Thermodynamic properties of cyclohexanone oxime

Kozyro, A.A.; Kabo, Gennady J.; Krouk, Vladimir; Sheiman, M. S.; Yursha, I. A.; Simirsky, V.V.; Krasulin, A.P.; Sevruk, V.M.; Gogolinsky, V.I.

doi:10.1016/s0021-9614(05)80233-2

Cited by 18 publications

(41 citation statements)

References 7 publications

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“…In addition, a previous determination of the enthalpy of combustion of cyclohexanone oxime was reported by Runge and Maass in 1953. 77 The values for the enthalpy of combustion of solid cyclohexanone oxime found in the literature search were ∆ c H°m(C 6 H 11 NO, cr, 298.15 K) ) -(3723 ( 4) kJ‚mol -1 by Runge and Maass, 77 76 Kozyro et al 76 reference another determination of the enthalpy of combustion of cyclohexanone oxime by Lebedev et al, 78 ∆ c H°m(C 6 H 11 NO, cr, 298.15 K) ) -(3785.7 ( 1.7) kJ‚mol -1 . (All efforts by us to obtain a copy of that reference proved unsuccessful.)…”

Section: Note In Proofsupporting

confidence: 89%

“…Thermodynamic property determinations on cyclohexanone oxime have been reported by Kozyro et al in three papers. [74][75][76] Measurements included in the communications were energies of combustion, heat capacities for the liquid and solid phases, vapor pressures and sublimation pressures, and experimental determination of the enthalpies of fusion, vaporization, and sublimation. In addition, a previous determination of the enthalpy of combustion of cyclohexanone oxime was reported by Runge and Maass in 1953.…”

Section: Note In Proofmentioning

confidence: 99%

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Thermodynamic Properties and Ideal-Gas Enthalpies of Formation for 1,4-Diisopropylbenzene, 1,2,4,5-Tetraisopropylbenzene, Cyclohexanone Oxime, Dimethyl Malonate, Glutaric Acid, and Pimelic Acid

Steele¹,

Chirico²,

Cowell³

et al. 2002

J. Chem. Eng. Data

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The results of a study aimed at improvement of group-contribution methodology for estimation of enthalpies of formation in the ideal-gas state for pure organic substances are reported. Specific weaknesses where particular group-contribution terms were unknown, or estimated because of lack of experimental data, are addressed by experimental studies of enthalpies of combustion in the condensed phase, vaporpressure measurements, and differential scanning calorimetric (DSC) heat-capacity measurements. Enthalpies of formation in the condensed phase were determined for 1,4-diisopropylbenzene, 1,2,4,5tetraisopropylbenzene, dimethyl malonate, glutaric acid, pimelic acid, and cyclohexanone oxime. Idealgas enthalpies of formation for each of the compounds except pimelic acid are also reported. Enthalpies of fusion and for crystalline phase transitions were determined for 1,2,4,5-tetraisopropylbenzene, cyclohexanone oxime, glutaric acid, and pimelic acid. Two-phase (solid + vapor) or (liquid + vapor) heat capacities were determined from 300 K to the critical region or earlier decomposition temperature for all the title compounds. For 1,4-diisopropylbenzene, 1,2,4,5-tetraisopropylbenzene, and dimethyl malonate, values of the critical temperature and critical density were determined from the DSC results and the corresponding critical pressure was derived from the fitting procedures. The results of all the measurements were combined to derive a series of thermophysical properties including critical temperature, critical density, critical pressure, acentric factor, enthalpies of vaporization (restricted to within (50 K of the temperature range of the vapor pressures), and heat capacities along the saturation line. Wagner-type vapor-pressure equations were derived for each compound. Enthalpies of sublimation were derived for cyclohexanone oxime and, using literature vapor pressures, glutaric acid. Group-additivity enthalpy of formation parameters and strain energies useful in the application of ideal-gas-phase group-contribution correlations were derived. Errors in the literature data for the enthalpy of formation of diethyl malonate are noted.

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Section: Note In Proofsupporting

confidence: 89%

Section: Note In Proofmentioning

confidence: 99%

Thermodynamic Properties and Ideal-Gas Enthalpies of Formation for 1,4-Diisopropylbenzene, 1,2,4,5-Tetraisopropylbenzene, Cyclohexanone Oxime, Dimethyl Malonate, Glutaric Acid, and Pimelic Acid

Steele¹,

Chirico²,

Cowell³

et al. 2002

J. Chem. Eng. Data

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“…Figure 3B shows the deviations of values calculated using eq 8 from the Knudsen effusion measurements reported by Aihara, 31 Kozyro et al, 27 and Kabo et al 28 and from the Project 801 Database 24 sublimation vapor-pressure correlation equation. Agreement with both the 1989 and the 1992 results 27,28 is excellent, showing that the liquid-phase vapor-pressure measurements reported here are thermodynamically consistent with the Russian thermodynamic property measurements. Not shown in Figure 3B are the results of Hoyer and Peperle, 32 who report an equation for the sublimation pressure in the temperature region 258 K to 308 K obtained using the Knudsen effusion technique.…”

Section: Discussionmentioning

confidence: 91%

“…Figure 3A compares the Project 801 Database 24 correlation equation and vapor-pressure measurements listed in the following references (Moravek, 25 Daubert et al, 26 Kozyro et al 27 ) with values for the saturation vapor pressure of -caprolactam obtained using eq 2 and the parameters listed in Table 5. Agreement with the measurements of Daubert et al 26 is within the error limit of 5% assigned to those measurements in the 801 Database (the tabulated vapor pressure at 361.47 °C, i.e., 447,330 Pa, is probably a typographical error and probably should read 557,330 Pa).…”

Section: Discussionmentioning

confidence: 99%

Measurements of Vapor Pressure, Heat Capacity, and Density along the Saturation Line for ε-Caprolactam, Pyrazine, 1,2-Propanediol, Triethylene Glycol, Phenyl Acetylene, and Diphenyl Acetylene

Steele¹,

Chirico²,

Knipmeyer³

et al. 2002

J. Chem. Eng. Data

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This paper reports measurements made for DIPPR Research Project 821 in the 1996 Project Year. Vapor pressures were measured to a pressure limit of 270 kPa (unless decomposition occurred) for all six compounds using a twin ebulliometric apparatus. Additionally, for -caprolactam, measurements at low pressures (0.043 kPa to 3.08 kPa) were performed using an inclined-piston apparatus. Liquid-phase densities along the saturation line were measured for each compound over a range of temperatures (ambient to a maximum of 548 K). A differential scanning calorimeter was used to measure two-phase (liquid + vapor) heat capacities for each compound in the temperature region ambient to the critical temperature or lower decomposition point. A critical temperature and the corresponding critical density were determined experimentally for pyrazine. The results of all the measurements were combined to derive a series of thermophysical properties including critical temperature, critical density, critical pressure, acentric factor, enthalpies of vaporization (within the temperature range ((50 K) of the vapor pressures), enthalpies of fusion if solid at ambient temperature, solubility parameter, and heat capacities along the saturation line. Wagner-type vapor-pressure equations were derived for each compound. In addition, the liquid-phase densities were compared with values derived using a four-term power series in [(1 -T r ) n/3 ]. For -caprolactam, the results of the present measurements were combined with literature values to derive a "Third Law" estimate of sublimation pressures in the region of ambient temperature. All measured and derived values were compared with those obtained in a search of the literature.

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“…Since D r G 0 as a thermodynamic value is only dependent on the initial and the end condition of the participating substances, the byproducts were formed directly out of the oxime without any intermediate state. The Gibbs standard heat of reaction of the Beckmannn rearrangement was calculated with thermodynamical data published by Kozyro and Kabo [15,16]. The data for ammonia and water were taken from [17].…”

Section: Discussionmentioning

confidence: 99%