1009. Thermodynamic properties of organic oxygen compounds. Part I. Preparation and physical properties of pure phenol, cresols, and xylenols

Abstract

Karr, " Physical Properties of Low-Boiling Phenols. the Interior, 1957, Information Circular 7802. F. p. 99.929 & 0.006 0.848" f 0.004" 40.84" f 0.01" F. p. 99.963 f 0.002 0-596 f 0.009 30.97 f 0.01 M. p. 99.917 & 0.020 0.749 f 0-040 12-16 f 0.01 F. p-99.963 f 0.021 0.915 f 0.051 34-65 f 0.01 M. p. 99.928 f 0.005 0.502 f 0.019 72-53 f 0.01 M. p. 99.972 f 0.002 0.576 f 0.030 24.52 f 0.01 M. p. 99.896 f 0.020 0.727 f 0.008 74.77 f 0.01 F. p. 99.886 f 0.008 0-558 f 0-016 45.56 f 0.01 M. p. 99.971 & 0.005 0.727 f 0.020 65-09 f 0.01 M. p. 99.960 f 0.004 0.520 f 0.059 63.24 f 0.01 I;. p. €or 100% purity 40.90" f 0.01" 30.99 & 0.01 34.69 -J= 0.02 72.57 f 0.02 24.54 & 0.01 74.85 f 0-02 45-62 & 0.01 65.11 f 0-01 63.27 f 0.02 (tf, 0 ) f 0-02Vapour pressure-temperature relationships, normal boiling points, values of (dtldp) 760 mm., and latent heats of vaporization. The vapour pressures of the liquid and solid xylenols were measured by ebulliometric and gas-saturation procedures previously described.4~ 1 3 ~~4 Detailed results for the six xylenols are given in Table 2.Antoine equations [i.e., equations of the form log,, P = A -B/(t + C)] were fitted to the data for higher temperatures, and the two-constant equation log,, P = A -B/(t + 273) was used for the lower temperature range. Table 3 gives the constants of these equations and Table 4 shows the normal b. p.s; values of (dt/dP),so-.

Energetics of Cresols and of Methylphenoxyl Radicals

“…Andon et al 16 derived ∆ sub H m°( o-CH 3 C 6 H 4 OH) ) 76.0 ( 0.8 kJ‚mol -1 based on vapor pressure against temperature data determined by ebulliometric and gas saturation methods. This value differs by 2.3 kJ‚mol -1 from that proposed in this work (73.74 ( 0.46 kJ‚mol -1 ).…”

“…9,10 It is therefore surprising that some significant discrepancies are found between the published enthalpies of formation, enthalpies of vaporization/sublimation, and DH°(O-H) values of cresols. Even excluding early results that are only of historical value, [11][12][13][14] it is possible to conclude that the published enthalpies of formation of o-cresol (cr), m-cresol (l), and p-cresol (cr), at 298.15 K, span ranges of 2.6 kJ‚mol -1 , [15][16][17][18] 17.0 kJ‚mol -1 , 15-19 and 6.3 kJ‚mol -1 , [15][16][17][18] respectively. The enthalpies of sublimation of both o-cresol and p-cresol at 298.15 K have been determined only once, 16,20 and the reported values of the enthalpy of vaporization of m-cresol at 298.15 K vary between 46.3 and 71.2 kJ‚mol -1 .…”

Thermodynamic properties of organic iodine compounds

“…The values given in the same table for the standard molal entropy (S ) and volume (V ) at 25°C and 1 bar, as well as for the heat capacity power function coefficients of the three isomers have been estimated from the group stoichiometry expressions shown in Table 8 together with group contributions taken from Table 9 and Richard and Helgeson (1998). The group properties and coefficients of the C OH (6) (C) (C) group were derived from those of crystalline phenol by considering the group stoichiometry expression shown in Table 8 for phenol together with the standard molal enthalpy of formation (DH f ¼ À165:1 kJ mol À1 ) reported by Andon et al (1960), a standard molal volume (V ¼ 83:1 cm 3 mol À1 ) derived from a density value reported by the same authors, the standard molal entropy (S ¼ 144:01 J mol À1 K À1 ) at 25°C and 1 bar determined by Andon et al (1963) and the following values for the a, b and c heat capacity coefficients: a = À118.7 J mol À1 K À1 , b = 726.7 Â 10 À3 J mol À1 K À2 , and c = 26.120 Â 10 5 J K mol À1 . The latter values have been obtained by regressing with Eq.…”

Standard partial molal properties of aqueous alkylphenols and alkylanilines over a wide range of temperatures and pressures

“…On the thermodynamic side, the most important contribution is that of Dohnal and Fenclova (1995) who published highly reliable Henry's law constants and limiting Andon et al (1960), the enthalpy of vaporization of subcooled p-cresol was obtained from Andon et al (1960), the enthalpy of vaporization of aniline was from the review of Majer and Svoboda (1985), respectively. Desnoyers et al (1973), Hamann and Linton (1974), Hamann and Lim (1954), and Hopkins et al (1976) for phenol; Indelli (1963) for o-, m-, and p-dihydroxybenzene; Shahidi et al (1977) for aniline.…”

“…k Estimated from Joback's group contribution scheme (Poling et al, 2001). of solution published in literature combined with the representative enthalpies of vaporization for their conversion to the enthalpy of hydration. In the case of phenolic compounds the enthalpies of vaporization and sublimation were obtained from the vapor pressure data published by Andon et al (1960) and in the case of aniline we used the Fig. 4.…”