Estimation des enthalpies de vaporisation des composes organiques liquides. Partie 1. Applications aux alcanes, cycloalcanes, alcenes, hydrocarbures benzeniques, alcools, alcanes thiols, chloro et bromoalcanes, nitriles, esters, acides et aldehydes

Ducros, M.; Gruson, J. F.; Sannier, H.

doi:10.1016/0040-6031(80)80109-2

Cited by 82 publications

(11 citation statements)

References 33 publications

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“…b Value estimated by group additivity contributions of ref . c Extrapolated using group additivity values of ref . In the case of undecanol, the value of 19.6 kcal/mol is clearly out of line with the extrapolation from the experimental values and tends to favor ref .…”

Section: Introductionmentioning

confidence: 98%

Some Observations on the Structures of Liquid Alcohols and Their Heats of Vaporization

Benson

1996

J. Am. Chem. Soc.

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From comparisons of the differences in heats of vaporization of alcohols (ROH) and their analogous hydrocarbons (RCH3) which turned out to be 6.1 ± 0.1 kcal/mol at 298 K it was concluded that this difference represents the contribution of the hydrogen bond to the value of ΔH vap(alcohol, 298 K). It is further concluded that alcohols are self associated in pure liquids in cyclic clusters each of four alcohols. These conclusions are supported by extensive, earlier studies of PVT relations in vapors, heat capacities, and IR spectra in solutions. Group additivity tables of Ducros et al. are shown to be in excellent agreement with directly measured ΔH vap(298 K) for both alcohols and alkanes. Similar analysis of amines shows a much weaker H-bond with a lower limit of about 2.2 kcal/mol between amines so that amines exist mostly as monomers. Scattered data on diols of lesser accuracy suggest compact sandwich structures with the hydrocarbon tying together two cyclic tetramer rings of H-bonded oxygen atoms.

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Section: Introductionmentioning

confidence: 98%

Some Observations on the Structures of Liquid Alcohols and Their Heats of Vaporization

Benson

1996

J. Am. Chem. Soc.

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“…However, the models proposed by Ducros et al [32,33], Guthrie and Taylor [36], Chickos et al [28], Domalski and Hearing [165] , Constantinou and Gani [29], and Kolská et al [37] predicts the dataset with an %AARD of 7%, 10.6%, 4.6%, 6.4%, 5.5%, 4.1% respectively. Therfore, the model predict the vaporization enthalpies of the selected 83 compounds better than these previous models.…”

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confidence: 99%

A group contribution model for determining the vaporization enthalpy of organic compounds at the standard reference temperature of 298K

Gharagheizi

Ilani-Kashkouli

Acree

et al. 2013

Fluid Phase Equilibria

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A group contribution model for determining the vaporization enthalpy of organic compounds at the standard reference temperature of 298 K, Fluid Phase Equilibria (2013), http://dx.doi.org/10. 1016/j.fluid.2013.09.021 This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. , recently published a comprehensive compilation of phase change enthalpies, including vaporization enthalpies of pure organic and organometallic compounds. This collection of vaporization enthalpies for 2811 compounds at the standard temperature of 298.15 K was used in this study for the development of a predictive model. The compounds in the collection are composed of a combination of the following atoms, viz. carbon, hydrogen, nitrogen, oxygen, phosphorous, sulfur, fluorine, chlorine, bromine, and iodine. This paper presents a reliable group contribution model for the prediction of the vaporization enthalpies of organic compounds. The group contribution model developed is able to predict the standard molar enthalpies of vaporization to within an average absolute relative deviation of 3.7%, which is of sufficient accuracy for many practical applications in chemical and petrochemical engineering.

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“…Table contains some of the group additivity values of Ducros et al − for estimating Δ vap H °(298) for the compound in Table together with the modified values selected by the author and used here.…”

Section: Heat Of Formation and Entropy Of Liquids At Their Boiling Po...mentioning

confidence: 99%

“…Group additivity provides great facility in estimating the thermochemistry of gas-phase reactions for species whose thermochemistry has not been measured. , To have equal facility in dealing with the much larger realm of condensed phase reactions it is important to have methods for evaluating the relevant thermochemistry of species in the liquid state. A major step in this direction was taken by Ducros and co-workers − who showed that group additivity could be used to estimate heats of vaporization of organic and metal organic compounds at 298 K with good precision. This made possible the evaluation of Δ f H ° 298 ( l ) for those compounds for which gas-phase group values were available.…”

Section: Introductionmentioning

confidence: 99%

New Methods for Estimating the Heats of Formation, Heat Capacities, and Entropies of Liquids and Gases

Benson

1999

J. Phys. Chem. A

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Using group additivity values to estimate Δvap H°(298) and the Kistiakowsky equation to estimate both Δvap S°(T b) and Δvap H°(T b) at the boiling point (T b), it is shown how an average value of Δvap C p° can be obtained which can then be used to calculate values of Δvap S°(298). This latter can then be used in conjunction with S°(g,298) to calculate S°(l,298). Alternatively, where values of S°(l,298) are available but not S°(g,298) the latter can be calculated. The method applies to regular liquids, even those with relatively large dipoles but not to H-bonded liquids. The accuracy of estimated values of S°(l,298) are 0.45 ± 0.16 cal/(mol K) with a maximum deviation of 1.0 cal/(mol K) for an assortment of 14 selected compounds and 0.3 ± 0.12 for another 17 liquids for which groups are not available but Δvap H°(298) and Δvap S°(298) are. Here the largest deviation is 1.9 cal/(mol K). Calculated values of C p°(l,298) are much less accurate, ±3 cal/(mol K) with a maximum deviation of 9.0 cal/(mol K). It is also shown that the best average value of C p° to use in calculating changes in ΔH° and ΔS° in a specified temperature interval, T 1 to T 2, is the arithmetic mean of the initial and final values, [C p°(T 1) + C p°(T 2)]/2. Changes are recommended in some of the group values for calculating Δvap H°(298) and also in the group O−(C)2 for calculating gas-phase entropies of ethers and for N−(C)2(H) for calculating entropies of secondary amines.

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Estimation des enthalpies de vaporisation des composes organiques liquides. Partie 1. Applications aux alcanes, cycloalcanes, alcenes, hydrocarbures benzeniques, alcools, alcanes thiols, chloro et bromoalcanes, nitriles, esters, acides et aldehydes

Cited by 82 publications

References 33 publications

Some Observations on the Structures of Liquid Alcohols and Their Heats of Vaporization

Some Observations on the Structures of Liquid Alcohols and Their Heats of Vaporization

A group contribution model for determining the vaporization enthalpy of organic compounds at the standard reference temperature of 298K

New Methods for Estimating the Heats of Formation, Heat Capacities, and Entropies of Liquids and Gases

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