Physico-chemical Studies of Isomeric Butanols in Aniline with m-Xylene

Abstract

The values of sound velocity, density and viscosity have been measured at 303 K in the ternary systems of aniline + m-xylene + n, sec, tert and iso-butanols. From these data, acoustical parameters such as molar volume, adiabatic compressibility, free length, free volume and internal pressure have been estimated using the standard relations. The results are interpreted in terms of molecular interaction between the components of the mixtures. The presence of weak dipole-induced dipole interactions of larger magnitude is confirmed in the ternary systems. Of all the isomeric butanols, 1-ol, and especially 2-ol are found to be good structure makers that make the ternary complexes. In addition the possible interactions between the components are further confirmed by their excess values.

Introduction

In many industrial applications, liquid mixtures rather than single component liquid system are used in processing and product formulations. Thermodynamic and transport properties of liquid mixtures have been extensively used [1,2,3] to study the departure of a real liquid mixture from ideality. A departure from linearity in the velocity versus composition behavior in liquid mixtures is taken as an indication of the existence of interaction between the different species [4,5,6].

During the last few decades, ultrasonic study of liquid mixtures has gained much importance in assessing the nature of molecular interactions and investigating the physico-chemical behavior of such system [7, 8]. Though, a number of investigations were carried out in liquid mixtures having alcohol as one of the component, ternary systems with isomeric butanol as one of the component are scarcely reported.

Further, as alcohols are highly polar, they can be made to form complexes with one of other component of the system that can trap the dissolved molecules. The binary complexes taken up for the present study is aniline + m-xylene both are symmetric, aniline is strong polar but m-xylene is weak polar. It will be interesting to study the influence of an asymmetric alcohol molecule in a symmetric molecular environment [9,10,11]. Though the alcohol molecule is in a symmetric molecular environment the environment is not fully symmetric. This asymmetric environment by symmetric molecules is expected to interact differently with a polar molecule such as alcohol [12]. On this basis the present work is the thorough study on the molecular interaction process of aniline + m-xylene + isomeric butanol, using the sound velocity data. The present work deals with the measurements of density, viscosity and ultrasonic velocity and the computation of related parameters in ternary systems of aniline + m-xylene + n, sec, tert and iso-butanol at 303 K.

Experimental Techniques

The mixtures of various concentrations in mole fraction were prepared by taking 99% purified AR grade samples at 303 K. The mole fraction of the second component, m-xylene (x2 = 0.3) was kept fixed, while the mole fractions of the remaining two were varied from ~ 0.0 to 0.7, so as to have the mixtures of different compositions. Further this fixed ~ 0.3 mol fraction of m-xylene is to discuss critically the system efficiency in absorption of m-xylene. The ultrasonic velocities in liquid mixtures have been measured using an ultrasonic interferometer (Mittal type) working at 2 MHz frequency with an accuracy of ± 0.1 ms−1. The density and viscosity are measured using a 5 ml specific gravity bottle and an Ostwald’s viscometer (using constant temperature bath), respectively with an accuracy of 0.1 kg m−3 for density and 0.001 m Nsm−2 for viscosity Using the measured data, the acoustical parameters such as molar volume (V), adiabatic compressibility (β), free length (Lf), free volume (Vf) and internal pressure (πi) and their excess parameters have been calculated using the standard expressions [13, 14].

Results

Ternary system was formed by adding aniline with the binary mixture of m-xylene + butanol isomer. The second component, m-xylene, mole fraction is maintained constant and the exact mole fractions of the components were calculated. For simplicity, they have been shown in rounded figures. The rounded mole fraction values shown in the Tables and their corresponding exact mole fraction values for all the ternary mixtures are presented in Table 1. Measured values of density, viscosity and sound velocity obtained for the present ternary mixtures are given in Table 2.

Table 1 Measured values in aniline + m-xylene + butanol isomer systems at 303 K
Table 2 Calculated values of molar volume (V), adiabatic compressibility (β), free length (Lf) and their excess values (VE), (βE) and (LEf), at 303 K for the systems of aniline + m-xylene + butanol isomers

The presentation of one calculated parameter along with its excess value offer a valid firm suggestion and will offer unanimous conclusion from different parameters and hence Table 2 and Fig. 1, represent calculated molar volume of all the isomeric butanol systems and its excess values. Further, Tables 2 to 3 and Figs. 1 and 2 are for adiabatic compressibility, free length free volume and internal pressure along with their excess values respectively.

Fig. 1
figure1

Trend of a molar volume, b excess molar volume, c adiabatic compressibility, d excess adiabatic compressibility, e free length and f excess free length of aniline + m-xylene + butanol isomers

Table 3 Calculated values of free volume (Vf), internal pressure (πi) and its excess values (VEf), (πEi) at 303 K for the systems of aniline + m-xylene + Butanol isomer
Fig. 2
figure2

Trend of a free volume, b excess free volume, c internal pressure and d excess internal pressure

Discussions

The perusal of Table 1 reveals that all the measured parameters such as ρ, η and U increases with increasing mole fraction of aniline. The rise of density in the mixture clearly reveals the inclusion of mass from the components. This reveals the significant character of the medium, i.e., though the density and sound velocity apparently seems to be independent of each other, in actual case, it is not so. For a single particle of a component in the mixture, the sound velocity depends on the size and mass of the particle. Size is important in offering cohesion effects whereas the mass is important regarding the inertial effects [15].

If the propagated sound energy is of enough strength, then only it can lift that mass and transfer energy to the next particle. If the neighboring particles are close, then transfer speed will be more. If the addition of aniline increases the density (mass appreciably) of the mixture, the medium is made to be more inertial and this leads to increase the sound velocity. But in this case, only a little detail may be obtained about the interactions. However in most cases, size will grow that increases the cohesion effects and so more information about the existing interactions can be obtained [16].

The continuous increase in the measured parameters indicates the enhancement of net intermolecular interaction with increasing mole fraction of aniline. The absence of 2-ol yields a more value whereas the absence of aniline leads to lower the parameters. This indicates that the weak polar m-xylene is influenced more by aniline than by butanol. Though aniline and alcohol, both are polar the weak polar m-xylene is attracted more by aniline due to the availability of more symmetry in aniline.

As per nature’s law, like dissolves like, m-xylene a hexagonal ring shaped carbon compound, though freely mixed with both aniline and alcohol, can easily dissolve into the same hexagonal ring shaped aniline than the straight chain/branched chain alcohol. Thus the observed non-linear variations in these parameters hint to the possible interaction between the components of the mixture.

The inspection of Table 2 reveals the behavior of molar volume with increasing mole fraction of aniline. Specific variations are existing for 1-ol and 2-ol but the other isomers show a decreasing trend [17]. The case of 1-butanol system is peculiar in the sense that the binary and the ternary have distinct variations. The ternary system behaves differently from binaries viz. aniline + m-xylene or m-xylene + 1-ol. In this ternary system, a peak exists at 0.3 mol fraction of aniline, indicating that the 1 mol of the components needs huge volume as they are held apart largely at this mole fraction. This suggests that interactions are fewer at this mole fraction. The existence of peak suggests that both aniline and butanol have influence over m-xylene but to different extent.

Further, for the 2-ol system, in addition to the distinct variation from binaries haphazard variations exist all along the mole fraction range. This may be an indication that the system comprises of unstable environments due to the temporary or induced dipoles. In the other two isomers, a monotonous decrease is observed with increase in aniline mole fraction. Every isomer behaves differently from that of the other especially at lower mole fraction of aniline (or higher mole fraction of butanol). However at higher mole fraction of aniline, all isomers almost resemble one another. This again suggests that aniline has much influence on m-xylene than butanol isomers.

The trend of molar volume assures that temporary or induced dipoles are formed in the systems in varying magnitude that depends on the type of isomer and the degree of interactions are larger in straight chain isomer than in branched type [18].

In order to substantiate the presence of interaction between the molecules, it is essential to study the excess parameters. The deviation of a physical property of the liquid mixtures from the ideal behavior is a measure of the interaction between the molecules which is attributed to either adhesive or cohesive forces [19]. Excess values are more meaningful than the calculated values and their trend follows the specific distinction of binary and ternary systems in all the isomeric butanols.

All the isomeric butanols show a positive excess molar volume that suggests that all systems have appreciable degree of interactions. Excess 1-ol molar volume trend is similar to that of molar volume trend. This reassures the mutual influence between the components of the system. 3-ol and iso-ol systems show a continuous decreasing trend and the sec-ol records a haphazard variation. Further in straight chain also the alcohol at the terminal carbon atom seems to be more influential in offering interactions that that at internal carbon atom. Positive magnitude hints that the existing interactions are weak type and the magnitude of variations assures that 3-ol has least interaction and 1-ol has large.

Table 2 presents the values of calculated adiabatic compressibility and its excess values for all the isomeric butanols. It is found that an exactly reverse trend of compressibility to that of ultrasonic velocity, as expected, is noticed [20]. The higher compressibility value reveals that the medium is loosely packed. The Table shows that as aniline concentration is increased, the compressibility values decrease. Thus, the deletion of alcohol molecules supports the available symmetry in the environment and makes the bonds between the species. Hence, the components of the mixtures are compact and it makes the sound velocity to increase. As the number of hydrocarbon group increases, the sound velocity is found to increases. This behavior at such concentrations for the mixtures which is different from the ideal mixture behavior, can be attributed to the intermolecular interactions in the systems studied [21,22,23].

Among the three components, aniline is symmetric as well as polar, butanol is non-symmetric and polar whereas m-xylene is symmetric but weak polar. The electro negativity of oxygen (3.5) is higher than all other atoms in the environment in the entire concentration range of the mixtures. However, in the absence of alcohol molecules, the nitrogen of aniline is not supposed to interact appreciably with carbon atoms of m-xylene as the electro negativity of these two values (3.04, 3.44) are close to each other. Further, the symmetry arrangement of m-xylene prevents the attraction of electron by nitrogen of aniline and so there would be almost no interaction between these two components. But the situation is reversed if the third component, butanol is added. The excess adiabatic compressibility value has been discussed along with the excess free length.

The existence of strong/weak interaction can also be best understood by referring the trend shown by free length. Adiabatic compressibility and free length, both are the replica of the actual intermolecular interaction. The calculated values of Lf, for all the isomeric butanol systems are presented in Table 2. Lf shows a similar trend as that of β with varying magnitude. These two parameters are found to be decreasing with increase in mole fraction of aniline. A decrease in β suggests that less space is available between the components so that the chance of compression is much lesser than at previous mole fraction, i.e., this leads to the suggestion that the intermolecular interaction is getting strengthened by the addition of aniline.

The absence of alcohol form a low β values whereas the absence of aniline leads to higher β (and Lf) value. i.e., aniline and m-xylene both are ring structured molecules, that can occupy a relatively small area and so the observed inter molecular free length is low. As the system is replaced by more and more number of butanol, the symmetry is lost and the system experiences the same type of dipole-induced dipole interactions but of weak magnitude [24, 25].

However, in the intermediate mole fractions, interactions are possible between the polar aniline and polar alcohol. i.e., strong dipole–dipole interaction are expected between the aniline-butanol components. The observed trend of β and Lf suggests that these strong interaction phenomena are overruled by the weak interaction exhibited by m-xylene. This is also quite possible because of free mixing nature of m-xylene with alcohol as well as aniline, whereas the solubility of alcohol in aniline (or reverse) is relatively poor as confirmed by Ernest Fick [26].

It is interesting to note that all the isomeric forms of butanol show the same trend of parameter with increasing mole fraction of aniline but the magnitude of variations are quite different. On comparing these values of tert-butanol with other isomers, it is observed that the tert-butanol shows a larger magnitude of variations.

A large value of β (and Lf) is an indication of existence of more free space. 3-ol systems initially have larger values that point that the components are set away due to lesser interactions. Hence of all the isomers of butanol, tert-ol is found to have least interaction. However, in general, the addition of aniline make the system to possess less free space as is evident from the trends of β and Lf. The trend as shown by the respective excess parameters will lead to a firm prediction and in this aspect the excess adiabatic compressibility and the excess free length both possess positive magnitudes. A positive value of these excess parameters is a clear indication of existence of weak interactions [27]. βE shows a monotonous increasing trend with increasing mole fraction of aniline whereas LEf exhibits a peak around 0.5 (or 0.4) mole fraction of aniline.

At lower mole fraction of aniline the magnitudes vary sharply but at higher mole fraction, the changes in the magnitudes are feeble and they resemble each other. Of all the isomers, the magnitude of tert-ol has large deviation from other isomers in the excess values of both parameters. This confirms that of all the isomers taken in the study, 3-ol has less degree of interactions.

Table 2 presents the values of free volume and excess free volume observed in all the isomeric systems. The respective trends can be referred from the Fig. 2a, b. Of all the five parameters calculated in the m-xylene ternary systems, free volume seems to offer sharp predictions than the other parameters. The free volume of 1-ol shows a continuous decrease with increasing mole fraction of aniline whereas it exhibits a peak at 0.4 mol fraction in 2-ol, and in other two isomers, a continuous increase can be observed. Of all the isomers, the free volume magnitudes observed is least for 3-ol. The average volume available among the species is taken to be the free volume and if this is high then it is a reflection that the components are held highly apart. Thus the observed free volume values suggest that at 0.1 mol fraction of aniline, 1-ol mixture has higher free volume and 3-ol has least free volume. The addition of aniline largely reduced the available free volume in 1-ol and this reduction is least in 3-ol that suggests that the interactions induced in 3-ol systems are least [23].

To be more general the branched chain isomers have least interactions and the straight chain isomers have more interactions. 1-ol and 2-ol both are straight chain isomers. Among these two isomers, 2-ol exhibits a peak at 0.4 mol fraction where as 1-ol changes are monotonous. The peak formation suggests that 2-ol may have complex formation at this mole fraction. For the 2-ol system Vf initially increases with increase in mole fraction of aniline, forms a peak at 0.4 mol fraction of aniline then decreases. The increase in free volume suggests the closeness of molecules. This is more at lower mole fraction of 2-ol and the variation are minimum as mole fraction approaches 0.4 mol fraction. However again as mole fraction deviates much from 0.4, Vf again shows larger difference. The complex formation tendency with weakening of intermolecular interaction is a peculiar type and is observed in the present system.

Dispersive type interactions are in general weak, whereas the dipolar interactions are strong. In this case of ternary system, two components are polar and the other is weak polar but can exhibit temporary dipoles. So, the dipole–dipole strong interaction exhibited by aniline-2-ol components is to be managed by either the induced dipole or by dispersive type interaction of m-xylene. The chance of managing a strong interaction by a weak interaction is somewhat ridiculous and so dispersive type interactions of m-xylene are over ruled. Thus, m-xylene in this present case is to exhibit only induced dipole interactions. Thus, the ternary complex of aniline + m-xylene + 2-ol is quite possible by dipole-induced dipole–dipole type interaction. The observed dip at 0.4 mol fraction of 2-ol confirms this view.

The mechanism of complex formation between aniline and 2-butanol can be explained as follows. The dipoles in aniline and alcohol arise due to difference in electro negativities of nitrogen, oxygen and hydrogen. They are in the order nitrogen > oxygen > hydrogen [28, 29]. Hence dipolar molecules are pictured as

figurea

There are three possibilities of dipole–dipole interactions.

  1. 1.

    Linkage between N−δ of amine will H alcohol, alcohol being proton donor.

  2. 2.

    Linkage between O−δ of alcohol with H of amine here amine acts as proton donor.

  3. 3.

    Linkage between O−δ of alcohol with N−δ of amine, alcohol being proton donor.

However, the third possibility is less likely, since electro negativities of N (3.5) and oxygen (3.0) are very close. Therefore, the aniline-alcohol complexation may arise due to first two possibilities.

The second possibility of linkage between O−δ alcohol and H of aniline is remote, because of steric hindrance of hydrogen groups from aniline to oxygen in alcohol. However the first possibility of dipole–dipole interactions between N−δ group of aniline with H+ group of alcohol is most likely, which can be represented as follows:

figureb

The N atom is sp3 hybridized and the shape of amine is pyramidal, there is a lot of space on the outside of the apex of pyramid (N atom position) for the OH to penetrate and enter into complexation.

Figure 2b shows the trend of excess free volume. It is negative for all the isomers. Negative VEf indicates that the actual available volume between the components is less than that is expected. This reduction in actual volume may be attributed to the fact that the induced dipole formation in m-xylene is continuously changing between the two forms of Kekule structures. Again the 3-ol system behave differently that is shows a continuous decreasing magnitude whereas other isomers shows an increasing trend. This suggests that 3-ol system approaches ideality due to very few interactions existing in the system [30].

The calculated values of internal pressure for all the isomeric butanols are shown in Table 3. By comparing free volume, it can be noticed that internal pressure behaves just opposite to that of free volume. The internal pressure for 1-ol system shows a continuous increase, for 2-ol system a dip formation at 0.4 mol fraction of aniline and for other two isomers a continuous decrease is observed with increasing mole fraction of aniline. This trend just re-suggests the same predictions as obtained from free volume trend.

As regards the excess internal pressure, all isomers show a shift from positive to negative magnitude Further it is observed from Fig. 2a, c that Vf shows peak in ternary mixtures whereas πi exhibit a dip at 0.4 mol fraction of 2-butanol. Aniline and 2-butanol both are polar. However, 2-butanol can show associative as well as dissociate nature depending on the environment [16]. This is highly reflected in the observed πi (and also Vf) values.

As long as aniline is sufficiently existing in the system (up to 0.4 mol fraction of aniline), πi exhibits a decreasing trend. This trend indicates that the added alcohol molecules are combining with the existing aniline—m-xylene complexes in such a way to reduce the size of ternary complex. This implies that the very strong dipole–dipole type and dipole-induced dipole type interactions are existing simultaneously with the formation of charge transfer complexation. Beyond this critical mole fraction, the further increase of alcohol shows its other side, that it tends to act in a dissociative way and hence πi start to increase. This is highly reflected if aniline is not present (0.7 mol fraction of butanol) in the system [31, 32].

The gradual increase in πi with the addition of tert-butanol or iso-butanol signifies that the polar alcohol molecules enhance the existing symmetry between the aniline—m-xylene components. At lower mole fraction, the πi variations are feeble indicate that the disturbances in symmetry are larger. As mole fraction of aniline is increased, the variation of πi are smaller which is due to the arrangement of alcohol molecule in the available void spaces, that filling the gaps. It means that finally when there is no alcohol in the system, the aniline interact strongly with the induced dipole of m-xylene due to Kekule structure conformation. As alcohol are having permanent dipoles, when they are added to the medium, they influence heavily than the induced dipoles of m-xylene and so structural deformation takes place. As ternary structure occupy much more space than binary structure, decrease in πi is sharp and large at lower mole fraction aniline and is maximum if aniline is absent [33].

Figure 2d shows the trend of excess internal pressure. For all the isomers, it shifts from negative to positive and is in increasing trend. Of course the variations have no specific features, all such trend hint to the existence of interactions of weak type in all the systems.

Conclusions

The above discussions lead to the following conclusions: The strength of interaction increases with addition of aniline. Existence of charge transfer complexation and dipole-induced dipole interaction are noticed. Dispersive type interactions are overruled by the induced dipole interactions in m-xylene. Aniline seems to exhibit more interactions with m-xylene than butanol. Presence of aniline is highly essential to maintain compactness of the system. Polar–polar and polar–weak polar combinations are behaving differently. A good degree of ternary complexation is found to exist in 1-ol and 2ol system in the mole fraction range of 0.3 to 0.4 of aniline. Among the various isomeric butanols, straight chain isomers seems to be the better options for forming ternary complex with m-xylene and aniline. And this may useful in the field of pharmacy, paint and etc.

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Palaniappan, L., Nithiyanantham, S. & Murugesan, S. Physico-chemical Studies of Isomeric Butanols in Aniline with m-Xylene. Chemistry Africa 3, 409–417 (2020). https://doi.org/10.1007/s42250-020-00120-z

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Keywords

  • Physicochemical study
  • Alcohol
  • Molecular interaction
  • Polar molecule