Thermodynamic properties and ideal-gas enthalpies of formation for dicyclohexyl sulfide, diethylenetriamine, di-n-octyl sulfide, dimethyl carbonate, piperazine, hexachloroprop-1-ene, tetrakis(dimethylamino)ethylene, N,N′-bis-(2-hydroxyethyl)ethylenediamine, and 1,2,4-triazolo[1,5-α]pyrimidine

Journal of Chemical and Engineering Data

Volumn 42, Issue 6, 1997, Pages 1037-1052

  Steele, W V ^a,b   Chirico, R D ^a,b   Knipmeyer, S E ^a,b   Nguyen, A ^a,b   Smith, N K ^a,b  

^a IIT RESEARCH INSTITUTE   (United States)

^b NORTHROP GRUMMAN MISSION SYSTEMS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CHLORINE COMPOUNDS; DENSITY MEASUREMENT (SPECIFIC GRAVITY); DIFFERENTIAL SCANNING CALORIMETRY; ENTHALPY; PRESSURE MEASUREMENT; SATURATION (MATERIALS COMPOSITION); SPECIFIC HEAT OF LIQUIDS; SULFUR COMPOUNDS; THERMAL VARIABLES MEASUREMENT; VAPOR PRESSURE;

DICYCLOHEXYL SULFIDE; DIETHYLENETRIAMINE; DIMETHYL CARBONATE; DIMETHYLAMINOETHYLENE; DIOCTYL SULFIDE; GROUP CONTRIBUTION METHODOLOGY; HEXACHLOROPROPENE; HYDROXYETHYLETHYLENEDIAMINE; PIPERAZINE; PYRIMIDINE;

ORGANIC COMPOUNDS;

EID: 0031276442     PISSN: 00219568     EISSN: None     Source Type: Journal    
DOI: 10.1021/je9700986     Document Type: Article

References (65)

1. Ambrose, D.; Walton, J. Vapor Pressures up to Their Critical Temperatures of Normal Alkanes and 1-Alkanols. Pure Appl. Chem. 1989, 61, 1395-1403.
2. Anderson, D. F. Gas Scintillation Proportionality Counters. IEEE Trans. Nucl. Sci. 1981, NS-28.
3. Anderson, D. F. Measurement of TMAE and TEA Vapor Pressures. Nucl. Instrum. Methods Phys. Res. 1988, A270, 416-418.
4. Bedford, A. F.; Beezer, A. E.; Mortimer, C. T. Heat of Formation and Bond Energies. X. 1,2,5,6-Tetrahydropyridine, Piperidine, and Piperazine. J. Chem. Soc. 1963, 2039-2043.
5. Benson, S. W. Thermochemical Kinetics, 2nd ed.; Wiley: New York, 1976.
6. Bobylev, V. A.; Kamakaya, O. I.; Kossoi, A. A.; Koludarova, E. Yu. Heat Capacity of Ethylene Amines by Differential Scanning Calorimetry. Zh. Obshch. Khim. 1988, 58, 2536-2538.
7. Chirico, R. D.; Steele, W. V. Reconciliation Of Calorimetrically And Spectroscopically Derived Thermodynamic Properties at Pressures Greater Than 0.1 MPa for Benzene and Methylbenzene: The Importance of the Third Virial Coefficient. Ind. Eng. Chem. Res. 1994, 33, 157-167.
8. Chirico, R. D.; Knipmeyer, S. E.; Nguyen, A.; Steele, W. V. The Thermodynamic Properties of Dibenzothiophene. J. Chem. Thermodyn. 1991, 23, 431-450.
9. Chirico, R. D.; Knipmeyer, S. E.; Nguyen, A.; Smith, N. K.; Steele, W. V. The Thermodynamic Properties of 4,5,9,10-Tetrahydropyrene and 1,2,3,6,7,8-Hexahydropyrene J. Chem. Thermodyn. 1993, 25, 729-761.
10. Cohen, E. R.; Taylor, B. N. The 1986 CODATA Recommended Values of the Fundamental Physical Constants. J. Phys. Chem. Ref. Data 1988, 17, 1795-1803.
11. Cox, J. D., Wagman, D. D., Medvedev, V. A., Eds.; CODATA Key Values for Thermodynamics; Hemisphere: New York, 1989.
12. Cross, J. D.; Hunter, R.; Stemson, V. R. The Thermal Decomposition of Simple Carbonate Esters. Aust. J. Chem. 1976, 29, 1477-1481.
13. Daubert, T. E.; Hutchison, G. Vapor Pressure of 18 Pure Industrial Chemicals. In Results from the Design Institute for Physical Property Data: Experimental Results and Data Compilation Procedures; Cunningham, J. R., Jones, D. K. Eds.; AIChE Symposium Series 279; AIChE: New York, 1990; pp 93-114.
14. Daubert, T. E.; Danner, R. P. Physical and Thermodynamic Properties of Pure Chemicals: Data Compilation; DIPPR Project 801; Hemisphere: New York, 1993.
15. Domalski, E. S.; Hearing, E. D. Heat Capacities and Entropies of Organic Compounds in the Condensed Phase, Volume II. J. Phys. Chem. Ref. Data 1990, 19, 881-1048.
16. Dreisbach, R. R. Physical Properties of Chemical Compounds II; ACS Advances in Chemistry Series 22. American Chemical Society: Washington, DC, March 1959.
17. Goldberg, R. N.; Weir, R. D. Conversion of Temperatures and Thermodynamic Properties to the Basis of the International Temperature Scale of 1990. Pure Appl. Chem. 1990, 64, 1545-1562.
18. Good, W. D. The Enthalpies of Combustion and Formation of 11 Isomeric Nonanes. J. Chem. Eng. Data 1969, 14, 231-235.
19. Good, W. D. The Enthalpies of Combustion of Nine Organic Nitrogen Compounds Related to Petroleum. J. Chem. Eng. Data 1972, 17, 231.
20. Good, W. D.; Smith, N. K. The Enthalpies of Combustion of Toluene, Benzene, Cyclohexane, Cyclohexene, Methylcyclopentane, 1-Methylcyclopentene, and n-Hexane. J. Chem. Eng. Data 1969, 14, 10106.
21. Good, W. D.; Moore, R. T. The Enthalpies of Formation of Ethylenediamine, 1,2-Propanediamine, 1,2-Butanediamine, 2-Methyl-1,2-propanediamine, and Isobutylamine. J. Chem. Eng. Data 1970, 15, 150-154.
22. Good, W. D.; Scott, D. W.; Waddington, G. Combustion Calorimetry of Organic Fluorine Compounds by a Rotating-Bomb Methodol. J. Phys. Chem. 1956, 60, 1080-1089.
23. Good, W. D.; Douslin, D. R.; Scott, D. W.; George, A.; Lacina, J. L.; Dawson, J. P.; Waddington, G. Thermochemistry and Vapor Pressure of Aliphatic Fluorocarbons. A Comparison of the C-F and C-H Thermochemical Bond Energies. J. Phys. Chem. 1959, 63, 1133-1138.
24. Guthrie, G. B.; Scott, D. W.; Hubbard, W. N.; Katz, C.; McCullough, J. P.; Gross, M. E.; Williamson, K. D.; Waddington, G. Thermodynamic Properties of Furan. J. Am. Chem. Soc. 1952, 74, 4662-4669.
25. Hales, J. L.; Townsend, R. Liquid Densities from 293 to 490 K of Nine Aromatic Hydrocarbons. J. Chem. Thermodyn. 1972, 4, 763-772.
26. Harrer, T. S. Sulfuric Acid and Sulfur Trioxide. In Kirk-Othmer Encyclopedia of Chemical Technology, 2nd ed.; Wiley: New York, 1969; Vol. 19, pp 441-482.
27. Holroyd, R. A.; Presses, J. M.; Woody, C. L. Measurement of the Absorption Length and Absolute Quantum Efficiency of Tetrakis(dimethylamino)ethylene from Threshold to 120 nm. Nucl. Instrum. Methods Phys. Res. 1987, A261, 440-444.
28. Hu, A. T.; Sinke, G. C. Combustion Calorimetry of Some Chlorinated Organic Compounds. J. Chem. Thermodyn. 1969, 1, 507-513.
29. Hu, A. T.; Sinke, G. C.; Mintz, M. J. The Enthalpy of Formation of 1,1,1-Trichloroethane from Enthalpy of Combustion and Equilibrium Studies. J. Chem. Thermodyn. 1972, 4, 239-245.
30. Hu, A. T.; Sinke, G. C.; Mansson, M.; Ringner, B. Test Substances for Bomb Combustion Calorimetry. p-Chlorobenzoic Acid. J. Chem. Thermodyn. 1974, 4, 283-299.
31. Hubbard, W. N.; Scott, D. W.; Waddington, G. Reduction to Standard States (at 25°C) of Bomb Calorimetric Data for Compounds of Carbon, Hydrogen, Oxygen and Sulfur J. Phys. Chem. 1954, 58, 152-162.
32. Hubbard, W. N.; Scott, D. W.; Waddington, G. Standard States and Corrections for Combustions in a Bomb at Constant Volume. In Experimental Thermochemistry. Rossini, F. D., Ed.; Interscience: New York, 1956; Chapter 5, pp 75-128.
33. IUPAC Commission on Atomic Weights and Isotopic Abundances. Atomic Weights of the Elements 1991. J. Phys. Chem. Ref. Data 1993, 22, 1571-1584.
34. Jiang, B.; Zhang, J. Determination and Correlation of Vapor Pressures of Dimethyl Carbonate and 2,3-Dichloropropene. Tianjin Daxue Xuebao (Journal of Tianjin University) 1987, 1, 54-62.
35. Kogerman, P. N.; Kranig, J. Physical Constants of Some Alkyl Carbonates. Acta Commentat. Univ. Tartu. (Dorpate.) 1927, 12 (7), 3-11.
36. Mangum, B. W.; Furukawa, G. T. Guidelines for Realizing the International Temperature Scale of 1990 (ITS-90). NIST Technical Note 1265; National Institute of Standards and Technology: Gaithersburg, MD, 1990.
37. c, and ω as Parameters. AIChE J. 1983, 29, 107-113.
38. Pedley, J. B., Naylor, R. D.; Kirby, S. P. Thermochemical Data of Organic Compounds, 2nd ed.; Chapman Hall: New York, 1986.
39. Pitzer, K. S.; Curl, R. F., Jr. The Volumetric and Thermodynamic Properties of Fluids. III. Empirical Equation for the Second Virial Coefficient. J. Am. Chem. Soc. 1957, 79, 2369-2370.
40. Reid, R. C., Prausnitz, J. M.; Poling, B. E. The Properties of Gases and Liquids, 4th ed.; McGraw-Hill: New York, 1987.
41. Riedel, L. Liquid Density in the Saturated State. Extension of the Theorem of Corresponding States II. Chem.-Ing.-Tech. 1954, 26, 259-264.
42. Rossini, F. D. Assignment of Uncertainties to Thermochemical Data. In Experimental Thermochemistry; Rossini, F. D., Ed.; Interscience: New York, 1956; Chapter 14, pp 297-320.
43. Scott, D. W., Finke, H. L.; Gross, M. E.; Guthrie, G. B.; Huffman, H. M. 2,3-Dithiabutane: Low Temperature Heat Capacity, Heat of Fusion, Heat of Vaporization, Vapor Pressure, Entropy, and Thermodynamic Functions J. Am. Chem. Soc. 1950, 72, 2424-2430.
44. Sivokova, M.; Matejicek, A.; Juracka, F. Vapor Pressures of Ethylenediamine, Diethylenetriamine, and Triethylenetetramine. Chem. Prum. 1967, 17, 213-214.
45. Smith, N. K.; Scott, D. W.; McCullough, J. P. Combustion Calorimetry of Organic Chlorine Compounds. The Heat of Combustion of 2,3,5,6-Tetrachloro-p-xylene. J. Phys. Chem. 1964, 68, 934-939.
46. Steele, W. V. Fifty Years of Thermodynamics Research at Bartlesville. The Hugh M. Huffman Legacy. J. Chem. Thermodyn. 1995, 27, 135-162.
47. Steele, W. V. Unpublished results, 1996.
48. Steele, W. V.; Archer, D. G.; Chirico, R. D.; Collier, W. B.; Hossenlopp, I. A.; Nguyen, A.; Smith, N. K.; Gammon, B. E. The Thermodynamic Properties of Quinoline and Isoquinoline. J. Chem. Thermodyn. 1988, 20, 1233-1264.
49. Steele, W. V.; Chirico, R. D.; Knipmeyer, S. E.; Nguyen, A. The Thermodynamic Properties of 2-Aminobiphenyl. J. Chem. Thermodyn. 1991a, 23, 957-977.
50. Steele, W. V.; Chirico, R. D.; Nguyen, A.; Hossenlopp, I. A.; Smith, N. K. DIPPR Project 871. Determination of Ideal-Gas Enthalpies of Formation for Key Compounds The 1989 Project Results. In Experimental Results for Phase Equilibria and Pure Component Properties; DIPPR Data Series 1; Cunningham, J. R., Jones, D. K., Eds.; AIChE: New York, 1991b; pp 101-134.
51. Steele, W. V.; Chirico, R. D.; Knipmeyer, S. E.; Nguyen, A. Vapor Pressure of Acetophenone, (±)-1,2-Butanediol, (±)-1,3-Butanediol, Diethylene Glycol Monopropyl Ether, 1,3-Dimethyladamantane, 2-Ethoxyethyl Acetate, Ethyl Octyl Sulfide, and Pentyl Acetate. J. Chem. Eng. Data 1996a, 41, 1255-1268.
52. Steele, W. V.; Chirico, R. D.; Knipmeyer, S. E.; Nguyen, A.; Smith, N. K.; Tasker, I. R. Thermodynamic Properties and Ideal-Gas Enthalpies of Formation for Cyclohexene, Phthalan (2,5-Dihydrobenzo-3,4-furan), Isoxazole, Octylamine, Dioctylamine, Trioctylamine, Phenyl Isocyanate, and 1,4,5,6-Tetrahydropyrimidine. J. Chem. Eng. Data 1996b, 41, 1269-1284.
53. Steele, W. V.; Chirico, R. D.; Knipmeyer, S. E.; Nguyen, A.; Smith, N. K. Thermodynamic Properties and Ideal-Gas Enthalpies of Formation for Butyl Vinyl Ether, 1,2-Dimethoxyethane, Methyl Glycolate, Bicyclo[2.2.1]hept-2-ene, 5-Vinylbicyclo[2.2.1]-hept-2-ene, trans-Azobenzene, Butyl Acrylate, Di-tert-butyl Ether, and Hexane-1,6-diol. J. Chem. Eng. Data 1996c, 41, 1285-1302.
54. Thiebaut, J.-M.; Rivail, J.-L.; Greffe, J.-L. Dielectric Studies of Non Electrolyte Solutions. Part 3. Conformational Equilibria in 1,2-Dichloroethane and Dimethyl Carbonate. J. Chem. Soc., Faraday Trans. 2 1976, 72, 2024-2034.
55. Tutubalina, V. P.; Gabdrakhmanov, F. G.; Konyukhova, T. M. Study of Heat Capacity of n-Sulfides. Teplo-Massoobmen Khim. Tekhnol. 1982, 27-28.
56. Vogel, A. I. XXIII Miscellaneous Compounds. Investigations of the So-Called Coordinate or Dative Link in Esters of Oxy Acids and in Nitro Paraffins by Molecular Refractivity Determinations. Atomic, Structural, and Group Parachors and Refractivities. J. Chem. Soc. 1948, 1833-1855.
57. Waddington, G.; Sunner , S.; Hubbard, W. N. Combustion on a Bomb of Organic Sulfur Compounds. In Experimental Thermochemistry; Rossini, F. D., Ed.; Interscience: New York, 1956; Chapter 7, pp 149-179.
58. Wagman, D. D.; Evans, W. H.; Parker, V. B.; Schumm, R. H.; Halow, I.; Bailey, S. M.; Churney, K. L.; Nuttall, R. L. The NBS Tables of Chemical Thermodynamics. J. Phys. Chem. Ref. Data 1982, 11 (Suppl. 2).
59. Wagner, W. New Vapor Pressure Measurements for Argon and Nitrogen and a New Method for Establishing Rational Vapor Pressure Equations. Cryogenics 1973, 13, 470-482.
60. Walton. J. Vapor Pressure and Critical Points of Liquids XII: Aromatic Nitrogen Compounds; Engineering Science Data Item Number 78011; Institute Chemical Engineers: London, March 1978.
61. Waring, W. Form of a Wide-Range Vapor Pressure Equation. Ind. Eng. Chem. 1954, 46, 762-763.
62. Wilson, A. L. New Aliphatic Amines. Ind. Eng. Chem. 1935, 27, 867-871.
63. Witschonke, C. R. Freezing Point and Purity Data for Some Organic Compounds. Anal. Chem. 1954, 26, 562-564.
64. Wright, F. J. Latent Heat of Vaporization and Composition. Recl. Trav. Chim. Pays-Bas 1960, 79, 784-789.
65. Yaws, C. L.; Ni, H. M.; Chiang, P. Y. Heat Capacity for 700 Chemicals. Chem. Eng. (N. Y.) 1988, 95 (7), 91-98.