Refractive properties, speed of sound and FT-IR study of binary mixtures of N-formylmorpholine with some halobenzenes at 303.15, 308.15 and 313.15 K
Introduction
It is very difficult to estimate the importance of intermolecular interaction forces in nature because the world would be a uniform ideal gas in absence of intermolecular interactions. The proper knowledge of mixing properties such as deviation in refractive index, deviation in speed of sound and other properties related to them are necessary to understand the molecular interactions between the components of binary mixtures [1], and also play important role in designing various chemical processes such as geometry at equilibrium position, the binding energy, characteristic spectra, ion exchange systems, gas adsorption solvents, mass transfer phenomena etc [2], [3], [4]. Various electrostatic interaction forces such as dipole-dipole forces, hydrogen bonding and repulsive forces play important role in biological systems such as DNA, RNA etc [5].
N-formylmorpholine which is used as a one of the main component of binaries in the present study plays important role for various industrial processes. Because of its specific nature of N-formylmorpholine is polar and dense solvent having good stability, it is widely used in extractive distillation of pure monocyclic aromatic hydrocarbons from petroleum feed stocks [6]. Halobenzenes are known for their higher electro negativity and are widely used in industries as nucleophilic reagents for synthesis processes. So the information related to deviation of physical properties such as density, viscosity, refractive index, speed of sound etc plays an important role for understanding behavior of components in binary and ternary mixtures.
In this present study, we report accurate data of refractive index and speed of sound for three binary mixtures, viz, N-formylmorpholine, + fluorobenzene, + chlorobenzene, + bromobenzene at temperature from 303.15, 308.15 and 313.15 K. Deviations in properties like nD, ΔRm, Δu, Δks and Δz are also reported. To understand more about these mixtures and their interaction behavior with each other, many theoretical relations of refractive indexes and speed of sound are also applied. The FT-IR study has been carried out for understanding inter or intra molecular hydrogen bonding between these binary mixtures.
Section snippets
Materials
In this present study, all organic liquid components use were of AR grade and were supplied by reputed companies. N-formylmorpholine (99.5% pure, supplied by Himedia chemical, India) and halobenzenes like fluorobenzene, chlorobenzene and bromobenzene (99.5% pure, supplied by S.D. fine chemicals, India) were used after purification using standard methods [7], [8] and their purity was confirmed by gas chromatography, which showed that the mass fraction purity was higher than 99.95%. The suppliers
Deviation in refractive index (ΔηD) and molar refraction (ΔRm)
Experimentally obtained values of refractive indexes (ηD) of pure components and their binary mixtures at 303.15, 308.15 and 313.15 K are listed in Table 3. Deviation in refractive index (ΔηD) and deviation in molar refraction (ΔRm) are calculated using following equations and their values are also listed in Table 3.where, , ; and are volume fraction, refractive index and molar refraction of components 1 and 2 respectively. ,
Conclusion
The refractive index (ηD), speed of sound (Δu) are experimentally measured at 303.15, 308.15 and 313.15 K for whole composition range. Using these values, various deviation properties like deviation in refractive index (ΔηD), deviation in molar refraction (ΔRm), deviation in speed of sound (Δu), deviation in isentropic compressibility (Δks and ) and deviation in acoustical impedance (Δz) have been calculated. Moreover nine theoretical refractive index calculating relations like Arago–Biot
References (53)
- et al.
Ultrasonic studies of some derivatives of 6-ethylbenzene-1,3-diol in 1,4-dioxane
Fluid Phase Equilib.
(2003) - et al.
Ultrasonic velocity, viscosity and excess properties of binary mixture of tetrahydrofuran with 1-propanol and 2-propanol
Fluid Phase Equilib.
(2006) Ultrasonic and viscometric study of molecular interactions in binary mixtures of aniline with 1-propanol, 2-propanol, 2-methyl-1-propanol, and 2-methyl-2-propanol at different temperatures
Fluid Phase Equilib.
(2007)- et al.
Excess and deviation properties for the binary mixtures of methylcyclohexane with benzene toluene, p-xylene, mesitylene, and anisole at T = (298.15, 303.15, and 308.15) K
J. Chem. Thermodyn.
(2006) - et al.
The refractivity intercept and the specific refraction equation of Newton. I. development of the refractivity intercept and comparison with specific refraction equations
J. Franklin Inst.
(1936) - et al.
Evaluation of excess isentropic compressibilities and isochoric heat capacities
J. Chem. Thermodyn.
(1979) - et al.
Thermodynamic characterization of the water + methanol system, at 298.15 K
Thermochim. Acta
(1989) - et al.
Ultrasonic and IR study of intermolecular association through hydrogen bonding in ternary liquid mixtures
Ultrasonics
(2003) - et al.
Thermodynamic properties of (tetradecane + benzene, + toluene, + chlorobenzene, + bromobenzene, + anisole) binary mixtures at T = (298.15, 303.15, and 308.15) K
J. Chem. Thermodyn.
(2006) - et al.
Excess molar enthalpies and excess molar volumes of binary mixtures containing dialkyl carbonates+ pine resins at (298.15 and 313.15) K
J. Chem. Eng. Data
(2001)
Intermolecular Interactions: Physical Picture, Computational Methods and Model Potentials Intermolecular Interactions
Thermodynamic properties of the binary and ternary systems containing N-formylmorpholine methanol, benzene and toluene at 298.15 K
J. Al-Nahrain Univ.
Organic Solvents: Physical Properties and Method of Purification
Vogel’s Textbook of Practical Organic Chemistry
Density viscosity, refractive index, excess molar volume, viscosity, and refractive index deviations and their correlations for the (formamide + water) system, isobaric (vapor + liquid) equilibrium at 2.5 kPa
J. Chem. Eng. Data
Refractive indices, molar volumes and molar refractions of binary liquid mixtures: concepts and correlations
Phys. Chem. Chem. Phys.
On the influence of temperature on the refraction of light
Phil. Trans. R. Soc. Lond.
On the relationship between the propagation of light and mass density
Wied. Ann. Phys.
Theory of refraction constants
Berichte (Leipzig)
The determination of refractive indices of colloidal particles by means of a new mixture rule or from measurements of light scattering
Phys. Rev.
The scattering of light and its applications to chemistry
Chem. Rev.
Significant Liquid Structures
Volumetric viscometric and ultrasonic studies on binary mixtures of oleic acid with alkyl esters at 303.15, 308.15 and 313.15 K
Int. J. Phys. Sci.
Physicochemical properties for binary mixtures of anisole with 1-hexanol 1-heptanol, 1-octanol, 1-nonanol, and 1-decanol at 298.15, 303.15, 308.15, and 313.15 K
Chem. Eng. Comm.
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