Vapor Pressure and Its Temperature Dependence of 28 Organic Compounds: Cyclic Amines, Cyclic Ethers, and Cyclic and Open Chain Secondary Alcohols

Abstract

The vapor pressures p of 28 organic compounds were accurately measured by a static method in the temperatures range (273 to 323) K. These include cyclic amines (CH 2 ) n NH with n = 2−7, N-methylpyrrolidine, N-methylpiperidine, morpholine, N-methylmorpholine, piperazine, N-methylpiperazine, N,N′-dimethylpiperazine), cyclic ethers (tetrahydrofuran, 2-methyltetrahydrofuran, 2,5-dimethyltetrahydrofuran, tetrahydropyran, 1,3-dioxolan, 1,4-dioxan), cyclic and open-chain secondary alcohols (cyclopentanol, cyclohexanol, cycloheptanol, 2-butanol, 3-pentanol, 3-hexanol, 4-heptanol), as well as 2-methoxyethylamine and 3-methoxypropylamine. For six substances, no p data were already available in the literature at any temperature, and for another eight only one paper each was found. The parameters of the Antoine equation were determined to allow interpolation and extrapolation of the experimental results. The enthalpy of vaporization, Δ vap H, at 298.15 was obtained for each compound from the derivative dp/dT. For nine compounds, Δ vap H values had not been determined before. Either p and Δ vap H at 298.15 K for all substances considered were compared with available literature values. For p, the disagreement is less than 1% for 10 substances and (1 to 3) % for another 8 compounds; for Δ vap H, it is less than 1% with respect to 18 literature data, of which 10 are calorimetric. All these confirm the high precision of p measurements here reported.

Calculation of Five Thermodynamic Molecular Descriptors by Means of a General Computer Algorithm Based on the Group-Additivity Method: Standard Enthalpies of Vaporization, Sublimation and Solvation, and Entropy of Fusion of Ordinary Organic Molecules and Total Phase-Change Entropy of Liquid Crystals

“…Experimental data of vaporization enthalpies have essentially been extracted for this work from the large collection of Acree, Jr. and Chickos [ 8 ] and Chickos et al [ 10 , 11 , 12 , 13 , 14 ], supplemented by recent data from a number of further authors publishing experimental vaporization values of several acetophenones [ 23 ], aliphatic tertiary amines [ 24 ], azidomethyl- N -nitrooxazolidines [ 25 ], benzamides [ 26 ], benzocaine [ 27 ], bisabolol and menthol [ 28 ], crown ethers [ 29 ], N , N -dialkyl monoamides [ 30 ], fenpropidin and phencyclidine [ 31 ], flavors [ 32 ], long-chain fluorinated alcohols [ 33 ], whiskey- and metha-lactone [ 34 ], halogenated fluorenes [ 35 ], ibuprofen and naproxen [ 36 ], imidazo[1,2- a ]pyrazine and phthalazine [ 37 ], insect pheromones [ 38 ], morpholines [ 39 ], organo(thio)phosphates [ 40 ], dialkyl phthalates [ 41 ], nitrogen heteroaromatics [ 42 ], phenylimidazoles [ 43 ], 2-acetylthiophene [ 44 ], dicarboxylic n -pentyl esters [ 45 ], and cyclic amines, ethers and alcohols [ 46 ]. The result of the atom-group parameters, based on 3581 compounds, is summarized in Table 1 .…”

Calculation of Five Thermodynamic Molecular Descriptors by Means of a General Computer Algorithm Based on the Group-Additivity Method: Standard Enthalpies of Vaporization, Sublimation and Solvation, and Entropy of Fusion of ordinary Organic Molecules and Total Phase-Change Entropy of Liquid Crystals

“…Experimental data of vaporization enthalpies have essentially been extracted for this work from the large collection of W. E. Acree Jr. and J. S. Chickos [8] and J. S. Chickos et al [10][11][12][13][14], supplemented by recent data from a number of further authors publishing experimental vaporization values of several acetophenones [23], aliphatic tertiary amines [24], azidomethyl-N-nitro-oxazolidines [25], benzamides [26], benzocaine [27], bisabolol and menthol [28], crown ethers [29], N,N-dialkyl monoamides [30], fenpropidin and phencyclidine [31], flavors [32], long-chain fluorinated alcohols [33], whiskey-and methalactone [34], halogenated fluorenes [35], ibuprofen and naproxen [36], imidazo[1,2-a]pyrazine and phthalazine [37], insect pheromones [38], morpholines [39], organo(thio)phosphates [40], dialkyl phthalates [41], nitrogen heteroaromatics [42], phenylimidazoles [43], 2-acetylthiophene [44], dicarboxylic n-pentyl esters [45], and cyclic amines, ethers and alcohols [46]. The result of the atom-group parameters, resting on 3581 compounds, is summarized in Table 1.…”

Solubilities of gases in cycloethers. The solubility of 13 nonpolar gases in 2,5-dimethyltetrahydrofuran at 273.15 to 303.15 K and 101.32 kPa

“…The refractive index was measured and 20 used together to its gas GLC chromatogram as purity criteria. Also our density and vapour pressure measurements can be compared with the existing data of literature [18][19][20][21][22][23][24] (Table 2). A Zeiss refractometer with interchangeable thermostated prisms was used for refractive index measurements, with an standard uncertainty of ±0.0001.…”