Vapor pressure, heat capacity, and density along the saturation line, measurements for dimethyl isophthalate, dimethyl carbonate, 1,3,5-triethylbenzene, pentafluorophenol, 4-tert-butylcatechol, α-methylstyrene, and N,N′-bis(2-hydroxyethyl)ethylenediamine

Journal of Chemical and Engineering Data

Volumn 42, Issue 6, 1997, Pages 1008-1020

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

^a IIT RESEARCH INSTITUTE   (United States)

^b NORTHROP GRUMMAN MISSION SYSTEMS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; BENZENE; DENSITY MEASUREMENT (SPECIFIC GRAVITY); ENTHALPY; ESTERS; PHENOLS; PRESSURE MEASUREMENT; SATURATION (MATERIALS COMPOSITION); SOLUBILITY; SPECIFIC HEAT OF LIQUIDS; STYRENE; VAPOR PRESSURE;

ACENTRIC FACTOR; BUTYLCATECHOL; DIMETHYL CARBONATE; DIMETHYL ISOPHTHALATE; EBULLIOMETERS; HYDROXYETHYLETHYLENEDIAMINE; METHYLSTYRENE; PENTAFLUOROPHENOL; TRIETHYLBENZENE; WAGNER VAPOR PRESSURE EQUATION;

ORGANIC COMPOUNDS;

EID: 0031269246     PISSN: 00219568     EISSN: None     Source Type: Journal    
DOI: 10.1021/je970102d     Document Type: Article

References (69)

1. Ambrose, D. Thermodynamic Properties of Fluorine Compounds. Part V. Vapour Pressures of Pentafluorobenzene, Chloropentafluorobenzene, 2,3,4,5,6-Pentafluorotoluene, and Pentafluorophenol. J. Chem. Soc. A 1968, 1381-1383.
2. Ambrose, D.; Sprake, C. H. S. Thermodynamic Properties of Fluorine Compounds. Part X. Critical Properties and Vapour Pressures of Pentafluorobenzene, Chloropentafluorobenzene, 2,3,4,5,6-Pentafluorotoluene, and Pentafluorophenol. J. Chem. Soc. A 1971, 1263-1266.
3. Ambrose, D.; Walton, J. Vapor Pressures up to Their Critical Temperatures of Normal Alkanes and 1-Alkanols. Pure Appl. Chem. 1989, 61, 1395-1403.
4. Ambrose, D.; Ewing, M. B.; Ghiassee, N. B.; Sanchez Ochoa, J. C. The Ebulliometric Method of Vapour-Pressure Measurement: Vapour Pressures of Benzene, Hexafluorobenzene, and Naphthalene. J. Chem. Thermodyn. 1990, 22, 589-605.
5. Andon, R. J. L.; Counsell, J. F.; Hales, J. L.; Lees, E. B.; Martin, J. F. Thermodynamic Properties of Fluorine Compounds. Part VII. Heat Capacity and Entropy of Pentafluorochlorobenzene and Pentafluorophenol. J. Chem. Soc. A 1968, 2357-2361.
6. Auwers, von K.; Roth, W. A.; Eisenlohr, F. Thermochemical Investigations. III. Heats of Combustion of Terpenes and Styrenes. Liebigs Ann. Chem. 1910, 373, 267-290.
7. Auwers, von K.; Roth, W. A.; Eisenlohr, F. Thermochemical Investigations. IV. Heats of Combustion of Terpenes and Styrenes and Calculated Heat of Combustion. Liebigs Ann. Chem. 1912, 385, 102-116.
8. Bodnaryuk, F. N.; Korshavov, M. A.; Kislev, V. Ya.; Sumin, I. G. A New Method for Synthesizing Oligoester Acrylates. Zh. Prikl. Khim. (Leningrad) 1972, 45, 2500-2505.
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. Colomina, M.; Laynez, J. L.; Perez-Ossono, R.; Turrion, C. Enthalpies of Combustion and Formation of Six Methyl Esters of Benzene Carboxylic Acids J. Chem. Thermodyn. 1972, 4, 499-506.
16. Cox, J. D.; Gundry, H. A.; Harrop, D.; Head, A. J. Thermodynamic Properties of Fluorine Compounds. 9. Enthalpies of Formation of some Compounds Containing the Pentafluorophenyl Group. J. Chem. Thermodyn. 1969, 1, 77-87.
17. Cross, J. D.; Hunter, R.; Stemson, V. R. The Thermal Decomposition of Simple Carbonate Esters. Aust. J. Chem. 1976, 29, 1477-1481.
18. Daubert, T. E.; Danner, R. P. Physical and Thermodynamic Properties of Pure Chemicals: Data Compilation; DIPPR Project 801; Hemisphere: New York, 1993.
19. Douslin, D. R.; McCullough, J. P. An Inclined-Piston Deadweight Pressure Gage. Bur. Mines Rep. Invest. 1963, No. 6149, 11 pp.
20. 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.
21. DuPont de Nemours. 4-Oxo-1,3-dioxanes. U.S. Patent 3,503,993, March 31, 1970; Chem. Abstr. 1970, 73, 14860Z.
22. Gibbons, L. C.; Thompson, J. F.; Reynolds, T. W.; Wright, J. I.; Chanan, H. H.; Lamberti, J. M.; Hipsher, H. F.; Karabinos, J. V. Purification and Physical Constants of Aromatic Hydrocarbons. J. Am. Chem. Soc. 1945, 68, 1130-1131.
23. 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.
24. Gray, P.; Williams, A. The Thermochemistry and Reactivity of Alkoxyl Radicals. Chem. Rev. 1959, 59, 239-328.
25. Green, J. H. S.; Harrison, D. J. Thermodynamic Properties of Fluorine Compounds. 19. Hexafluorobenzene, Pentafluorophenol, 1,3,5-Trichlorotrifluorobenzene, and Pentafluorobenzaldehyde: Vibrational Assignments and Chemical Thermodynamic Properties. J. Chem. Thermodyn. 1976, 8, 529-544.
26. Hales, J. L.; Townsend, R. Liquid Densities from 293 to 490 K of Nine Aromatic Hydrocarbons. J. Chem. Thermodyn. 1972, 4, 763-772.
27. Hales, J. L.; Townsend, R. Liquid Densities from 293 K to 490 K of Eight Fluorinated Aromatic Compounds. J. Chem. Thermodyn. 1974, 6, 111-116.
28. Hamdouni, A.; Leonard, J.; Bui, Van Tam Modeling Vapor Pressure Data of Ternary α-Methylstyrene-Toluene-Poly(α-methylstyrene) System. Polym. J. (Tokyo) 1991, 23, 219-226.
29. Hildebrand, J. H.; Scott, R. L. Regular Solutions; Prentice Hall: Englewood Cliffs, NJ, 1962.
30. IUPAC Commission on Atomic Weights and Isotopic Abundances. Atomic Weights of the Elements 1991. J. Phys. Chem. Ref. Data 1993, 22, 1571-1584.
31. 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.
32. Kerr, J. A. Bond Dissociation Energies by Kinetic Methods. Chem. Rev. 1966, 66, 465-500.
33. 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.
34. Kogerman, P. N.; Kranig, J. Physical Constants of Some Alkyl Carbonates. Acta Commentat. Univ. Tartu. (Dorpat.) 1927, 12 (7), 3-11.
35. Kucharenko, T. A.; Grigor'eva, E. A. Neftekhymia 1970, 10, 303-305.
36. Kraus, M.; Beranck, L.; Kochloefl, K.; Bazant, V. Vapor Pressure of Benzenecarboxylic Acids and their Derivatives. Chem. Prum. 1962, 12, 649-652.
37. Laevskaya, N. S.; Bagrov, I. V.; Dobroserdov, I. L.; Sokolkina, T. P. Liquid-Vapor Equilibrium of Systems Formed by Styrene with Benzene and a Series of its Derivatives. Zh. Prikl. Khim (Leningrad) 1979, 52, 687-689.
38. Lebedev, B. V.; Rabinovich, I. B. Heat Capacities and Thermodynamic Functions of α-Methyl-styrene and Poly(α-methylstyrene). Tr. Khim. Khim. Tekhnol. 1971, 1, 12-15.
39. 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.
40. Murogova, R. A.; Tudorosvakaya, G. L.; Laufer, V. V.; Kozlova, V. D.; Serafimov, L. A. Liquid-Vapor Equilibrium in Systems Formed by Esterification Products of Isophthalic Acid at a Pressure of 15 mm Mercury. J. Appl. Chem. USSR 1974, 47, 2079-2081.
41. Muthu, O.; Munjal, S.; Smith, B. D. Total Pressure Vapor-Liquid Equilibria Data for Binary Systems of Acetone with Isopropylbenzene and Isopropenylbenzene. J. Chem. Eng. Data 1983, 28, 192-196.
42. c, and ω as Parameters. AIChE J. 1983, 29, 107-113.
43. Osborn A. G.; Douslin, D. R. Vapor Pressure Relations of 36 Sulfur Compounds Present in Petroleum. J. Chem. Eng. Data 1966, 11, 502-509.
44. Paukov, I. E.; Lavrent'eva, M. N.; Anisimov, M. P. Heat Capacity, Phase Transitions, Entropy, and Enthalpy of Pentafluorophenol at Low Temperatures. Russ. J. Phys. Chem. 1969, 43, 436-438.
45. 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.
46. Ribeiro da Silva, M. D. M. C.; Ribeiro da Silva, M. A. V.; Pilcher, G. Enthalpies of Combustion Of 1,2-Dihydroxybenzene and of Six Alkylsubstituted 1,2-Dihydroxybenzenes. J. Chem. Thermodyn. 1984, 16, 1149-1155.
47. Riedel, L. Liquid Density in the Saturated State. Extension of the Theorem of Corresponding States II. Chem.-Ing.-Tech. 1954, 26, 259-264.
48. 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.
49. Smith, B. D.; Srivastava, R. Thermodynamic Data for Pure Compounds. Part B. Halogenated Hydrocarbons and Alcohols; Physical Sciences Data 25; Elsevier: New York, 1986.
50. Steele, W. V. Fifty Years of Thermodynamics Research at Bartlesville. The Hugh M. Huffman Legacy. J. Chem. Thermodyn. 1995, 27, 135-162.
51. Steele, W. V. Unpublished results, 1996.
52. 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.
53. 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.
54. Steele, W. V.; Chirico, R. D.; Knipmeyer, S. E.; Nguyen, A. The Thermodynamic Properties of 2-Aminobiphenyl. J. Chem. Thermodyn. 1991, 23, 957-977.
55. 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.
56. 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.
57. 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.
58. 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.
59. Stull, D. R. Vapor Pressures of Pure Substances. Organic Compounds. Ind. Eng. Chem. 1947, 39, 518-550; 1947, 39, 1684.
60. Stull, D. R. Vapor Pressures of Pure Substances. Organic Compounds. Ind. Eng. Chem. 1947, 39, 518-550; 1947, 39, 1684.
61. Swietoslawski, W. Ebulliometric Measurements; Reinhold: New York, 1945.
62. 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.
63. Tiffeneau, M. Benzene Hydrocarbons with a Pseudo-Allyl Side Chain: Methovinyl Benzene and its Homologues. Ann. Chim. Phys. (Paris) 1907, 10, 145-198.
64. TRC Thermochemical Tables-Hydrocarbons. (Formerly API Research Project 44, then TRC Hydrocarbon Project. Selected Values of Properties of Hydrocarbons and Related Compounds, Category A. Tables of Physical and Thermodynamic Properties.) Thermodynamics Research Center, Texas A&M University: College Station, TX, Extant 1996.
65. 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.
66. Voronkov, M. G.; Broun, A. S.; Karpenko, G. P.; Gol'shtein, B. L. Reactions of Sulfur with Unsaturated Compounds. III. Synthesis of 2-Phenylthiophene. Zh. Obshch. Khim. 1949, 19, 1356-1364.
67. 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.
68. Wegscheider, R.; Perdanner, H. I.; Auspitzer, O. Esterification of Unsymmetric Di- and Polybasic Acids. XXXIII. Trimellitic Acid. Monatsh. Chem. 1911, 31, 1253-1301.
69. Wright, F. J. Latent Heat of Vaporization and Composition. Recl. Trav. Chim. Pays-Bas 1960, 79, 784-789.