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Liquid Phase Behavior of 1-Butyl-1-methylpyrrolidinium Bis(triuoromethylsulfonyl)imide with 1-Butanol or Hexan-1-ol: Measurements of Coexistence Curves, Density, and Interfacial Tension
Monika Geppert-Rybczyns ka,*, Anne Knorr, Jochen K. Lehmann, and Andreas Heintz

University of Silesia, Szkolna 9, 40-006 Katowice, Poland University of Rostock, Dr.-Lorenz-Weg 1, 18059 Rostock, Germany

ABSTRACT: The liquidliquid equilibria of two binary systems containing 1-butyl-1-methylpyrrolidinium bis(triuoromethylsulfonyl)imide with butan-1-ol or hexan-1-ol at atmospheric pressure have been investigated. The two-phase line was observed as function of temperature using light scattering or visual detection. In addition, other physical properties such as the densities of phases in equilibrium and the interfacial tension were determined. The results obtained were compared with the literature and briey discussed in terms of possible interactions that may occur in ionic liquid + alkan-1-ol solutions.

INTRODUCTION The aim of this work is to investigate the liquid-phase behavior of two binary systems containing the ionic liquid (IL) 1-butyl1-methylpyrrolidinium bis(tri uoromethylsulfonyl)imide [BMPyr][NTf2] and an alcohol with a medium-length chain (butan-1-ol or hexan-1-ol). Other IL + alcohol binary mixtures were previously characterized in the literature.17 They were mainly the subject of comparative studies carried out to determine the inuence of changing the ILs anion or some chemical groups of its cation structure (e.g., the length of hydrocarbon chain) on the properties of the whole binary system. In our work, we chose to study [BMPyr][NTf2], which is a nonaromatic alternative to the very often studied IL 1butyl-3-methylimidazolium bis(triuoromethylsulfonyl)imide, [BMIm][NTf2]. The [BMPyr+] cation is similar in size to [BMIm+] but has a dierent structure, which may promote or reduce the solubility of [BMPyr][NTf2] in alcohols compared with [BMIm][NTf2]. The properties we studied are liquid liquid equilibria, densities, and interfacial tensions. We expect that our results will provide some new facts to discuss in regard to the nature of ILs and the intermolecular interactions occurring in their binary mixtures with alcohols. EXPERIMENTAL SECTION Chemicals. The sources and basic characteristics of the chemicals used, including the water content (as determined using a Karl Fischer titrator, Titroline KF Trace, Schott Instruments GmbH) are presented in Table 1. Prior to use, [BMPyr][NTf2] was dried under vacuum for around 48 h in
2012 American Chemical Society

order to reduce the water content below 100 ppm and to remove other volatile impurities as well. Butan-1-ol and hexan1-ol were used without purication after the amount of water was checked and their densities and refractive indices were compared with the literature values (see Table 1). Mixtures were prepared by weighing directly before measurements. The general uncertainty in the mole fractions was 0.0002. Since the experimental work encompasses three dierent techniques, the quality of chemicals was periodically monitored by checking the density and the amount of water. LiquidLiquid Equilibrium Measurements. Liquid liquid equilibria (LLE) of the mixtures under study were determined using a cloud-point method described previously.3,8 The basic temperature range was (287.15 to 348.15) K, and the samples were cooled slowly under continuous stirring of liquid in the vial. The cooling and heating cycles were repeated several times, shortening the range stepwise from (1.0 to 0.1) K. Determination of the cloud-point temperature of [BMPyr][NTf2] + butan-1-ol solution was performed as previously by means of a laserdetector set.3,8 In the case of the [BMPyr][NTf2] + hexan-1-ol system, the detection of the temperature of phase separation had to be done by visual observation because of the very small dierences in the refractive indexes (nD) of the compounds (below 0.5%). The
Received: December 30, 2011 Accepted: June 20, 2012 Published: June 28, 2012
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Journal of Chemical & Engineering Data Table 1. Characteristics of Pure Compounds at 298.15 K
/gcm3 compound butan-1-ol hexan-1-ol [BMPyr] [NTf2]
a

Article

nD literature AAD/ %b 0.009 0.024 0.025 this work 1.3973 1.4167 1.4229 literature 1.3973,n 1.3974,o,p 1.3975q 1.4163,r 1.4166,s 1.4167t 1.42304l AAD/ %b 0.072 0.012 0.005

source, puritya Merck, 0.999 Merck, 0.999 Io-li-tec, 0.99

amount of water 90.0 ppm 56.8 ppm 68.6 ppm

this work 0.80568 (0.80565c) 0.81512 (0.81486c) 1.39516 (1.39455c)

0.80562,d 0.80569,e 0.80575f,g,h 0.81495,i 0.81505,j 0.81516e 1.394,k 1.39459,l 1.395m

Mass fraction purity. bAbsolute average deviation, dened as AAD = [n i=1|(sexp slit,i)/sexp|/n]100 %, where s is density () or refractive index (nD) and n is the number of literature data. cDensity after viscosity correction; viscosities were taken from ref 13 for butan-1-ol, ref 14 for hexan-1-ol, and ref 15 for [BMPyr][NTf2]. dReference 16. eReference 17. fReference 18. gReference 19. hReference 20. iReference 21. jReference 22. kReference 23. l Reference 24. mReference 15. nReference 25. oReference 26. pReference 14. qReference 27. rReference 28. sReference 29. tReference 30.

uncertainty in the temperature determination in both cases was estimated as 0.1 K. Density Measurements. The densities () of the pure substances as well as of the homogeneous solutions in the neighborhood of the two-phase line at given temperature were determined using a vibrating tube densimeter (DMA 602, Anton Paar/Austria) as described previously.5,10 Samples were taken from carefully thermostatted and equilibrated two-phase systems. Pure liquids and solutions were degassed directly in an ultrasonic bath before measurements. The general uncertainty in the density measurements was 0.00002 gcm3. However, because of the lack of viscosity corrections and common diculties during the work with the two-phase systems, the uncertainties of the homogeneous solutions at the phase boundaries were estimated to be 0.0001 gcm3. Refractive Index Determination. Refractive indexes of pure substances used for testing their purity (see Table 1) were determined using an Abbe refractometer (AR2, Kruss Optronic GmbH). The general uncertainty in nD was 0.0003. Interfacial Tension Measurements. Liquidliquid interfacial tension () measurements were carried out using the pendant-drop method. The experimental procedure and the apparatus have been described previously.8,11,12 Two-phase samples were equilibrated, and a drop of the denser liquid phase was formed in the lighter one after complete phase separation. The uncertainty in these measurements was 0.1 mNm1. All of the data reported represent mean values of several results obtained by tting Laplaces equation to the shape of the drops photographed by a CCD camera with standard deviations of 0.01 to 0.03 mNm1.

Table 2. Experimental Cloud Points for the System [BMPyr][NTf2] (1) + Butan-1-ol or Hexan-1-ol (2)a
x1 0.0096 0.0160 0.0318 0.0520 0.0707 0.0833 0.0910 0.1097 0.0224 0.0399 0.0721 0.1050 0.1370 0.1572 0.1776
a

T/K

x1

T/K 312.4 312.2 312.0 310.8 308.2 303.4 293.6 285.2 347.6 345.9 344.0 337.8 330.5 317.0

[BMPyr][NTf2] (1) + Butan-1-ol (2) 287.8 0.1280 296.6 0.1535 306.2 0.1787 310.4 0.2180 311.6 0.2676 312.2 0.3388 312.2 0.4427 312.4 0.5111 [BMPyr][NTf2] (1) + Hexan-1-ol (2) 335.1 0.2127 342.3 0.2691 346.7 0.3117 347.9 0.4026 348.0 0.4849 347.9 0.5943 347.9

Uncertainties (u) are u(T) = 0.1 K and u(x1) = 0.0002.

respect to the experimental data [(T)] was calculated from the following equation:
N (T T )2 1/2 i ,exp i ,cal (T ) = N n i=1

(4)

RESULTS AND DISCUSSION The temperatures and compositions of the two phases for [BMPyr][NTf2] + butan-1-ol or hexan-1-ol systems determined in this work are listed in Table 2. The data were tted to eq 1, which shows an exponential dependence of temperature on composition near the critical point:3133
T /K = Tc/K + k|y yc |m
(1)

where
y= x1 1 + x1( 1)
(2)

yc =

x1c 1 + x1c( 1)

(3)

Tc and x1c are the coordinates of the critical point, and m, k, and are tting parameters. The standard deviation of eq 1 with
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where N is the number of data points and n the number of tting parameters. All of the parameter values are listed in Table 3. As discussed previously by Ott and coauthors,31 deviations of from 1 skew the coexistence curve, and this is especially pronounced in a case of binary mixtures having compounds with dierent molar masses, such as IL + alcohol systems.1,6,9 In the classical case, the parameter m should be equal to 2, but in our work as well as in the literature,3133 its values are distinctly higher. As found for many other binary mixtures of ILs with alcohols, the systems in this study show an upper critical solution temperature (UCST) with a low solubility of the IL in the alcohol and high solubility of the alcohol in the IL.1,35,7,9 According to the observations reported in previous works,1,35 elongation of the hydrocarbon chain of an alcohol diminishes its mutual solubility with an IL. Our results conrm this rule, as the replacement of butan-1-ol by hexan-1-ol in a mixture with [BMPyr][NTf2] increased the UCST by 35.7 K, while the
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Table 3. Values of Parameters in Equations 1 to 3 with Their Standard Deviations (in Parentheses) and the Mean Deviation from the Regression Line, (T), Dened by Equation 4 for the Systems [BMPyr][NTf2] (1) + Butan-1-ol or or Hexan-1-ol (2)
m 4.05 (0.12) 3.79 (0.17) k 957 (105) 727 (113) Tc/K x1c 0.1132 (0.0020) 0.1418 (0.0032) (T)/K 0.39 0.35 [BMPyr][NTf2] (1) + Butan-1-ol (2) 6.774 (0.218) 312.10 (0.14) [BMPyr][NTf2] (1) + Hexan-1-ol (2) 4.809 (0.281) 347.78 (0.15)

position of the maximum on concentration scale changed very slightly (Table 3). Figure 1 shows our results and additional data taken from literature for two binary systems containing [BMIm][NTf2]

Table 4. Densities of the Upper and Lower Phases (u and l) in the Two-Phase Equilibrium, Density Dierences (), and Interfacial Tensions () in the LiquidLiquid Equilibrium of [BMPyr][NTf2] (1) + Butan-1-ol (2)a
T/K 293.15 295.65 298.15 300.65 303.15 305.65 308.15 310.65 312.65 313.15 315.65 318.15 320.65
a

u/gcm3 0.8334 0.8356 0.8378 0.8416 0.8464 0.8545 0.8706 0.8905 0.9763 0.9770 0.9746 0.9726 0.9704

l/gcm3 1.2384 1.2247 1.2101 1.1929 1.1734 1.1513 1.1176 1.0810 0.9763 0.9770 0.9746 0.9726 0.9704

/gcm3 0.4050 0.3891 0.3723 0.3513 0.3270 0.2968 0.2470 0.1905 0 0 0 0 0

/mNm1 0.67 0.58 0.44 0.37 0.28 0.16

Standard uncertainties are u(T) = 0.02 K, u() = 0.0001 gcm3, and u() = 0.1 mNm1. Figure 1. Tx diagram. Experimental results from this work: , [BMPyr][NTf2] (1) + 1-butanol (2); , [BMPyr][NTf2] (1) + 1hexanol (2). Literature data1 for comparison: , [BMIM][NTf2] (1) + 1-butanol (2); , [BMIM][NTf2] (1) + 1-hexanol (2). Lines were determined using eqs 1 to 3.3133

and butan-1-ol or hexan-1-ol.1 The comparison indicates the inuence of the cation structure on the mutual solubility of the IL with alcohols. [BMIm][NTf2] has similar molar volume (291.97 cm3mol1 at 298.15 K) as [BMPyr][NTf2] (302.90 cm3mol1 at 298.15 K), but the dierence in the chemical character of the cation causes dierences in the LLE curves. The nonaromaticity of [BMPyr][NTf2] obviously leads to signicantly lower mutual solubility of this IL with alcohols in comparison with [BMIm][NTf2]. Since the Laplace equation used for evaluation the interfacial tensions from the drop shape contains , the dierence in the densities of the two phases, the densities of the two liquid phases in thermodynamic equilibrium must be known. Density measurements on the [BMPyr][NTf2] + butan-1-ol system were carried out for the two phases as a function of the temperature using the vibrating tube instrument (DMA 602). The results are listed in Table 4 and illustrated in Figure 2. The interfacial tension () of the [BMPyr][NTf2] + butan-1ol system was determined at a few temperature points from (293.15 to 305.15) K using the pendant-drop technique. The results are given in Table 4 and presented in Figure 3 as a function of (Tc T). It is noticeable that the interfacial tensions of the system under study are extremely small (below 1 mNm1) but still measurable using the pendant-drop technique.8 For comparison, typical values of in [CnMIm]1925

Figure 2. Densities of the phases in two- and one-phase regions for [BMPyr][NTf2] (1) + 1-butanol (2) mixtures: , lower phase; , upper phase; , single phase above the UCST. Solid lines are the bestt lines; the dotted line shows the UCST (312.10 K; see Table 3).

[PF6] or [CnMIm][NTf2] with normal alkanes are 1 order of magnitude higher.34,35 Inspection of Table 4 and Figures 2 and 3 shows that both and tend to vanish close to the UCST and that the (x) curves of the two phases change their slope very signicantly as T approaches the UCST. To describe the liquidliquid interfacial tension at each temperature, the following expression was used:34
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Figure 3. Interfacial tension () between the equilibrated phases in the [BMPyr][NTf2] (1) + 1-butanol (2) system as a function of (Tc T). The symbols show the experimental data, and the dotted line is the best-t line; the error bars show the uncertainty in .

Figure 4. Linear correlation between the experimental interfacial tensions of equilibrated phases in the [BMPyr][NTf2] (1) + 1-butanol (2) system and those calculated according eq 5.34

P1 P22 cal1/4 = A + B 1 M2 M1

AUTHOR INFORMATION

Corresponding Author
(5)

*E-mail: mong@o2.pl.
Notes

where A and B are constants, subscripts 1 and 2 refer to the IL and alcohol, respectively, M is molecular mass, is the density, and P is the parachor calculated from the molar volume (V) and their liquidair interfacial tension () of the substance using the relation P = V1/4. Density and liquidair interfacial tension values of pure substances at 298.15 K were taken from our work or from the literature.36,37 The constants in eq 5 were found by minimization of the objective function (OF):34
2 P1 P22 1 OF = exp A B M 2 M1 i i=1 n

The authors declare no competing nancial interest.

ACKNOWLEDGMENTS The authors are grateful to Dagmar Klasen and Anika Rose for technical assistance during the experimental work. REFERENCES

(6)

where n is the number of experimental points. The values of the parameters in eq 5 are A = 7.1926 and B = 33.89, with the average absolute deviations (AADs) equal to 6.1%. The interfacial tension values obtained from eq 5 are plotted versus experimental values in Figure 4. The relationship between cal and exp seems to be not strictly linear, but the equation cal = exp(1.043 0.073) is able to describe the interfacial tension within the experimental uncertainty.

CONCLUSIONS The results obtained for the LLE of the binary systems [BMPyr][NTf2] + butan-1-ol or hexan-1-ol reveal that the UCST values are higher than in case of the corresponding [BMIm][NTf2] mixtures. This leads to the conclusion that the anity of the [BMIm+] cation for the alcohols is larger than in case of the [BMPyr+] cation, most probably because of the preferred interaction of the OH group of the alcohol molecules with the electrons of the aromatic imidazolium ring system. For the binary mixtures studied here as well as for [BMIm][NTf2] + alcohol systems,1,2 elongation of the hydrocarbon chain of the alcohol causes a shift of the UCST to higher values. Very small values of the interfacial tension between the two liquid phases in the [BMPyr][NTf2] + alcohol systems compared with [BMIm][NTf2] systems were also found.8,11
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