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Densities and Excess Molar Volume for the Ternary Systems

Densities and Excess Molar Volume for the Ternary Systems (1-Butyl-3-methylimidazolium methyl sulphate + Nitromethane + Methanol or Ethanol or 1-Propanol) at

T = (303.15 and 313.15) K

Indra Bahadur and Nirmala Deenadayalu*

Department of Chemistry, Durban University of Technology, Steve Biko Campus, P.O. Box 1334, Durban 4000, South Africa.

Received 10 September 2012, revised 16 May 2013, accepted 7 June 2013.

ABSTRACT

The densities of the ternary systems containing the ionic liquid1-butyl-3-methylimidazolium methyl sulphate

([BMIM]+[MeSO

4]–)were determined.The ternary systems studied were([BMIM]+[MeSO

4

]–+nitromethane+methanol or

ethanol or1-propanol)at the temperatures(303.15and313.15)K.The ternary excess molar volumes were calculated from the

experimental densities at each temperature,being negative for all mole fractions of the ionic liquid.The minimum ternary excess molar volumes increase with an increase in temperature for the systems([BMIM]+[MeSO

4

]–+nitromethane+methanol or

ethanol),and decrease for the system([BMIM]+[MeSO

4

]–+nitromethane+1-propanol).The results are interpreted in terms of the alcohol chain length and the intermolecular interactions.

KEYWORDS

Density, excess molar volume, ionic liquid, alcohol, nitromethane.

1.Introduction

Ionic liquids(ILs)are low-melting molten salts which are

composed of organic cations,and inorganic anions and their

properties depend on the type of cation and anion.1ILs are

studied as‘green solvents’for organic reactions,combined with a

catalyst to extend its life span,and as reagents for nanomaterials.2,3

The physical properties of ILs such as density,viscosity,melting

point,polarity and miscibility with water or molecular solvents,

can be finely tuned by changing either the anion or the cation.2–6

ILs have other properties such as very low vapour pressure,

wide electrochemical window,high recyclability,good ionic

conductivities,thermal stability and nonflammability7,8making

them useful solvents for a wide range of applications.9,10The

applications of ILs are rapidly increasing in all modern scientific

fields such as,separations,11organic synthesis,12homogeneous

two-phase catalysis,13extractions,14electrochemistry,15and poly-

merization processes.16

Thermophysical properties of mixtures of ILs with different

solvents are useful for the design of chemical separation pro-

cesses.17,18

Ternary excess molar volumes,V E

123,for IL systems have

been reported by various researchers.19–28In this paper the densities were measured for the ter nary systems

([BMIM]+[MeSO

4]–+nitromethane+methanol or ethanol or

1-propanol)over the entire composition range at T=(303.15

and313.15)K and at atmospheric pressure.V E

123data were

calculated at T=(303.15and313.15)K and at atmospheric pressure for IL systems by using the experimental density values.The results are interpreted in terms of intermolecular interactions and the alcohol chain length.This work is a continu-ation of our research group’s work on thermodynamic proper-ties of ILs.21–26,29–352.Experimental

2.1. Materials

The chemicals were purchased from Aldrich or Merck or Fluka and used without further purification.The chemicals,supplier, purity and the literature and experimental density(r)are given in Table1.The density of the pure chemicals was determined at T=(303.15and313.15)K and at atmospheric pressure.The water content in the IL was determined by using a Karl-Fischer coulometer(Metrohm797,Herisau,Switzerland)and the mass percent water content was found to be<0.0024.The purity of the pure chemicals was assessed by a comparison of the experimental density values with the literature density values where avail-able.31,36The structure of the IL used in this work is given in Fig.1.

2.2. Apparatus and Procedure

The ternary mixtures were prepared by transferring the pure liquids into stoppered bottles to prevent evaporation.The IL was first filled into the air-tight glass stoppered5cm3glass vial and weighed.An OHAUS(Pine Brook,NJ,USA)mass balance was used to determine the mass of each component of the mix-ture.The mass balance has a precision of0.0001g.The uncer-tainty in the mole fraction was estimated to be0.0006.The ternary mixtures were prepared from a spreadsheet calculation to obtain a constant z ratio(z=x

2

/x

1

)where x

1

and x

2

are the mole fractions of the ionic liquid and nitromethane,respectively,with varying

Figure1Structure of1-butyl-3-methylimidazolium methyl sulphate [BMIM]+[MeSO

4

]–.

DMA 38vibrating U-tube densimeter.Ultra-pure water supplied by SH Calibration Service GmbH Graz,Austria and dried air were used for the calibration of the densimeter at T =298.15K.29The temperature maintenance and control were regulated by a built-in thermostat controller with a temperature uncertainty of ±0.02K.The repeatability and accuracy in experimental measurements was (±0.0002and ±0.001)g cm –3for density.The uncertainty in density for the ternary system was ±0.001g cm –3.

The ternary excess molar volumes V E

123

were calculated from the experimental density.The experimental uncertainty in V E

123was ±0.2cm 3mol –1.The experimental technique was validated by measuring the density for the test system (octane +toluene)at T =298.15K and comparing it with the literature density.37The difference between experimental and literature density for the test system was within the experimental error.

3.Results and Discussion

Densities,r ,and ternary excess molar volumes,V E

123

,for the (IL +nitromethane +methanol or ethanol or 1-propanol)systems as a function of composition at T =(303.15and 313.15)K

are given in Tables 2–4.The V E

123

was calculated by using Equation (1):

V x M x M x M x M x M x M E

123112233111222333=++???

r r r r (1)where M 1,M 2and M 3are the molecular masses,r 1,r 2,and r 3are

the densities of pure components 1,2,or 3,respectively,where ‘1’refers to the IL,‘2’to nitromethane and ‘3’to methanol or ethanol or 1-propanol and r is the density of the mixture.

The binary V m

E

data for (IL +methanol)31,(IL +ethanol)31,(IL +1-propanol)31,(IL +nitromethane)36,(methanol +nitromethane)38,(ethanol +nitromethane)38and (1-propanol +nitromethane)38were published in the literature.For each ternary system there are three sets of binary data:(i)(IL +an alcohol)(ii)(IL + nitromethane) and (iii) (an alcohol + nitromethane).(i) (IL + nitromethane + methanol)

The binary V m

E

data for (IL +methanol)at the temperatures (303.15and 313.15)K are negative for all mole fractions of the IL due to the more efficient packing and/or attractive interaction

between the IL and the methanol molecules.31The V m E

values at the temperatures (303.15and 313.15)K are –1.444cm 3

mol –1at x 1= 0.4386 and –1.531 cm 3mol –1at x 1= 0.5589, respectively.31

For the system (IL +nitromethane)V m E

are negative at the temperatures (303.15and 313.15)K,and at all mole fractions of

the IL.25The V m E

,min values at the temperatures (303.15and 313.15)K are –0.602cm 3mol –1and –0.667cm 3mol –1,respectively,both occurring at x 1= 0.2998.36

For the binary system (methanol +nitromethane)V m E

is nega-tive at the temperature 303.15K,and both positive and negative contributions)and dipole–dipole interactions and geometrical fitting of the nitromethane into the methanol structure (negative

contributions).38The V m E

,min values at the temperatures (303.15and 313.15)K are –0.1687cm 3mol –1at x 1=0.6500and –0.1523cm 3mol –1at x 1= 0.7500, respectively.38

Figures 2and 3are the plots of V E

123vs.mole fraction of metha-nol for the ternary system (IL +nitromethane +methanol).V E 123values are negative for the ternary composition curves,as can be

T able 1Pure compound specifications: supplier, purity, literature and experimental density at T = (303.15 and 313.15) K.Chemical

Supplier

Purity/mole fraction

r /g cm –3

Literature Experimental

T = 303.15 K

T =303.15 K T

T = 303.15 K Methanol Sigma-Aldrich 0.9980.7836a 0.7830.775Ethanol Sigma-Aldrich 0.9980.7821a 0.7820.7731-Propanol Merck

0.9950.7962a 0.7960.788Nitromethane Sigma-Aldrich 0.990 1.12439b 1.124 1.112[BMIM]+[MeSO 4]–

Sigma-Aldrich 0.970 1.20448b

1.205

1.199

a

Reference 31.b Reference 36.

Figure 2Graph of excess molar volumes,V E

123,for the ternary mixture [BMIM]+[MeSO 4]-(x 1)+

nitromethane (x 2)+methanol (x 3)against mole fraction of methanol at T =303.15K at constant z =x 2/x 1.The symbols represent experimental results:D ,z =4.21; ,z =1.87; ,z =0.70; ,z = 0.23;u ,z = 0.04.

Figure 3Graph of excess molar volumes,V E

123,for the ternary mixture

[BMIM]+[MeSO 4]–

(x 1)+nitromethane (x 2)+methanol (x 3)against mole fraction of methanol at T =313.15K at constant z =x 2/x 1.The symbols

expected,since the three binary V m E

,min values are all negative.

The negative values of V E

123for (IL +nitromethane +methanol)show that the (ion-dipole)interactions and packing effect between methanol,nitromethane and the IL are dominating over the dissociation of any intermolecular hydrogen bonds in methanol and nitromethane.27

From Table 2,it can be seen that for the system ([BMIM]+

[MeSO 4]–+nitromethane +methanol)V E

123,min decreases with a decreasing z values (increasing mole fractions of IL)except at z =0.70at the temperatures (303.15and 313.15)K and also at z = 0.04 for the temperature 313.15 K.

From Table 2,it can also be seen that the V E

123,min

increases with an increase in temperature for the system ([BMIM]+[MeSO 4]–+

nitromethane +methanol).The V E

123,min

values of (–2.0and –1.9)cm 3mol –1

at each temperature are similar in magnitude to

the V m

E

values for the ([BMIM]+[MeSO 4]–+methanol)binary system.31

(ii) (IL + nitromethane + ethanol)

The binary V m E

data for (IL +ethanol)at the temperatures (303.15and 313.15)K are negative for all mole fractions of the IL due to the same effects that occur in the binary system (IL +

methanol).The V m E

,min values at the temperatures (303.15and 313.15)K both occur at x 1=0.4056and are –0.775cm 3mol –1and –0.869cm 3mol –1,respectively.31The binary excess molar volumes of (IL +ethanol)are greater than for the (IL +methanol)systems.31

For the binary system (ethanol +nitromethane)V m E

are both positive and negative at the temperatures (303.15and 313.15)K due to the same effects that occur in the binary system (methanol +

nitromethane).38The V m E

,min values at the temperatures (303.15and 313.15)K are –0.0292cm 3mol –1at x 1=0.8500x 1

x 3

r /g cm –3

V E 123/cm mol 3–1

[BMIM]+[MeSO 4]–(x 1) + nitromethane (x 2)+ methanol (x 3)

T =303.15K

z = 4.21

0.04850.74710.956–0.90.09030.5290 1.044–0.90.10990.4269 1.076–0.90.14520.2429 1.130–1.20.17710.0765 1.159–0.80.1917

0.0000

1.172

–0.7

z = 1.87

0.13320.6173 1.054–1.60.19980.4256 1.112–1.50.23900.3114 1.137–1.20.29710.1467 1.164–0.90.3482

0.0000

1.185

–0.6

z = 0.70

0.06030.89740.914–0.70.15910.7290 1.036–1.40.24940.5752 1.098–1.50.31190.4692 1.127–1.40.37050.3690 1.146–1.10.47200.1965 1.174–0.90.52710.1026 1.186–0.70.5875

0.0000

1.197

–0.6

z = 0.23

0.23010.7162 1.072–1.80.37060.5428 1.126–1.40.46920.4211 1.152–1.20.54940.3222 1.167–0.90.61510.2409 1.178–0.80.72420.1053 1.193–0.60.8106

0.0000

1.203

–0.4

z = 0.04

0.84680.1150 1.194–0.20.44660.5333 1.137–1.30.33400.6509 1.106–1.60.72000.2475 1.181–0.50.60310.3697 1.165–0.80.95680.000 1.204–0.10.2165

0.7737

1.058

–2.0

T = 313.15K z = 4.21

0.11970.87490.982–1.50.04850.74710.946–0.90.09030.5290 1.035–1.00.10990.4269 1.066–0.90.14520.2429 1.120–1.20.17710.0765 1.152–1.00.1917

0.0000

1.166

–1.0

z = 1.87

0.13320.6173 1.048–1.80.19980.4256 1.104–1.50.23900.3114 1.129–1.313

123z = 0.70

0.06030.89740.906–0.70.15910.7290 1.028–1.40.24940.5752 1.092–1.60.31190.4692 1.120–1.50.37050.3690 1.140–1.30.47200.1965 1.167–0.90.52710.1026 1.179–0.80.58750.0000

1.190–0.6

z = 0.23

0.23010.7162 1.066–1.90.37060.5428 1.120–1.50.46920.4211 1.145–1.20.54940.3222 1.161–1.00.61510.2409 1.171–0.80.72420.1053 1.186–0.50.81060.0000

1.196–0.4

z = 0.04

0.84680.1150 1.188–0.30.44660.5333 1.129–1.10.33400.6509 1.098–1.50.72000.2475 1.175–0.60.60310.3697 1.159–0.80.95680.0000 1.198–0.00.21650.7737 1.048–1.80.11970.87490.974–1.6

23

than those for the binary system (methanol + nitromethane).

Figures 4and 5are the plots of V E

123

versus mole fraction of ethanol for the ternary system (IL +nitromethane +ethanol).V E

123

values are negative for the ternary composition curves.The negative values of V E

123

for the ternary system (IL +nitro-methane +ethanol)are due to the same effects that occur in the ternary (IL + nitromethane + methanol) system.

From Table 2,it is evident that for the system ([BMIM]+

[MeSO 4]–+nitromethane +ethanol)V m E

,min decreases with a decreasing z value except at z =0.23and 0.04for both the tem-peratures (303.15and 313.15)K.Also,V m E

,min increases with an increase in temperature for the system ([BMIM]+[MeSO 4]–+

nitromethane +ethanol).The V m E ,min values of (–1.8and –1.7)cm

3

mol –1at each temperature are similar in magnitude to the V m E

values for the ([BMIM]+[MeSO 4]–+ethanol)binary system.31

The V E

123,min of (IL +nitromethane +ethanol)is greater than (IL+ nitromethane + methanol) for each temperature.

x 1

x 3

r/g cm –3

V E 123/cm mol 3–1

[BMIM]+[MeSO 4]–(x 1) + nitromethane (x 2) + ethanol (x 3)

T = 303.15K

z = 4.21

0.06280.67260.949–0.80.10760.4385 1.038–0.80.12630.3412 1.071–0.70.15680.1824 1.124–0.90.18130.0545 1.159–0.80.1917

0.0000

1.172

–0.7

z = 1.87

0.16400.5288 1.049–1.70.22970.3403 1.106–1.20.28980.1676 1.149–0.90.31090.1070 1.163–0.80.3481

0.0000

1.186

–0.7

z = 0.70

0.08290.85880.911–0.90.20450.6517 1.035–1.80.30240.4850 1.094–1.50.36380.3807 1.121–1.10.41750.2891 1.143–1.00.50200.1454 1.172–0.70.5875

0.0000

1.197

–0.5

z = 0.23

0.29420.6370 1.063–1.60.44390.4523 1.123–1.30.53830.3359 1.149–1.00.66370.1808 1.176–0.60.74820.0757 1.192–0.50.8106

0.0000

1.202

–0.3

z = 0.04

0.87750.0829 1.193–0.10.53320.4428 1.132–1.00.41660.5646 1.100–1.40.77870.1862 1.179–0.30.67960.2898 1.164–0.70.95680.0000 1.204–0.00.2833

0.7039

1.045

–1.4

T =313.15K z = 4.21

0.16320.82940.967–1.00.06280.67260.940–0.80.10760.4385 1.029–0.80.12630.3412 1.062–0.80.15680.1824 1.112–0.70.18130.0545 1.148–0.70.1917

0.0000

1.162

–0.6

z = 1.87

0.16400.5288 1.040–1.70.22970.3403 1.099–1.40.28980.1676 1.141–0.90.31090.1070 1.154–0.70.3481

0.0000

1.176

–0.6

z = 0.70

131230.3024

0.4850 1.087–1.60.36380.3807 1.115–1.30.41750.2891 1.136–1.10.50200.1454 1.165–0.80.5875

0.0000

1.188

–0.4

z = 0.23

0.29420.6370 1.055–1.50.44390.4523 1.116–1.40.53830.3359 1.143–1.10.66370.1808 1.170–0.60.74820.0757 1.184–0.30.81060.0000

1.194–0.1

z = 0.04

0.87750.0829 1.187–0.10.53320.4428 1.127–1.10.41660.5646 1.093–1.40.77870.1862 1.173–0.30.67960.2898 1.158–0.70.95680.0000 1.198–0.00.28330.7039 1.036–1.20.16320.82940.958–0.9

2

3Figure 4Graph of excess molar volumes,V E

123,for the ternary mixture

[BMIM]+[MeSO 4]–

(x 1)+nitromethane (x 2)+ethanol (x 3)against mole fraction of ethanol at T =303.15K at constant z =x 2/x 1.The symbols rep-

(iii) (IL + nitromethane + 1-propanol)

The binary V m

E

data for (IL +1-propanol)at the temperatures (303.15and 313.15)K are negative for all mole fractions of the IL due to the same effects that occur in the binary systems (IL +

methanol or ethanol).The V m E

,min values at the temperatures (303.15and 313.15)K both occur at x 1=0.4756are –0.251cm 3mol –1and –0.260cm 3mol –1,respectively.31The binary excess molar volumes of (IL +1-propanol)are greater than (IL +ethanol)that are greater than the (IL +methanol)system due to the increase in the alcohol chain length.31

x 1

x 3

r/g cm –3

V E 123/cm mol 3–1

[BMIM]+[MeSO 4]–(x 1) + nitromethane (x 2) + 1-propanol (x 3)

T =303.15K

z = 4.21

0.09790.4893 1.001–0.70.13720.2842 1.075–0.70.16370.1460 1.122–0.60.18360.0423 1.157–0.60.19130.0000 1.171–0.60.07450.61160.955–0.60.11990.3745 1.043–0.70.05390.71870.913–0.50.0350

0.8172

0.872

–0.3

z = 1.87

0.18710.4625 1.046–1.10.24950.2834 1.105–0.80.28030.1947 1.131–0.70.31880.0841 1.162–0.60.34810.0000 1.185–0.60.1454

0.5823

1.002

–1.1

z = 0.70

0.16390.72080.975–1.00.10370.82340.920–0.80.24120.5892 1.033–1.00.34100.4193 1.093–1.00.39930.3203 1.122–0.80.44770.2377 1.143–0.70.51970.1153 1.171–0.50.5875

0.0000

1.195

–0.3

z = 0.23

0.34560.5736 1.062–0.90.49640.3876 1.122–0.80.58410.2794 1.148–0.70.69300.1447 1.176–0.40.8106

0.0000

1.201

–0.1

z = 0.04

0.89480.0648 1.194–0.10.59460.3786 1.133–0.70.47980.4985 1.099–0.80.81410.1492 1.180–0.20.72890.2382 1.164–0.40.95680.0000 1.204–0.00.33900.6457 1.045–0.80.2024

0.7885

0.971

–0.6

T =313.15K z = 4.21

0.09790.48930.992–0.70.13720.2842 1.066–0.70.16370.1460 1.113–0.70.18360.0423 1.148–0.70.19130.0000 1.162–0.70.07450.61160.946–0.60.11990.3745 1.034–0.70.05390.71870.905–0.50.0350

0.8172

0.866

–0.4

z = 1.87

131230.2803

0.1947 1.124–0.80.31880.0841 1.155–0.70.34810.0000 1.177–0.70.1454

0.5823

0.995

–1.2

z = 0.70

0.16390.72080.969–1.20.10370.82340.914–1.10.24120.5892 1.026–1.20.34100.4193 1.086–1.00.39930.3203 1.115–0.90.44770.2377 1.136–0.80.51970.1153 1.165–0.60.58750.0000

1.189–0.5

z = 0.23

0.34560.5736 1.055–1.00.49640.3876 1.115–0.90.58410.2794 1.142–0.80.69300.1447 1.170–0.40.81060.0000

1.195–0.2

z = 0.04

0.89480.0648 1.188–0.10.59460.3786 1.127–0.80.47980.4985 1.093–0.90.81410.1492 1.174–0.20.72890.2382 1.158–0.50.95680.0000 1.198–0.00.33900.6457 1.038–0.80.20240.78850.964–0.6

2

3Figure 5Graph of excess molar volumes,V E

123,for the ternary mixture

[BMIM]+[MeSO 4]–

(x 1)+nitromethane (x 2)+ethanol (x 3)against mole fraction of ethanol at T =313.15K at constant z =x 2/x 1.The symbols

For the binary system (1-propanol +nitromethane)V m E

is positive at the temperatures (303.15and 313.15)K due to a

decrease in the intermolecular interactions.The V m E

,min values at the temperatures (303.15and 313.15)K both occur at x 1=0.9500and are 0.0374cm 3mol –1and 0.0542cm 3mol –1,respectively.38The excess molar volumes of (1-propanol +nitromethane)are greater than (ethanol +nitromethane)are greater than (metha-nol +nitromethane)system due to the increase in the alcohol chain length.38

Figures 6–7are the plots of V E

123versus mole fraction of 1-propanol for the ternary system (IL +nitromethane +

1-propanol).V E

123

values are negative for all ternary composition curves.The negative values of V E

123

for (IL +nitromethane +1-propanol)are due to similar effects that occur in the ternary (IL + nitromethane + methanol or ethanol) systems.

From Table 4it can be seen that for the ternary system

([BMIM]+[MeSO 4]–+nitromethane +1-propanol)V E

123,min increases with decreasing z values for both temperatures and

E

+ethanol)is greater than (IL +nitromethane +methanol)systems due to a decrease in intermolecular interactions among the three components and a less compact structure (a decrease in the packing effect)possibly due to the larger 1-propanol molecules.

The V E

123,min increases in the order (IL +nitromethane +1-propanol)>(IL +nitromethane +ethanol)>(IL +nitromethane + methanol) at each temperature.

4.Conclusions

In this paper,the densities and V E

123

have been reported for the ternary systems (IL +nitromethane +methanol or ethanol or

1-propanol)at the temperatures (303.15and 313.15)K.The V E

123

values are negative for all compositions of the IL and V E

123,min increases with an increase in temperature for the systems (IL +nitromethane +methanol or ethanol)and decreases for the

system (IL +nitromethane +1-propanol).The negative V E

123values are due to strong intermolecular interactions,as well as,a more efficient packing effect among the alcohol,nitromethane and the IL.The IL,an alcohol and/or the nitromethane are engaged in specific interactions,and the ability of the alcohol to form hydrogen bonds with the IL is increased by the presence of

the nitromethane molecules.V E

123,min

values increase in the order (IL +nitromethane +1-propanol)>(IL+nitromethane +etha-nol) > (IL+ nitromethane + methanol) at each temperature.Acknowledgements

The authors acknowledge the National Research Foundation,South Africa,and Durban University of Technology for a post-doctoral scholarship for Dr I. Bahadur.References

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Figure 6Graph of excess molar volumes,V E

123,for the ternary mixture

[BMIM]+[MeSO4]-(x 1)+nitromethane (x 2)+1-propanol (x 3)against

mole fraction of 1-propanol at T =303.15K at constant z =x 2/x 1.The symbols represent experimental results:D ,z =4.21; ,z =1.87; ,z =0.70; ,z =0.23;u ,z =

0.04.

Figure 7Graph of excess molar volumes,,for the ternary mixture [BMIM]+[MeSO 4]-(x 1)+nitromethane (x 2)+1-propanol (x 3)against mole fraction of 1-propanol at T =313.15K at constant z =x 2/x 1.The symbols represent experimental results:D ,z =4.21; ,z =1.87; ,z = 0.70; ,z = 0.23;u ,z = 0.04.

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