Density, Speed of Sound, and Viscosity of Aqueous Solutions

Jun 20, 2017 - The effect of some 1-alkyl-4-methylpyridinium based ionic liquids on the thermodynamic and transport properties of l(+)-lactic acid in ...
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Density, Speed of Sound, and Viscosity of Aqueous Solutions Containing 1‑Alkyl-4-methylpyridinium Bromide, Lactic Acid, and Polyethylene Glycol Abbas Mehrdad,* Hemayat Shekaari, and Narmin Noorani Department of Physical Chemistry, Faculty of Chemistry, University of Tabriz, Tabriz, Iran S Supporting Information *

ABSTRACT: The effect of some 1-alkyl-4-methylpyridinium based ionic liquids on the thermodynamic and transport properties of L(+)-lactic acid in aqueous polyethylene glycol solutions have been studied. Density, speed of sound, and viscosity of L(+)-lactic acid in the aqueous solutions of polyethylene glycol, (polyethylene glycol + 1-hexyl-4-methylpyridinium bromide) and (polyethylene glycol + 1-octyl-4methylpyridinium bromide) were measured at T = (288.15, 298.15, 308.15, and 318.15) K. Apparent molar volume, transfer apparent molar volume, apparent molar isentropic compressibility and viscosity B-coefficient of L(+)-lactic acid were calculated using experimental data and were discussed in terms of solute−solute and solute− solvent interactions. The results indicate that solute−solvent interactions were decreased by increasing the concentration of ionic liquid, length of alkyl group of ionic liquid, and temperature.

1. INTRODUCTION L(+)-lactic acid (LaH) is an industrially important organic acid that has widespread applications for preservation and acidification of products in food industries and for drug delivery control in the pharmaceutical industries.1,2 LaH is produced by both chemical synthesis and fermentation processes. Several techniques were proposed for the separation and recovery of LaH from the fermentation process.3−5 Among the various methods to recover LaH, liquid−liquid extraction based on aqueous biphasic systems is an alternative method which has been widely used for separation and purification of biological materials.6,7 Recently, a new type of aqueous biphasic system based on ionic liquid (IL)−polymer has been reported.8−12 Polyethylene glycol (PEG) as an effective and useful polymer in these type of aqueous biphasic systems is extensively used due to its low melting point, low cost, hydrophilic nature, and low toxicity.13,14 ILs are known as green solvents due to their unique properties such as low vapor pressure, high thermal stability, nonflammability under ambient conditions, low toxicity, and strong solubility power. Thereby, ILs have many attractive applications in biotechnology for separation and purification of organic acids.15−20 Extraction of LaH using ionic liquids has been studied in recent years.21−24 Solvent extraction of organic acids with ionic liquids was also investigated by Huddleston.25 Oliveira et al. investigated the extraction of L-lactic, L-malic, and succinic acid from aqueous solutions using hydrophobic ILs.26 Having information about the thermodynamic and transport properties of LaH in aqueous (IL + polymer) systems is useful to design and optimize the extraction process using the aqueous biphasic systems method and selection of the proper ionic liquid. Moreover, knowledge of © XXXX American Chemical Society

volumetric, acoustical, and viscometric properties is useful to evaluate the solute−solute and solute−solvent interactions. Recently, the effect of some imidazolium-based ionic liquids on the volumetric properties of acetaminophen were investigated.27,28 Also the effect of some ionic liquids on the volumetric properties of sucrose were investigated to understand solute−solute and solute−solvent interactions.29−31 In the present study, volumetric and transport properties of lactic acid in the aqueous solution of (PEG + IL) were investigated at different temperatures to provide information about the interactions of LaH in the aqueous solutions of (PEG + IL). The apparent molar volume (Vϕ), infinite dilution apparent molar volume (Voϕ), transfer volume (ΔtrVoϕ), apparent molar isentropic compressibility (κϕ) and the viscosity B-coefficient were used to interpret the solute−solute and solute−solvent interactions of LaH in the aqueous solutions of (PEG + IL).

2. EXPERIMENTAL SECTION 2.1. Chemicals. The names, CAS numbers, abbreviations, purities in mass fraction of the chemicals used and analysis methods are listed in Table 1. Double distilled water was used to prepare the solutions. 2.2. Synthesis of Ionic Liquids. The ionic liquids, 1-hexyl4-methylpyridinium bromide ([HMPyr]Br) and 1-ocyl-4methylpyridinium bromide ([OMPyr]Br) were prepared using the procedure described in the literature.32 To direct Received: January 12, 2017 Accepted: June 7, 2017

A

DOI: 10.1021/acs.jced.7b00033 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

Journal of Chemical & Engineering Data

Article

Table 1. Table of the Materials Used in This Study chemical name L(+)−lactic

acid polyethylene glycola 4 − methylpyridine 1−bromohexane 1−bromooctane toluene ethyl acetate 1−hexyl-4-methyl pyridinium bromide 1−octyl-4-methyl pyridinium bromide a

CAS no. 79-33-4 25322-68-3 108-89-4 111-25-1 111-83-1 108-88-3 141-78-6

supplier

purity (mass fraction)

purification method

≥0.98 >0.99 >0.99 >0.99 >0.99 >0.99 >0.99 >0.98

none none none none none none none rotary/evaporator and vacuum

Karl Fischer titration

[HMPyr]Br

Sigmaaldrich Merck Merck Merck Merck Merck Merck synthesized

[OMPyr]Br

synthesized

>0.98

rotary/evaporator and vacuum

Karl Fischer titration and 1H NMR

abbreviation LaH PEG

analysis method

Karl Fischer titration and 1H NMR

The reported average molar mass was 20 kg·mol−1.

respectively. Viscosity of the solutions was measured by digital viscometer (Lovis 2000M, Anton Paar). This viscometer is based on the concept of a falling sphere inside a capillary of known diameter. Two laser sensors at the two ends of the capillary detect the metal sphere, and the time elapsed during its fall between the two positions can be recorded. An average time is automatically recorded for the desired number of successive runs. The temperature of the capillary is controlled by a Peltier device within a precision of 0.01 K. The uncertainty of viscosity measurements was 0.001 mPa·s.

alkylation, 1-bromoalkane (1-bromohexane and 1-bromooctane) was slowly added to 4-methylpyridin at ambient temperature, and then the mixture was refluxed at T = 323 K for 72 h under an argon atmosphere. To enhance the reaction rate, toluene was added as cosolvent. Solvent was removed by a rotary evaporator in reduced pressure. The obtained solid was washed several times with ethyl acetate and separated from reagent. The volatile compounds in product were eliminated at about T = 353 K by rotary evaporator. The purification procedure is the same as described in the literature.32 The moisture of ionic liquids was measured by Karl Fischer titrator (720-KSS-Metrohm Herisau, Switzerland) and it was found to be 0.012 and 0.01 mass fraction for [HMPyr]Br and [OMPyr]Br, respectively. The synthesized ionic liquids were analyzed by 1H NMR (Bruker Av-400) and FT-IR (Bruker, Tensor 27) to confirm the absence of any major impurities. 1 H NMR and FT-IR spectra of synthesized ionic liquids are shown in Figures S1 to S4 (Supporting Information). The purity of the synthesized ionic liquids was determined using the procedure described in the literature.33 As shown in the 1 H NMR spectrum, there is not a detectable peak belonging to any impurity; therefore the purity of synthesized ionic liquids was >0.98. The details of 1H NMR chemical shifts and FT-IR data of the synthesized ionic liquids are as follows: [HMPyr]Br: 1 H NMR (400 MHz, D2O): δ/ppm = 0.70 (3H, hex-CH3), 1.13 (6H, CH2), 1.84 (2H, CH2), 2.51 (3H, C−CH3), 4.40 (2H, N−CH2), 7.74 (2H, CH), 8.52 (2H, N−CH). [HMPyr]Br: FT−IR: υ/cm−1 = 3432, 3016, 2930, 2861, 1640, 1470, 1518, 1378, 1313, 1116, 831. [OMPyr]Br: 1H NMR (400 MHz, D2O): δ/ppm = 0.71 (3H, hex-CH3), 1.15 (10H, CH2), 1.87 (2H, CH2), 2.53 (3H, C−CH3), 4.42 (2H, N−CH2), 7.76 (2H, CH), 8.53 (2H, N−CH). [OMPyr]Br: FT−IR: υ/cm−1 = 3435, 3020, 2928, 2858, 1642, 1469, 1518, 1391, 1323, 1121, 833. 2.3. Apparatus and Procedure. LaH solutions were prepared in the aqueous solutions of (PEG + IL) (wPEG = 0.020 and wIL = 0.010, 0.015, and 0.020). The solutions were prepared in glass vials using an analytical balance (CP224 S Sartorius Co.) with a precision of 1 × 10−7 kg. The calculated uncertainty for molality of LaH with a confidence level of 95% was 0.0002 mol·kg−1. Density and speed of sound were measured by a density and sound velocity analyzer (DSA5000, Anton Paar). The apparatus was calibrated with double distilled and degassed water and dry air at atmospheric pressure. The temperature was kept constant within ±1.0 × 10−3 K using the Peltier device built-in densimeter. The uncertainty of density and speed of sound measurements were 0.15 kg·m−3 and 0.5 m·s−1,

3. RESULTS AND DISCUSSION 3.1. Apparent Molar Volume. Density (d) and speed of sound (u) for LaH in the aqueous solutions of PEG and in the aqueous solutions of (PEG + IL) (wPEG = 0.020 and wIL = 0.010, 0.015, and 0.020) at T = (288.15, 298.15, 308.15, and 318.15) K are reported in Table 2. The measured density of the binary system (water + PEG) is in agreement with the literature. Comparison of density data with the literature is illustrated in Figure S5 (Supporting Information). With the use of density data, the apparent molar volumes of lactic acid were calculated by the following equation;34 Vϕ =

1000(do − d) M + d mdod

(1)

where M and m are the molar mass and molality of LaH, d0 and d represent the density of the solvent and solution, respectively. In the case of ternary systems, (PEG + water) is taken as the solvent and in quaternary systems, (PEG + IL + water) is taken as the solvent. The values of apparent molar volumes of LaH and their uncertainties with confidence level of 95% are given in Table 3. The values of apparent molar volumes as a function of LaH concentration are shown in Figures 1 and 2. The apparent molar volumes were correlated to the following equation;34 Vϕ = V ϕo + Svm

(2)

where Sv is the experimental slope and Voϕ is the infinite dilution apparent molar volumes. Voϕ and Sv are attributed to solute− solvent and solute−solute interactions, respectively. The calculated values of Vϕo and Sv and their uncertainties with confidence level of 95% are listed in Table 4. The values of Sv are negative in the all of the studied systems. The values of Sv were decreased by the addition of ionic liquid and increasing temperature. This behavior shows that solute−solute interaction weakens by the addition of ionic liquid and increasing B

DOI: 10.1021/acs.jced.7b00033 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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Table 2. Density (d), Speed of Sound (u), and Viscosity (η) of L(+)-Lactic Acid in the Aqueous Solutions of PEG and in the Aqueous Solutions of (PEG + ILs) at Different Temperatures and Pressure p = 0.1 MPaa T/K = 288.15 mLaH mLaH/ mol·kg

d −1

−3

kg·m

T/K = 298.15 η

u −1

m·s

mPa·s

0.0000 0.0391 0.0587 0.0782 0.0980 0.1176 0.1377 0.1564 0.1787 0.1959

1002.60 1003.29 1003.64 1003.99 1004.34 1004.68 1005.04 1005.37 1005.76 1006.06

1479.8 1480.7 1481.2 1481.7 1482.3 1482.8 1483.3 1483.8 1484.4 1484.9

2.284 2.303 2.310 2.319 2.329 2.336 2.346 2.357 2.368 2.377

0.0000 0.0354 0.0527 0.0705 0.0887 0.1058 0.1237 0.1421 0.1599 0.1776

1004.50 1005.15 1005.48 1005.84 1006.21 1006.57 1006.97 1007.39 1007.80 1008.24

1471.5 1472.2 1472.6 1473.0 1473.4 1473.8 1474.2 1474.7 1475.1 1475.5

2.401 2.416 2.425 2.433 2.444 2.453 2.463 2.472 2.482 2.491

0.0000 0.0358 0.0539 0.0702 0.0879 0.1064 0.1259 0.1432 0.1587 0.1771

1005.38 1006.01 1006.35 1006.67 1007.03 1007.44 1007.88 1008.28 1008.68 1009.14

1472.4 1473.1 1473.5 1473.8 1474.2 1474.5 1474.9 1475.3 1475.6 1476.0

2.451 2.471 2.480 2.488 2.498 2.508 2.518 2.527 2.534 2.543

0.0000 0.0353 0.0524 0.0706 0.0889 0.1061 0.1244 0.1416 0.1602 0.1779

1006.70 1007.23 1007.51 1007.83 1008.18 1008.52 1008.90 1009.27 1009.70 1010.11

1473.5 1474.2 1474.6 1474.9 1475.3 1475.7 1476.1 1476.4 1476.9 1477.3

2.516 2.536 2.546 2.557 2.567 2.577 2.585 2.596 2.606 2.614

0.0000 0.0362 0.0530 0.0729 0.0898 0.1071 0.1250 0.1416 0.1615 0.1789

1004.63 1005.27 1005.59 1005.99 1006.34 1006.72 1007.13 1007.51 1007.99 1008.42

1488.4 1489.2 1489.6 1490.0 1490.4 1490.9 1491.3 1491.7 1492.3 1492.8

2.403 2.422 2.432 2.445 2.452 2.462 2.469 2.479 2.489 2.500

0.0000 0.0358 0.0555 0.0716

1005.46 1006.00 1006.32 1006.61

1490.1 1491.0 1491.5 1492.0

2.458 2.481 2.489 2.500

d

T/K = 308.15 η

u −3

kg·m

m·s

−1

mPa·s

d −3

kg·m

Water + PEG (wPEG = 0.020) 1000.31 1507.6 1.725 997.10 1001.00 1508.5 1.735 997.76 1001.34 1509.0 1.741 998.10 1001.68 1509.5 1.747 998.43 1002.03 1510.0 1.756 998.76 1002.37 1510.5 1.761 999.10 1002.73 1511.0 1.771 999.44 1003.06 1511.4 1.778 999.76 1003.45 1512.0 1.783 1000.14 1003.75 1512.5 1.791 1000.44 Water + PEG (wPEG = 0.020) + [HMPyr]Br (wIL= 1002.19 1501.6 1.816 998.82 1002.79 1502.2 1.828 999.37 1003.10 1502.5 1.835 999.66 1003.43 1502.9 1.841 999.98 1003.79 1503.3 1.848 1000.31 1004.13 1503.6 1.854 1000.63 1004.51 1504.0 1.862 1000.99 1004.91 1504.4 1.869 1001.37 1005.31 1504.8 1.876 1001.75 1005.72 1505.2 1.882 1002.14 Water + PEG (wPEG = 0.020) + [HMPyr]Br (wIL= 1003.21 1502.7 1.851 999.87 1003.77 1503.3 1.865 1000.40 1004.08 1503.6 1.871 1000.70 1004.37 1503.9 1.880 1000.98 1004.71 1504.2 1.886 1001.32 1005.07 1504.5 1.891 1001.67 1005.49 1504.8 1.902 1002.07 1005.86 1505.2 1.908 1002.44 1006.21 1505.5 1.913 1002.79 1006.67 1505.9 1.919 1003.22 Water + PEG (wPEG = 0.020) + [HMPyr]Br (wIL= 1004.25 1503.9 1.889 1001.02 1004.74 1504.5 1.903 1001.46 1005.01 1504.9 1.911 1001.70 1005.30 1505.2 1.919 1001.98 1005.62 1505.6 1.926 1002.28 1005.94 1506.0 1.933 1002.57 1006.30 1506.4 1.940 1002.90 1006.65 1506.8 1.947 1003.23 1007.05 1507.3 1.954 1003.60 1007.44 1507.7 1.960 1003.97 Water + PEG (wPEG = 0.020) + [OMPyr]Br (wIL= 1002.40 1514.9 1.810 999.20 1002.98 1515.5 1.825 999.71 1003.27 1515.8 1.831 999.98 1003.64 1516.2 1.839 1000.31 1003.98 1516.5 1.846 1000.62 1004.34 1516.9 1.852 1000.95 1004.73 1517.3 1.858 1001.32 1005.11 1517.6 1.865 1001.68 1005.58 1518.1 1.874 1002.11 1006.02 1518.5 1.880 1002.52 Water + PEG (wPEG = 0.020) + [OMPyr]Br (wIL= 1003.13 1516.5 1.851 999.76 1003.63 1517.1 1.866 1000.21 1003.93 1517.5 1.873 1000.48 1004.19 1517.9 1.881 1000.72 C

T/K = 318.15 η

u −1

m·s

1529.0 1529.8 1530.3 1530.7 1531.2 1531.6 1532.1 1532.6 1533.1 1533.5 0.010) 1522.9 1523.4 1523.7 1524.0 1524.3 1524.7 1525.0 1525.4 1525.7 1526.2 0.015) 1523.5 1523.9 1524.2 1524.4 1524.7 1525.0 1525.3 1525.5 1525.8 1526.1 0.020) 1524.1 1524.6 1524.9 1525.2 1525.5 1525.8 1526.2 1526.5 1527.0 1527.4 0.010) 1534.4 1534.9 1535.2 1535.5 1535.8 1536.1 1536.4 1536.7 1537.2 1537.5 0.015) 1536.4 1536.9 1537.2 1537.5

d

η

u −3

−1

mPa·s

kg·m

m·s

mPa·s

1.345 1.354 1.357 1.362 1.367 1.372 1.380 1.385 1.39 1.393

993.17 993.80 994.12 994.44 994.77 995.10 995.44 995.75 996.14 996.43

1543.8 1544.6 1545.0 1545.5 1545.9 1546.3 1546.8 1547.2 1547.7 1548.1

1.072 1.082 1.085 1.089 1.094 1.096 1.103 1.105 1.109 1.113

1.420 1.429 1.435 1.440 1.445 1.450 1.455 1.460 1.466 1.472

995.23 995.69 995.94 996.22 996.51 996.80 997.12 997.46 997.81 998.17

1539.8 1540.4 1540.7 1541.0 1541.3 1541.6 1542.0 1542.4 1542.7 1543.1

1.132 1.139 1.143 1.147 1.151 1.154 1.158 1.162 1.166 1.171

1.451 1.462 1.467 1.473 1.478 1.484 1.489 1.494 1.499 1.504

996.65 997.13 997.41 997.67 997.97 998.31 998.69 999.04 999.34 999.75

1540.3 1540.7 1540.9 1541.1 1541.3 1541.5 1541.8 1542.1 1542.3 1542.6

1.158 1.166 1.170 1.174 1.179 1.182 1.186 1.190 1.193 1.197

1.476 1.486 1.491 1.497 1.503 1.509 1.515 1.521 1.526 1.532

998.02 998.41 998.62 998.87 999.14 999.41 999.72 1000.03 1000.36 1000.71

1540.6 1541.1 1541.4 1541.7 1542.0 1542.3 1542.7 1543.0 1543.4 1543.8

1.179 1.187 1.191 1.195 1.199 1.203 1.207 1.211 1.215 1.219

1.417 1.426 1.431 1.438 1.444 1.449 1.454 1.459 1.465 1.470

995.27 995.72 995.96 996.25 996.54 996.84 997.17 997.49 997.90 998.29

1548.4 1548.8 1549.1 1549.4 1549.6 1549.9 1550.2 1550.5 1550.9 1551.2

1.126 1.134 1.136 1.143 1.147 1.152 1.155 1.159 1.164 1.170

1.442 1.453 1.458 1.464

995.93 996.32 996.56 996.78

1549.9 1550.2 1550.5 1550.7

1.145 1.153 1.157 1.162

DOI: 10.1021/acs.jced.7b00033 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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Table 2. continued T/K = 288.15 mLaH mLaH/ mol·kg

a

d −1

T/K = 298.15 η

u −3

kg·m

−1

m·s

mPa·s

0.0889 0.1073 0.1248 0.1423 0.1609 0.1795

1006.93 1007.28 1007.62 1007.98 1008.38 1008.78

1492.5 1493.0 1493.6 1494.2 1494.9 1495.6

2.510 2.519 2.528 2.537 2.550 2.557

0.0000 0.0349 0.0528 0.0706 0.0887 0.1043 0.1234 0.1427 0.1594 0.1772

1006.40 1006.90 1007.18 1007.49 1007.81 1008.11 1008.50 1008.92 1009.29 1009.71

1495.8 1496.6 1497.0 1497.4 1497.9 1498.3 1498.8 1499.3 1499.7 1500.3

2.535 2.555 2.564 2.578 2.587 2.598 2.609 2.619 2.633 2.645

d

T/K = 308.15 η

u −3

kg·m

m·s

−1

mPa·s

Water + PEG (wPEG = 0.020) 1004.49 1518.3 1004.82 1518.7 1005.15 1519.2 1005.50 1519.7 1005.88 1520.2 1006.29 1520.7 Water + PEG (wPEG = 0.020) 1004.03 1518.0 1004.49 1518.6 1004.76 1519.0 1005.04 1519.3 1005.36 1519.7 1005.64 1520.1 1006.00 1520.5 1006.40 1521.0 1006.76 1521.5 1007.18 1521.9

d −3

−1

kg·m

T/K = 318.15 η

u m·s

+ [OMPyr]Br (wIL= 0.015) 1.889 1000.99 1537.8 1.894 1001.29 1538.2 1.903 1001.60 1538.6 1.910 1001.92 1539.0 1.919 1002.29 1539.4 1.926 1002.67 1539.7 + [OMPyr]Br (wIL= 0.020) 1.895 1000.57 1538.9 1.910 1001.01 1539.3 1.917 1001.26 1539.6 1.926 1001.53 1539.9 1.933 1001.83 1540.2 1.940 1002.11 1540.5 1.947 1002.47 1541.0 1.954 1002.85 1541.4 1.961 1003.19 1541.8 1.967 1003.60 1542.3

d

η

u −3

−1

mPa·s

kg·m

m·s

mPa·s

1.469 1.474 1.479 1.484 1.490 1.498

997.02 997.31 997.58 997.89 998.21 998.56

1551.0 1551.3 1551.7 1552.0 1552.4 1552.7

1.165 1.169 1.173 1.177 1.181 1.188

1.471 1.482 1.487 1.494 1.499 1.504 1.510 1.515 1.520 1.525

996.82 997.19 997.43 997.68 997.95 998.21 998.55 998.90 999.23 999.60

1551.3 1551.7 1551.9 1552.2 1552.5 1552.8 1553.2 1553.6 1553.9 1554.2

1.171 1.179 1.183 1.187 1.191 1.196 1.201 1.206 1.211 1.216

Standard uncertainties are s(m) = 0.0002 mol·kg−1, s(d) = 0.15 kg·m−3, s(η) = 0.001 mPa·s, s(u) = 0.5 m·s−1, s(p) = 5 kPa.

Table 3. Apparent Molar Volume (Vϕ) and Apparent Molar Isentropic Compressibility (κϕ) of L(+)-Lactic Acid in the Aqueous Solutions of PEG and in the Aqueous Solutions of (PEG + ILs) at Different Temperatures and at Pressure p = 0.1 MPaa T/K = 288.15

T/K = 298.15

T/K = 308.15

T/K = 318.15

mLaH

106Vϕ

1014κϕ

106Vϕ

1014κϕ

106Vϕ

1014κϕ

106Vϕ

1014κϕ

mol·kg−1

m3·mol−1

m3·mol−1·Pa−1

m3·mol−1

m3·mol−1·Pa−1

m3·mol−1

m3·mol−1·Pa−1

m3·mol−1

m3·mol−1·Pa−1

1.173 1.158 1.145 1.132 1.123 1.108 1.094 1.080 1.066

74.31 74.18 74.12 74.01 73.92 73.85 73.77 73.65 73.61

1.276 1.259 1.244 1.232 1.220 1.207 1.195 1.180 1.172

1.653 1.598 1.545 1.500 1.445 1.389 1.320 1.271 1.198

77.20 76.81 76.31 75.88 75.40 74.97 74.48 74.06 73.61

1.815 1.760 1.704 1.633 1.579 1.514 1.468 1.416 1.377

1.860 1.789 1.740 1.680 1.613 1.567 1.513 1.464 1.396

76.75 76.15 75.62 75.10 74.49 73.91 73.41 73.07 72.52

2.052 1.984 1.952 1.902 1.833 1.761 1.703 1.657 1.596

1.953 1.901 1.809

79.08 78.66 78.04

2.135 2.064 1.983

0.0391 0.0587 0.0782 0.0980 0.1176 0.1377 0.1564 0.1787 0.1959

72.08 72.07 72.05 72.06 72.05 72.03 72.02 72.02 72.01

0.933 0.922 0.915 0.902 0.891 0.883 0.873 0.861 0.853

0.0354 0.0527 0.0705 0.0887 0.1058 0.1237 0.1421 0.1599 0.1776

71.53 71.21 70.82 70.47 70.13 69.73 69.31 68.99 68.59

1.205 1.150 1.091 1.030 0.977 0.934 0.873 0.829 0.770

0.0358 0.0539 0.0702 0.0879 0.1064 0.1259 0.1432 0.1587 0.1771

72.35 71.84 71.37 70.95 70.33 69.78 69.38 68.85 68.38

1.227 1.192 1.157 1.094 1.064 1.015 0.989 0.942 0.887

0.0353 0.0524 0.0706

74.52 74.02 73.54

1.518 1.477 1.418

Water + PEG (wPEG = 0.020) 72.49 1.057 73.28 72.48 1.041 73.23 72.46 1.031 73.22 72.43 1.015 73.19 72.40 1.001 73.14 72.37 0.987 73.09 72.33 0.972 73.07 72.30 0.958 73.02 72.27 0.944 72.94 Water + PEG (wPEG = 0.020) + [HMPyr]Br (wIL= 0.010) 73.01 1.435 74.47 72.68 1.383 74.09 72.30 1.319 73.63 71.91 1.251 73.23 71.50 1.203 72.85 71.09 1.147 72.42 70.65 1.097 72.04 70.28 1.047 71.61 69.90 0.991 71.22 Water + PEG (wPEG = 0.020) + [HMPyr]Br (wIL= 0.015) 74.25 1.624 75.09 73.77 1.581 74.59 73.31 1.515 74.13 72.75 1.451 73.53 72.26 1.400 73.05 71.62 1.357 72.48 71.18 1.295 71.94 70.79 1.250 71.46 70.16 1.172 70.92 Water + PEG (wPEG = 0.020) + [HMPyr]Br (wIL= 0.020) 75.96 1.682 77.55 75.40 1.609 76.87 74.87 1.542 76.27 D

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Table 3. continued T/K = 288.15

mol·kg

a

−1

−1

m ·mol 3

T/K = 298.15

1014κϕ

106Vϕ

mLaH

−1

m ·mol ·Pa 3

0.0889 0.1061 0.1244 0.1416 0.1602 0.1779

72.90 72.41 71.85 71.37 70.79 70.32

1.359 1.296 1.233 1.174 1.097 1.026

0.0362 0.0530 0.0729 0.0898 0.1071 0.1250 0.1416 0.1615 0.1789

72.00 71.66 71.06 70.65 70.19 69.71 69.29 68.83 68.38

1.180 1.129 1.060 0.993 0.907 0.839 0.786 0.718 0.656

0.0367 0.0531 0.0706 0.0891 0.1070 0.1224 0.1429 0.1599 0.1788

74.72 74.26 73.69 73.20 72.69 72.33 71.92 71.42 71.05

1.192 1.065 0.999 0.907 0.845 0.757 0.686 0.587 0.505

0.0349 0.0528 0.0706 0.0887 0.1043 0.1234 0.1427 0.1594 0.1772

75.57 74.91 74.31 73.71 73.23 72.57 71.92 71.43 70.87

1.517 1.426 1.327 1.224 1.157 1.061 0.978 0.921 0.846

−1

m ·mol 3

−1

Water + PEG 74.31 73.76 73.22 72.74 72.18 71.73 Water + PEG 73.94 73.45 72.80 72.28 71.71 71.16 70.61 70.04 69.50 Water + PEG 75.91 75.42 74.98 74.54 74.02 73.57 73.08 72.61 72.05 Water + PEG 76.60 76.03 75.41 74.78 74.30 73.70 73.04 72.51 71.87

T/K = 308.15

1014κϕ

106Vϕ

−1

m ·mol ·Pa 3

(wPEG = 0.020) 1.469 1.399 1.327 1.253 1.172 1.113 (wPEG = 0.020) 1.525 1.474 1.376 1.317 1.235 1.155 1.117 1.043 0.971 (wPEG = 0.020) 1.669 1.566 1.491 1.413 1.320 1.234 1.145 1.083 0.996 (wPEG = 0.020) 1.782 1.694 1.594 1.502 1.432 1.344 1.259 1.172 1.082

−1

−1

m ·mol 3

+ [HMPyr]Br (wIL= 75.74 75.24 74.71 74.23 73.69 73.21 + [OMPyr]Br (wIL= 75.96 75.36 74.75 74.16 73.64 73.02 72.46 71.91 71.33 + [OMPyr]Br (wIL= 77.60 77.11 76.66 76.16 75.69 75.21 74.73 74.18 73.68 + [OMPyr]Br (wIL= 77.59 77.04 76.46 75.80 75.23 74.50 73.89 73.42 72.74

T/K = 318.15

1014κϕ

106Vϕ

−1

m ·mol ·Pa 3

1014κϕ

106Vϕ −1

−1

m ·mol 3

m ·mol−1·Pa−1 3

0.020) 1.760 1.689 1.619 1.539 1.454 1.382

77.46 76.93 76.37 75.86 75.40 74.86

1.892 1.811 1.742 1.659 1.588 1.514

1.843 1.757 1.669 1.606 1.545 1.468 1.404 1.313 1.255

77.85 77.41 76.85 76.20 75.61 75.01 74.50 73.86 73.28

2.085 1.997 1.907 1.834 1.769 1.695 1.630 1.552 1.490

2.080 1.960 1.852 1.752 1.667 1.583 1.515 1.456 1.403

79.52 78.94 78.43 77.98 77.44 76.97 76.45 76.03 75.51

2.322 2.193 2.123 2.047 1.963 1.869 1.803 1.739 1.670

2.041 1.913 1.821 1.743 1.669 1.552 1.446 1.371 1.280

79.57 78.76 78.05 77.44 76.83 76.11 75.55 74.96 74.35

2.309 2.185 2.058 1.957 1.865 1.771 1.685 1.609 1.547

0.010)

0.015)

0.020)

Standard uncertainties are s(Vϕ) = 0.01 × 10−6 m3·mol−1, s(κϕ) = 0.002 × 10−14 m3·mol·Pa−1, s(p) = 5 kPa.

Figure 1. Apparent molar volume of LaH as a function of molality m of LaH in aqueous solutions of (PEG+[HMPyr]Br) with (wPEG = 0.020) at T = 298.15 K; ●, wIL = 0.000; ○, wIL = 0.010; ▲, wIL = 0.015; △, wIL = 0.020.

Figure 2. Apparent molar volume of LaH as a function of molality m of LaH in aqueous solutions of (PEG+[OMPyr]Br) with wPEG = 0.020 at T = 298.15 K; ●, wIL = 0.000; ○, wIL = 0.010; ▲, wIL = 0.015; △, wIL = 0.020. E

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Table 4. Apparent Molar Volume at Infinite Dilution (Voϕ), Experimental Slope (Sv), Transfer Volume (ΔtrVoϕ), Apparent Molar Isentropic Compressibility at Infinite Dilution (κoϕ), Experimental Slope (Sκ) and Viscosity B-Coefficients (B) for L(+)-Lactic Acid in the Aqueous Solutions of PEG and in the Aqueous Solutions of (PEG + ILs) at Different Temperatures T

106Voϕ

K

m ·mol

−1

3

106Sv −2

m ·mol ·kg 3

288.15 298.15 308.15 318.15

72.10 72.56 73.37 74.46

± ± ± ±

0.01 0.01 0.02 0.02

−0.45 −1.4 −2.0 −4.4

288.15 298.15 308.15 318.15

72.30 73.84 75.27 78.12

± ± ± ±

0.03 0.03 0.02 0.03

−20.8 −22.2 −22.9 −25.4

288.15 298.15 308.15 318.15

73.36 75.31 76.18 77.74

± ± ± ±

0.05 0.05 0.03 0.07

−28.2 −28.9 −29.6 −29.9

288.15 298.15 308.15 318.15

75.58 76.96 78.46 80.15

± ± ± ±

0.04 0.04 0.08 0.06

−29.8 −29.8 −29.9 −30.0

288.15 298.15 308.15 318.15

72.95 75.09 77.09 79.11

± ± ± ±

0.04 0.03 0.04 0.06

−25.7 −31.4 −32.4 −32.6

288.15 298.15 308.15 318.15

75.58 76.90 78.61 80.46

± ± ± ±

0.10 0.03 0.02 0.05

−25.8 −26.8 −27.4 −27.8

288.15 298.15 308.15 318.15

76.66 77.75 78.83 80.68

± ± ± ±

0.04 0.03 0.06 0.10

−32.9 −33.1 −34.4 −36.2

106ΔtrVoϕ

1014κoϕ

−1

m ·mol 3

−1

m ·mol ·Pa 3

1014Sκ −1

Water + PEG (wPEG = 0.020) 0.04 0.953 ± 0.001 0.1 1.085 ± 0.001 0.2 1.198 ± 0.002 0.2 1.298 ± 0.002 Wate r+ PEG (wPEG = 0.020) + [HMPyr]Br (wIL= 0.010) ± 0.2 0.20 ± 0.03 1.306 ± 0.006 ± 0.3 1.28 ± 0.03 1.539 ± 0.008 ± 0.2 1.90 ± 0.03 1.769 ± 0.009 ± 0.2 3.66 ± 0.04 1.921 ± 0.012 Water + PEG (wPEG = 0.020)+[HMPyr]Br (wIL = 0.015) ± 0.4 1.26 ± 0.05 1.315 ± 0.009 ± 0.4 2.75 ± 0.05 1.738 ± 0.011 ± 0.3 2.81 ± 0.04 1.965 ± 0.008 ± 0.7 3.28 ± 0.07 2.172 ± 0.010 Water + PEG (wPEG = 0.020) + [HMPyr]Br (wIL = 0.020) ± 0.3 3.48 ± 0.04 1.658 ± 0.012 ± 0.4 4.40 ± 0.04 1.823 ± 0.005 ± 0.8 5.09 ± 0.08 2.106 ± 0.013 ± 0.5 5.69 ± 0.06 2.289 ± 0.008 Water + PEG (wPEG = 0.020) + [OMPyr]Br (wIL = 0.010) ± 0.4 0.85 ± 0.04 1.323 ± 0.011 ± 0.2 2.53 ± 0.03 1.667 ± 0.014 ± 0.3 3.72 ± 0.04 1.977 ± 0.010 ± 0.5 4.65 ± 0.06 2.216 ± 0.012 Water + PEG (wPEG = 0.020) + [OMPyr]Br (wIL = 0.015) ± 0.9 3.48 ± 0.10 1.337 ± 0.014 ± 0.2 4.34 ± 0.03 1.827 ± 0.011 ± 0.2 5.24 ± 0.03 2.204 ± 0.039 ± 0.5 6.00 ± 0.05 2.451 ± 0.021 Water + PEG (wPEG = 0.020) + [OMPyr]Br (wIL = 0.020) ± 0.4 4.56 ± 0.04 1.664 ± 0.020 ± 0.2 5.19 ± 0.03 1.945 ± 0.008 ± 0.5 5.46 ± 0.06 2.206 ± 0.014 ± 0.9 6.22 ± 0.10 2.454 ± 0.033 ± ± ± ±

−2

B

kg m ·mol ·Pa 3

−1

dm ·mol−1 3

−0.51 −0.72 −0.66 −0.66

± ± ± ±

0.01 0.01 0.02 0.02

0.203 0.188 0.181 0.170

± ± ± ±

0.004 0.007 0.008 0.006

−3.03 −3.12 −3.15 −3.16

± ± ± ±

0.06 0.08 0.08 0.11

0.209 0.205 0.198 0.193

± ± ± ±

0.005 0.003 0.004 0.003

−3.12 −3.13 −3.20 −3.24

± ± ± ±

0.09 0.10 0.07 0.09

0.217 0.212 0.205 0.195

± ± ± ±

0.002 0.004 0.003 0.003

−3.48 −4.02 −4.02 −4.40

± ± ± ±

0.11 0.04 0.11 0.07

0.224 0.218 0.213 0.200

± ± ± ±

0.003 0.003 0.004 0.002

−3.76 −3.93 −4.08 −4.12

± ± ± ±

0.10 0.12 0.08 0.11

0.225 0.218 0.211 0.199

± ± ± ±

0.004 0.003 0.004 0.006

−4.65 −4.69 −4.73 −4.48

± ± ± ±

0.13 0.09 0.34 0.19

0.231 0.227 0.217 0.203

± ± ± ±

0.003 0.002 0.005 0.007

−4.74 −4.87 −5.26 −5.35

± ± ± ±

0.18 0.07 0.13 0.30

0.237 0.232 0.222 0.210

± ± ± ±

0.004 0.003 0.003 0.006

of IL. This phenomenon can be interpreted on the basis of the cosphere overlap model.36 According to this model, the important interactions between LaH and IL can be classified as follows: (i) Polar−ionic interactions between COOH, OH of LaH, and cation of 1-alkyl-4-methylpyridinium. (ii) Polar− polar interactions between the polar groups of LaH and pyrdinium via the hydrogen bonding. (iii) Polar−nonpolar group interactions between the COOH, OH of LaH, and alkyl chain of 1-alkyl-4-methylpyridinium cation. (iv) Nonpolar− nonpolar group interactions between the nonpolar groups of LaH and alkyl chain of 1-alkyl-4-methylpyridinium cation. By transfer LaH from aqueous solutions of PEG to the aqueous solutions of (PEG + IL), some of hydrogen bound between LaH and PEG were replaced with hydrogen bound between LaH and IL. Consequently, ΔtrVoϕ becomes positive. 3.2. Apparent Molar Isentropic Compressibility. The apparent molar isentropic compressibility κϕ, is calculated as follows:37

temperature. Also this behavior can be attributed to the acidic nature of the pyridinium cation. Dissociation degree of LaH decreases in the presence of an ionic liquid because of the acidic nature of the pyridinium cation. Consequently, the values of Sv decreased by the addition of an ionic liquid. At infinite dilution, the solute−solute interaction is negligible; therefore the values of the infinite dilution apparent molar volumes provide valuable information about the solute−solvent interaction.35 The obtained results show that Voϕ values of LaH in the aqueous solutions of (PEG + IL) was increased by increasing the concentration of IL, alkyl chain length of IL, and temperature. This behavior can be interpreted in terms of dissociation degree of LaH. Dissociation degree of LaH decreases by the addition of IL. Considering that the intrinsic volume of LaH is larger than those of lactate anion, it can be concluded that the Voϕ values of LaH were increased by the addition of IL. The values of ΔtrVoϕ for the transfer of LaH from aqueous solutions of PEG to aqueous solutions of (PEG + IL) [ΔtrVoϕ = Voϕ (aqueous PEG + IL solution) − Voϕ (aqueous PEG solution)] are given in Table 4. As can be seen from Table 4, the values of ΔtrVoϕ at all concentrations of ILs are positive and increase by increasing the concentration and alkyl chain length

κϕ = F

(κSdo − κSod) κM + s mddo d

(3) DOI: 10.1021/acs.jced.7b00033 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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1

positive and increased by increasing the concentration and alkyl chain length of ionic liquid. Therefore, solute−solvent interactions decreases by increasing the concentration and alkyl chain length of IL. Moreover the results of Table 4 indicate that the values of κoϕ increases by increasing temperature. Therefore, it can be concluded that solute−solvent interactions decrease by increasing temperature. This behavior can be attributed to the stronger interactions of LaH and PEG with respect to interactions of LaH and IL. The values of Sκ are negative in all of the studied systems. The values of Sκ were decreased by the addition of ionic liquid and increasing temperature. Therefore, it can be concluded that solute−solute interactions weakened with the addition of ionic liquid and increasing temperature. 3.3. Viscosity B-Coefficients. Viscosity of solution provides useful information about the nature of interactions. The measured viscosity, η, for the LaH in the aqueous solutions of PEG and in the aqueous solutions of (PEG + IL) at T = (288.15−318.15) K are listed in Table 2. The obtained data for viscosity of binary system (water + PEG) is slightly smaller than those of literature. Comparison of the obtained viscosity with the literature is illustrated in Figure S6 (Supporting Information). The concentration dependency of viscosity was given by the Jones−Dole equation:39

where κs = du2 is the isentropic compressibility and u is the sound velocity. The values of κϕ for LaH in the aqueous solutions of PEG and in the aqueous solutions of (PEG + IL) at different temperatures are listed in Table 3. The apparent molar isentropic compressibility of LaH was correlated via molality of LaH according to the following equation:38 κϕ = κϕo + Sκm

(4)

κoϕ

where is the apparent molar isentropic compressibility at infinite dilution and Sκ is the experimental slope. The apparent molar isentropic compressibility of LaH in the aqueous solutions of (PEG + IL) was shown in Figures 3 and 4. The calculated

η = ηo(1 + AC1/2 + BC)

(5)

where η and ηo are the viscosity of the solution and solvent, respectively, C is molarity of the solution. The A-coefficient is related to solute−solute interactions but is often small; hence it is neglected in many correlations. The viscosity B-coefficient is an experimental coefficient which can be attributed to the solute−solvent interactions and depends on shape and size of solute molecules.40 The plots of η versus C are illustrated in Figure 5. The viscosity B-coefficients are calculated from the

Figure 3. Apparent molar isentropic compressibility of LaH as a function of molality m of LaH in the aqueous solutions of (PEG + [HMPyr]Br) with wPEG = 0.020, wIL = 0.010; ●, 288.15 K; ○, 298.15 K; ▲, 308.15 K; △, 318.15 K.

Figure 4. Apparent molar isentropic compressibility of LaH as a function of molality m of LaH in the aqueous solutions of (PEG + [OMPyr]Br) with wPEG = 0.020, wIL = 0.010; ●, 288.15 K; ○, 298.15 K; ▲, 308.15 K; △, 318.15 K.

Figure 5. Viscosity of (LaH + PEG + ILs) as a function of molarity C of LaH in the aqueous solution at T = 288.15 K; [HMPyr]Br; ●, wIL= 0.010; ▲,wIL = 0.015; ◆,wIL = 0.020; [OMPyr]Br; ○, wIL = 0.010; △, wIL = 0.015 ; ◇,wIL = 0.020.

slope of linear plot of η versus C and the obtained B-coefficients are given in Table 4. The results of Table 4 reveal that the viscosity B-coefficients increased with increasing the concentration and alkyl chain length of IL which can be attributed to increment of apparent molar of LaH rather than solute−solvent

values of κoϕ, Sκ, and their uncertainties with confidence level of 95% are given in Table 4. The infinite dilution apparent molar isentropic compressibility is an important property and provides valuable information about the solute−solvent interactions. The results of Table 4 show that the values of κoϕ are G

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(4) Schäfer, T.; Rodrigues, C. M.; Afonso, C. A. M.; Crespo, J. G. Selective recovery of solutes from ionic liquids by pervaporation−a novel approach for purification and green processing. Chem. Commun. 2001, 17, 1622−1623. (5) Chooklin, S.; Kaewsichan, L.; Kaewsrichan, J. Potential use of oil palm sap on lactic acid production and product adsorption on Dowex 66 resin as adsorbent. Asia-Pac. J. Chem. Eng. 2013, 1, 23−31. (6) Albertson, P. A. Partitioning of Cell Particles and Macromolecules; Wiley−Interscience: New York, 1986. (7) Walter, H.; Brooks, D. E.; Fisher, D. Partitioning in Aqueous TwoPhase Systems; Academic Press: New York, 1985. (8) Zaslavsky, B. Y. Aqueous Two-Phase Partitioning: Physical Chemistry and Bioanalytical Applications; Marcel Dekker: New York, 1995. (9) Wu, C.; Wang, J.; Pei, Y.; Wang, H.; Li, Z. Salting-out effect of ionic liquids on poly(propylene glycol) (PPG): formation of PPG + ionic liquid aqueous two-phase systems. J. Chem. Eng. Data 2010, 55, 5004−5008. (10) Freire, M. G.; Pereira, J. F. B.; Francisco, M.; Rodriguez, H.; Rebelo, L. P. N.; Rogers, R. D.; Coutinho, J. A. P. Insight into the interactions that control the phase behavior of new aqueous biphasic systems composed of polyethylene glycol polymers and ionic liquids. Chem. - Eur. J. 2012, 18, 1831−1839. (11) Liu, X.; Li, Z.; Pei, Y.; Wang, H.; Wang, J. Liquid−Liquid equilibria for (cholinium-based ionic liquids + polymers) aqueous twophase systems. J. Chem. Thermodyn. 2013, 60, 1−8. (12) Sadeghi, R.; Ebrahimi, N.; Mahdavi, A. Thermodynamic studies of the ionic liquid 1-hexyl-3-methylimidazolium chloride in polyethylene glycol aqueous solutions. J. Chem. Thermodyn. 2012, 47, 48− 55. (13) Moradian, T.; Sadeghi, R. Isopiestic investigations of the interactions of water-soluble polymers with imidazolium-based ionic liquids in aqueous solutions. J. Phys. Chem. B 2013, 117, 7710−7717. (14) Helfrich, M. R.; El-Kouedi, M.; Etherton, M. R.; Keating, C. D. Partitioning and assembly of metal particles and their bioconjugates in aqueous two-phase systems. Langmuir 2005, 21, 8478−8486. (15) Yankov, D. S.; Trusler, J. P. M.; Yordanov, B. Y.; Stateva, R. P. Influence of Lactic Acid on the Formation of Aqueous Two-Phase Systems Containing Poly(ethylene glycol) and Phosphates. J. Chem. Eng. Data 2008, 53, 1309−1315. (16) Guo, W. J.; Hou, Y. C.; Wu, W. Z.; Tian, S. D.; Marsh, K. N. Separation of phenol from model oils with quaternary ammonium salts via forming deep eutectic solvents. Green Chem. 2013, 15, 226−229. (17) Wang, C. M.; Zheng, J. J.; Cui, G. K.; Luo, X. Y.; Guo, Y.; Li, H. Highly efficient SO2 capture through tuning the interaction between anion-functionalized ionic liquids and SO2. Chem. Commun. 2013, 49, 1166−1168. (18) Wang, C. M.; Luo, X. Y.; Luo, H. M.; Jiang, D. E.; Li, H.; Dai, S. Tuning the basicity of ionic liquids for equimolar CO2 capture. Angew. Chem., Int. Ed. 2011, 50, 4918−4922. (19) Brandt, A.; Grasvik, J.; Hallett, J. P.; Welton, T. Deconstruction of lignocellulosic biomass with ionic liquids. Green Chem. 2013, 15, 550−583. (20) Kurane, R.; Jadhav, J.; Khanapure, S.; Salunkhe, R.; Rashinkar, G. Synergistic catalysis by an aerogel supported ionic liquid phase (ASILP) in the synthesis of 1,5-benzodiazepines. Green Chem. 2013, 15, 1849−1856. (21) Martak, J.; Schlosser, S. Phosphonium ionic liquids as new, reactive extractants of lactic acid. Chem. Pap. 2006, 60, 395−398. (22) Martak, J.; Schlosser, S. Extraction of lactic acid by phosphonium ionic liquids. Sep. Purif. Technol. 2007, 57, 483−494. (23) Matsumoto, M.; Mochiduki, K.; Fukunishi, K.; Kondo, K. Extraction of organic acids using imidazolium-based ionic liquids and their toxicity to Lactobacillus rhamnosus. Sep. Purif. Technol. 2004, 40, 97−101. (24) Yankov, D. S.; Beschkov, V. N.; Stateva, R. P. Influence of acid solutes on the phase behaviour of aqueous two-phase systems, containing poly(ethylene glycol) and poly(ethylene imine). Bulg. Chem. Commun. 2010, 42, 327−334.

interactions. Because in addition solute-solvent interactions, viscosity B-coefficient is depends on the shape and size of solute molecules. The results of volumetric proved that the apparent molar volume of LaH increased by addition of IL; therefore viscosity B-coefficients are increase by increasing the concentration of IL. The values of B-coefficients for all the investigated systems are positive and decrease with increasing temperature, therefore, the thermal coefficient (dB/dT) is negative and this phenomena may be due to stronger solute− solvent interactions in the lower temperature. The negative thermal coefficient (dB/dT) indicate that hydrodynamic volume of solute were decreased by increasing temperature; in other words LaH molecules are solvated in low temperature rather than high temperature.

4. CONCLUSIONS Density, speed of sound, and viscosity of aqueous solutions containing 1-alkyl-4-methylpyridinium bromide, lactic acid, and polyethylene glycol were measured at different temperatures. Volumetric and viscometric properties of LaH in the aqueous solutions of (PEG + IL) were calculated from density, speed of sound, and viscosity data. The infinite dilution apparent molar volume Voϕ, transfer volume ΔtrVoϕ, the limiting value of apparent molar isentropic compressibility κoϕ increased with increasing temperature, concentration, and alkyl chain length of ionic liquid. Therefore, solute−solvent interactions decreased with increasing temperature, concentration, and alkyl chain length of ionic liquid. Viscosity B-coefficients decreased by increasing temperature which reveals that solute−solvent interactions were decreased by increasing temperature. Also viscosity B-coefficients were increased by the addition of ionic liquid and this behavior can be attributed to an increment of apparent molar LaH rather than solute−solvent interactions.

■

ASSOCIATED CONTENT

S Supporting Information *

The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jced.7b00033. 1 H NMR and FT-IR spectra of 1-hexyl-3-methylpyridinium bromide and 1-octyl-3-methylpyridinium bromide (PDF)

■

AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected]. ORCID

Abbas Mehrdad: 0000-0002-1181-3512 Notes

The authors declare no competing financial interest.

■

REFERENCES

(1) Hong, W. H.; Kim, Y. J.; Wozny, G. Effect of recycle and feeding method on batch reactive recovery system of lactic acid. Korean J. Chem. Eng. 2002, 19, 808−814. (2) Matsumoto, A.; Matsukawa, Y.; Suzuki, T.; Yoshino, H. Drug release characteristics of multi-reservoir type microspheres with poly(DL-lactide-co-glycolide) and poly(DL-lactide). J. Controlled Release 2005, 106, 172−180. (3) Cheng, K.; Zhao, X.; Zeng, J.; Wu, Y.-Z.; Xu, Y.-Z.; Liu, D.-H.; Zhang, J.-A. Downstream processing of biotechnological produced succinic acid. Appl. Microbiol. Biotechnol. 2012, 4, 841−850. H

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(25) Huddleston, J. G.; Willauer, H. D.; Swatloski, R. P.; Visser, A. E.; Rogers, R. D. Room temperature ionic liquids as novel media for ‘clean’ liquid−liquid extraction. Chem. Commun. 1998, 16, 1765−1766. (26) Oliveira, F. S.; Araújo, J. M.; Ferreira, R.; Rebelo, L. P. N.; Marrucho, I. M. Extraction of L-lactic, L-malic, and succinic acids using phosphonium-based ionic liquids. Sep. Purif. Technol. 2012, 85, 137− 146. (27) Shekaari, H.; Zafarani Moattar, M. T.; Ghaffari, F. Solvation properties of acetaminophen in aqueous ionic liquid 1-hexyl-3methylimidazolium bromide solutions at different temperatures. J. Mol. Liq. 2015, 202, 86−94. (28) Shekaari, H.; Zafarani Moattar, M. T.; Ghaffari, F. Volumetric, acoustic and conductometric studies of acetaminophen in aqueous ionic liquid, 1-octyl-3-methylimidazolium bromide at T = 293.15− 308.15 K. Phys. Chem. Res. 2016, 4, 119−141. (29) Jin, H. X.; Chen, H. Y. Volumetric properties for ionic liquid− sucrose−water Systems. J. Chem. Eng. Data 2011, 56, 4392−4395. (30) Singh, V.; Chhotaray, P. K.; Gardas, R. L. Effect of protic ionic liquid on the volumetric properties and taste behavior of sucrose. Food Chem. 2015, 169, 478−483. (31) Zafarani Moattar, M. T.; Shekaari, H.; Mazaher, E. The study of solute−solute and solute−solvent interactions in aqueous solutions containing sucrose and ionic liquid, 1-butyl-3-methylimidazolium bromide at different temperatures. J. Mol. Liq. 2015, 212, 930−940. (32) Tiago, G.; Restolho, J.; Forte, A.; Colaço, R.; Branco, L. C.; Saramago, B. Novel ionic liquids for interfacial and tribological applications. Colloids Surf., A 2015, 472, 1−8. (33) Stark, A.; Ott, D.; Kralisch, D.; Kreisel, G.; Ondruschka, B. Ionic liquids and green chemistry: a lab experiment. J. Chem. Educ. 2010, 87, 196−201. (34) Pal, A.; Kumar, H.; Maan, R.; Kumar Sharma, H. Solute−solvent interactions of glycine, L-alanine, and L-valine in aqueous 1-methyl-3octylimidazolium chloride ionic liquid solutions in the temperature interval (288.15−308.15) K. Thermochim. Acta 2014, 590, 127−137. (35) Shekaari, H.; Kazempour, A.; Ghasedi, Z. Structure-making tendency of ionic liquids in the aqueous D-glucose solutions. Fluid Phase Equilib. 2012, 316, 102−108. (36) Desnoyers, J. E.; Joly, M.; Perron, G.; Jolicoeur, C. Apparent molal volumes of alkali halides in water at 25.deg. Influence of structural hydration interactions on the concentration dependence. J. Phys. Chem. 1969, 73, 3346−3351. (37) Kumar, H.; Singla, M.; Katal, A. Effect of N-acetylglycine on volumetric, acoustic and viscometric behavior of aqueous amoxicillin solutions. Thermochim. Acta 2014, 583, 49−58. (38) Millero, F. J.; Surdo, A. L.; Shin, S. C. The apparent molal volumes and adiabatic compressibilities of aqueous amino acids at 25°C. J. Phys. Chem. 1978, 82, 784−792. (39) Jones, G.; Dole, M. The viscosity of aqueous solutions of strong electrolytes with special reference to barium chloride. J. Am. Chem. Soc. 1929, 51, 2950−2964. (40) Iqbal, M. J.; Chaudhry, M. A. Volumetric and viscometric studies of antidepressant drugs in aqueous medium at different temperatures. J. Chem. Eng. Data 2009, 54, 2772−2776.

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DOI: 10.1021/acs.jced.7b00033 J. Chem. Eng. Data XXXX, XXX, XXX−XXX