Thermodynamics of ionic liquid precursors. 1-bromobutane and its isomers

Journal of Chemical and Engineering Data

Volumn 56, Issue 12, 2011, Pages 4891-4899

  Paulechka, Yauheni U ^a   Kabo, Gennady J ^a   Blokhin, Andrey V ^a   Firaha, Dzmitry S ^a  

^a BELARUSIAN STATE UNIVERSITY   (Belarus)

Author keywords

[No Author keywords available]

Indexed keywords

1-BUTYL-3-METHYLIMIDAZOLIUM BROMIDE; 1-METHYLIMIDAZOLE; ADIABATIC CALORIMETRY; BROMOALKANES; ENTHALPIES OF FORMATION; ENTHALPY CHANGE; EXPERIMENTAL DATA; GASPHASE; LIQUID PHASE; LIQUID PRECURSORS; LIQUID STATE; LIQUID-PHASE REACTION; LITERATURE DATA; NEGATIVE ENTROPIES; QUANTUM-CHEMICAL CALCULATION; RECOMMENDED VALUES; SPECTROSCOPIC DATA; TEMPERATURE RANGE; THERMODYNAMIC FUNCTIONS;

BROMINE COMPOUNDS; ENTHALPY; ENTROPY; ISOMERS; QUANTUM CHEMISTRY; QUANTUM THEORY; STATISTICAL MECHANICS; SYNTHESIS (CHEMICAL); THERMODYNAMICS;

IONIC LIQUIDS;

EID: 83455260266     PISSN: 00219568     EISSN: 15205134     Source Type: Journal    
DOI: 10.1021/je200814m     Document Type: Article

References (42)

1. Wasserscheid, P.; Welton, T. Ionic Liquids in Synthesis; Wiley-VCH Verlag, GmbH&Co. KGaA: Weinheim, 2008.
2. Paulechka, Y. U.; Kabo, G. J.; Blokhin, A. V.; Shaplov, A. S.; Lozinskaya, E. I.; Vygodskii, Ya. S. Thermodynamic properties of 1-alkyl-3-methylimidazolium bromide ionic liquids J. Chem. Thermodyn. 2007, 39, 158-166
3. Verevkin, S. P.; Zaitsau, Dz. H.; Emel'yanenko, V. N.; Paulechka, Y. U.; Blokhin, A. V.; Bazyleva, A. B.; Kabo, G. J. Thermodynamics of Ionic Liquids Precursors: 1-Methylimidazole J. Phys. Chem. B 2011, 115, 4404-4411
4. Paulechka, Y. U.; Kabo, A. G.; Blokhin, A. V. Calorimetric Determination of the Enthalpy of 1-Butyl-3-methylimidazolium Bromide Synthesis: A Key Quantity in Thermodynamics of Ionic Liquids J. Phys. Chem. B 2009, 113, 14742-14746
5. Shehatta, I. Heat capacity at constant pressure of some halogen compounds Thermochim. Acta 1993, 213, 1-10
6. Chorazewski, M.; Goralski, P.; Tkaczyk, M. Heat Capacities of 1-Chloroalkanes and 1-Bromoalkanes within the Temperature Range from 284.15 K to 353.15 K. A Group Additivity and Molecular Connectivity Analysis J. Chem. Eng. Data 2005, 50, 619-624
7. Kurbatov, V. Ya. Heat capacities of liquids. Heat capacity and temperature dependence of heat capacity for haloderivatives of acyclic hydrocarbons Zh. Obshch. Khim. 1948, 18, 372-389
8. Deese, R. F., Jr. Thermal Energy Studies. IV. Comparison of Continuous and Discontinuous Methods of Measuring Heat Capacities. Heat Capacities of Some Aliphatic Bromides J. Am. Chem. Soc. 1931, 53, 3673-3683
9. Tschamler, H.; Richter, E.; Wettig, F. Über die Mischbarkeit von Chlorex (β,β′-Dichlordiäthyläther) mit Halogenkohlenwasserstoffen Monatsh. Chem. 1949, 80, 856-863
10. Timmermans, J. Recherches sur la Tháorie des Solutions concentrées.-XII. Application de l'analyse thermique á la determination de la chaleur de fusion de quelques composes organiques Bull. Soc. Chim. Belg. 1934, 43, 626-638
11. Wadsö, I. Heats of Vaporization for a Number of Organic Compounds at 25 °C Acta Chem. Scand. 1966, 20, 544-552
12. Wadsö, I. Heats of Vaporization of Organic Compounds. II. Chlorides, Bromides, and Iodides Acta Chem. Scand. 1968, 22, 2438-2444
13. Chickos, J. S.; Hosseini, S.; Hesse, D. G. Determination of vaporization enthalpies of simple organic molecules by correlations of changes in gas chromatographic net retention times Thermochim. Acta 1995, 249, 41-62
14. Svoboda, V.; Majer, V.; Vesely, F.; Pick, J. Heats of vaporization of alkyl bromides Collect. Czech. Chem. Commun. 1977, 42, 1755-60
15. Garriga, R.; Martínez, S.; Pérez, P.; Gracia, M. Vapor Pressures at Several Temperatures between 278.15 and 323.15 K and Excess Functions at T = 298.15 K for 1-Bromobutane with 1-Butanol or 2-Methyl-2-propanol J. Chem. Eng. Data 2002, 47, 322-328
16. Milazzo, G. Messung kleiner Dampfdrucke Chem. Ing. Tech. 1956, 28, 646-654
17. 2] in the Condensed State J. Chem. Eng. Data 2006, 51, 1377-1388
18. Hoge, H. J. Heat capacity of a two-phase system, with applications to vapor corrections in calorimetry J. Res. Natl. Bur. Stand. 1946, 36, 111-118
19. Cibulka, I.; Takagi, T.; Růžička, K. P -ρ- T Data of Liquids: Summarization and Evaluation. 7. Selected Halogenated Hydrocarbons J. Chem. Eng. Data 2001, 46, 2-28
20. Granovsky, A. A. Firefly, version 7.1.G; MSU: Moscow, 2010.
21. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S.; Windus, T. L.; Dupuis, M.; Montgomery, J. A. General atomic and molecular electronic structure system J. Comput. Chem. 1993, 14, 1347-1363
22. McQuarrie, D. A. Statistical Mechanics; Harper & Row: New York, 1976.
23. Kabo, G. J.; Roganov, G. N.; Frenkel, M. L. Thermodynamics and Equilibria of Isomers (in Russian); Universitetskoye Publ.: Minsk, 1986.
24. Pitzer, K. S. Energy Levels and Thermodynamic Functions for Molecules with Internal Rotation: II. Unsymmetrical Tops Attached to a Rigid Frame J. Chem. Phys. 1946, 14, 239-243
25. Aarset, K.; Hagen, K.; Stølevik, R.; Sæbø, P. C. Molecular Structure and Conformational Composition of 1-Chlorobutane, 1-Bromobutane, and 1-Iodobutane as Determined by Gas-Phase Electron Diffraction and ab Initio Calculations Struct. Chem. 1995, 6, 197-205
26. Ogawa, Y.; Imazeki, S.; Yamaguchi, H.; Matsuura, H.; Harada, I.; Shimanouchi, T. Vibration Spectra and Rotational Isomerism of Chain Molecules. VII. 1-Chloro-, 1-Bromo-, and 1-Iodopropanes, and 1-Chloro-, 1-Bromo-, and 1-Iodobutanes Bull. Chem. Soc. Jpn. 1978, 51, 748-767
27. Durig, J. R.; Zhu, X.; Shen, S. Conformational and structural studies of 1-chloropropane and 1-bromopropane from temperature-dependant FT-IR spectra of rare gas solutions and ab initio calculations J. Mol. Struct. 2001, 570, 1-23
28. Bjellerup, L. Heats of Combustion and Formation of the 1-Bromoalkanes from C4 through C8 Acta Chem. Scand. 1961, 15, 231-241
29. Cox, J. D.; Pilcher, G. Thermochemistry of Organic and Organometallic Compounds; Academic Press: London, 1970.
30. Holm, T. Thermochemistry of grignard reagents. Enthalpies of formation of alkylmagnesium bromides and of alkyl bromides J. Organomet. Chem. 1973, 56, 87-93
31. Holm, T. Thermochemical Bond Dissociation Energies of Carbon-Magnesium Bonds J. Chem. Soc., Perkin Trans. II 1981, 464-467
32. Smyth, C. P.; Engel, E. W. Molecular Orientation and the Partial Vapor Pressures of Binary Mixtures. I. Systems Composed of Normal Liquids J. Am. Chem. Soc. 1929, 51, 2646-2660
33. Bjellerup, L. On the Accuracy of Heat of Combustion Data Obtained with a Precision Moving-Bomb Calorimetric Method for Organic Bromine Compounds Acta Chem. Scand. 1961, 15, 121-140
34. Lacher, J. R.; Billings, T. J.; Campion, D. E.; Lea, K. R.; Park, J. D. Vapor Phase Heats of Hydrobromination of the Isomeric Butenes J. Am. Chem. Soc. 1952, 74, 5291-5292
35. Bryce-Smyth, D.; Howlett, K. E. The Preparation and Properties of tert -Butyl Bromide J. Chem. Soc. 1951, 1141-1142
36. Howlett, K. E. The Use of Equilibrium Constants to calculate Thermodynamic Quantities. Part III. Equilibria in the System tert -Butyl Bromide-iso Butene-Hydrogen Bromide J. Chem. Soc. 1957, 2834-2836
37. Kistiakowsky, G. B.; Stauffer, C. H. The Kinetics of Gaseous Addition of Halogen Acids to Isobutene J. Am. Chem. Soc. 1937, 59, 165-170
38. Clarke, E. C. W.; Glew, D. N. Evaluation of thermodynamic functions from equilibrium constants Trans. Faraday Soc. 1966, 62, 539-547
39. Pedley, J. B. Thermochemical data and structures of organic compounds; CRC Press: Boca Raton, FL, 1994.
40. Frenkel, M.; Chirico, R. D.; Diky, V.; Muzny, C. D.; Kazakov, A. F.; Lemmon, E. W. NIST ThermoData Engine 103b - Pure Compounds and Binary Mixtures Version, 3.0 NIST, Standard Reference Database 103b, Boulder, Colorado, 2009,: http://www.nist.gov/srd/nist103b.htm.
41. Chase, M. W., Jr. NIST-JANAF Thermochemical Tables, 4 th ed. J. Phys. Chem. Ref. Data, Monograph 9, 1998.
42. Nesterova, T. N.; Rozhnov, A. M. Izv. Vuzov. Khim. Khim. Tekhnol. 1974, 17, 556-558