.03 K, U(p) = 2.0 kPa, and Ur(x1) = 0.03, with a 0.95 level of confidence (k = 2). C
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Table 4. Mole-Fraction Solubilities of R1234ze(E) in [Hmim][BF4]a x1 T/K = 283.15 0.0511 0.0990 0.1503 0.1950 0.2387 0.2827 0.3241 T/K = 323.15 0.0248 0.0454 0.0667 0.0868 0.1063 0.1266 0.1464 a
p/MPa 0.044 0.082 0.117 0.150 0.180 0.210 0.237 0.062 0.118 0.174 0.228 0.279 0.333 0.384
x1 T/K = 293.15 0.0437 0.0852 0.1233 0.1604 0.1959 0.2327 0.2680 T/K = 333.15 0.0201 0.0374 0.0550 0.0718 0.0880 0.1049 0.1218
p/MPa
x1 T/K = 303.15 0.0367 0.0689 0.1001 0.1301 0.1591 0.1894 0.2184 T/K = 343.15 0.0160 0.0305 0.0450 0.0590 0.0725 0.0867 0.1003
0.049 0.091 0.133 0.173 0.210 0.247 0.282 0.066 0.125 0.185 0.242 0.298 0.355 0.409
p/MPa 0.053 0.101 0.149 0.193 0.236 0.280 0.321
x1 T/K = 313.15 0.0307 0.0560 0.0813 0.1058 0.1295 0.1543 0.1782
p/MPa 0.057 0.110 0.162 0.212 0.259 0.308 0.355
0.069 0.132 0.195 0.256 0.315 0.375 0.434
The combined expanded uncertainties U are U(T) = 0.03 K, U(p) = 2.0 kPa, and Ur(x1) = 0.03, with a 0.95 level of confidence (k = 2).
Table 5. Mole-fraction solubilities of R1234ze(E) in [Omim][BF4]a x1 T/K = 283.15 0.0595 0.1144 0.1692 0.2204 0.2689 0.3176 0.3614 T/K = 323.15 0.0302 0.0544 0.0784 0.1025 0.1260 0.1498 0.1722 a
p/MPa 0.045 0.082 0.117 0.150 0.181 0.211 0.236 0.062 0.118 0.173 0.227 0.279 0.334 0.383
x1 T/K = 293.15 0.0529 0.0984 0.1406 0.1830 0.2230 0.2650 0.3032 T/K = 333.15 0.0246 0.0451 0.0657 0.0856 0.1053 0.1257 0.1447
p/MPa
x1 T/K = 303.15 0.0450 0.0805 0.1153 0.1502 0.1835 0.2189 0.2513 T/K = 343.15 0.0200 0.0375 0.0545 0.0716 0.0881 0.1050 0.1209
0.049 0.091 0.133 0.173 0.211 0.248 0.281 0.066 0.125 0.184 0.242 0.298 0.356 0.409
p/MPa 0.053 0.101 0.148 0.194 0.237 0.280 0.320
x1 T/K = 313.15 0.0368 0.0658 0.0948 0.1236 0.1513 0.1804 0.2067
p/MPa 0.058 0.110 0.161 0.212 0.260 0.309 0.354
0.070 0.132 0.194 0.256 0.315 0.377 0.433
The combined expanded uncertainties U are U(T) = 0.03 K, U(p) = 2.0 kPa, and Ur(x1) = 0.03, with a 0.95 level of confidence (k = 2).
Figure 3. Solubility in mole fraction for R1234ze(E) in [Emim][BF4] at different temperatures: ■, 283.15 K; ●, 293.15 K; ★, 303.15 K; ☆, 313.15 K; ◆, 323.15 K; ○, 333.15 K; □, 343.15 K.
Figure 4. Solubility in mole fraction for R1234ze(E) in [Hmim][BF4] at different temperatures: ■, 283.15 K; ●, 293.15 K; ★, 303.15 K; ☆, 313.15 K; ◆, 323.15 K; ○, 333.15 K; □, 343.15 K. D
DOI: 10.1021/acs.jced.7b00047 J. Chem. Eng. Data XXXX, XXX, XXX−XXX
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Figure 5. Solubility in mole fraction for R1234ze(E) in [Omim][BF4] at different temperatures: ■, 283.15 K; ●, 293.15 K; ★, 303.15 K; ☆, 313.15 K; ◆, 323.15 K; ○, 333.15 K; □, 343.15 K.
Figure 6. Deviations between experimental data and the calculated values for R1234ze(E) + [Emim][BF4]: ■, 283.15 K; ●, 293.15 K; ★, 303.15 K; ☆, 313.15 K; ◆, 323.15 K; ○, 333.15 K; □, 343.15 K.
of τ12 and τ21 are τ12 = τ120 +
1 τ12 T
(11)
1 τ21 (12) T 0 1 0 1 The parameters (τ12, τ12, τ21, and τ21) were determined based on solubility experimental data, and the objective function is 0 τ21 = τ21 +
N
obj =
∑
|piexp − pical |
i=1
piexp
(13)
of τ012, τ112, τ021, and τ121 for
The optimized values R1234ze(E) with [Emim][BF4], [Hmim][BF4], and [Omim][BF4] are tabulated in Table 6. Deviations in pressure are presented in Figures 6−8. Table 6. Coefficients of the NRTL Model by Fitting the Experimental Solubility Data system
τ012
τ112
τ021
τ121
R1234ze(E) + [Emim][BF4] R1234ze(E) + [Hmim][BF4] R1234ze(E) + [Omim][BF4]
6.78 4.042 4.056
84.57 143.0 152.2
1.616 0.48 0.029
−397.8 −367.1 −284.7
Figure 7. Deviations between experimental data and the calculated values for R1234ze(E) + [Hmim][BF4]: ■, 283.15 K; ●, 293.15 K; ★, 303.15 K; ☆, 313.15 K; ◆, 323.15 K; ○, 333.15 K; □, 343.15 K.
The ARD between experimental and calculated results was 1.77%, 2.07%, and 2.32% for R1234ze(E)/[Emim][BF4], R1234ze(E)/[Hmim][BF4], and R1234ze(E)/[Omim][BF4], respectively. The maximum deviation was 4.06%, 4.01%, and 4.10%. 3.2. The Cation Alkyl Length Effect on R1234ze(E) Solubility. As mentioned above, the ILs investigated have the same anion [BF4]. Hence, the effect of the different cations [Emim], [Hmim], and [Omim] on the solubility was compared. Figure 9 illustrates the comparison of the solubilities of R1234ze(E) in the three ionic liquids at 323.15 K. It is obviously that the magnitudes of solubilities are in the following order: [Emim][BF4] < [Hmim][BF4] < [Omim][BF4]. Moreover, the solubilities of R1234ze(E) with [Hmim][BF4] and [Omim][BF4] at a constant pressure is markedly higher than that with [Emim][BF4]. However, solubilities of R1234ze(E) with [Omim][BF4] is slightly higher than that of [Hmim][BF4].
Figure 8. Deviations between experimental data and the calculated values for R1234ze(E) + [Omim][BF4]: ■, 283.15 K; ●, 293.15 K; ★, 303.15 K; ☆, 313.15 K; ◆, 323.15 K; ○, 333.15 K; □, 343.15 K. E
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A larger anion ([Tf2N] > [BF4]) has a more dispersed negative charge and can be easily solvated by R1234ze(E) or R134a, resulting in better miscibility at a given temperature and pressure.
4. CONCLUSIONS The solubilities of R1234ze(E) in [Emim][BF4], [Hmim][BF4], and [Omim][BF4] were reported from (283.15 to 343.15) K. Solubilities decrease with increasing temperature and increase with increasing pressure for the three systems. Experimental solubility data were correlated based on the NRTL model. In addition, while at the same anion [BF4], the effect of cation alkyl length on the solubility was analyzed; the solubilities will increase with increasing cation alkyl group length. Because of lower solubilities, R1234ze(E) with imidazolium IL pairs will have a much lower cooling capacity and energy efficiency compared to R134a with the same ionic liquids and the LiBr-H2O or NH3−H2O system. Hence, further research should be carried out to seek new R1234ze(E)/ionic liquid mixtures as the working pairs of absorption refrigeration system.
Figure 9. Cation effects on the solubilities of R1234ze(E) in different ionic liquids at 323.15 K: ■, [Emim][BF4]; ●, [Hmim][BF4]; ▲, [Omim][BF4].
■
This phenomena can be explaned that by increasing the cation alkyl-group length (from [Emim] to [Omim]), the dispersion forces of the cation will increase, and the longer cation alkyl chain will then have a better interaction with R1234ze(E). Similar phenomena were also observed by several researchers. Ren and Scurto11 measured the phase equilibrium data of R134a/[Emim][Tf2N] and R134a/[Hmim][Tf2N]. Results showed that at the same anion [Tf2N], the solubility of R134a increases from [Emim] to [Hmim]. Shiflett and Yokozeki27 reported the solubilities of R32 with several ILs at the same [TFES] anion. R32 solubility also increased in the following order: [Emim] < [Bmim] < [Dmim] ∼ [Hmim]. In addition, Aki,28 Blanchard,29 and Shariati30,31 also found the solubility of CO2 in ILs will increase with alkyl chain length increasing. 3.3. Anion Effect on R1234ze(E) Solubility. Solubility data of R1234ze(E) with [Hmim][Tf2N] were reported by Liu et al.19 The effect of anion on the solubilities of R1234ze(E) with [Hmim] ILs at 293.15 K is shown in Figure 10. It indicates that the solubility of R1234ze(E) with [Hmim][Tf2N] are higher than [Hmim][BF4]. This trend is consistent with the solubilities of R134a with [Hmim][Tf2N] and [Hmim][BF4]. The reason is probably related to the anion’s diameter or charge density.
AUTHOR INFORMATION
Corresponding Author
*E-mail:
[email protected]. Fax: 86-29-82668789. Tel: 86-29-82668210. ORCID
Xiaopo Wang: 0000-0002-5550-2193 Funding
This research was supported by NSFC (Grant 51476129) and the Key Laboratory of Cryogenics, TIPC CAS. Notes
The authors declare no competing financial interest.
■
REFERENCES
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Figure 10. Anion effects on the solubilities of R1234ze(E) in different ionic liquids at 293.15 K: ■, [Hmim][BF4] (this work); ●, [Hmim][Tf2N].19 F
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DOI: 10.1021/acs.jced.7b00047 J. Chem. Eng. Data XXXX, XXX, XXX−XXX
