density and speed of sound for binary mixtures of 1,4-dioxane with propanol and butanol isomers at...

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Journal of Molecular Liquids xxx (2013) xxx–xxx

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MOLLIQ-03932; No of Pages 9

Contents lists available at ScienceDirect

Journal of Molecular Liquids

j ourna l homepage: www.e lsev ie r .com/ locate /mol l iq

Density and speed of sound for binary mixtures of 1,4-dioxane withpropanol and butanol isomers at different temperatures

OFAmalendu Pal a, Harsh Kumar b,⁎, Bhupinder Kumar a, Rekha Gaba b

a Department of Chemistry, Kurukshetra University, Kurukshetra 136119, Haryana, Indiab Department of Chemistry, Dr B R Ambedkar National Institute of Technology, Jalandhar 144 011, Punjab, India

⁎ Corresponding author. Tel.: +91 9876498660.E-mail addresses: [email protected], manchandah

0167-7322/$ – see front matter © 2013 Published by Elsehttp://dx.doi.org/10.1016/j.molliq.2013.08.009

Please cite this article as: A. Pal, et al., Journ

Oa b s t r a c t
a r t i c l e i n f o
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Article history:Received 28 December 2012Received in revised form 22 July 2013Accepted 20 August 2013Available online xxxx

Keywords:DensitySpeed of sound1,4-DioxaneApparent molar volumeMolecular interaction

3233
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ED P

RThe densities, ρ and the speeds of sound, u, for binary liquid mixtures of 1,4-dioxane with 1-propanol, 2-propanol, 1-butanol, and 2-butanol have been measured as a function of composition using an Anton-Paar DSA5000 densimeter at temperatures (293.15, 298.15, 303.15 and 308.15) K and atmospheric pressure. The excessmolar volumes, VE, and excess molar isentropic compressibilities, KS,m

E , were calculated from the experimentaldata. The computed quantities were fitted to Redlich–Kister equation to derive the coefficients and estimatethe standard error values. Also, apparent molar volume, Vϕ,i and partial molar volume, Vi , excess partial molar

volume, VEi and their limiting values at infinite dilution, V

0ϕ;i , V

0i and V

E;∞m;i respectively have been calculated

from the experimental densitymeasurements. Excess partialmolar isentropic compression,KS,iE , of both componentsand their respective limits at infinite dilution, KS,iE,∞,were analytically obtained using Redlich–Kister type equations.The variation of these properties with composition and temperature of the mixtures are discussed in terms ofmolecular interactions.

© 2013 Published by Elsevier B.V.

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UNCO

RRE1. Introduction

1,4-Dioxane is a cyclic molecule used in variety of applications inindustrial sectors e.g. as a stabilizer for storing and transporting 1,1,1-trichloroethane in aluminium containers, and in a variety of applicationsas a solvent, e.g. in inks and adhesives. Also, oxygenated compoundssuch as ethers and alcohols are used as gasoline additives and havebeen extensively investigated due to their great industrial interest [1].Interactions of 1,4-dioxane with different types of liquids as studied byvarious researchers in previous years [2–12] are important from afundamental viewpoint. Although the excess properties of 1,4-dioxanewith n-alkanols have been measured by some researchers mainly at298.15 K [13–20], references for the acoustic properties of 1,4-dioxanewith n-alkanols at different temperature are scare.

As a part of our ongoing programme of research on thermodynamicand acoustic properties of binary liquidmixtures containing linear cyclicethers, we report here the experimental data for density and speed ofsound of binary mixtures of cyclic ether with 1-propanol, 2-propanol,1-butanol, and 2-butanol and those of pure liquids at temperatures(293.15, 298.15, 303.15 and 308.15) K and atmospheric pressure overthe entire composition range. The results will enable us to comprehendthe effect of specific interactions on the excess properties, the dependenceon the position of the OH group and the alkyl chain length in the alcohol,

@nitj.ac.in (H. Kumar).

vier B.V.

al of Molecular Liquids (2013

and also the influence of temperature on the composition dependentbehaviour of these mixtures. An attempt is also made to ascertainwhether the thermophysical properties of the cyclic ether + alkanolresemble those of linear ether + alkanol [21,22].

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2. Experimental

2.1. Materials

1-Propanol, 2-propanol, 1-butanol, and 2-butanol (all S D FineChemicals, India, spectroscopic and analytical grade) were stored oversodium hydroxide pellets for several days and fractionally distilledtwice [19]. The middle fraction of the distillate was used. 1,4-Dioxane(Acros, USA) was used without further purifications. Prior to experi-mental measurements, all liquids were stored in dark bottles over0.4 nm molecular sieves to reduce water content, and were partiallydegassed with a vacuum pump under a nitrogen atmosphere. Theestimated purities determined by gas chromatographic analysiswere better than 99.5 mol% for all the liquid samples. The watercontent, measured by Karl-Fischer titration for each sample, wasalways found to be less than 0.002 mass %. The details of thechemicals used in the present work are also given in Table 1. Further,the purities of liquids were checked by comparing their densitiesand speeds of sound with their corresponding literature values[5,8,13,16,20,24–34] and are reported in Table 2. The experimentaland literature values compare well in general.

), http://dx.doi.org/10.1016/j.molliq.2013.08.009

http://dx.doi.org/10.1016/j.molliq.2013.08.009

mailto:[email protected]

mailto:[email protected]


http://www.sciencedirect.com/science/journal/01677322


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Table 1t1:1

t1:2 Specification of chemical samples.

t1:3 Chemical name Provenance CAS number Purity (supplier) Purity (GC) Water content (supplier) Water content (KF)

t1:4 1,4-Dioxane Acros, USA 123-91-1 ≥0.995 N0.995 ≤0.1% b0.002%t1:5 1-Propanol SD Fine Chem Ltd, India 71-23-8 N0.995 N0.995 0.1% b0.002%t1:6 2-Propanol SD Fine Chem Ltd, India 67-63-0 N0.995 N0.995 0.1% b0.002%t1:7 1-Butanol SD Fine Chem Ltd, India 71-36-3 N0.995 N0.995 0.1% b0.002%t1:8 2-Butanol SD Fine Chem Ltd, India 78-92-2 N0.995 N0.995 0.1% b0.002%

t2:1

t2:2

t2:3

t2:4

t2:5

t2:6

t2:7

t2:8

t2:9

t2:10

t2:11

t2:12

t2:13

t2:14

t2:15

t2:16

t2:17

t2:18

t2:19

t2:20

t2:21

t2:22

t2:23

t2:24

t2:25

t2:26

2 A. Pal et al. / Journal of Molecular Liquids xxx (2013) xxx–xxx

2.2. Apparatus and procedure

The densities, ρ and speeds of sound, u, of both pure liquids and ofthe mixtures were simultaneously, and automatically measured, usingan Anton Paar DSA 5000 densimeter. Both the density and speed ofsound are extremely sensitive to temperature, so it was controlled to±1 × 10−2 K by built-in solid state thermostat. Before each series ofmeasurements, the apparatus was calibrated with double-distilled anddegassed water, n-hexane, n-heptane, n-octane, cyclohexane, andbenzene. The sensitivity of the instrument corresponds to a precisionin density and speed of sound measurements of 1 × 10−6 g cm−3

and 1 × 10−2 m s−1. The uncertainty of the density and speed ofsound are ±3 × 10−6 g cm−3 and ±1 × 10−1 m s−1, respectively.

The mixtures were prepared by mass and were kept in specialairtight stoppered glass bottles to avoid evaporation. The weighingswere done on an A&D company limited electronic balance (Japan,Model GR-202) having a precision of ±0.01 mg. The probable errorin the mole fraction was estimated to be less than ±1 × 10−4. Allmolar quantities were based on the IUPAC relative atomic masstable [35].

UNCO

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Table 2Thermodynamic parameter for pure components.

Component T/(K) ρ × 103/(kg·m−3) α × 10−3/(K−1) CP⁎/(J·m

Exp. Lit.

1,4-Dioxane 293.15 1.033782 1.096a 148.68298.15 1.028118 1.02809 [5]

1.0283 [8]1.02797 [16]

1.102a 150.61

303.15 1.022455 1.0283 [8]1.02230 [13]1.0223 [20]

1.119a 152.56

308.15 1.01668 1.0178 [8] 1.136a 154.591-Propanol 293.15 0.803731 0.8034 [25] 1.005a 140.84

298.15 0.799714 0.7995 [25] 1.007a 144.10303.15 0.795676 0.7955 [25]

0.79601 [27]1.020a 147.36

308.15 0.791602 0.79146 [28] 1.029a 150.622-Propanol 293.15 0.785282 0.78507 [29] 1.055a 151.69

298.15 0.781073 0.780942 [24] 1.087a 158.8 [303.15 0.776790 0.776601 [24] 1.112a 159.91308.15 0.772434 0.772559 [24] 1.128a 164.01

1-Butanol 293.15 0.809164 0.80917 [32] 0.902a 173.85

298.15 0.8055704 0.80575 [29]0.80554 [32]

177.10

303.15 0.801899 0.80180 [29]0.80190 [32]

0.907a 180.37

308.15 0.798242 0.79825 [32] 0.916a 183.612-Butanol 293.15 0.806854 0.80684 [29]

0.80657 [32]1.004a 192.79

298.15 0.802728 0.80228 [32] 1.039a 196.9 [

303.15 0.798513 0.79799 [32] 1.045a 201.02308.15 0.794211 0.79372 [32] 1.083a 205.13

a Derived from our measured densities.b Calculated using group additivity.

Please cite this article as: A. Pal, et al., Journal of Molecular Liquids (2013

ED P

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3. Equations

3.1. Ultrasonic speeds and isentropic compressibilities

With the assumption that the absorption of the acoustic wave isnegligible [36], the isentropic compressibility, κS, can be calculatedusing the Newton–Laplace's equation:

κS ¼ 1=u2ρ ¼ V Mu2� �−1

: ð1Þ

The molar isentropic compressibilities KS,m, can be obtained fromEq. (2):

KS;m ¼ − δV=δPð Þs ¼ VκS ¼ ΣxiMi= ρuð Þ2; ð2Þ

where ρ is the density, V, is themolar volume, and xi andMi are themolefraction and molar mass of component i in the mixture, respectively.

ol−1·K−1) u/(m·s−1) KS,m∗ × 109/(m3·mol−1·MPa−1)

Exp. Lit.

b 1367.26 44.101[18] 1344.20 1345 [8]

1345.5 [16]46.131

b 1321.83 48.236

b 1300.34 50.411b 1223.17 1223.0 [25] 62.103[26] 1206.47 1206.0 [25] 64.530b 1189.86 1189.0 [25]

1189.0 [27]67.066

b 1172.04 1171.41 [28] 69.741b 1157.78 1156 [29] 72.70130] 1140.24 1139 [29] 75.765b 1122.59 1121 [29] 79.031[30] 1104.51 1104.04 [31] 82.563b 1272.81 1257 [29]

1256.8 [33]69.880

b 1255.81 1240 [29]1239.8 [33]

72.426

b 1238.85 1224 [29]1222.9 [33]

75.106

b 1221.96 1206.2 [33] 77.906b 1230.49 1230 [29]

1230.1 [33]75.198

34] 1212.54 1212 [29]1212.1 [33]

78.239

b 1194.48 1194 [29,33] 81.476b 1176.34 1175 [34] 84.921



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Table 3t3:1

t3:2 Values of densities, ρ and ultrasonic speeds, u, of binary mixtures as a function of mole fraction, x1, of 1,4-dioxane at different temperatures.

t3:3 x1 ρ × 103/(kg·m−3) u/(m·s−1)

t3:4 293.15(K)

298.15(K)

303.15(K)

308.15(K)

293.15(K)

298.15(K)

303.15(K)

308.15(K)

t3:5 1,4-Dioxane (1) + 1-propanol (2)t3:6 0.0252 0.810148 0.806076 0.801878 0.797743 1227.53 1210.18 1193.07 1176.03t3:7 0.1288 0.836284 0.831995 0.827657 0.823309 1242.94 1225.13 1207.41 1189.87t3:8 0.2202 0.858780 0.854298 0.849787 0.845252 1256.44 1238.14 1220.01 1202.09t3:9 0.3097 0.880249 0.875612 0.870922 0.866217 1269.28 1250.57 1232.05 1213.75t3:10 0.4066 0.902979 0.898157 0.893314 0.888441 1283.20 1264.04 1245.10 1226.38t3:11 0.5092 0.926523 0.921552 0.916555 0.911534 1298.60 1279.05 1259.59 1240.37t3:12 0.6058 0.948295 0.943159 0.937997 0.932819 1313.25 1293.19 1273.32 1253.70t3:13 0.7330 0.976355 0.971054 0.965708 0.960329 1331.13 1310.40 1289.82 1269.68t3:14 0.8024 0.991552 0.986048 0.980625 0.975087 1341.40 1320.31 1299.41 1278.70t3:15 0.9021 1.012892 1.007251 1.001625 0.995947 1353.79 1332.13 1310.91 1290.87t3:16t3:17 1,4-Dioxane (1) + 2-propanol (2)t3:18 0.0222 0.791256 0.786884 0.782463 0.782225 1163.09 1145.37 1127.72 1110.06t3:19 0.1123 0.815208 0.810626 0.806085 0.805271 1183.38 1165.16 1146.80 1128.13t3:20 0.1541 0.826037 0.821466 0.816837 0.815849 1192.20 1173.61 1155.05 1136.25t3:21 0.2244 0.844298 0.839546 0.834828 0.833508 1206.62 1187.70 1168.94 1150.06t3:22 0.2634 0.854255 0.849473 0.844644 0.843163 1214.68 1195.57 1176.62 1157.55t3:23 0.3133 0.867044 0.862186 0.857274 0.855512 1224.96 1205.80 1186.61 1167.51t3:24 0.4013 0.889184 0.884223 0.879176 0.876901 1241.61 1222.07 1202.53 1183.15t3:25 0.5096 0.916034 0.910891 0.905818 0.902902 1265.72 1245.64 1225.78 1206.00t3:26 0.6124 0.941375 0.936105 0.930814 0.927285 1287.35 1266.90 1246.65 1226.49t3:27 0.7122 0.965463 0.960089 0.954701 0.950576 1308.15 1287.36 1266.75 1246.26t3:28 0.8314 0.994135 0.988552 0.982948 0.978139 1332.76 1311.45 1290.33 1269.43t3:29 0.9464 1.021127 1.015439 1.009730 1.004107 1357.41 1335.70 1314.04 1292.65t3:30t3:31 1,4-Dioxane (1) + 1-butanol (2)t3:32 0.0366 0.816644 0.812927 0.809046 0.805236 1272.81 1255.81 1238.85 1221.96t3:33 0.1449 0.838854 0.834903 0.830786 0.826683 1274.43 1257.49 1240.64 1224.01t3:34 0.2574 0.862409 0.858244 0.853920 0.849508 1280.90 1263.69 1246.54 1229.58t3:35 0.3700 0.886532 0.882101 0.877533 0.872928 1287.75 1270.07 1252.34 1235.1t3:36 0.4302 0.899592 0.894982 0.890319 0.885662 1296.04 1277.82 1259.70 1241.98t3:37 0.4433 0.902438 0.897810 0.893104 0.888432 1300.89 1282.45 1263.95 1245.92t3:38 0.5795 0.932693 0.927843 0.922857 0.917865 1301.96 1283.54 1264.94 1246.85t3:39 0.6291 0.943952 0.939016 0.933958 0.928821 1314.49 1295.17 1275.89 1257.21t3:40 0.7603 0.974842 0.969522 0.964050 0.958611 1319.92 1300.25 1280.61 1261.68t3:41 0.8075 0.986197 0.980765 0.975202 0.969540 1335.40 1314.86 1294.53 1274.89t3:42 0.8328 0.992470 0.986883 0.981367 0.975544 1341.05 1320.31 1299.87 1280.18t3:43 0.9201 1.013809 1.008202 1.002467 0.996479 1344.01 1323.27 1302.57 1283.07t3:44t3:45 1,4-Dioxane (1) + 2-butanol (2)t3:46 0.0340 0.813426 0.809235 0.804967 0.800518 1233.05 1215.23 1197.22 1179.35t3:47 0.1197 0.830301 0.825952 0.821544 0.816988 1240.56 1222.77 1204.56 1186.68t3:48 0.1741 0.841148 0.836710 0.832208 0.827572 1246.63 1228.64 1210.27 1192.17t3:49 0.2178 0.850109 0.845596 0.841027 0.836295 1251.20 1233.04 1214.42 1196.32t3:50 0.2877 0.864919 0.860290 0.855607 0.850579 1258.56 1240.32 1221.39 1203.33t3:51 0.3219 0.872026 0.867339 0.862609 0.857735 1262.60 1244.15 1225.04 1206.67t3:52 0.4196 0.893358 0.888521 0.883638 0.878522 1273.93 1255.04 1235.51 1216.87t3:53 0.5364 0.919545 0.914546 0.909515 0.904249 1288.96 1269.59 1249.48 1230.46t3:54 0.6147 0.937496 0.932385 0.927249 0.921884 1300.52 1280.72 1260.29 1241.01t3:55 0.7117 0.960712 0.955398 0.950097 0.944601 1316.19 1295.84 1274.93 1255.12t3:56 0.8040 0.983240 0.977871 0.972479 0.966870 1331.85 1310.84 1289.77 1269.65t3:57 0.9102 1.010141 1.004624 0.999090 0.993342 1350.82 1329.24 1307.76 1287.24

3A. Pal et al. / Journal of Molecular Liquids xxx (2013) xxx–xxx

UN

3.2. Excess molar volumes and excess molar isentropic compressibilities

The experimental results of the density, ρ and speed of sound, u,measurements of binary mixtures of 1,4-dioxane + n-alkanols as afunction of mole fractions, x1, of 1,4-dioxane (0 ≤ x1 ≤ 11) at differenttemperatures are reported in Table 3. Excess molar volume VE andexcess molar isentropic compressibility, KS,m

E have been calculatedfrom experimental ρ and u values as follows:

VE ¼ Σi¼1

xiMi ρ−1−ρ�i−1

� �; ð3Þ

KES;m ¼ KS;m−Kid

S;m; ð4Þ


where [37]:

KidS;m ¼ Σxi K�

S;i−TA�P;i ΣxiA

�P;i=ΣxiC

�P;i

� �− A�

P;i=C�P;i

� �n oh i; ð5Þ

where ϕi(=xiVi/Vid) is the volume fraction, AP,i⁎ , is the product ofthe molar volume, Vi

⁎ and the isobaric expansivities, αP,i⁎ and CP,i⁎ ,are the isobaric molar heat capacity, and KS,i⁎ , the product of themolar volume, Vi

⁎ and the isentropic compressibility, κS,i⁎ . The accu-racy in the values of VE and KS,m

E is found to be ±0.003 cm3·mol−1

and ±0.04 mm3·mol−1·MPa−1. The calculated values of VE and KS,

mE are reported in Table S1 in Supplementary data.



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147148149

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155156157158

159

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163164165

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169170171

172173174

175176

t4:1

t4:2

t4:3

t4:4

t4:5

t4:6

t4:7

t4:8

t4:9

t4:10

t4:11

t4:12

t4:13t4:14

t4:15

t4:16

t4:17

t4:18

t4:19

t4:20

t4:21

t4:22

t4:23t4:24

t4:25

t4:26

t4:27

t4:28

t4:29

t4:30

t4:31

t4:32

t4:33t4:34

t4:35

t4:36

t4:37

t4:38

t4:39

t4:40

t4:41

t4:42


The calculated values of VE and KS,mE of the binary mixtures, at each

investigated temperature,werefitted to a Redlich–Kister type polynomialEq. (6):

YE ¼ x1x2 Σi¼0

ai x1−x2ð Þi; ð6Þ

where YE stands for VE or KS,mE . The coefficients ai of Eq. (6), evaluated

using least-squares method along with the standard deviations, σ(YE)are summarized in Table 4. Results on VE and KS,m

E are shown graphicallyin Figs. 1 and 2 at 298.15 K.

3.3. Partial molar volumes and its relation to excess partial molar volumesand limiting excess partial molar volumes

Thepartialmolar volumes,V1 andV2, in these systemswere evaluatedover the entire composition range by using of Eqs. (7) and (8):

V1 ¼ VE þ V�1 þ x2 δVE

=δx1� �

P;T; ð7Þ

V2 ¼ VE þ V�2−x1 δVE

=δx1� �

P;T: ð8Þ

These calculated values are reported in Table S2 given in Supple-mentary data.

The derivatives of Eqs. (7) and (8) were obtained by differentiationof VE from Eq. (6). We have also calculated excess partial molar volumeof 1,4-dioxaneV

E1 ¼ V1−V∗

1

� �from VE. The limiting excess partial molar

volumes of alcohol in ether, and of ether in alcohol VE;∞i can be easily

UNCO

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Table 4Coefficients, ai, from Eq. (6) and standard deviation, σ for the binary mixtures at different tem

Property T a0 a1

1,4-Dioxane (1) + 1-propanol (2)VE × 106/(m3·mol−1) 293.15 0.6395 0.21

298.15 0.6798 0.19303.15 0.7326 0.18308.15 0.7624 0.15

KS,mE × 109/(m3·mol−1·MPa−1) 293.15 −6.6700 0.49

298.15 −6.9908 0.29303.15 −7.2650 0.22308.15 −7.5690 0.36

1,4-Dioxane (1) + 2-propanol (2)VE × 106/(m3·mol−1) 293.15 0.8824 0.04

298.15 0.9455 0.04303.15 1.0081 −0.05308.15 1.0556 −0.08

KS,mE × 109/(m3·mol−1·MPa−1) 293.15 −11.5008 1.88

298.15 −11.9527 1.56303.15 −12.2776 1.52308.15 −12.9673 1.54

1,4-Dioxane (1) + 1-butanol (2)VE × 106/(m3·mol−1) 293.15 0.9767 0.35

298.15 1.0522 0.34303.15 1.1576 0.37308.15 1.2457 0.30

KS,mE × 109/(m3·mol−1·MPa−1) 293.15 −2.1279 −0.19

298.15 −2.2432 0.04303.15 −2.3911 0.09308.15 −2.5137 0.12

1,4-Dioxane (1) + 2-butanol (2)VE × 106/(m3·mol−1) 293.15 1.8714 −0.16

298.15 1.9363 −0.17303.15 1.9946 −0.19308.15 2.1067 −0.21

KS,mE × 109/(m3·mol−1·MPa−1) 293.15 −2.7546 −0.78

298.15 −2.8515 −0.70303.15 −2.9243 −0.69308.15 −3.0420 −0.59


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obtained by simple graphical extrapolation of VE1 to x1 = 0 (x2 = 1)

and of VE2 to x2 = 0 (x1 = 1). All of these limiting excess partial molar

volumes are listed in Table 5.Eqs. (7) and (8) lead to Eqs. (9) and (10) for the partial molar

volumes of the solute in 1,4-dioxane (1) (V1) and the cosolvent alkanol(2) (V2):

V1 ¼ V�1 þ 1−x1ð Þ2

Xi¼1

ai 2x1−1ð Þi−1 þ x1 1−x1ð Þ2Xi¼1

2 i−1ð Þai 2x1−1ð Þi−2

" #; ð9Þ

V2 ¼ V�2 þ 1−x2ð Þ2

Xi¼1

ai 1−2x2ð Þi−1 þ x2 1−x2ð Þ2Xi¼1

−2ð Þ i−1ð Þai 1−2x2ð Þi−2

" #: ð10Þ

Weare interested to focus on the partialmolar volume of 1,4-dioxaneat infinite dilution (x1 = 0) in alkanol and the partial molar volume ofalkanol at infinite dilution (x2 = 0) in 1,4-dioxane. Setting x2 = 1(corresponding to x1 = 0) in Eq. (9) leads

V01 ¼ V�

1 þXni¼1

ai −1ð Þi−1: ð11Þ

Similarly, setting x2 = 0 in Eq. (10) leads to

V02 ¼ V�

2 þXni¼1

ai: ð12Þ

In Eqs. (11) and (12), V01 and V

02 represent the partial molar volume

of 1,4-dioxane at infinite dilution in n-alkanol and the partial molarvolume of n-alkanol at infinite dilution in 1,4-dioxane, respectively.

ED

peratures.

a2 a3 a4 σ

95 −0.1583 −0.0530 0.3251 0.003021 −0.1549 0.0789 0.4485 0.001235 −0.2600 0.0808 0.7771 0.004332 −0.2302 0.1614 0.8077 0.004328 −1.8055 1.1709 2.5175 0.024449 −1.7956 1.1627 2.2702 0.024838 −1.7874 0.7575 2.1133 0.028875 −1.0761 0.0119 0.1079 0.0292

53 −0.1031 0.005757 0.0087 0.007541 −0.2186 0.1797 0.6784 0.006054 −0.1433 0.2919 0.7712 0.007077 −2.8381 2.2321 0.045778 −2.6641 2.3233 0.041673 −3.0894 1.3811 0.060083 −1.0315 1.4916 −3.4283 0.0637

66 −0.2407 −0.4829 0.006244 −0.1223 −0.3359 0.002720 −0.0541 −0.3564 0.3044 0.003937 0.1520 −0.0426 0.5770 0.00359 −1.8605 −0.3602 1.9134 0.018571 −1.6693 −0.6321 0.9443 0.015504 −1.3823 −0.8337 0.016830 −1.7045 −0.9383 0.0167

06 0.2192 0.007893 0.2188 0.007543 0.2137 0.007450 0.2464 0.005278 −1.9257 −1.7359 2.9125 0.013977 −1.9208 −1.9608 2.0737 0.013913 −2.1316 −2.2101 1.3843 0.013921 −1.8656 −2.3480 0.0123



T

PRO

OF

177178179180

181

182

183

184

185186

187188189

190

191

192

193

194

195196

Fig. 1.Variation of excess molar volumes, VE, with mole fraction, x1, of 1,4-dioxane forthe binary mixtures at 298.15 K. (ο, 1-propanol; ×, 1-propanol41; ● 2-propanol; ✱,2-propanol41;□, 1-butanol;x, 1-butanol16; ----, 1-butanol18;■, 2-butanol;+, 2-butanol16).Smooth curves have been drawn from polynomial curve fitting.

Table 5 t5:1

t5:2Values of VE;∞1 and KS,1

E,∞ and VE;∞2 and KS,2

E,∞ for 1,4-dioxane + n-alkanol binary mixtures att5:3different temperatures.

t5:4293.15(K)

298.15(K)

303.15(K)

308.15(K)

t5:51,4-Dioxane (1) + 1-propanol (2)t5:6V

E;∞m;1 � 106/(m3·mol−1) 0.491 0.539 0.619 0.683

t5:7VE;∞m;2 � 106/(m3·mol−1) −0.702 −0.796 −0.830 −0.959

t5:8KS,1E,∞ × 109/(m3·MPa−1·mol−1) −4.294 −5.059 −5.958 −8.158

t5:9KS,2E,∞ × 109/(m3·MPa−1·mol−1) −7.622 −8.269 −7.920 −8.917

t5:10t5:111,4-Dioxane (1) + 2-propanol (2)t5:12V

E;∞m;1 � 106/(m3·mol−1) 0.759 0.892 1.071 1.177

t5:13VE;∞m;2 � 106/(m3·mol−1) −0.430 −0.558 −0.907 −1.119

t5:14KS,1E,∞ × 109/(m3·MPa−1·mol−1) −10.219 −10.726 −12.459 −14.387

t5:15KS,2E,∞ × 109/(m3·MPa−1·mol−1) −18.459 −18.508 −18.275 −20.467

t5:16t5:171,4-Dioxane (1) + 1-butanol (2)t5:18V

E;∞m;1 � 106/(m3·mol−1) 0.719 0.808 1.001 1.144

t5:19VE;∞m;2 � 106/(m3·mol−1) −0.435 −0.694 −1.050 −1.655

t5:20KS,1E,∞ × 109/(m3·MPa−1·mol−1) −2.634 −3.553 −4.517 −5.034

t5:21KS,2E,∞ × 109/(m3·MPa−1·mol−1) −1.516 −2.383 −3.030 −3.403

t5:22t5:231,4-Dioxane (1) + 2-butanol (2)t5:24V

E;∞m;1 � 106/(m3·mol−1) 1.935 2.007 2.072 2.200

t5:25VE;∞m;2 � 106/(m3·mol−1) −0.857 −0.860 −0.862 −0.909

t5:26KS,1E,∞ × 109/(m3·MPa−1·mol−1) −4.292 −5.367 −6.573 −7.848

t5:27KS,2E,∞ × 109/(m3·MPa−1·mol−1) 0.756 −0.030 −0.770 −0.732

Table 6 t6:1

t6:2Values of V1⁎, V01 , V

0ϕ;1 , and K

0ϕ;1 for 1,4-binary dioxane + n-alkanol mixtures at different

t6:3temperatures.


REC

Partial molar volumes V01 and V

02 at infinite dilution are included in

Tables 6 and 7. All these partial molar volumes at infinite dilutionwere evaluated at different temperatures using Redlich–Kister coeffi-cients (Table 4).

3.4. Apparent molar properties

The apparentmolar volume (Vϕ,2) and apparentmolar compressibil-ity (Kϕ,2) of cosolvent alkanols (2) in 1,4-dioxane defined in terms ofmole fraction concentration unit are calculated from the relations

Vϕ;2 ¼ V�ϕ;2 þ VE

=x2� �

ð13Þ

Kϕ;2 ¼ K�ϕ;2 þ KE

S;m=x2� �

ð14Þ

where Kϕ,2∗ is the molar isentropic compressibility same as KS,m

∗ (2).Simple graphical extrapolation of Vϕ,1 and Kϕ,1 values for dilute

solution of 1,4-dioxane in n-alkanol to x1 = 0 (x2 = 1) and of Vϕ,2

UNCO

R

Fig. 2. Variation of excess molar isentropic compressibilities, KS,mE with mole fraction,

x1, of 1,4-dioxane for the binary mixtures at 298.15 K. (o, 1-propanol; ● 2-propanol;□, 1-butanol; ■, 2-butanol). Smooth curves have been drawn from polynomial curvefitting.


EDand Kϕ,2 values for dilute solution of n-alkanol in 1,4-dioxane x2 = 0

(x1 = 1) gives values of Vϕ,10 or Vϕ,20 and Kϕ,10 or Kϕ,2

0 at infinite dilutions.These are also the desired partial molar volumes and partial molar

compressibilities at infinite dilution represented by V01 or V

02 and K

0ϕ;1

or K0ϕ;2. The methods of obtaining V

01 and V

02, using Eqs. (11) and (12)

and by extrapolatingVϕ,2 (orVϕ,1 ) values fromEq. (13) are all satisfactory

t6:4293.15(K)

298.15(K)

303.15(K)

308.15(K)

t6:51,4-Dioxane (1) +1-propanol (2)t6:6V1

⁎ × 106/(m3·mol−1) 85.227 85.697 86.171 86.661

t6:7V01 � 106/(m3·mol−1) 85.718 86.236 86.790 87.344

t6:8V0ϕ;1 � 106/(m3·mol−1) 85.786 86.304 87.064 87.615

t6:9K0ϕ;1 × 109/(m3·MPa−1·mol−1) 27.445 29.751 31.616 31.912

t6:10t6:111,4-Dioxane (1) + 2-propanol (2)t6:12V1

⁎ × 106/(m3·mol−1) 85.227 85.697 86.171 86.661

t6:13V01 � 106/(m3·mol−1) 85.986 86.589 87.242 87.838

t6:14V0ϕ;1 � 106/(m3·mol−1) 85.928 86.823 87.689 88.371

t6:15K0ϕ;1 × 109/(m3·MPa−1·mol−1) 36.495 38.367 40.616 42.320

t6:16t6:171,4-Dioxane (1) + 1-butanol (2)t6:18V1

⁎ × 106/(m3·mol−1) 85.227 85.697 86.171 86.661

t6:19V01 � 106/(m3·mol−1) 85.946 86.505 87.172 87.805

t6:20V0ϕ;1 � 106/(m3·mol−1) 85.894 86.502 87.363 88.072

t6:21K0ϕ;1 × 109/(m3·MPa−1·mol−1) 41.935 43.635 45.522 46.994

t6:22t6:231,4-Dioxane (1) + 2-butanol (2)t6:24V1

⁎ × 106/(m3·mol−1) 85.227 85.697 86.171 86.661

t6:25V01 � 106/(m3·mol−1) 87.162 87.704 88.243 88.861

t6:26V0ϕ;1 � 106/(m3·mol−1) 87.330 87.885 88.420 89.148

t6:27K0ϕ;1 × 109/(m3·MPa−1·mol−1) 43.155 44.695 46.303 47.856



T

197

198

199

200

201

202

203

204205206

207

208

209

210

211

212

213214215

216

217218219

220221222

223

224

225

226

227

228229230

231232

233234235

236

237

238239

240241242

243

244245246

247

248

249250251252

Table 7t7:1

t7:2 Values of V2⁎, V02 , V

0ϕ;2 , and K

0ϕ;2 for 1,4-dioxane + n-alkanol binary mixtures at different

t7:3 temperatures.

t7:4 293.15(K)

298.15(K)

303.15(K)

308.15(K)

t7:5 1,4-Dioxane (1) +1-propanol (2)t7:6 V2

⁎ × 106/(m3·mol−1) 74.772 75.147 75.528 75.917

t7:7 V02 � 106/(m3·mol−1) 74.070 74.351 74.698 74.958

t7:8 V0ϕ;2 � 106/(m3·mol−1) 74.551 76.009 75.897 75.442

t7:9 K0ϕ;2 × 109/(m3·MPa−1·mol−1) 61.606 63.333 65.775 68.902

t7:10t7:11 1,4-Dioxane (1) + 2-propanol (2)t7:12 V2

⁎ × 106/(m3·mol−1) 76.528 76.940 77.364 77.801

t7:13 V02 � 106/(m3·mol−1) 76.098 76.382 76.457 76.682

t7:14 V0ϕ;2 � 106/(m3·mol−1) 76.401 76.691 76.910 77.140

t7:15 K0ϕ;2 × 109/(m3·MPa−1·mol−1) 56.177 58.022 59.971 61.795

t7:16t7:17 1,4-Dioxane (1) + 1-butanol (2)t7:18 V2

⁎ × 106/(m3·mol−1) 91.604 92.013 92.433 92.857

t7:19 V02 � 106/(m3·mol−1) 91.169 91.319 91.383 91.202

t7:20 V0ϕ;2 � 106/(m3·mol−1) 91.846 92.046 92.162 91.963

t7:21 K0ϕ;2 × 109/(m3·MPa−1·mol−1) 67.088 69.143 71.480 73.840

t7:22t7:23 1,4-Dioxane (1) + 2-butanol (2)t7:24 V2

⁎ × 106/(m3·mol−1) 91.866 92.339 92.826 93.329

t7:25 V02 � 106/(m3·mol−1) 91.009 91.479 91.964 92.420

t7:26 V0ϕ;2 � 106/(m3·mol−1) 91.822 92.339 92.848 93.2945

t7:27 K0ϕ;2 × 109/(m3·MPa−1·mol−1) 70.890 73.510 76.234 79.300

Fig. 3. Variation of excess molar volumes, VE, with mole fraction, x1, of 1,4-dioxane + 1-propanol binary mixtures at different temperatures. (o, 293.15 K; Δ, 298.15 K;□, 303.15 K; w , 308.15 K).


UNCO

RREC

and lead to similar results, as listed in Tables 6 and 7. The values ofK0ϕ;1 or

K0ϕ;2 are also listed in Tables 6 and 7.

3.5. Excess molar and limiting partial molar isentropic compression

In order to separate the contributions of each component to theexcess molar isentropic compression, excess partial molar isentropiccompression of both components Ks,i

E , over the entire compositionrange was then obtained from Eq. (15):

KES;i ¼ KE

S;m þ 1−xið ÞdKES;m

dxi: ð15Þ

The derivatives of Eq. (15) were obtained by differentiation ofKS,mE from Eq. (6) with respect to x2.Using the concept of apparent molar properties, limiting excess

partial molar isentropic compressions of alcohol in cyclic ether, and ofcyclic ether in alcohol, KS,i

E,∞ can easily be obtained from Eq. (6). Theexcess apparent molar isentropic compression as reported in Table S3of both components, KS,ϕ,1

E , can be expressed as a function of KS,mE :

KES;ϕ;1 ¼ KE

S;m=x1: ð16Þ

Substituting,KS,mE in Eq. (16)with the expression given in Eq. (6) and

setting x1 = 1 (corresponding to x2 = 0) in Eq. (6) leads to

limx2→0

KES;ϕ;2 ¼ KE;∞

S;2 ¼X

ai: ð17Þ

Similarly, setting x1 = 0 in Eq. (6) leads to

limx1→0

KES;ϕ;1 ¼ KE;∞

S;1 ¼Xi¼odd

ai−Xi¼even

ai: ð18Þ

The KS,iE,∞ values thus obtained are listed in Table 5. The resulting

Eqs. (17) and (18) were used by many authors [37–40].


ED P

RO

OF

3.6. Ideal and excess apparent ultrasonic speeds

The partial and apparent speeds of sound in these systems wereevaluated over the entire composition range by Eqs. (19)–(25) suggestedby Reis et al. [41].:

u1 ¼ uþ 1−x1ð Þ ∂u.

∂x1

� �T;P

: ð19Þ

The apparent speed of sound were calculated using the Eq. (20):

uϕ;1 ¼ u−x2u�2

� �=x1 ð20Þ

uϕ;2 ¼ u−x1u�1

� �=x2: ð21Þ

In analogy with Eq. (20), we defined the ideal apparent speed ofsound of component 1, uϕ,id1, and component 2 uϕ,

id2 using Eqs. (22)

and (23):

uidϕ;1 ¼ uid−x2u

�2

� �=x1 ð22Þ

uidϕ;2 ¼ uid−x1u

�1

� �=x2: ð23Þ

Implementation of the concept of an excess apparent speed ofsound, leads to Eq. (24):

uEϕ;i ¼ uϕ;i−uid

ϕ;i calculatedfromEqs:22and23ð Þ ¼ u−uid=xi

� �¼ uE

=xi ¼ uEϕ;i: ð24Þ

In so far as theNewton–Laplace equation is valid, the ideal ultrasonicspeed uid may be expressed correctly in term of thermodynamicproperties of an ideal mixture:

uid ¼ Vidm

� �1=2: Kid

S;m Σiϕiρ

�i

� �−1=2; ð25Þ

where ϕi is the volume fraction of component i. The values of uid anduϕ,iE are given in Table S4 and S5, respectively as Supplementary

information.



T

OO

F

253

254

255

256

257

258

259

260

261

262

263

264

265

266

267

268

269

270

271

272

273

274

275

276

277

278

279

280

281

282

283

284

285

286

287

288

289

290

291

292

293

294

295

296

297

298

299

300

301

302

303

304 Q3

305

306

307

308

309

310

311

312

0.0 0.2 0.4 0.6 0.8 1.0

-0.2

0.0

0.2

0.4

0.6

0.8

1.0

1.2

1.4

1.6

1.81,4-dioxane + 1-propanol1,4-dioxane + 2-propanol1,4-dioxane + 1-butanol1,4-dioxane + 2-butanol

Vm

,2E

,h x

106 (

mm

3 mol

-1)

x1

Fig. 5. Variation of excess partial molar volumes at infinite dilution, VE∞m;2 , for the binary

mixtures at 298.15 K.


REC

4. Discussion

For all themixtures,VE is positive over thewholemole fraction rangeand at all temperatures. Figs. 1 and 2, show the values of the excessmolar volume and excess molar isentropic compressibility at 298.15 K.Fig. 3 shows the variation of VE for 1,4-dioxane with 1-propanol atdifferent temperatures. The experimental data from the literaturefor the presentmixtures have also been included in Fig. 1 for comparison.For 1,4-dioxane + 1-propanol [42];+ 2-propanol [18] and+1-butanol[16,18] a close agreement is observed between our values and literaturevalues at 298.15 K. Similar behaviour is observed for 1,4-dioxane + 2-butanol [16] although there is a significant difference between thevalues. Further, the experimental VE values for 1,4-dioxane + 1-butanolat 303.15 and 308.15 K are very close to the VE values reported by Rajaand Kubendran [20]. For the investigated systems at any particulartemperature, the VE values increase in the sequence: 1-propanol b 2-propanol b 1-butanol b 2-butanol. The excess molar volumes curvesare symmetrical at x1 = 0.5 for 2-butanol, but the curves are unsymmet-rical for other systems, the position of the maximum being at x1 N 0.5.However, the magnitude of excess molar volumes increases with anincrease in temperature. The excess molar volume values increase withan increase in the alkyl chain length both for 1-alkanol and 2-alkanol.Remarkably, VE is less positive for the mixtures with 1-alkanol thanthat with 2-alkanol. From the experimental results, it can be said that1,4-dioxane + 2-alkanol complex formation is relatively weaker thanthe formation of complex between 1,4-dioxane and 1-alkanol. This isdue to the increase of steric hindrance of the alkyl groups in 2-alkanol.However, the effects of steric hindrance on the properties of mixturesbetween two alkanols are not so important here. Similar to thoseobserved for mixtures of 1-alkoxypropane-2-ols with 1-butanoland 2-butanol [43]: VE value is less negative with 2-butanolthan with 1-butanol. Again, with increasing the chain length of then-alkanol, the strength of the specific interaction between unlikemolecules is expected to decrease or become less important: VE

increases and becomes more positive for the larger n-alkanols.This behaviour may be compared with the VE result for mixtures of1-propanol or 1-butanol with linear ether EGDME [21,22]: VE

increases as the alkyl chain length of the alkanol increases.For each of the mixtures studied, KS,m

E is negative over the wholemole fraction range at all temperatures and shows a minimum inthe sequence 2-propanol N 1-propanol N 2-butanol N 1-butanol insteadof the order 1-propanol N 2-propanol N 1-butanol N 2-butanol if the

UNCO

R

0.0 0.2 0.4 0.6 0.8 1.0

0.0

0.5

1.0

1.5

2.0

2.5

1,4-dioxane + 1-propanol1,4-dioxane + 2-propanol1,4-dioxane + 1-butanol1,4-dioxane + 2-butanol

Vm

,1E

h x 1

06 (m

m3 m

ol-1

)

x1

Fig. 4. Variation of excess partial molar volumes at infinite dilution, VE∞m;1 , for the binary

mixtures at 298.15 K.


ED P

Rorder is compared with volumetric behaviour. Royo et al. [16] havealso reported the negative values of excess isentropic compressibilitiesfor 1,4-dioxane + 1-butanol and + 2-butanol mixtures at 298.15 and313.15 K. The order gets reversed in the case of both alkanols whenbranching occurs. Negative values of KS,mE mean that the mixture is lesscompressible than the corresponding ideal mixture, suggesting thattheremaybe disruptionof the non-hydrogen bonded structure of alcoholby the non-polar dioxane as in the case of branched alkanols as comparedto n-alkanols. As the ether is added to alcohol thereby causing abreakdown of branched alcohol structure, with a consequence increasein u, KS,m

E decreases. The effect of temperature on KS,mE depends on the

isomers of alkanols: systems containing 1-propanol or 1-butanol areshifted toward less negative values when the temperature increases.Nevertheless mixtures of 1,4-dioxane with 2-propanol or 2-butanolbecome more negative when temperature rises. Negative values ofKS,mE are indicative of specific interaction among the components in

the mixture [44] but positive values of VE and excess enthalpies[45,46] indicate that specific interactions are not very strong in thebinary mixtures of 1,4-dioxane with alkanol molecules which suggests

Fig. 6. Variation of limiting excess partial molar isentropic compressibility KE∞S;1 for the

binary mixtures at 298.15 K.



T

F

313

314

315

316

317318319320321322323324325326327

328

329

330

331

332

333

334

335

336

337

338339340341342343344345346347

348349350351352

353

354355356357358359360361362363364365366367368

369

370

371

372

Fig. 8.Variation of excess apparent speeds of sound,UEwithmole fraction, x1, of 1,4-dioxanefor the binary mixtures at 298.15 K. (o, 1-propanol; ● 2-propanol; □, 1-butanol; ■, 2-butanol).


EC

that the structural effects like interstitial accommodation, packingeffect, molecular size and shape are playing an important role [47] inour mixtures and are responsible of the shape of the curves obtained.

Negative values of VE;∞2 of the component (2) as reported in Table 5

and Figs. 4 and 5 reflects the solute–solvent interaction, in the case ofthe solvent being alkanol, is stronger than the intermolecular interactionin the pure components. As the temperature decreases, the strengthof the solute–solvent interaction increases. On the other hand the largerpositive values forV

E;∞1 of the component (1) (Table 5)would result from

the two factors, namely the changes in the 1,4-dioxane conformation(the structural changes arise due to the addition of alcohol molecules)which is infinitely diluted in alcohol and the weak solute–solventinteraction due to the presence of intermolecular interactions inthe pure component alcohol.

Table 5 also reports the values of KS,iE,∞ for the present systems at all

studied temperatures. These values are also graphically represented inFigs. 6 and 7. Table 5 shows that 1,4-dioxane at infinite dilution inalcohols has negative KS,i

E,∞, and its magnitude decreases as thetemperature increases. The behaviour of 1,4-dioxane in the alcohol-rich region reflects that in this region there is better heteroassociationof ether in an alcohol environment in relation to the pure state.This behaviour seems to diminish as the alkyl chain length/branchingof the alcohol increases.

Partial molar volumes and partial molar isentropic compressibilities

at infinite dilution are listed in Tables 6 and 7. All of theseV0ϕ;1 values for

1,4-dioxane in various alkanols (Table 6) are higher than the corre-sponding V1

∗ of pure 1,4-dioxane. This observation is consistent withthe idea that the partial molar volume of 1,4-dioxane is the result ofthe actual molecular volume of 1,4-dioxane plus the additional volumethat arises from the rupture of interactions between the components ofthe mixture. The difference increases with an increase in size of thealcohol. That is, the structure formation in these systems is hinderedand is one of the causes behind an increase in VE while increasing thealcohol chain length.

We also observe that all of theV0ϕ;2 values for alkanols in 1,4-dioxane

(Table 7) are smaller than the corresponding molar volumes V2∗ of thealkanol with 1,4-dioxane both at lower and higher temperatures exceptin 1-butanol. One can say that the heteroassociation between alcoholand cyclic ethermolecule decreaseswhen the hydrocarbon chain lengthof the alkanol increases.

UNCO

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Fig. 7. Variation of limiting excess partial molar isentropic compressibility KE∞S;2 for the

binary mixtures at 298.15 K.


ED P

RO

OThe difference betweenV0ϕ;1 and V1

∗ values for 1,4-dioxane in variousalkanols (Table 6) increases with increasing number of atoms of carbonper molecule of alkanol. This observation and the positive VE valuesobtained, suggest that the structure breaking effect between likemolecules exceed the structure formation between unlike molecules.Repulsive interaction is relatively strong between 1,4-dioxane and 2-butanol, as suggested from VE data. Increasing the chain length of thealcohol, that is from 1-propanol to 1-butanol tends to increase thedispersive interactions between 1,4-dioxane and alcohol. Further, thedifference between V

0ϕ;2 and V2

∗ is smaller with 1,4-dioxane + primaryalcohol than with 1,4-dioxane + secondary alcohol, indicating that onmixing there is an expansion in volume more with the latterone.Further, the difference between V

0ϕ;2 and V2

∗ decreases as thetemperature increases which suggest an increase of interactionsbetween two unlike molecules.

Further from Fig. 8 and Table S5, it is observed that, large positiveuϕ,iE values were observed for all binary mixtures. These values result

from a pronounced increase in the speed of sound that occurs due toheteroassociation of alcohols with 1,4-dioxane molecules.

373

374

375

376

377

378

379

380

381

382

383

384

385

386

387

388

389

390

391

392

5. Conclusions

Results on density and speeds of sound measurements for 1,4-dioxane + alkanols at different temperatures have been reported inthe present study. Experimental density and speeds of sound data wasused to calculate excessmolar volume, excess isentropic compressibilityapparent molar volume, partial molar volume, excess partial molarvolume, and their limiting values at infinite dilution. Experimentalspeeds of sound data were used to estimate apparent molar adiabaticcompressibility, limiting apparent molar adiabatic compressibility,transfer parameter and hydration number. Excess partial molar isen-tropic compression of both components and their respective limits atinfinite dilution were obtained using Redlich–Kister parameters. TheVE values are positive over the whole mole fraction range and at alltemperatures and the magnitude of excess molar volumes increaseswith an increase in temperature and also for increase in the alkylchain length both for 1-alkanol and 2-alkanol. It is also observedthat KS,m

E is negative over the whole mole fraction range at alltemperatures. Negative values ofKS,m

E are indicative of specific interactionamong the binary mixtures of 1,4-dioxane with alkanol molecules. Theapparent properties calculated were discussed in terms of interactionsbetween molecules.

393 Q4

394

6. Uncited reference

[23]



395

396

397

398

399

400

401

402

403404405406407408Q6409410411412413414415416417418419420421422423424425426

427428429430431432433434435436437438439440441442443444445446447448449450451452453454455456457458459460461462463464465466467

469


Acknowledgement

Financial support for this project (Grant No. SR/S1/PC-55/2008) bythe Government of India through the Department of Science andTechnology (DST), is gratefully acknowledged.

Appendix A. Supplementary data

Supplementary data to this article can be found online at http://dx.doi.org/10.1016/j.molliq.2013.08.009.

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