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

Journal of Chemical and Engineering Data

Volumn 41, Issue 6, 1996, Pages 1285-1302

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

^a IIT RESEARCH INSTITUTE   (United States)

^b BDM Oklahoma Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; DECOMPOSITION; DENSITY MEASUREMENT (SPECIFIC GRAVITY); DIFFERENTIAL SCANNING CALORIMETRY; ENTHALPY; ETHANE; ETHERS; PRESSURE MEASUREMENT; SPECIFIC HEAT; TEMPERATURE MEASUREMENT; THERMAL EFFECTS;

BUTYL ACRYLATE; HEPTENE; HEXANE DIOL; IDEAL GAS ENTHALPY; METHYL GLYCOLATE;

ORGANIC COMPOUNDS;

EID: 0030281948     PISSN: 00219568     EISSN: None     Source Type: Journal    
DOI: 10.1021/je960117w     Document Type: Article

References (85)

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. Ambrose, D.; Ellender, J. H.; Sprake, C. H. S.; Townsend, R. Thermodynamic Properties of Organic Oxygen Compounds. XLIII. Vapour Pressures of Some Ethers. J. Chem. Thermodyn. 1976, 8, 165-178.
3. Benson, S. W. Thermochemical Kinetics, 2nd ed.; Wiley: New York, 1976.
4. Bouwstra, J. A.; de Leeuw, V. V.; Van Miltenburg, J. C. Properties of Mixed-Crystalline Organic Materials Prepared by Zone Levelling. IV. Melting Properties and Excess Enthalpies of (trans-Azobenzene + trans-Stilbene). J. Chem. Thermodyn. 1985, 17, 685-695.
5. Bright, N. F. H.; Carson, T.; Dyson, T. A. Azobenzene Part I: Vapour Pressure of cis- and trans- Azobenzene. Research (London) 1950, 3, 185-186.
6. Carvajal, C.; Töle,K. J.; Smid, J.; Szwarc, M. Studies of Solvation Phenomena of Ions and Ion Pairs in Dimethoxyethane and Tetrahydrofuran. J. Am. Chem. Soc. 1965, 87, 5548-5553.
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. Thermodynamic Properties of Biphenyl. J. Chem. Thermodyn. 1989a, 21, 1307-1331.
9. 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.
10. Chirico, R. D.; Knipmeyer, S. E.; Nguyen, A.; Steele, W. V. The Thermodynamic Properties of Dibenzothiophene. J. Chem. Thermodyn. 1991, 23, 431-450.
11. 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.
12. 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.
13. Cole, L. G.; Gilbert, E. C. The Heat of Combustion of Some Nitrogen Compounds and the Apparent Energy of the N-N Bond. J. Am. Chem. Soc. 1951, 73, 5423-5427.
14. Corruccini, R. J.; Gilbert, E. C. The Heat of Combustion of cis- and trans-Azobenzene. J. Am. Chem. Soc. 1939, 61, 2925-2927.
15. Cox, J. D.; Wagman, D. D.; Medvedev, V. A. editors. CODATA Key Values for Thermodynamics; Hemisphere: New York, 1989.
16. de Kruif C. G.; van Ginkel, C. H. D. Torsion-Weighing Effusion Vapour-Pressure Measurements on Organic Compounds. J. Chem. Thermodyn. 1977, 9, 725-730.
17. Dias, A. R.; Minas Da Piedade, M. E.; Martinho Simões, J. A.; Simoni, J. A.; Teixeira, C.; Diogo, H. P.; Meng-Yan, Yang; Pilcher, G. The Enthalpies of Formation of cis- and trans-Azobenzenes. J. Chem. Thermodyn. 1992, 34, 439-447.
18. Douslin, D. R.; McCullough, J. P. An Inclined-Piston Deadweight Pressure Gage. Bur. Mines Rep., Invest. 1963, No. 6149, 11 pp.
19. 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.
20. Eigenmann, H. K.; Golden, D. M.; Benson, S. W. Revised Group Additivity Parameters for the Enthalpies of Formation of Oxygen-Containing Organic Compounds. J. Phys. Chem. 1973, 77, 1687-1691.
21. Engineering Science Data Item Number 78011. Vapor Pressure and Critical Points of Liquids XII: Aromatic Nitrogen Compounds; Institute Chemical Engineers: London, March 1978.
22. Fenwick, J. O.; Harrop, D.; Head, A. J. Thermodynamic Properties of Organic Oxygen Compounds. 41. Enthalpies of Formation of Eight Ethers. J. Chem. Thermodyn. 1975, 7, 943-954.
23. Figurski, Von G.; von Weber, U. Some Physical Properties of the Cyclic Hydrocarbons 1-Vinylcyclohex-3-ene; 5-Vinyl-bicyclo[2.2.1]hept-2-ene; 4,7,8,9-Tetrahydroindene, and endo-Dicyclopentadiene; the Free Excess Enthalpies of Their Binary Mixtures at 80° and 90°C. Wiss. Z. Wilhelm-Pieck-Univ. Rostock, Math.-Naturwiss. Reihe 1976, 25, 1071-1074.
24. 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.
25. Good, W. D. The Enthalpies of Combustion and Formation of 11 Isomeric Nonanes. J. Chem. Eng. Data 1969, 14, 231-235.
26. Good, W. D. The Enthalpies of Combustion of Nine Organic Nitrogen Compounds Related to Petroleum. J. Chem. Eng. Data 1972, 17, 28-31.
27. 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.
28. 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.
29. 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.
30. 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.
31. 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.
32. 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.
33. 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.
34. Hales, J. L.; Townsend, R. Liquid Densities from 293 to 490 K of Nine Aromatic Hydrocarbons. J. Chem. Thermodyn. 1972, 4, 763-772.
35. Hall, H. K.; Smith, C. D.; Baldt, J. H. Enthalpies of Formation of Nortricyclene, Norbornene, Norbornadiene, and Quadricyclane. J. Am. Chem. Soc. 1973, 95, 3197-3201.
36. 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.
37. Inque, Y. Useful Synthetic Routes to Pure exo-5-Vinyl-2-norbornene and endo-5-Vinyl-2-norbornene. Bull. Chem. Soc. Jpn. 1987, 60, 1954-1956.
38. IUPAC Commission on Atomic Weights and Isotopic Abundances. Atomic Weights of the Elements 1991. J. Phys. Chem. Ref. Data 1993, 22, 1571-1584.
39. 3,7]-decane (Adamantane). J. Chem. Thermodyn. 1982, 14, 395-398.
40. Jordache, I.; Lipkovics, R.; Mihailesau, M.; Andreescu, G. Data on Liquid-Vapor Equilibrium during the Synthesis of Ethylidenenorbornene. I. Concentration of Vinylnorbornene. Rev. Chim. 1979, 30, 999-1003.
41. 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.
42. Kobe, K. A.; Ravicz, A. E.; Vohra, S. P. Critical Properties and Vapor Pressures of Some Ethers and Heterocyclic Compounds. Ind.. Eng. Chem. Chem. Eng. Data Ser. 1956, 1, 50-56.
43. Kozina, M. P.; Bychikhina, L. V.; Gal'shenko, G. L.; Milwitskaya, E. M.; Ordubadi, M.; Plate, A. F. Enthalpies of Nortricyclene and Norbornene Formation. Dokl. Akad. Nauk SSSR 1976, 226, 1105-1106.
44. Kusano, K. Densities, Refractive Indexes, and Normal Boiling Points of 1,2-Disubstituted Ethylene Glycol Derivatives. J. Chem. Eng. Data 1978, 23, 141-143.
45. Kusano, K.; Wadsö, I. Enthalpies of Vaporization of Organic Compounds. VI. Some Disubstituted Ethylene Glycols. Acta Chem. Scand. 1970, 24, 2037-2042.
46. Kusano, K.; Suurkuush, J.; Wadsö, I. Thermochemistry of Solutions of Biochemical Model Compounds. 2. Alkoxyethanols and 1,2-Dialkoxyethanes in Water. J. Chem. Thermodyn. 1973, 5, 757-767.
47. Lebedev, B.; Smirnova, N.; Kiparisova, V.; Makovetsky, K. Thermodynamics of Norbornene, of its Polymerization Process and of Polynorbornene from 0 to 400 K at Standard Pressure. Makromol. Chem. 1992, 193, 1399-1411.
48. Majury, T. G. Vapor Pressures and Heats of Sublimation of p-Nitroaniline, N,N′-Dimethyl-p-nitroaniline, p-Aminoazobenzene, and N,N-Dimethyl-p-aminoazobenzene. Chem. Ind. 1956, 349-350.
49. 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.
50. McCurdy, K. G.; Laidler, K. J. Thermochemical Studies of Some Acrylate and Methacrylate Polymerizations in Emulsion Systems. Can. J. Chem. 1964, 42, 818-824.
51. 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.
52. Obama, M.; Oodera, Y.; Kohama, N.; Yanase, T.; Salto, Y.; Kusano, K. Densities, Molar Volumes, and Cubic Expansion Coefficients of 78 Aliphatic Ethers. J. Chem. Eng. Data 1985, 30, 1-5.
53. c, and ω as Parameters. AIChE J. 1983, 29, 107-113.
54. Osborn, A. G.; Douslin, D. R. Vapor Pressure Relations of 36 Sulfur Compounds Present in Petroleum. J. Chem. Eng. Data 1966, 11, 502-509.
55. Papayoanou, A.; Christopulos, J. A. Thermodynamic and Ultrasonic Properties of Acrylic Monomers. U.S. Natl. Tech. Inform. Serv. AD Rep. 1973, No. 766263/9, 22 pp. Available from NTIS.
56. 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.
57. Quadri, S. K.; Kudchadker, A. P. Measurements of the Critical Temperatures and Critical Pressures of some Thermally Stable or Mildly Unstable Esters, Ketones, and Ethers. J. Chem. Thermodyn. 1991, 23, 129-134.
58. Reid, R. C.; Prausnitz, J. M.; Poling, B. E. The Properties of Gases and Liquids, 4th ed.; McGraw-Hill: New York, 1987.
59. Riedel, L. Liquid Density in the Saturated State. Extension of the Theorem of Corresponding States II. Chem.-Ing.-Tech. 1954, 26, 259-264.
60. 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.
61. Schulze, F. W.; Patrick, H. J.; Cammenge, H. K.; Klinge, H. Z. Thermodynamic Properties of the Structural Analogues Benzo[c]-cinnoline, trans-Azobenzene, and cis-Azobenzene. Z. Phys. Chem. 1977, 107, 1-19.
62. 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.
63. σ Dependencies of Ethylene Glycol Dimethyl Ether. Izv. Vyssh. Uchebn. Zaved. Neft Gaz 1978, 21 (8), 62-64.
64. 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.
65. Smutny, E. J.; Bondi, A. Di-t-butyl Ether; Strain Energy and Physical Properties. J. Phys. Chem. 1961, 65, 546-550.
66. 7 Bridged-Ring Hydrocarbons: Norbornane, Norbornene, Nortricyclene, Norbornadiene and Quadricyclane. J. Chem. Thermodyn. 1978, 10, 919-927.
67. Steele, W. V. Fifty Years of Thermodynamics Research at Bartlesville. The Hugh M. Huffman Legacy. J. Chem. Thermodyn. 1995, 27, 135-162.
68. 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.
69. 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 1998b. Available from NTIS Order No. DE89000709.
70. Steele, W. V.; Chirico, R. D.; Knipmeyer, S. E.; Nguyen, A. The Thermodynamic Properties of 2-Aminobiphenyl. J. Chem. Thermodyn. 1991a, 23, 957-977.
71. 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. Experimental Results for Phase Equilibria and Pure Component Properties; DIPPR Data Series No. 1; Cunningham, J. R., Jones, D. K.,Eds.; AIChE: New York, 1991b; pp 101-134.
72. 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. Experimental Results for DIPPR 1990-91 Projects on Phase Equilibria and Pure Component Properties; DIPPR Data Series No. 2; Cunningham, J. R., Jones, D. K., Eds.; AIChE: New York, 1994a; pp 154-173.
73. Steele, W. V.; Chirico, R. D.; Hossenlopp, I. A.; Knipmeyer, S. E.; Nguyen, A.; Smith, N. K. DIPPR Project 871. Determination of Ideal-Gas Enthalpies of Formation for Key Compounds. The 1990 Project Results. Experimental Results for DIPPR 1990-91 Projects on Phase Equilibria and Pure Component Properties; DIPPR Data Series No. 2; Cunningham, J. R., Jones, D. K., Eds.; AIChE: New York, 1994b; pp 188-215.
74. Stull, D. R. Vapor Pressure Of Pure Substances. Organic Compounds. Ind. Eng. Chem. 1947, 39, 518-550. Errata 1947, 39, 1684.
75. Swietoslawski, W. Ebulliometric Measurements; Reinhold: New York, 1945.
76. Syverud, A. N. Personal communications. The Dow Chemical Company, 1991.
77. Titiva, L. F.; Chaplits, D. N.; Dudorova, G. S. Relation of Saturated Vapour Pressure to Temperature and Heat of Vaporization of the Products of the Diels-Alder Reaction of Butadiene and Cyclopentadiene. Promst. Sint. Kauch. Ref. Sb. 1972, No. 5, 1-3.
78. Trofimov, B. A.; Nedolya, N. A.; Lebedev,N. D.; Ryadnenko, V. L.; Masalitinova, T. N.; Dobychin, S. L.; Zacheslavskaya, R. Kh.; Petrov, G. N. Thermochemical and Quantum-Chemical Estimation of Conjugation Energy in Vinyl Ethers. Izv. Akad. Nauk SSSR Ser. Khim. 1981, 4, 751-753.
79. Van Miltenburg, J. C.; Bouwstra, J. A. Thermodynamic Properties of trans-Azobenzene and trans-Stilbene. J. Chem. Thermodyn. 1984, 16, 61-65.
80. Varushchenko, R. M.; Druzhinina, A. C.; Belikova, N. A.; Bobyleva, A. A.; Plate, A. F. The Vapour Pressures and Boiling Points of Certain Bicyclic Hydrocarbons and 4-Vinylcyclohex-1-ene. All Union Institute of Scientific & Technical Information VINITI No. 6970-73; VINITI: Moscow, Deposited October 9, 1973; 10 pp.
81. Varushchenko, R. M.; Druzhinina, A. C.; Belikova, N. A.; Bobyleva, A. A.; Plate, A. F. The Vapour Pressures and Boiling Points of Certain Bicyclic Hydrocarbons and 4-Vinylcyclohex-1-ene. Russ. J. Phys. Chem. 1974, 48, 282.
82. 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.
83. 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.
84. Walsh, R.; Wells, J. W. The Enthalpy of Formation and Thermodynamic Functions of Bicyclo[2.2.1]hept-2-ene. J. Chem. Thermodyn 1976, 8, 55-60.
85. Werblan, L.; Leinski, J. Phase Velocity of Sound, Viscosity, and Density in Mixtures of gamma-Butyrolactone with Water and Ethers-1,1-Dimethoxyethane and 1,2-Dimethoxyethane. Polish J. Chem. 1980, 54, 507-516.