ABSTRACT

Thermodynamic properties of 2-(1'-hydroxycyclohexyl)cyclohexanone (ketol) are reported. The investigated compound is a byproduct from the caprolactam manufacture. The heat capacity of ketol was measured by vacuum adiabatic calorimetry (T = 5 K to T = 310 K) and by differential scanning calorimetry (T = 294 K to T = 370 K). The fusion temperature Tfus = 306.75 K and the mole fraction of the ketol sample (x = 0.9982) were found by fractional melting analysis. The molar enthalpy of fusion fus = (20.81 +- 0.02) kJ*mol-1 was determined in the adiabatic calorimeter. The standard molar thermodynamic functions of ketol in the condensed state were obtained with the use of these calorimetric measurements. The standard molar enthalpy of combustion of ketol c(cr, 298.15 K) = -(6963.0 +- 1.8) kJ*mol-1 was found by bomb calorimetry, and the standard molar enthalpy of formation f(cr, 298.15 K) = -(597.6 +- 2.4) kJ*mol-1 was derived. The equilibrium of dimerization of cyclohexanone with ketol formation was investigated in the temperature range 294 K to 367 K. The equilibrium constants (Ka) were obtained at five temperatures, and the enthalpy of the reaction at the average temperature rHm(330.5 K) = -(34.4 +- 3.3) kJ*mol-1 was derived.

Compounds

#	Formula	Name
1	CO2	carbon dioxide
2	H2O	water
3	O2	oxygen
4	C6H10O	cyclohexanone
5	C12H20O2	1'-hydroxy-[1,1'-bicyclohexyl]-2-one

Datasets

The table above is generated from the ThermoML associated json file (link above). POMD and RXND refer to PureOrMixture and Reaction Datasets. The compound numbers are included in properties, variables, and phases, if specificied; the numbers refer to the table of compounds on the left.
Type	Compound-#	Property	Variable	Constraint	Phase	Method	#Points
POMD	5	Molar enthalpy of transition or fusion, kJ/mol ; Crystal			Crystal Liquid Gas	Adiabatic calorimetry	1
POMD	5	Molar enthalpy of transition or fusion, kJ/mol ; Crystal			Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	5	Triple point temperature, K ; Crystal			Crystal Liquid Gas	Adiabatic calorimetry	1
POMD	5	Triple point temperature, K ; Crystal			Crystal Liquid Air at 1 atmosphere	DSC	1
POMD	5	Mass density, kg/m3 ; Crystal	Temperature, K; Crystal Pressure, kPa; Crystal		Crystal	Pycnometric method	1
POMD	5	Molar heat capacity at constant pressure, J/K/mol ; Crystal	Temperature, K; Crystal	Pressure, kPa; Crystal	Crystal	VADIAC:UFactor:4	36
POMD	5	Molar heat capacity at constant pressure, J/K/mol ; Liquid	Temperature, K; Liquid	Pressure, kPa; Liquid	Liquid	Large sample (1 g) DSC	8
POMD	5	Molar heat capacity at saturation pressure, J/K/mol ; Crystal	Temperature, K; Crystal		Crystal Gas	VADIAC:UFactor:4	168
POMD	5	Molar heat capacity at saturation pressure, J/K/mol ; Liquid	Temperature, K; Liquid		Liquid Gas	VADIAC:UFactor:4	3
POMD	5	Molar enthalpy function {Hm(T)-Hm(0)}/T, J/K/mol ; Crystal	Temperature, K; Crystal	Pressure, kPa; Crystal	Crystal	VADIAC:UFactor:4	36
POMD	5	Molar enthalpy function {Hm(T)-Hm(0)}/T, J/K/mol ; Liquid	Temperature, K; Liquid	Pressure, kPa; Liquid	Liquid	Vacuum adiabatic calorimetry	2
POMD	5	Molar entropy, J/K/mol ; Crystal	Temperature, K; Crystal	Pressure, kPa; Crystal	Crystal	Vacuum adiabatic calorimetry	36
POMD	5	Molar entropy, J/K/mol ; Liquid	Temperature, K; Liquid	Pressure, kPa; Liquid	Liquid	VADIAC:UFactor:4	2
POMD	4 2 5	Liquid-liquid equilibrium temperature, K ; Liquid mixture 1	Solvent: Mole fraction - 5; Liquid mixture 1 Mole fraction - 2; Liquid mixture 1	Pressure, kPa; Liquid mixture 1	Liquid mixture 1 Liquid - 2	VISOBS	12
RXND	5 1 2 3	Specific internal energy of reaction at constant volume, J/g				Static bomb calorimetry	1
RXND	4 5	Equilibrium constant in terms of mole fraction				Chromatography	10

Thermodynamics Research Center / ThermoML | Journal of Chemical and Engineering Data

Thermodynamic Properties for 2-(1'-Hydroxycyclohexyl)cyclohexanone and Equilibrium of Dimerization of Cyclohexanone

Shevelyova, M. P.[Marina P.], Kabo, G. J., Blokhin, A. V.[Andrey V.], Kabo, A. G.[Andrey G.], Jursha, J. A.[Joseph A.], Rajko, A. A.[Anna A.]

ABSTRACT