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Experimental Solubility and Density Studies on Aqueous Solutions of Quaternary
Ammonium Halides, and Thermodynamic Modeling for Melting Enthalpy
Estimations
Sérgio M. Vilas-Boasa,b,c, Dinis O. Abranchesc, Emanuel A. Crespoc, Olga Ferreiraa,b, João A. P. Coutinhoc, Simão P. Pinho*a,b
aCentro de Investigação de Montanha (CIMO), Instituto Politécnico de Bragança, Campus de Santa Apolónia, 5300-253 Bragança, Portugal
bLaboratory of Separation and Reaction Engineering - Laboratory of Catalysis and Materials (LSRE-LCM), Instituto Politécnico de Bragança, Campus de Santa Apolónia, 5300-253 Bragança, Portugal
cCICECO − Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal.
*Corresponding author: Simão P. Pinho
Telephone: +351 273 303 086
Fax: +351 273 313 051
E-mail: [email protected]
Table S1. Experimental densities (ρ) of tetramethylammonium bromide ([N1111]Br) and tetrapropylammonium
bromide ([N3333]Br) in water solutions.
Temperature (K)
[N1111]Br [N3333]Br
ρ/(kg m-3) ρ/(kg m-3)
xs =
0.050a
xs = 0.090 1
xs =
0.050
xs =
0.100
xs =
0.135
293.2 1085.66 1134.96 1064.73 1093.00 1102.96
298.2 1083.76 1132.75 1061.53 1089.25 1099.18
303.2 1081.74 1130.46 1058.25 1085.47 1095.38
308.2 1079.59 1128.09 1054.91 1081.65 1091.57
313.2 1077.33 1125.64 1051.50 1077.81 1087.73
318.2 1074.96 1123.12 1048.03 1073.94 1083.88
323.2 1072.49 1120.52 1044.49 1070.04 1080.01
328.2 1069.91 1117.85 1040.89 1066.12 1076.13
333.2 1067.23 1115.11 1037.23 1062.16 1072.23
338.2 1064.46 1112.26 1033.51 1058.19 1068.31
343.2 1061.60 1109.37 1029.74 1054.19 1064.37
348.2 1058.65 1106.53 1025.97 1050.24 1060.52a xs represents the mole fraction of the salt in the solutions.
Table S2. Experimental densities (ρ) of tetraethylammonium bromide ([N2222]Br) in water solutions.
Temperature (K)
[N2222]Br
ρ/(kg m-3)
xs =
0.050a
xs =
0.100a
xs =
0.149a
xs =
0.183a
293.2 1082.00 1136.45 1172.28 1187.19
298.2 1079.65 1133.33 1168.67 1183.73
303.2 1077.18 1130.17 1165.07 1180.25
308.2 1074.61 1126.96 1161.42 1176.76
313.2 1071.93 1123.69 1157.89 1173.23
318.2 1069.16 1120.38 1154.33 1169.68
323.2 1066.29 1117.02 1150.75 1166.10
328.2 1063.32 1113.61 1147.14 1162.49
333.2 1060.27 1110.17 1143.51 1158.86
338.2 1057.13 1106.67 1139.86 1155.21
343.2 1053.91 1103.13 1136.18 1151.54
348.2 1050.67 1099.61 1132.67 1147.92a xs represents the mole fraction of the salt in the solutions.
Table S3. Experimental densities (ρ) of tetrabutylammonium bromide ([N4444]Br) in water solutions.
[N4444]Br
Temperature
(K)
ρ/(kg m-3)
xs =
0.050-a
xs =
0.100a
xs =
0.148a
xs =
0.176a
xs =
0.199a
xs =
0.247a
xs =
0.296a
293.2 1042.83 1052.56 1055.78 1056.78 1057.60 1058.61 1059.55
298.2 1039.19 1048.82 1052.12 1053.16 1054.03 1055.12 1056.15
303.2 1035.54 1045.05 1048.44 1049.52 1050.44 1051.61 1052.73
308.2 1031.85 1041.25 1044.74 1045.88 1046.85 1048.09 1049.29
313.2 1028.13 1037.43 1041.02 1042.22 1043.24 1044.56 1045.84
318.2 1024.38 1033.60 1037.29 1038.55 1039.63 1041.03 1042.38
323.2 1020.58 1029.73 1033.54 1034.86 1036.01 1037.49 1038.92
328.2 1016.76 1025.84 1029.78 1031.17 1032.38 1033.95 1035.47
333.2 1012.89 1021.93 1026.00 1027.46 1028.74 1030.40 1032.01
338.2 1008.98 1018.00 1022.20 1023.74 1025.09 1026.86 1028.55
343.2 1005.04 1014.03 1018.40 1020.02 1021.44 1023.32 1025.10
348.2 1001.05 1010.02 1014.58 1016.29 1017.84 1019.80 1021.65
a xs represents the mole fraction of the salt in the solutions.
Table S4. Experimental densities (ρ) of tetramethylammonium bromide ([Ch]Br) in water solutions.
Temperature
(K)
[Ch]Br
ρ/(kg m-3)
xs =
0.050a
xs =
0.100-
xs =
0.149
xs =
0.199
xs =
0.248
xs =
0.300
293.2 1114.92 1186.92 1231.24 1266.50 1292.76 1314.17
298.2 1112.92 1184.53 1228.67 1263.79 1289.95 1311.30
303.2 1110.80 1182.09 1226.06 1261.06 1287.13 1308.42
308.2 1108.58 1179.59 1223.41 1258.31 1284.31 1305.54
313.2 1106.25 1177.03 1220.72 1255.54 1281.48 1302.65
318.2 1103.83 1174.41 1217.99 1252.74 1278.65 1299.76
323.2 1101.31 1171.73 1215.21 1249.92 1275.80 1296.86
328.2 1098.69 1169.00 1212.39 1247.08 1272.95 1293.95
333.2 1095.96 1166.21 1209.55 1244.22 1270.09 1291.04
338.2 1093.08 1163.37 1206.69 1241.33 1267.22 1288.12
343.2 1090.19 1160.48 1203.83 1238.42 1264.34 1285.19
348.2 1087.37 1157.53 1200.94 1235.50 1261.44 1282.26
a xs represents the mole fraction of the salt in the solutions.
Table S5. Experimental densities (ρ) of tetramethylammonium chloride ([N1111]Cl) in water solutions.
Temperature
(K)
([N1111]Cl)
ρ/(kg m-3)
xs = 0.051axs =
0.100axs = 0.150a xs = 0.200a xs = 0.250a
293.2 1004.43 1012.49 1020.50 1027.11 1032.55
298.2 1002.74 1010.56 1018.43 1024.93 1030.31
303.2 1000.94 1008.56 1016.31 1022.74 1028.08
308.2 999.030 1006.50 1014.17 1020.53 1025.83
313.2 997.006 1004.37 1011.98 1018.30 1023.57
318.2 994.877 1002.19 1009.75 1016.04 1021.29
323.2 992.647 999.935 1007.48 1013.77 1019.00
328.2 990.321 997.625 1005.17 1011.47 1016.69
333.2 987.899 995.257 1002.83 1009.16 1014.36
338.2 985.391 992.830 1000.44 1006.83 1012.01
343.2 982.796 990.346 998.011 1004.48 1009.65
348.2 980.213 987.864 995.604 1002.15 1007.28axs represents the mole fraction of the salt in the solutions.
\
Table S6. Experimental densities (ρ) of tetraethylammonium chloride ([N2222]Cl) in water solutions.
Temperature (K)
([N2222]Cl)
ρ/(kg m-3)
xs = 0.051a xs = 0.102a xs = 0.151a
293.2 1009.22 1024.41 1033.14
298.2 1006.98 1021.49 1030.02
303.2 1004.64 1018.54 1026.89
308.2 1002.21 1015.54 1023.72
313.2 999.689 1012.50 1020.53
318.2 997.083 1009.43 1017.32
323.2 994.375 1006.32 1014.08
328.2 991.592 1003.17 1010.82
333.2 988.733 999.979 1007.54
338.2 985.796 996.756 1004.25
343.2 982.785 993.502 1000.93
348.2 979.757 990.267 997.782
a xs represents the mole fraction of the salt in the solutions.
Table S7. Experimental densities (ρ) of tetrapropylammonium chloride ([N3333]Cl) in water solutions.
Temperature
(K)
([N3333]Cl)
ρ/(kg m-3)
xs = 0.050a xs = 0.100a xs = 0.151a xs = 0.200a xs = 0.250a
293.2 996.458 998.607 993.19 988.60 984.99
298.2 994.255 995.117 989.81 985.36 981.89
303.2 991.912 991.599 986.42 982.11 978.78
308.2 989.439 988.063 983.01 978.86 975.67
313.2 986.842 984.499 979.59 975.60 972.54
318.2 984.122 980.913 976.15 972.32 969.41
323.2 981.287 977.306 972.70 969.03 966.26
328.2 978.348 973.681 969.23 965.73 963.11
333.2 975.306 970.038 965.75 962.43 959.95
338.2 972.169 966.379 962.27 959.11 956.78
343.2 968.938 962.701 958.77 955.79 953.61
348.2 965.678 959.064 955.26 952.48 950.43a xs represents the mole fraction of the salt in the solutions.
Table S8. Experimental densities (ρ) of tetrabutylammonium chloride ([N4444]Cl) in water solutions.
Temperature
(K)
([N4444]Cl)
ρ/(kg m-3)
xs = 0.039a xs = 0.100a xs = 0.150a xs = 0.201a xs = 0.220a
293.2 988.324 971.13 961.44 955.74 954.28
298.2 984.924 967.64 958.10 952.51 951.10
303.2 981.506 964.13 954.75 949.28 947.90
308.2 978.057 960.60 951.39 946.03 944.69
313.2 974.576 957.05 948.01 942.78 941.47
318.2 971.062 953.49 944.62 939.52 938.24
323.2 967.505 949.90 941.21 936.24 935.00
328.2 963.911 946.30 937.79 932.96 931.76
333.2 960.276 942.67 934.36 929.67 928.51
338.2 956.603 939.03 930.92 926.38 925.26
343.2 952.882 935.37 927.46 923.07 922.00
348.2 949.183 931.76 924.05 919.76 918.73a xs represents the mole fraction of the salt in the solutions.
Table S9. Experimental densities (ρ) of choline chloride ([Ch]Cl) in water solutions.
Temperature (K)
([Ch]Cl)
ρ/(kg m-3)
xs = 0.100axs =
0.150-xs = 0.200 xs = 0.251 xs = 0.301
293.2 1057.29 1074.21 1085.94 1094.79 1102.38
298.2 1055.26 1072.04 1083.70 1092.50 1100.05
303.2 1053.18 1069.85 1081.45 1090.21 1097.73
308.2 1051.04 1067.63 1079.17 1087.90 1095.39
313.2 1048.84 1065.37 1076.88 1085.59 1093.05
318.2 1046.59 1063.08 1074.57 1083.26 1090.71
323.2 1044.28 1060.76 1072.24 1080.91 1088.36
328.2 1041.93 1058.41 1069.89 1078.55 1086.00
333.2 1039.16 1056.02 1067.51 1076.18 1083.63
338.2 1037.52 1053.59 1065.12 1073.79 1081.26
343.2 1034.54 1051.13 1062.71 1071.39 1078.87
348.2 1031.98 1048.64 1060.28 1068.97 1076.47a xs represents the mole fraction of the salt in the solutions.
Table S10. Overview of the density data found in literature.
Ammonium
Salt
Range of salt mole
fraction
Temperature
range (K)
Number of
pointsReference
[N1111]Br
0.10 298.2 1 [1]
0.004 298.2 – 313.2 4 [10]
0.0002 – 0.04 298.2 9 [11]
0.0003 – 0.002 298.2 11 [12]
0.0003 – 0.003 288.2 – 318.2 77 [13]
0.050 – 0.090 293.2 – 348.2 24 this work
[N2222]Br 0.0001 – 0.0007 298.2 9 [11]
0.0003 – 0.003 298.2 11 [12]
0.0003 – 0.003 288.2 – 318.2 77 [13]
0.005 – 0.026 298.2 5 [14]
0.01 – 0.04 308.2 10 [15]
0.0002 – 0.004 298.2 – 308.2 18 [16]
0.050 – 0.183 293.2 – 348.2 48 this work
[N3333]Br
0.0004 – 0.126 278.15 – 308.2 119 [2]
0.02 – 0.068 298.2 7 [3]
0.004 298.2 – 313.2 4 [10]
0.0003 – 0.003 298.2 11 [12]
0.0003 – 0.003 288.2 – 318.2 77 [13]
0.002 – 0.013 303.9 – 322.4 12 [17]
0.0002 293.2 – 318.2 6 [18]
0.050 – 0.135 293.2 – 348.2 36 this work
[N4444]Br
0.002 – 0.067 298.2 8 [3]
0.004 – 0.05 293.2 – 333.2 90 [4]
0.0002 – 0.007 298.2 10 [11]
0.0003 – 0.003 298.2 11 [12]
0.0003 – 0.003 288.2 – 318.2 77 [13]
0.009 – 0.03 308.2 10 [15]
0.002 – 0.009 303.9 – 322.4 8 [17]
0.0002 293.2 – 318.2 6 [18]
0.006 – 0.04 283.2- 303.2 31 [19]
0.050 – 0.296 293.2 – 348.2 84 this work
[N1111]Cl
0.0001 – 0.157 288.2 – 308.2 65 [6]a
0.026 – 0.283 298.2- 358.2 30 [7]
0.0006 288.2 – 313.2 6 [20]
0.051 – 0.250 293.2 – 348.2 60 this work
[N2222]Cl
0.017 – 0.199 298.2 – 358.2 31 [7]
0.0007 – 0.160 288.2 – 308.2 60 [8]a
0.001 – 0.016 288.2 – 308.2 15 [21]
0.0006 – 0.016 293.2 – 308.2 38 [22]
0.051 – 0.151 293.2 – 348.2 36 this work
[N3333]Cl
0.013 – 0.157 298.2- 358.2 31 [7]
0.0008 – 0.030 288.2 – 303.2 36 [23]
0.050 – 0.250 293.2 – 343.2 60 this work
[N4444]Cl0.0009 – 0.075 276.2 – 298.2 154 [5]a
0.039 – 0.220 293.2 – 348.2 60 this work
ChCl 0.099 – 0.303 293.2 – 353.2 65 [9]
0.001 – 0.035 278.2 – 318.2 45 [24]
0.100 – 0.301 293.2 – 348.2 60 this worka The data was calculated from the correlated parameters presented by the authors.
Figure S1. Comparison of experimental density measured in this work with the literature data [1–5] from 293.15 K
to 348.15 K at 0.1 MPa for: a) [N1111]Br; b) [N2222]Br; c) [N3333]Br; d) [N4444]Br.
Figure S2. Comparison of experimental density measured in this work with the literature data [6–8] from 293.15 K
to 348.15 K at 0.1 MPa for a) [N1111]Cl; b) [N2222]Cl; c) [N3333]Cl; d) [N4444]Cl.
Figure S3. Comparison of experimental density measured in this work with the literature data [9] from 293.15 K to
348.15 K at 0.1 MPa for: a) [Ch]Br; b) [Ch]Cl.
Table S11. Experimental solubilities (g of solute/ g of water) of the studied tetraalkylammonium bromides between
25 ºC and 70 ºC.
Temperature (K) [N1111]Br [N2222]Br [N3333]Br [N4444]Bra [Ch]Br
298.15 0.981 ± 0.001 3.301 ± 0.001 2.686 ± 0.001 7.006 ± 0.005 5.030 ± 0.004
303.15 1.029 ± 0.001 3.402 ± 0.002 2.886 ± 0.003 7.591 ± 0.012 5.378 ± 0.004
308.15 1.075 ± 0.002 3.517 ± 0.002 3.102 ± 0.002 8.552 ± 0.016 5.747 ± 0.003
313.15 1.130 ± 0.001 3.636 ± 0.002 3.335 ± 0.004 9.445 ± 0.016 6.145 ± 0.008
318.15 1.178 ± 0.001 3.763 ± 0.004 3.585 ± 0.002 10.836 ± 0.026 6.588 ± 0.003
323.15 1.229 ± 0.001 3.895 ± 0.003 3.814 ± 0.002 11.806 ± 0.026 7.041 ± 0.032
328.15 1.271 ± 0.001 4.046 ± 0.003 4.106 ± 0.003 7.620 ± 0.004
333.15 1.320 ± 0.001 4.191 ± 0.001 4.381 ± 0.003 8.181 ± 0.006
338.15 1.374 ± 0.007 4.355 ± 0.004 4.723 ± 0.003 8.783 ± 0.022
343.15 1.431 ± 0.003 4.527 ± 0.003 5.075 ± 0.002 9.444 ± 0.011
a The solubility experiments of [N4444]Br in water could not be performed in temperatures higher than 323.15 K due to the high viscosity of
the samples.
Table S12. Experimental solubilities (g of solute/ g of water) of the studied tetraalkylammonium chlorides between
25 ºC and 70 ºC.
Temperature (K) [N1111]Cl [N2222]Cl [N3333]Cl [N4444]Cla [Ch]Cl
298.15 2.580 ± 0.001 1.555 ± 0.001 3.678 ± 0.004 5.173 ± 0.002 4.430 ± 0.004
303.15 2.619 ± 0.001 1.838 ± 0.001 3.956 ± 0.002 7.214 ± 0.007 4.666 ± 0.023
308.15 2.657 ± 0.003 3.037 ± 0.002 4.199 ± 0.005 11.672 ± 0.080 4.944 ± 0.001
313.15 2.703 ± 0.003 3.136 ± 0.001 4.516 ± 0.002 17.940 ± 0.085 5.223 ± 0.002
318.15 2.745 ± 0.003 3.286 ± 0.001 4.835 ± 0.003 24.765 ± 0.215 5.522 ± 0.001
323.15 2.794 ± 0.002 3.435 ± 0.001 5.266 ± 0.004 5.847 ± 0.005
328.15 2.833 ± 0.002 3.620 ± 0.001 5.794 ± 0.004 6.164 ± 0.004
333.15 2.877 ± 0.002 3.784 ± 0.001 6.470 ± 0.004 6.591 ± 0.006
338.15 2.923 ± 0.002 3.990 ± 0.007 6.999 ± 0.003 7.037 ± 0.009
343.15 2.978 ± 0.004 4.124 ± 0.003 7.364 ± 0.010 7.321 ± 0.011
a The solubility experiments of [N4444]Cl in water could not be performed at temperatures higher than 318.15 K due to the high viscosity of
the samples.
.
Table S12. Overview of the solubility data for the selected quaternary ammonium salts measured in this work and
found in literature at 298.2 K.
Ammonium
SaltSolubility (g g⸱ -1 of water)
xSalt ARD(%
)Reference
[N1111]Br
0.975 0.102 0.5 [1]
0.97 ± 0.03 0.10 1.0 [34]
0.981 ± 0.001 0.103 this work
[N2222]Br3.15 ± 0.04 0.213 3.6 [34]
3.301 ± 0.001 0.221 this work
[N3333]Br
2.86 0.16 5.4 [27]
2.77 0.16 2.6 [34]
2.686 ± 0.001 0.154 this work
[N4444]Bra6.92 0.279 0.9 [27]
7.006 ± 0.005 0.281 this work
[N1111]Cla2.09 0.256 14.1 [27]
2.580 ± 0.001 0.298 this work
[N2222]Cl1.57 0.146 0.8 [27]
1.555 ± 0.001 0.145 this work
[N3333]Cl4.21 0.255 10.8 [27]
3.678 ± 0.004 0.230 this work
[N4444]Cl5.71 0.270 7.6 [27]
5.173 ± 0.002 0.251 this workaThis data is referenced by Nakayama [27] and the original reference could not be found by us.
Figure S4. Water activity coefficients in aqueous solutions of symmetrical tetraalkylammonium bromides. Symbols
represent experimental data obtained from the osmotic coefficient data reported by Lindenbaum and Boyd [35].
References
[1] B.J. Levien, Some physical properties of aqueous solutions of tetramethylammonium bromide and
tetramethylammonium iodide, Aust. J. Chem. 18 (1965) 1161–1170.
[2] G. Jákli, Thermal expansion and structure of tetrapropylammonium bromide aqueous solutions derived
from density measurements, J. Chem. Thermodyn. 43 (2011) 284–289.
[3] J.T. Slusher, P.T. Cummings, Y. Hu, C.A. Vega, J.P. O’Connell, Vapor-Liquid Equilibrium and Density
Measurements of Tetraalkylammonium Bromide + Propanol + Water Systems, J. Chem. Eng. Data. 40
(1995) 792–798.
[4] V. Belandria, A.H. Mohammadi, D. Richon, Volumetric properties of the (tetrahydrofuran + water) and
(tetra- n -butyl ammonium bromide + water) systems : experimental measurements and correlations, J.
Chem. Thermodyn. 41 (2009) 1382–1386.
[5] G. Jákli, tetrabutylammonium Bromide Aqueous Solutions Derived from Density Measurements †, J.
Chem. Eng. Data. 54 (2009) 2656–2665.
[6] G. Jákli, K. Jerie, A. Baranowski, J. Glínski, Structure of aqueous solutions of tetramethylammonium
chloride investigated by positron annihilation and ultrasonic methods, Acta Phys. Pol. A. 93 (1998) 649–
658.
[7] P.V.A. Pontes, E.A. Crespo, M.A.R. Martins, L.P. Silva, C.M.S.S. Neves, G.J. Maximo, M.D. Hubinger,
E.A.C. Batista, S.P. Pinho, J.A.P. Coutinho, G. Sadowski, C. Held, Measurement and PC-SAFT
modeling of solid-liquid equilibrium of deep eutectic solvents of quaternary ammonium chlorides and
carboxylic acids, Fluid Phase Equilib. 448 (2017) 69–80.
[8] K. Jerie, A. Baranowski, G. Jákli, J. Glinski, Structure of aqueous solutions of tetraethylammonium
chloride investigated by positron annihilation and ultrasonic methods, J. Radioanal. Nucl. Chem. 240
(1999) 223–229.
[9] M. Francisco, A.S.B. González, S.L. García de Dios, W. Weggemans, M.C. Kroon, Comparison of a low
transition temperature mixture (LTTM) formed by lactic acid and choline chloride with choline lactate
ionic liquid and the choline chloride salt: physical properties and vapour–liquid equilibria of mixtures
containing water and ethanol, RSC Adv. 3 (2013) 23553.
[10] A. Ali, Shahjahan Shahjahan, Volumetric behaviour of amino acids and their group contributions in
aqueous lactose solutions at different temperatures, Z. Phys. Chem. 222 (2008) 1591–1532.
[11] L.H. Blanco, E.F. Vargas, Apparent molar volumes of symetric and asymetric tetraalkylammonium salts
in dilute aqueous solutions, J. Solution Chem. 35 (2006) 21–28.
[12] P.A. Tomar, V.R. Shaikh, K.J. Patil, Tetraalkylammonium bromide-water mixtures revisited: Isothermal
compressibility and internal pressure variation in limiting concentration range at 298.15 K, J. Chem.
Thermodyn. 126 (2018) 119–125.
[13] W. Grzybkowski, D. Warmińska, Apparent Molar Volumes and Isentropic Compressibilities of
Tetraalkylammonium Bromides in Aqueous Propane-1,2-diol. An Attempt to Design Hydraulic Liquids,
J. Chem. Eng. Data. 61 (2016) 2933–2945.
[14] T. Banerjee, N. Kishore, Interactions of peptides and lysozyme with aqueous tetraethylammonium
bromide at 298.15 K, J. Solution Chem. 35 (2006) 1389–1399.
[15] K. Roy Choudhury, D.K. Majumdar, Viscocity of tetraethylammonium bromide and
tetrabutylammonium bromide: High concentration range, Electrochim. Acta. 29 (1984) 1371–1373.
[16] J. Doménech, J.M. Costa, Viscosity of tetraethylammonium bromide solutions in N,N-
dimethylformamide-water mixtures, Electrochim. Acta. 27 (1982) 1789–1793.
[17] M. Lucas, A. Feillolay, The Enthalpy of Solution of Some Molecules in Aqueous Tetraalkylammonium
Bromide Solutions and the Apparent Expansion Coefficient of the Aqueous Salt Solution, J. Phys.
Chem. 75 (1971) 2330–2335.
[18] S. Chauhan, M. Kaur, D.S. Rana, M.S. Chauhan, Volumetric Analysis of Structural Changes of Cationic
Micelles in the Presence of Quaternary Ammonium Salts, J. Chem. Eng. Data. 61 (2016) 3770–3778.
[19] W. Lin, D. Dalmazzone, W. Fürst, A. Delahaye, L. Fournaison, P. Clain, Thermodynamic studies of
CO2 + TBAB + water system: experimental measurements and correlations, J. Chem. Eng. Data. 58
(2013) 2233–2239.
[20] R. Golabiazar, R. Sadeghi, Salt-effects in aqueous surface-active ionic liquid 1-dodecyl-3-
methylimidazolium bromide solutions: Volumetric and compressibility property changes and critical
aggregation concentration shifts, J. Chem. Thermodyn. 76 (2014) 29–44.
[21] I.M.S. Lampreia, M.S.T. Neves, Limiting partial molar volumes and expansions for triethylamine in
water and in aqueous tetraethylammonium chloride solutions from 15 to 35 oC, J. Chem. Soc. Faraday
Trans. 93 (1997) 2277–2281.
[22] Â.F.S.S. Mendonça, D.T.R. Formigo, I.M.S. Lampreia, Solubility of triethylamine in calcium chloride
aqueous solutions from 20 to 35°C, J. Solution Chem. 31 (2002) 653–670.
[23] J.W. M’David, Specific volume of solutions of tetra-propyl-ammonium chloride, Proc. R. Soc.
Edinburgh. 23 (1910) 515–520.
[24] S. Shaukat, R. Buchner, Densities, viscosities [from (278.15 to 318.15) K], and electrical conductivities
(at 298.15 K) of aqueous solutions of choline chloride and chloro-choline chloride, J. Chem. Eng. Data.
56 (2011) 4944–4949.
[25] D.O. Abranches, L.P. Silva, M.A.R. Martins, L. Fernandez, S.P. Pinho, J.A.P. Coutinho, Can cholinium
chloride form eutectic solvents with organic chloride-based salts?, Fluid Phase Equilib. 493 (2019) 120–
126.
[26] D.R. Lide, CRC Handbook of chemistry and physics, 89th ed., 2009.
[27] H. Nakayama, Solid-liquid and liquid-liquid phase equilibria in the symmetrical tetraalkylammonium
halide-water systems, Bull. Chem. Soc. Jpn. 54 (1981) 3717–3722.
[28] T.. G. Coker, J. Ambrose, G.J. Janz, Fusion Properties of Some Ionic Quaternary Ammonium
Compounds, J. Am. Chem. Soc. 92 (1970) 5293–5297.
[29] A.K.R. Unni, L. Elias, H.I.. Schiff, The Conductivities of some quaternary ammonium chlorides and
bromides at 25oC, J. Phys. Chem. 67 (1963) 1216–1219.
[30] L. Fernandez, L.P. Silva, M.A.R. Martins, O. Ferreira, J. Ortega, S.P. Pinho, J.A.P. Coutinho, Indirect
assessment of the fusion properties of choline chloride from solid-liquid equilibria data, Fluid Phase
Equilib. 448 (2017) 9–14.
[31] V. Petrouleas, R.M. Lemmon, Calorimetric studies of choline chloride, bromide, and iodide, J. Chem.
Phys. 69 (1978) 1315–1316.
[32] A.P. Abbott, G. Capper, D.L. Davies, R.K. Rasheed, V. Tambyrajah, Novel solvent properties of choline
cholride urea mixtures, Chem. Commun. (2003) 70–71.
[33] R. Craveiro, I. Aroso, V. Flammia, T. Carvalho, M.T. Viciosa, M. Dionísio, S. Barreiros, R.L. Reis,
A.R.C. Duarte, A. Paiva, Properties and thermal behavior of natural deep eutectic solvents, J. Mol. Liq.
215 (2016) 534–540.
[34] J.A. Burns, W.F. Furter, Effects of salts having large organic ions on vapor-liquid equilibrium, Adv.
Chem. 155 (1976) 99–127.
[35] S. Lindenbaum, G.E. Boyd, Osmotic and Activity Coefficients for the Symmetrical Tetraalkyl
Ammonium Halides in Aqueous Solution at 25o, J. Phys. Chem. 68 (1964) 911–917.
