Enthalpies of Vaporization of Organic Compounds. VII. Some Carboxylic Acids.

Konicek, Jiri; Wadsö, Ingemar; Munch‐Petersen, Jon; Ohlson, Ragnar; Shimizu, Akira

doi:10.3891/acta.chem.scand.24-2612

Cited by 39 publications

(45 citation statements)

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“…Therefore the experimental vaporization and sublimation enthalpies for these materials reported in this and previous publications [1] are not state properties and should not be used in adjusting heats of formation data or in any other thermochemical cycle without appropriate adjustments for the equilibrium observed in the gas phase as reported previously for the mono-carboxylic acids [13]. The vaporization enthalpies of the smaller homologues are for the most part consistent with previous literature results on sublimation enthalpies.…”

Section: Discussionsupporting

confidence: 87%

Vaporization, fusion and sublimation enthalpies of the dicarboxylic acids from C4 to C14 and C16

Roux

Temprado

Chickos

2005

The Journal of Chemical Thermodynamics

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Section: Discussionsupporting

confidence: 87%

Vaporization, fusion and sublimation enthalpies of the dicarboxylic acids from C4 to C14 and C16

Roux

Temprado

Chickos

2005

The Journal of Chemical Thermodynamics

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“…Use of ΔS vap = 0.025 cal/(mol K) yields a liquid heat of formation that is 2 kcal/mol too positive as compared to experiment. 61,72 The calculated gas-phase heat of formation of succinic acid is in good agreement with the experiment to within 1 kcal/mol. 47,59 For the trans-n-pentenoic acids, estimated values of ΔS vap are 0.034, 0.031, and 0.032 cal/(mol K) for n = 2, 3, and 4, respectively.…”

Section: ' Results and Discussionsupporting

confidence: 52%

Prediction of the Thermodynamic Properties of Key Products and Intermediates from Biomass

2011

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The high-level G3MP2 computational chemistry method was used to predict the thermodynamic properties of a wide range of compounds relevant to the conversion of biomass-derived oxygenated feedstocks into fuels or chemical feedstocks. The starting compounds were glucose, 5-hydroxy-methyl furfural, sorbitol, levulinic acid, succinic acid, γ-valerolactone, and glycerol. The calculated G3MP2 gas-phase heats of formation were mostly within ±2 kcal/mol of the available experimental values. Heats of formation of the liquid were obtained from calculations of the boiling point combined with the rule of Pictet and Trouton using modified values for ΔS vap. The modified values for ΔS vap arise because of the presence of intermolecular hydrogen bonding, ΔS vap = 0.031 cal/(mol K) for carboxylic acids, 0.035 cal/(mol K) for dialcohols, and 0.040 cal/(mol K) for higher polyalcohols. The thermodynamics of a wide range of reactions were predicted. Reaction energies in the aqueous phase at 298 K were estimated from self-consistent reaction field calculations of the solvation energy using the COSMO parametrization. Most of the reactions were exothermic, and the reaction products were stabilized by aqueous solvation. Exceptions include dehydrogenation, decarbonylation, ring-opening, and dehydration reactions when only one mole of water is eliminated.

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“…results (Verevkin et al, 2000) at 298.15 K for the ethanoic [∆ l g H°m ) (42.43 ( 0.83) kJ‚mol -1 ] and propanoic [∆ l g H°m ) (51.40 ( 0.38) kJ‚mol -1 ] acids from transpiration shows the clear disagreement with those from Konicek and Wadsö (1970); see Table 2 (column 11). Following, the vapor phase contains associated molecules of acid in the transpiration experiments on both compounds.…”

Section: Comparison Of the ∆ L G H°m Values Obtained By Transpirationmentioning

confidence: 98%

“…It is not possible to assess the degree of dimerization of the vapor phase in the transpiration experiments quantitatively. But, the enthalpies of vaporization obtained from calorimetry (Konicek and Wadsö, 1970) and corrected to the process RCOOH(liquid, 298.15 K) S RCOOH(gas, monomer, 298.15 K) using data for dimerization enthalpies could be used as a criterion of the correctness of the enthalpies of vaporization measured by the transpiration method for lower carboxylic acids. Comparison of our a Derived from the transpiration in this work (see Table 1).…”

Section: Comparison Of the ∆ L G H°m Values Obtained By Transpirationmentioning

confidence: 99%

Measurement and Prediction of the Monocarboxylic Acids Thermochemical Properties

Verevkin

2000

J. Chem. Eng. Data

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The standard molar enthalpies of vaporization ∆ l g H°m or sublimation ∆ cr g H°m of 2-methylpropanoic, butanoic, 2-methylbutanoic, 3-methylbutanoic, pentanoic, 2,2-dimethylpropanoic, 3,3-dimethylbutanoic, hexanoic, heptanoic, and octanoic acids were measured by the transpiration method. The enthalpies of vaporization ∆ l g H°m of ethanoic, propanoic, 2-methylpropanoic, and butanoic acids were measured using correlation gas chromatography. The enthalpies of the phase transitions of 2,2-dimethylpropanoic acid were measured using differential scanning calorimetry. The values of ∆ l g H°m of the compounds studied were taken as a basis for the development of a group-additivity predictive scheme. The standard molar enthalpies of formation ∆ f H°m(g) at the temperature T ) 298.15 K of monocarboxylic acids were derived using the data for ∆ f H°m(l or cr) from the literature and the present results for the enthalpies of vaporization or sublimation. The improved group-contribution method was used for the estimation of the gaseous enthalpies of formation of monocarboxylic acids.

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Enthalpies of Vaporization of Organic Compounds. VII. Some Carboxylic Acids.

Cited by 39 publications

References 0 publications

Vaporization, fusion and sublimation enthalpies of the dicarboxylic acids from C4 to C14 and C16

Vaporization, fusion and sublimation enthalpies of the dicarboxylic acids from C4 to C14 and C16

Prediction of the Thermodynamic Properties of Key Products and Intermediates from Biomass

Measurement and Prediction of the Monocarboxylic Acids Thermochemical Properties

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