DOI QR코드

DOI QR Code

Optical and Acoustic Properties of Binary Mixtures of Butanol Isomers as Oxygenates with Cyclohexane, Benzene and Toluene at 308.15 K

  • Verma, Sweety (Department of Chemistry, Deenbandhu Chhotu Ram University of Science and Technology) ;
  • Gahlyan, Suman (Department of Chemistry, Deenbandhu Chhotu Ram University of Science and Technology) ;
  • Rani, Manju (Department of Chemical Engineering, Deenbandhu Chhotu Ram University of Science and Technology) ;
  • Maken, Sanjeev (Department of Chemistry, Deenbandhu Chhotu Ram University of Science and Technology)
  • Received : 2018.05.14
  • Accepted : 2018.08.31
  • Published : 2018.10.01

Abstract

Refractive index and speeds of sound for the binary mixture of isomer of butanol (1) + cyclohexane, benzene and toluene (2) were measured at 308.15 K. The measured data were used to calculate deviation in refractive index ${\Delta}n$, ultrasonic speed ${\Delta}u$, isentropic compressibility $K_s^E$, available volume $V_a$, excess intermolecular free length $L_f$ and molecular association $M_A$. All the derived properties were correlated with polynomial equation. Ultrasonic speed data were predicted using various empirical correlations like Nomoto, van Dael, impedance dependence and theoretically with Schaaff's collision factor theory (CFT). Jacobson free length theory (FLT) was used to calculate $L_f$. The measured refractive index was also correlated with various mixing rules. The deviation in refractive index Δn and ultrasonic speed ${\Delta}u$ was used to determine the intermolecular interactions.

Keywords

Oxygenates;Hydrocarbon;Refractive index;Speed of sound;Molecular interactions

References

  1. Hajbabaei, M., Karavalakis, G., Johnson, K. C., Guthrie, J., Mitchell, A. and Durbin, T. D., "Impacts of Biodiesel Feedstock and Additives on Criteria Emissions from a Heavy-duty Engine," Fuel Process Technol., 126, 402-414(2014). https://doi.org/10.1016/j.fuproc.2014.04.030
  2. Kim, K. H., Choi, I. S., Kim, H. M., Wi, S. G. and Bae, H.-J., "Bioethanol Production from the Nutrient Stress-induced Microalga Chlorella Vulgaris by Enzymatic Hydrolysis and Immobilized Yeast Fermentation," Bioresource Technol., 153, 47-54(2014). https://doi.org/10.1016/j.biortech.2013.11.059
  3. Surisetty, V. R., Dalai, A. K. and Kozinski, J., "Alcohols as Alternative Fuels: An Overview," Applied Catalysis A: General, 404, 1-11(2011).
  4. Karabektas, M., Ergen, G. and Hosoz, M., "The Effects of Using Diethylether as Additive on the Performance and Emissions of a Diesel Engine Fuelled with CNG," Fuel, 115, 855-860(2014). https://doi.org/10.1016/j.fuel.2012.12.062
  5. Ezeji, T. C. and Blaschek, H. P., Butanol Production from Lig- nocellulosic Biomass, in: H. P. Blaschek, T. C. Ezeji, J. Sheffran (Eds.), Biofuels from Agricultural Wastes and Byproducts, Wiley- Blackwell, Oxford, UK (2010).
  6. Luque, R., Menendez, J. A., Arenillas, A. and Cot, J., "Microwave-assisted Pyrolysis of Biomass Feedstocks: the Way Forward," Energy & Environl. Sci., 5, 5481-5488(2012). https://doi.org/10.1039/C1EE02450G
  7. Regulation 715/2007 of the European Parliament ad of the Council on type approval of motor vehicles with respect to emissions from light passenger and commercial vehicles (Euro 5 and Euro 6) (2007).
  8. Directive 2009/30/EC of the European Parliament ad of the Council on the specification of petrol, diesel and gas-oil and introducing a mechanism to monitor and reduce greenhouse gas emissions (2009).
  9. Dees, C., Askari, M. and Henley, D., "Carcinogenic Potential of Benzene and Toluene When Evaluated Using Cyclin-dependent Kinase Activation and p53-DNA Binding," Environ. Health Persp., 104, 1289-1292(1996).
  10. Belda, R., Herraez, J. V. and Diez, O., "Rheological Study and Thermodynamic Analysis of the Binary System (water/ethanol): Influence of Concentration," Phys. Chem. Liq., 42, 467-479(2004). https://doi.org/10.1080/00319100410001700850
  11. Belda, R., Herraez, J. V. and Diez, O., "A Study of the Refractive Index and Surface Tension Synergy of the Binary Water/Ethanol: Influence of Concentration," Phys. Chem. Liq., 43, 91-101(2005). https://doi.org/10.1080/00319100512331327342
  12. Adhikhari, A. B., Rahman, I. M. M., Uddin, M. A., Hasegawa, H. and Majid, M. A., "Volumetric Behavior of the Binary Mixtures of Methyl Ethyl Ketone with n-Hexane, Cyclohexane, and Benzene at T = (303.15, 313.15, and 323.15) K," J. Chem Eng. Data, 54, 1138-1141(2009). https://doi.org/10.1021/je800883b
  13. Al-Jimaz, A. S., Al-Kandary, J. A. and Abdul-Latif, A.-H.M., "Densities and Viscosities for Binary Mixtures of Phenetole with 1-pentanol, 1-hexanol, 1-heptanol, 1-octanol, 1-nonanol, and 1-decanol at Different Temperatures," Fluid Phase Equilibri., 218, 247-260(2004). https://doi.org/10.1016/j.fluid.2003.12.007
  14. Gahlyan, S., Rani, M., Lee, I., Moon, I. and Maken, S., "Measurement and Correlation of Excess Molar Volumes for Mixtures of 1-propanol and Aromatic Hydrocarbons," Korean J. Chem. Eng., 32, 168-177(2015). https://doi.org/10.1007/s11814-014-0200-6
  15. Gahlyan, S., Rani, M. and Maken, S., "Excess Molar Volume of Binary Mixtures Containing an Oxygenate," J. Mol. Liq., 199, 42-50(2014). https://doi.org/10.1016/j.molliq.2014.08.011
  16. Gahlyan, S., Verma, S., Rani, M. and Maken, S., "Application of Flory-Treszczanowicz-Benson Model and Prigogine-Flory-Patterson Theory to Excess Molar Volumes of Isomers of Propanol with Cyclohexane or n-hexane," Korean Chem. Eng. Res., 56(2018). In press.
  17. Gahlyan, S., Rani, M., Maken, S., Kwon, H., Tak, K. and Moon, I., "Modeling of Thermodynamic Properties of An Oxygenate+aromatic Hydrocarbon: Excess Molar Enthalpy," J. Ind. Eng. Chem., 23, 299-306(2015). https://doi.org/10.1016/j.jiec.2014.08.032
  18. Gahlyan, S., Verma, S., Rani, M. and Maken, S., "Ultrasonic Speed and Isentropic Compressibility of 2-propanol with Hydrocarbons at 298.15 and 308.15 K," Korean Chem Eng. Res., 55, 668-678(2017).
  19. Gahlyan, S., Verma, S., Rani, M. and Maken, S., "Viscometric Studies of Molecular Interactions in Binary Mixtures of Forma- mide with Alkanol at 298.15 and 308.15 K," Korean Chem Eng. Res., 55, 520-529(2017).
  20. Gahlyan, S., Verma, S., Rani, M. and Maken, S., "Volumetric Stud- ies of Isomers of Propanol and Butanol with n-decane: Flory-Treszczanowicz-Benson Model and Prigogine-Flory-Patterson Theory," J. Mol. Liq., 244, 233-240(2017). https://doi.org/10.1016/j.molliq.2017.09.015
  21. Gahlyan, S., Verma, S., Rani, M. and Maken, S., "Excess Molar Enthalpy of Oxygenate+hydrocarbon Mixtures: Application of Flory-Treszczanowicz-Benson Model and Graph Theoretical Approach," J. Mol. Liq., 258, 142-146(2018). https://doi.org/10.1016/j.molliq.2018.03.003
  22. Gahlyan, S., Verma, S., Rani, M. and Maken, S., "Viscometric and FTIR Studies of Molecular Interactions in 2-propanol+hydrocarbons Mixtures at 298.15 and 308.15 K," Korean J. Chem. Eng., 35(2018).
  23. Gahlyan, S., Verma, S., Rani, M. and Maken, S., "Measurements and Modeling of Excess Molar Enthalpy of Binary Mixtures of Oxygenate and Hydrocarbons," Asian J. Chem., 30, 731-735(2018). https://doi.org/10.14233/ajchem.2018.20685
  24. Partibha, Kumar, K., Gahlyan, S., Rani, M. and Bhankar, V., "Measurement and Correlation of Thermodynamic Properties of Amine and Esters," J. Mol. Liq., 259, 167-178(2018). https://doi.org/10.1016/j.molliq.2018.03.025
  25. Rani, M., Agarwal, S., Lahot, P. and Maken, S., "Excess Molar Enthalpies of Binary Mixtures of Formamide with Butanol at 298.15 K: Application of Prigogine-Flory-Patterson Theory and Treszczanowicz-Benson Association Model," J. Ind. Eng. Chem., 19, 1715-1721(2013). https://doi.org/10.1016/j.jiec.2013.02.011
  26. Rani, M., Gahlyan, S., Gaur, A. and Maken, S., "Ultrasonic Study on Molecular Interactions in Binary Mixtures of Formamide with 1-propanol or 2-propanol," Chinese J. Chem Eng., 23, 689-698 (2015). https://doi.org/10.1016/j.cjche.2014.12.003
  27. Kashyap, P., Rani, M., Gahlyan, S., Tiwari, D. P. and Maken, S., "Volumetric, Acoustic and Optical Properties of Binary Mixtures of 2-propanol with n-alkanes (C6-C10) from 293.15 K to 303.15 K," J. Mol. Liq., 268, 304-314(2018).
  28. Rani, M. and Maken, S., "Topological Studies of Molecular Interactions of Formamide with Propanol and Butanol at 298.15 K," J. Ind. Eng. Chem., 18, 1694-1704(2012). https://doi.org/10.1016/j.jiec.2012.03.011
  29. Gahlyan, S., Rani, M. and Maken, S., "Ultrasonic Speeds, Viscosities, Refractive Indices and FT-IR Spectroscopic Studies of an Oxygenate with Aliphatic and Aromatic Hydrocarbons at 298.15 K and 308.15 K," J. Mol. Liq., 219, 1107-1123(2016). https://doi.org/10.1016/j.molliq.2016.04.011
  30. Rani, M., Gahlyan, S., Om, H., Verma, N. and Maken, S., "Ultrasonic Studies of Molecular Interactions in Binary Mixtures of Formamide with Some Isomers of Butanol at 298.15 K and 308.15 K," J. Mol. Liq., 194, 100-109(2014). https://doi.org/10.1016/j.molliq.2014.01.016
  31. Gahlyan, S., Verma, S., Rani, M. and Maken, S., "Transport Properties and Modeling of Viscosity for Binary Mixtures of Butanol Isomers + Hydrocarbons," Arab. J. Sci.CI Eng., https://doi.org/10.1007/s13369-018-3276-1R.
  32. Schaaffs, W., Molekularakustik, Springer-Verlag, 1963.
  33. Schaaffs, W., "Das Problem Der Theoretischen Bereehnung Der Schallgeschwindigkeit in Binaren Flussigkeitsmischungen," Acustica, 33, 272-276(1975).
  34. Jacobson, B., "Association Numbers in Liquid Systems from Intermolecular Free Length Relationships," Acta. Chem. Scand., 9, 997-1008(1955). https://doi.org/10.3891/acta.chem.scand.09-0997
  35. Jacobson, B., "Ultrasonic Velocity in Liquids and Liquid Mixtures," J. Chem. Phys., 20, 927-928(1952).
  36. Jacobson, B., "Intermolecular Free Lengths in the Liquid State. I. Adiabaic and Isothermal Compressibilities," Acta. Chem. Scand., 6, 1485-1498(1952). https://doi.org/10.3891/acta.chem.scand.06-1485
  37. Riddick, J. A., Bunger, W. B. and Sakano, T. K., "Organic Solvents. Physical Properties and Methods of Purification," 4th ed., Wiley, New York(1986).
  38. Vogel, A. I., "A Text Book of Practical Organic Chemistry, 4th ed.," ELBS Longman, London(1978).
  39. Barta, L., Kooner, Z. S., Hepler, L. G., Roux-Desgranges, G. and Grolier, J. P. E., "Thermodynamics of Complex Formation in Chloroform + 1,4-dioxane," Can. J. Chem., 67, 1225-1229(1989). https://doi.org/10.1139/v89-185
  40. de Cominges, B. E., Pineiro, M. M., Mosteiro, E., Mascato, E., Mato, M. M., Iglesias, T. P. and Legido, J. L., "'Temperature Depen- dence of Thermophysical Properties of Octane+1-butanol System," J. Therm. Anal. Calorim., 70, 217-227(2002). https://doi.org/10.1023/A:1020626205538
  41. Nain, A. K., Srivastava, T., Pandey, J. D. and Gopal, S., "Densities, Ultrasonic Speeds and Excess Properties of Binary Mixtures of Methyl Acrylate with 1-butanol, or 2-butanol, or 2-methyl-1-propanol, or 2-methyl-2-propanol at Temperatures from 288.15 to 318.15K," J. Mol. Liq., 149, 9-17(2009). https://doi.org/10.1016/j.molliq.2009.07.005
  42. Troncoso, J., Tovar, C. A., Cerdeirina, C. A., Carballo, E. and Romani, L., "'Temperature Dependence of Densities and Speeds of Sound of Nitromethane + Butanol Isomers in the Range (288.15−308.15) K," J. Chem.& Eng. Data, 46, 312-316(2001). https://doi.org/10.1021/je0002641
  43. Chandra Sekhar, M., Madhu Mohan, T., Vijaya Krishna, T., Venkatesulu, A. and Siva Kumar, K., "Density, Refractive Index, Speed of Sound and Computational Studies of Intermolecular Interactions in Binary Mixtures of 2-Chloroaniline with Butanols (1-Buta- nol, 2-Butanol) at T = (303.15-318.15) K," J. Sol.Chem, 44, 237-263(2015). https://doi.org/10.1007/s10953-015-0306-4
  44. Sastry, N. V. and Patel, S. R., " Excess Volumes and Dielectric Properties for (methyl methacrylate + a branched alcohol) at T= 298.15 K and T = 308.15 K," J. Chem. Thermodyn., 32, 1669-1682(2000). https://doi.org/10.1006/jcht.2000.0707
  45. Kijevcanin, M. L., Radovic, I. R., Djordjevic, B. D., Tasic, A. Z. and Serbanovic, S. P., "Experimental Determination and Modeling of Densities and Refractive Indices of the Binary Systems Alcohol+dicyclohexylamine at T = (288.15-323.15)K," Thermochim Acta, 525, 114-128(2011). https://doi.org/10.1016/j.tca.2011.08.002
  46. Ghanadzadeh Gilani, A., Paktinat, N. and Moghadam, P. M., "'Relative Permittivity Data of Binary Mixtures Containing 2-butanol, 2-butanone, and cyclohexane," J. Chem. Thermodyn., 43, 569-575(2011). https://doi.org/10.1016/j.jct.2010.11.009
  47. George, J. and Sastry, N. V., "Densities, Excess Molar Volumes, Viscosities, Speeds of Sound, Excess Isentropic Compressibilities, and Relative Permittivities for $C_mH_{2m}+1(OCH_2CH_2)_nOH$ (m = 1 or 2 or 4 and n = 1) + benzene, + toluene, + (o-, m-, and p-) xylenes, + ethylbenzene, and + cyclohexane," J. Chem. Eng. Data, 48, 977-989(2003). https://doi.org/10.1021/je034005y
  48. Nayak, J. N., Aralaguppi, M. I. and Aminabhavi, T. M., "Density, Viscosity, Refractive Index, and Speed of Sound in the Binary Mixtures of Ethyl Chloroacetate with Aromatic Liquids at 298.15, 303.15, and 308.15 K," J. Chem. Eng. Data, 47, 964-969(2002). https://doi.org/10.1021/je0200158
  49. Sastry, N. V., Patel, M. C. and Patel, S. R., "Ultrasonic Behaviour of Methyl Methacrylate+hydrocarbon Mixtures at 298.15 and 308.15 K," Fluid Phase Equilib, 155, 261-276(1999). https://doi.org/10.1016/S0378-3812(98)00470-1
  50. Nayak, J. N., Aralaguppi, M. I. and Aminabhavi, T. M., "Density, Viscosity, Refractive Index, and Speed of Sound for the Binary Mixtures of Ethyl Chloroacetate with n-alkanes (C6 to C12) at (298.15, 303.15, and 308.15) K," J. Chem.Eng. Data, 46, 891-896(2001). https://doi.org/10.1021/je010020w
  51. Kiyohara, O. and Benson, G. C., "Ultrasonic Speeds and Isentropic Compressibilities of n-alkanol + n-heptane Mixtures at 298.15 K," J. ChemThermodyn., 11, 861-873(1979).
  52. Troncoso, J., Carballo, E., Cerdeirina, C. A., Gonzalez, D. and Romani, L., "Systematic Determination of Densities and Speeds of Sound of Nitroethane + isomers of Butanol in the Range (283.15−308.15) K," J. Chem. Eng. Data, 45, 594-599(2000). https://doi.org/10.1021/je990325z
  53. Sharma, V. K., Dua, R., Dimple and Jangra, S. K., "Heat Capacities of Binary and Ternary Mixtures Containing o-chlorotoluene, Cyclic Ether and Aromatic Hydrocarbons," Fluid Phase Equilib., 378, 83-92(2014). https://doi.org/10.1016/j.fluid.2014.06.024
  54. Troncoso, J. and Valencia, J. L., Souto-Caride, M., Gonzalez-Salgado, D. and Peleteiro, J., "Thermodynamic Properties of Dodecane + 1-butanol and + 2-butanol Systems," J. Chem Eng. Data, 49, 1789-1793(2004). https://doi.org/10.1021/je0497810
  55. Paramo, R., Zouine, M. and Casanova, C., "New Batch Cells Adapted to Measure Saturated Heat Capacities of Liquids," J. Chem. Eng. Data, 47, 441-448(2002). https://doi.org/10.1021/je0155103
  56. Oswal, S. L., Prajapati, K. D., Oswal, P., Ghael, N. Y. and Ijardar, S.P., "Viscosity of Binary Mixtures of 1-alkanol+cyclohexane, 2-alkanol+cyclohexane and 1-alkanol + methylcyclohexane at 303.15 K," J. Mol. Liq., 116, 73-82(2005). https://doi.org/10.1016/j.molliq.2004.05.004
  57. Bhardwaj, U., Maken, S. and Singh, K. C., "MExcess Volumes of 1-butanol, 2-butanol, 2-methylpropan-1-ol, and 2-methylpro- pan-2-ol with Xylenes at 308.15 K," J. Chem. Eng. Data, 41, 1043-1045 (1996). https://doi.org/10.1021/je960070e
  58. Bhardwaj, U., Maken, S. and Singh, K. C., "Molar Excess Enthal- pies and Molar Excess Volumes of all Isomers of Butanol with Cyclohexane at 308.15 K in terms of an Associated Model with a Flory Contribution Term," Indian J. Chem., 37A, 316-322(1998).
  59. Bhardwaj, U., Maken, S. and Singh, K. C., "Excess Molar Volumes of (an isomer of butanol+ benzene or toluene) at the Temperature 308.15 K," J. Chem. Thermodyn., 28, 1173-1177(1996). https://doi.org/10.1006/jcht.1996.0103