Thermochemical and vapor pressure behavior of anthracene and brominated anthracene mixtures

Fu, Jinxia; Suuberg, Eric M.

doi:10.1016/j.fluid.2012.12.036

Cited by 3 publications

(3 citation statements)

References 40 publications

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“…It is known from Kitaigorodskii’s “geometrical approach” that the formation of solid solutions in mixed crystals is substantially influenced by the similarity of molecular size and shape as well as similar crystal packing of the components. ,− As it has been shown that DHAC and DHAN exhibit comparable molecular skeletons and isostructural crystallization behavior, it seemed appealing to determine and analyze the crystal structure of a DHAC/DHAN mixture. The received X-ray analysis of the crystalline DHAC/DHAN mixture confirmed the presence of a mixture (Table ).…”

Section: Resultsmentioning

confidence: 99%

Isostructural Crystallization Behavior of Dihydroanthracene and Dihydroacridine

Kupka

Schauerte

Merz

2014

Crystal Growth & Design

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The crystal packing motifs of acenes are usually built up by heringbone C−H•••π interactions; on the contrary, N-heteroacenes form C−H•••N contacts. In the case of dihydroazaacenes the molecular structure of a rigid aromatic system is interrupted by a flexible part. The influence of heterocyclic CH 2 /NH substitution on the crystallization behavior and crystal packing of 9,10-dihydroacridine (DHAC) and 9,10-dihydroanthracene (DHAN) as well as a 1:1 mixture of both compounds was investigated by differential scanning calorimetry (DSC) measurements, hot stage microscopy methods, and crystal structure determination.

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Section: Resultsmentioning

confidence: 99%

Isostructural Crystallization Behavior of Dihydroanthracene and Dihydroacridine

Kupka

Schauerte

Merz

2014

Crystal Growth & Design

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“…Thus, the reduced eq with only Δ H (H → Hal) could be recommended for reliable assessment of anthracenes vaporization enthalpies. In order to be more confident with this recommendation, we have involved an additional experimental data for 2-chloroanthracene, 2-bromoanthracene, and 1,5-dibromoanthracene reported recently (see Table ). As can be seen from this table the agreement of the experimental and estimated enthalpies of vaporization for these additional substituted anthracenes was also within the experimental uncertainties of (2 to 4) kJ·mol –1 proving the validity of the reduced eq .…”

Section: Discussionmentioning

confidence: 99%

Enthalpies of Vaporization and Sublimation of the Halogen-Substituted Aromatic Hydrocarbons at 298.15 K: Application of Solution Calorimetry Approach

et al. 2015

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Recently, the solution calorimetry has been shown to be a valuable tool for the indirect determination of vaporization or sublimation enthalpies of low volatile organic compounds. In this work we studied 16 halogen-substituted derivatives of benzene, naphthalene, biphenyl, and anthracene using a new solution calorimetry based approach. Enthalpies of solution at infinite dilution in benzene as well as molar refractions for the chlorine-, bromine-, and iodine-substituted aromatics were measured at 298.15 K. Vaporization and sublimation enthalpies of these compounds at 298.15 K were indirectly derived from the solution calorimetry data. In order to verify results obtained by using solution calorimetry, vaporization/sublimation enthalpies for 1,2-, 1,3-, 1,4-dibromobenzenes, 4-bromobiphenyl, and 4,4′-dibromobiphenyl were additionally measured by using the well established transpiration method. Experimental data available in the literature were collected and evaluated in this work for the sake of comparison with our own results. Vaporization and sublimation enthalpies of halogen-substituted aromatics under study derived by using solution calorimetry approach have been in a good agreement with those measured by conventional methods. This fact approves using of solution calorimetry for determination or validation of sublimation/vaporization enthalpies for different aromatic compounds at reference temperature 298.15 K, where the conventional experimental data are absent or in disarray. Evaluated in this work a data set has been used to establish a simple group additivity scheme for prediction of vaporization enthalpies for halogen-substituted aromatic hydrocarbons.

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“…So far, the GC-RT method has been used to determine subcooled liquid vapor pressures for PBDEs − and hexabromobenzene (HBB), whereas the vapor pressures of PBDEs, − HBCDs, HBB, tetrabromobisphenol A (TBBPA), , and 1,2-bis(2,4,6-tribromophenoxy)ethane (BTBPE) have been measured using either the Knudsen effusion ,, or the gas saturation method . As for other brominated aromatic compounds, the vapor pressures of polybrominated dibenzo- p -dioxins (PBDDs), derivatives of BFRs, and brominated aromatic compounds with fewer Br substituents − have also been measured using the Knudsen effusion method, ,− , gas saturation method, , or other static methods using a manometer. , Besides vapor pressures, water solubilities, 1-octanol/water partition coefficients, and Henry’s law constants of BFRs have also been measured or estimated, and we have previously reported experimentally determined properties other than vapor pressure for TBBPA, brominated phenols, brominated benzenes, and PBDEs …”

Section: Introductionmentioning

confidence: 99%

Measurement of Vapor Pressures and Melting Properties of Five Polybrominated Aromatic Flame Retardants

et al. 2018

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While vapor pressure is among the most important properties used in the environmental fate assessment of organic contaminants, measured vapor pressures exist only for a few representatives of the group of novel brominated flame retardants (BFRs). To expand on this limited set of data, the vapor pressures of five BFRs1,2,4,5,-tetrabromo-dimethylbenzene (TBX), 1,2,3,4,5-pentabromo-6-methyl-benzene (PBT), 1,2,3,4,5-pentabromo-6-ethyl-benzene (PBEB), 2,3,4,5,6-pentabromo-phenol (PBP), and 1,3,5-tribromo-2(2,3-dibromopropoxy)-benzene (TBP-DBPE)were measured in the temperature range 322.7–367.7 K with the gas saturation method. Enthalpies of sublimation or vaporization were determined from the slopes of semilogarithmic plots of measured vapor pressure against reciprocal temperature. The melting temperature and enthalpy of fusion were measured using differential scanning calorimetry. From these experimental data, the vapor pressures and subcooled liquid vapor pressures at 298.2 K, p i ° and p i °,sl, respectively, were derived and compared with values estimated using group contribution methods, polyparameter linear free energy relationships, as well as EPISuite, SPARC, and COSMOtherm. Depending on the method and compound, deviations between measured and estimated log(p i °) or log(p i °,sl) values ranged from 8 to 77% of the measured values. The gas/particle partitioning behavior of the five BFRs was estimated using the measured p i °,sl values and the Junge–Pankow model. This estimation could account for the observed partitioning behavior of PBT and TBP-DBPE.

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Thermochemical and vapor pressure behavior of anthracene and brominated anthracene mixtures

Cited by 3 publications

References 40 publications

Isostructural Crystallization Behavior of Dihydroanthracene and Dihydroacridine

Isostructural Crystallization Behavior of Dihydroanthracene and Dihydroacridine

Enthalpies of Vaporization and Sublimation of the Halogen-Substituted Aromatic Hydrocarbons at 298.15 K: Application of Solution Calorimetry Approach

Measurement of Vapor Pressures and Melting Properties of Five Polybrominated Aromatic Flame Retardants

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