An Examination of the Thermodynamics of Fusion, Vaporization, and Sublimation of Several Parabens by Correlation Gas Chromatography

Umnahanant, Patamaporn; Chickos, James S.

doi:10.1002/jps.22423

Cited by 19 publications

(6 citation statements)

References 23 publications

(20 reference statements)

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“…However, as discussed in Section 3.1, the reason for this discrepancy lies in the few incorrect pressures that Kahlbaum measured at the lower and upper temperatures. It should also be noted that the enthalpies of vaporisation derived for this compound by correlation with gas chromatography [29][30][31] are systematically somewhat higher than those determined by conventional methods. The reason for this discrepancy is that the correlations made in these papers are based on the data set of alkyl parabens by Perlovich et al 33 However, as shown in our earlier work, 22 this data set is in conflict with other data available for alkyl parabens.…”

Section: Pccp Papermentioning

confidence: 81%

Experimental and computational thermochemistry: how strong is the intramolecular hydrogen bond in alkyl 2-hydroxybenzoates (salicylates)

Verevkin¹,

Portnova²,

Emel´yanenko³

et al. 2023

Phys. Chem. Chem. Phys.

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Section: Pccp Papermentioning

confidence: 81%

Experimental and computational thermochemistry: how strong is the intramolecular hydrogen bond in alkyl 2-hydroxybenzoates (salicylates)

Verevkin¹,

Portnova²,

Emel´yanenko³

et al. 2023

Phys. Chem. Chem. Phys.

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“…In the cream mixture, the liquid vapor pressure is necessary to calculate relative fugacity. Since BP is a solid at 32 °C, the relative fugacity is corrected by the ratio of the predicted liquid and solid phase vapor pressures, P v ,BP,liquid and P v ,BP,solid : where, R is the gas constant (8.314 J/mol K), and the enthalpy of fusion, Δ H fus (26.3 kJ/mol) and melting point temperature T mp (340 K) are taken from Umnahant & Chickos …”

Section: Methodsmentioning

confidence: 99%

“…R is the gas constant (8.314 J/mol K), and the enthalpy of fusion, ΔH fus (26.3 kJ/mol) and melting point temperature T mp (340 K) are taken from Umnahant & Chickos. 70 2.4. Relative Fugacity Based on Raoult's Law.…”

Section: Introductionmentioning

confidence: 99%

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Predicting Transdermal Uptake of Phthalates and a Paraben from Cosmetic Cream Using the Measured Fugacity

Eftekhari

Frederiksen

Andersson

et al. 2020

Environ. Sci. Technol.

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Transdermal uptake models compliment in vitro and in vivo experiments in assessing risk of environmental exposures to semi-volatile organic compounds (SVOCs). A key parameter for mechanistic models is a chemical driving force for mass transfer from environmental media to human skin. In this research, we measure this driving force in the form of fugacity for chemicals in cosmetic cream and use it to model uptake from cosmetics as a surrogate for condensed environmental media. A simple cosmetic cream, containing no target analytes, was mixed with diethylphthalate (DEP), di-n-butylphthalate (DnBP), and butyl paraben (BP) and diluted to make creams with concentrations ranging from 0.025% to 6%. The fugacity, relative to the pure compound, was measured using solid-phase micro extraction (SPME). We found that the relationship between the concentration and fugacity is highly non-linear. The relative fugacity of Page 1 of 43 ACS Paragon Plus Environment Environmental Science & Technology 2 the chemicals for a 2% w/w formulation was used in a diffusion-based model to predict transdermal uptake of each chemical and compared with excretion data from a prior human subject study with the same formulation. Dynamic simulations of excretion are generally consistent with the results of the human subject experiment but sensitive to the input parameters, especially the time between cream application and showering.

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“…The result for p-fluoroanisole is reassuring since it suggests that the combination of two functional groups, an ether oxygen and a fluorine substituent, both previously demonstrated to correlate individually with hydrocarbons, continue to due so when used in combination. 6,23,24 The agreement observed between these results and the literature values suggests that it may be possible to obtain good correlations with other partially fluorinated aromatic ethers and hydrocarbons. Results for the fully fluorinated aromatic compounds investigated clearly indicate that these compounds do not correlate either with hydrocarbons or with themselves.…”

Section: Table 4 Literature Vaporization Enthalpies Of Some Fluorocar...mentioning

confidence: 99%

Applications of Correlation Gas Chromatography and Transpiration Studies for the Evaluation of the Vaporization and Sublimation Enthalpies of Some Perfluorinated Hydrocarbons

et al. 2012

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The fusion, vaporization, and sublimation enthalpies of a series of perfluorinated alkanes have been measured by combining measurements obtained by differential scanning calorimetry (DSC), transpiration, and correlation-gas chromatography and comparing the results to available data in the literature. Additionally, experiments are reported to provide a guide in identifying appropriate structural features of fluorinated compounds suitable for use as standards in correlation gas chromatography measurements. Fusion enthalpies and fusion temperatures by DSC for the following compounds were measured (in kJ•mol −1 ; K): decafluorobiphenyl (20.5 ± 0.6, 339.6), perfluorododecane (24.2 ± 0.6, 346.6), perfluorotridecane (27.9 ± 0.4, 361.7), perfluorotetradecane (31.5 ± 0.3, 375.6), perfluoropentadecane (35.1 ± 0.2, 388.1), perfluorohexadecane (38.7 ± 0.1, 399.7), perfluoroeicosane (50.3 ± 0.3, 436.2), and perfluorotetracosane (63.2 ± 0.6, 461.1). Sublimation enthalpies for the following compounds were measured by transpiration (in kJ•mol −1 ; T = 298.15 K): perfluorododecane (85.8 ± 0.6), perfluorotridecane (94.3 ± 0.5), perfluorotetradecane (102.4 ± 1.0), and perfluoropentadecane (109.4 ± 0.4). Vaporization and sublimation enthalpies, respectively, were also evaluated for the following compounds (kJ•mol −1 ; T/K = 298.15): perfluorohexadecane (88.6 ± 4.0, 117.6 ± 4.9), perfluoroeicosane (113.7 ± 7.4, 148 ± 8.8), and perfluorotetracosane (141.4 ± 2.2, 168.3 ± 11.1). The measured vaporization enthalpies of the perfluorinated alkanes behave linearly as a function of the number of CF 2 groups similar to what is observed with n-alkanes. Correlation-gas chromatography experiments confirmed previous findings that hydrocarbons can be used as standards for compounds containing a few fluorine atoms but otherwise standards need to be chosen with similar fluorine substitution and functionality.

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An Examination of the Thermodynamics of Fusion, Vaporization, and Sublimation of Several Parabens by Correlation Gas Chromatography

Cited by 19 publications

References 23 publications

Experimental and computational thermochemistry: how strong is the intramolecular hydrogen bond in alkyl 2-hydroxybenzoates (salicylates)

Experimental and computational thermochemistry: how strong is the intramolecular hydrogen bond in alkyl 2-hydroxybenzoates (salicylates)

Predicting Transdermal Uptake of Phthalates and a Paraben from Cosmetic Cream Using the Measured Fugacity

Applications of Correlation Gas Chromatography and Transpiration Studies for the Evaluation of the Vaporization and Sublimation Enthalpies of Some Perfluorinated Hydrocarbons

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