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

Journal of Chemical and Engineering Data

Volumn 41, Issue 6, 1996, Pages 1269-1284

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

^a IIT RESEARCH INSTITUTE   (United States)

^b BDM Oklahoma Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; COMBUSTION; DENSITY MEASUREMENT (SPECIFIC GRAVITY); DIFFERENTIAL SCANNING CALORIMETRY; ENTHALPY; PRESSURE MEASUREMENT; SPECIFIC HEAT; TEMPERATURE MEASUREMENT; THERMAL EFFECTS; VAPOR PRESSURE;

CYCLOHEXENE; FURAN; IDEAL GAS ENTHALPY; ISOXAZOLE; PHENYL ISOCYANATE; TETRAHYDROPYRIMIDINE;

ORGANIC COMPOUNDS;

EID: 0030282108     PISSN: 00219568     EISSN: None     Source Type: Journal    
DOI: 10.1021/je960093t     Document Type: Article

References (82)

1. Ambrose, D. Correlations and Estimations of Vapor-Liquid Critical Properties. I. Critical Temperatures of Organic Compounds. NPL Rep. Chem. 82; National Physical Laboratory, Teddington, England, September 1978; corrected March 1980.
2. Ambrose, D. Correlations and Estimations of Vapor-Liquid Critical Properties. II. Critical Pressures and Volumes of Organic Compounds. NPL Rep. Chem. 98; National Physical Laboratory, Teddington, England, September 1979.
3. Ambrose, D.; Cox, J. D.; Townsend, R. The Critical Temperatures of Forty Organic Compounds. Trans. Faraday Soc. 1960, 56, 1452-1459.
4. Ambrose, D.; Walton, J. Vapor Pressures up to Their Critical Temperatures of Normal Alkanes and 1-Alkanols. Pure Appl. Chem 1989, 61, 1395-1403.
5. Benson, S. W. Thermochemical Kinetics, 2nd ed., Wiley: New York 1976.
6. Cardillo, P. Thermal Decomposition of Isoxazoles. Chem. Ind. (Milan) 1988, 70 (6), 90-92.
7. Carothers, W. H. The Isosterism of Phenyl Isocyanate and Diazobenzene-Imide. J. Am. Chem. Soc. 1923, 45, 1734-1738.
8. Carroll, K. K.; Wright, G. F. Catalyzed Nitration of Amines. VI. The Nitration of Dioctylamine. Can. J. Res. 1948, 26B, 271-283.
9. 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.
10. Chirico, R. D.; Knipmeyer, S. E.; Nguyen, A.; Steele, W. V. Thermodynamic Properties of Biphenyl. J. Chem. Thermodyn. 1989a, 21, 1307-1331.
11. Chirico, R. D.; Nguyen, A.; Steele, W. V.; Strube, M. M.; Tsonopoulos, C. The Vapor Pressure of n-Alkanes Revisited. New Vapor Pressure Data on n-Decane, n-Eicosane and n-Octacosane. J. Chem. Eng. Data 1989b, 34, 149-156.
12. Chirico, R. D.; Knipmeyer, S. E.; Nguyen, A.; Steele, W. V. The Thermodynamic Properties of Dibenzothiophene. J. Chem. Thermodyn. 1991, 23, 431-450.
13. 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.
14. 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.
15. Cox, J. D., Wagman, D. D., Medvedev, V. A., Eds. CODATA Key Values for Thermodynamics; Hemisphere: New York, 1989.
16. Dolliver, M. A.; Gresham, T. L.; Kistiakowsky, G. B.; Vaughan, W. E. Heats of Organic Reactions. V. Heats of Hydrogenation of Various Hydrocarbons. J. Am. Chem. Soc. 1937, 59, 831-841.
17. Douslin, D. R.; McCullough, J. P. An Inclined-Piston Deadweight Pressure Gage. Bur. Mines Rep. Invest. 1963, No. 6149, 11.
18. Douslin, D. R.; Osborn, A. G. Pressure Measurements in the 0.01-30 mm Range with an Inclined-Piston Gauge. J. Sci. Instrum. 1965, 42, 369-373.
19. Evans, E. B. The Viscosities of Hydrocarbons. Parts IV-VI. J. Inst. Petrol. Technol. 1941, 24, 321-337.
20. Forziati, A.; Camin, D. L.; Rossini, F. D. Density, Refractive Index, Boiling Point, and Vapor Pressure of Eight Monoolefin (1-Alkene), Six Pentadiene, and Two Cyclomonoolefin Hydrocarbons. J. Res. Natl. Bur. Stand. 1950, 45, 406-410.
21. 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.
22. Good, W. D. The Enthalpies of Combustion and Formation of 11 Isomeric Nonanes. J. Chem. Eng. Data 1969, 14, 231-235.
23. Good, W. D. The Enthalpies of Combustion of Nine Organic Nitrogen Compounds Related to Petroleum. J. Chem. Eng. Data 1972, 17, 28-31.
24. Good, W. D.; Smith, N. K. The Enthalpies of Combustion of Toluene, Benzene, Cyclohexane, Cyclohexene, Methylcyclopentane, 1-Methyl-cyclopentene, and n-Hexane. J. Chem. Eng. Data 1969, 14, 102-106.
25. 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.
26. Good, W. D.; Scott, D. W.; Waddington, G. Combustion Calorimetry of Organic Fluorine Compounds by a Rotating-Bomb Method. J. Phys. Chem. 1956, 60, 1080-1089.
27. 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.
28. Goodwin, R. D. Benzene Thermophysical Properties from 279 to 900 K at Pressures to 1000 Bar. J. Phys. Chem. Ref. Data 1988, 17, 1541-1636.
29. Goodwin, R. D. Toluene Thermophysical Properties from 178 to 800 K at Pressures to 1000 Bar. J. Phys. Chem. Ref. Data 1989, 18, 1565-1636.
30. 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.
31. Hales, J. L.; Townsend, R. Liquid Densities from 293 to 490 K of Nine Aromatic Hydrocarbons. J. Chem. Thermodyn. 1972, 4, 763-772.
32. 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.
33. 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.
34. Huggins, M. L. Densities and Optical Properties of Organic Compounds in the Liquid State. IV. The Densities of α-Substituted Normal Alkanes. J. Am. Chem. Soc. 1954, 76, 845-847.
35. IUPAC Commission on Atomic Weights and Isotopic Abundances. Atomic Weights of the Elements 1991. J. Phys. Chem. Ref. Data 1993, 22, 1571-1584.
36. Knipmeyer, S. E.; Archer, D. G.; Chirico, R. D.; Gammon, B. E.; Hossenlopp, I. A.; Nguyen, A.; Smith, N. K.; Steele, W. V.; Strube, M. M. High Temperature Enthalpy and Critical Property Measurements using a Differential Scanning Calorimeter. Fluid Phase Equilib. 1989, 52, 185-192.
37. Korovin, A. I.; Margolin, L. N. Thermodynamic Functions of Phenyl Isocyanate. Russ. J. Phys. Chem. 1976, 50, 1735-1736.
38. Labbauf, A.; Rossini, F. D. Heats of Combustion, Formation, and Hydrogenation of 14 Selected Cyclomonoolefin Hydrocarbons. J. Phys. Chem. 1961, 65, 476-480.
39. Lebedeva, N. D. Heats of Combustion and Formation of Aliphatic Tertiary Amine Homologues. Russ. J. Phys. Chem. 1966, 40, 1465-1467.
40. 6 Hydrocarbons J. Chem. Thermodyn. 1975, 7, 205.
41. Letcher, T. M. The Excess Volumes of Some Mixtures of Saturated and Unsaturated Ce Hydrocarbons. Part II. J. Chem. Thermodyn. 1977, 9, 661-664.
42. 6 Acyclic and Cyclic Hydrocarbons Between 300 and 320 K. J. Chem. Thermodyn. 1974, 6, 509-514.
43. Lister, M. A. Heats of Organic Reactions. X. Heats of Bromination of Cyclic Olefins. J. Am. Chem. Soc. 1941, 63, 143-149.
44. 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: Gaithersburgh, MD, 1990.
45. McCormick, D. G.; Hamilton, W. S. The Enthalpies of Combustion and Formation of Oxazole and Isoxazole. J. Chem. Thermodyn. 1978, 10, 275-278.
46. Meyer, E. F.; Hotz, R. D. High-Precision Vapor-Pressure Data for Eight Organic Compounds. J. Chem. Eng. Data 1973, 18, 359-362.
47. Mraw, S. C.; Naas, D. F. The Measurement of Accurate Heat Capacities by Differential Scanning Calorimetry. Comparison of dsc Results on Pyrite (100 to 800 K) with Literature Values from Precision Adiabatic Calorimetry. J. Chem. Thermodyn. 1979, 11, 567-584.
48. c, and ω as Parameters. AIChE J. 1983, 29, 107-113.
49. Osborn A. G.; Douslin, D. R. Vapor Pressure Relations of 36 Sulfur Compounds Present in Petroleum. J. Chem. Eng. Data 1966, 11, 502-509.
50. Pedley, J. B.; Naylor, R. D.; Kirby, S. P. Thermochemical Data of Organic Compounds, 2nd ed.; Chapman and Hall: New York, 1986.
51. 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.
52. Ralston, A. W.; Selby, W. M.; Pool, W. O.; Potts, R. H. Boiling Points of n-Alkyl Primary Amines. Ind. Eng. Chem. 1940, 32, 1093-1094.
53. Raltson, A. W.; Horner, C. W.; Hoffman, E. J. Studies on High Molecular Weight Aliphatic Amines and their Salts. VII. The Systems Octylamine-, Dodecylamine- and Octadecylamine-Water. J. Am. Chem. Soc. 1942, 64, 1516-1523.
54. Reid, R. C.; Prausnitz, J. M.; Poling, B. E. The Properties of Gases and Liquids, 4th ed.; McGraw-Hill: New York, 1987.
55. Riedel, L. Liquid Density in the Saturated State. Extension of the Theorem of Corresponding States II. Chem.-Ing.-Tech. 1954, 26, 259-264.
56. Rogers, D. W.; McLafferty, F. J. A New Hydrogen Calorimeter. Heats of Hydrogenation of Allyl and Vinyl Unsaturation Adjacent to a Ring. Tetrahedron 1971, 27, 3765-3775.
57. Rogers, D. W.; Munoz-Hresko, B. A Microcomputer-Controlled Microcalorimeter Calibration Circuit. 2. Enthalpies of Hydrogenation of Cyclopentene, Cyclohexene, and Cis-3-hexene. Mikrochim. Acta (Wien) 1984, 2, 427-435.
58. Rogers, D. W.; Dejroongruang, K. Enthalpies of Hydrogenation of the n-Heptenes and the Methylhexenes. J. Chem. Thermodyn. 1988, 20, 675-680.
59. Rogers, D. W.; Dejroongruang, K. Enthalpies of Hydrogenation of the Dimethylpentenes, Ethylpentenes, Methylethylbutene, and Trimethylbutene. J. Chem. Thermodyn. 1989, 21, 1115-1120.
60. Rogers, D. W.; Crooks, E.; Dejroongruang, K. Enthalpies of Hydrogenation of the Hexenes. J. Chem. Thermodyn. 1987, 19, 1209-1215.
61. Rogers, D. W.; Dejroongruang, K.; Samuel, S. D.; Fang, W.; Zhoo, Y. Enthalpies of Hydrogenation of the Octenes and the Methylheptenes. J. Chem. Thermodyn. 1992, 24, 561-565.
62. 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.
63. Roth, W. R.; Lennartz, H-W. Heats of Hydrogenation. I. Determination of Heats of Hydrogenation with an Isothermal Titration Calorimeter. Chem. Ber. 1980, 113, 1806-1817.
64. 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.
65. Simonson, J. M.; Oakes, C. S.; Bodnar, R. J. Densities of NaCl(aq) to the Temperature 523 K at Pressures to 40 MPa Measured with a New Vibrating-Tube Densitometer. J. Chem. Thermodyn. 1994, 26, 345-359.
66. Steele, W. V. Fifty Years of Thermodynamics Research at Bartlesville. The Hugh M. Huffman Legacy. J. Chem. Thermodyn. 1995, 27, 135-162.
67. Steele, W. V.; Chirico, R. D. Thermodynamics and the Hydrodeoxygenation of 2,3-Benzofuran. In three parts: Part I. Thermodynamic Properties of 2,3-Benzofuran and 4,5-Dihydro-2,3-benzofuran, Part II. Gibbs Energies of Reaction in the Hydrodeoxygenation of 2,3-Benzofuran, Part III. Thermodynamic Equilibria. NIPER-457; DOE Fossil Energy, Bartlesville Project Office: Bartlesville, OK, November 1989. Available from NTIS, Report No. DE90000218.
68. 4). J. Phys. Chem. Ref. Data 1993, 22, 377-430.
69. 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. 1988a, 20, 1233-1264.
70. Steele, W. V.; Chirico, R. D.; Knipmeyer, S. E.; Smith, N. K. High-Temperature Heat-Capacity Measurements and Critical Property Determinations using a Differential Scanning Calorimeter. (Development of Methodology and Application to Pure Organic Compounds). NIPER-360; DOE Fossil Energy, Bartlesville Project Office: Bartlesville, OK, December 1988b. Available from NTIS Order No. DE89000709.
71. Steele, W. V.; Chirico, R. D.; Hossenlopp, I. A.; Nguyen, A.; Smith, N. K. In Experimental Results from the Design Institute for Physical Property Data: Phase Equilibria and Pure Component Properties Part II; Shih, T. T., Jones, D. K., Eds.; AIChE Symposium Series No. 271; AIChE: New York, 1989; Vol. 85, pp 140-162.
72. Steele, W. V.; Chirico, R. D.; Knipmeyer, S. E.; Nguyen, A. The Thermodynamic Properties of 2-Aminobiphenyl. J. Chem. Thermodyn. 1991, 23, 957-977.
73. Steele, W. V.; Chirico, R. D.; Knipmeyer, S. E.; Nguyen, A. DIPPR Project 821. Vapor Pressure of Organic Compounds of Industrial Interest. The 1991 Project Results. In Experimental Results for DIPPR 1990-91 Projects on Phase Equilibria and Pure Component Properties; Cunningham, J. R., Jones, D. K., Eds.; DIPPR Data Series No. 2; AIChE: New York, 1994, pp 154-173.
74. Steele, W. V.; Chirico, R. D.; Nguyen, A.; Knipmeyer, S. E. Vapor Pressures, High-Temperature Heat Capacities, Critical Properties, Derived Thermodynamic Functions, and Barriers to Methyl-Group Rotation, for the Six Dimethylpyridines. J. Chem. Thermodyn. 1995, 27, 311-334.
75. Strepikheev, Yu. A.; Baranov, Yu. I.; Burmistrova, O. A. Determination of the Heats of Combustion and the Heat Capacities of Several Mono- and Di-isocyanates. Izv. Vyssh. Uchebn. Zaved. Khim. Khim. 1962, 5, 387-90.
76. Stull, D. R. Vapor Pressure Of Pure Substances. Organic Compounds. Ind. Eng. Chem. 1947, 39, 518-550; errata 1947, 39, 1684.
77. Swietoslawski, W. Ebulliometric Measurements; Reinhold: New York, 1945.
78. TRC. TRC Thermodynamic Tables-Nonhydrocarbons; Thermodynamics Research Center Texas A&M University: College Station, TX, extant 1990.
79. Vogel, A. I. Physical Properties and Chemical Constitution. Part XXII. Some Primary, Secondary, and Tertiary Amines. J. Chem. Soc. 1948, 1825-1833.
80. Waddington, G.; Sunner, S.; Hubbard, W. N. Combustions in a Bomb of Organic Sulfur Compounds. In Experimental Thermochemistry; Rossini, F. D., Eds.; Interscience: New York, 1956; Chapter 7, pp 149-179.
81. 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.
82. Wagner, W.; Pruss, A. International Equations for the Saturation Properties of Ordinary Water Substance. Revised According to the International Temperature Scale Of 1990. J. Phys. Chem. Ref. Data 1993, 22, 783-787.