Solid−Liquid Equilibria under High Pressure of Eight Pure<i>n</i>-Alkylcyclohexanes

Milhet, Michel; Pauly, Jérôme; Coutinho, João A. P.; Daridon, Jean-Luc

doi:10.1021/je600575r

Cited by 6 publications

(11 citation statements)

References 40 publications

(65 reference statements)

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“…The difference between both values is 1.7 K, which is higher than experimental uncertainty. On the other hand, no metastable solid phase was detected by Milhet et al [34] for dodecylcyclohexane, although the heating thermograms presented in Fig. 1 show evidence of other transitions that may be associated to polymorphism.…”

Section: Resultsmentioning

confidence: 71%

“…Other literature data for the melting point of dodecylcyclohexane show high discrepancies as well: 282.3 K [35], 285 K [36] and 285.8 K (for the triple point) [37]. As Milhet et al [34] point out, dodecylcyclohexane and other naphthenes are difficult to crystallize as they may present high degree of sub-cooling: for dodecylcyclohexane, according to the thermograms presented in Fig. 1, we estimated the difference in temperature of crystallization and melting as approximately 22 K. These kinetic effects may account for the discrepancies found in the value of the melting temperature.…”

Section: Resultsmentioning

confidence: 93%

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Solid-liquid equilibrium of binary and ternary systems formed by ethyl laurate, ethyl palmitate and dodecylcylohexane: Experimental data and thermodynamic modeling

Robustillo

Meirelles

Filho

2016

Fluid Phase Equilibria

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a b s t r a c tThe solideliquid equilibrium diagrams of binary and ternary mixtures formed by dodecylcyclohexane and the fatty acid esters ethyl laurate and ethyl palmitate was determined herein. The liquidus and solidus lines were obtained through differential scanning calorimetry. The thermograms of pure compounds were resolved into the corresponding overlapping peak components by a fitting analysis, allowing a better estimation of phase-change properties of polymorphs. All binary systems show immiscibility in the solid phase, although those containing dodecylcyclohexane present small regions of partial miscibility. The system formed by ethyl palmitate and dodecylcyclohexane presents a peritectic transition, which was also observed in the ternary system. The thermodynamic modeling was conducted using different models for liquid-phase non-ideality and considering different polymorphs in solid phase. The modeling shows that a probable inversion of polymorphs relative stability occurs for the binary system formed by ethyl laurate and dodecylcyclohexane. The results from this work may contribute to enhancing the understanding and description of the complex behavior of biodiesel/diesel mixtures at low temperatures.

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Section: Resultsmentioning

confidence: 71%

Section: Resultsmentioning

confidence: 93%

Solid-liquid equilibrium of binary and ternary systems formed by ethyl laurate, ethyl palmitate and dodecylcylohexane: Experimental data and thermodynamic modeling

Robustillo

Meirelles

Filho

2016

Fluid Phase Equilibria

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“…The classical amphiphilic nature of fatty acids is such that they adopt organised supramolecular assemblies in the solid state or on the surface of water supported by hydrogen bonding of the carboxylate head groups and van der Waals interactions of the aliphatic chains, typical of lipid membranes. 25 In the solid state such arrangements can be interdigitated to form a repeat monolayer or the molecules can arrange head to head and form bilayers. On water, the carboxylate head groups associate with the aqueous subphase and chains aggregate into monolayer or bilayer assemblies, a process that can be monitored in a Langmuir trough through pressure area isotherm analysis.…”

Section: Resultsmentioning

confidence: 99%

Supramolecular packing of alkyl substituted Janus face all-cis 2,3,4,5,6-pentafluorocyclohexyl motifs

et al. 2021

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“…Finally, Milhet et al used DSC to observe the melting behavior of n-alkyl cyclohexanes. Their observations revealed that melting temperature increases as chain length increases, but that odd carbon length chains behaved differently from even carbon length chains (Milhet et al, 2007). Adding an extra CH2 to an alkyl chain with an odd number of carbons increased the melting temperature more than if a CH2 was added to an alkyl chain length with an even number of carbons.…”

Section: Monosubstituted Linear Cycloalkanementioning

confidence: 99%

Building Structure-Property Relationships of Cycloalkanes in Support of Their Use in Sustainable Aviation Fuels

et al. 2022

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In 2018 13.7 EJ of fuel were consumed by the global commercial aviation industry. Worldwide, demand will increase into the foreseeable future. Developing Sustainable Aviation Fuels (SAFs), with decreased CO2 and soot emissions, will be pivotal to the on-going mitigation efforts against global warming. Minimizing aromatics in aviation fuel is desirable because of the high propensity of aromatics to produce soot during combustion. Because aromatics cause o-rings to swell, they are important for maintaining engine seals, and must be present in at least 8 vol% under ASTM-D7566. Recently, cycloalkanes have been shown to exhibit some o-ring swelling behavior, possibly making them an attractive substitute to decrease the aromatic content of aviation fuel. Cycloalkanes must meet specifications for a number of other physical properties to be compatible with jet fuel, and these properties can vary greatly with the cycloalkane chemical structure, making their selection difficult. Building a database of structure-property relationships (SPR) for cycloalkanes greatly facilitates their furthered inclusion into aviation fuels. The work presented in this paper develops SPRs by building a data set that includes physical properties important to the aviation industry. The physical properties considered are energy density, specific energy, melting point, density, flashpoint, the Hansen solubility parameter, and the yield sooting index (YSI). Further, our data set includes cycloalkanes drawn from the following structural groups: fused cycloalkanes, n-alkylcycloalkanes, branched cycloalkanes, multiple substituted cycloalkanes, and cycloalkanes with different ring sizes. In addition, a select number of cycloalkanes are blended into Jet-A fuel (POSF-10325) at 10 and 30 wt%. Comparison of neat and blended physical properties are presented. One major finding is that ring expanded systems, those with more than six carbons, have excellent potential for inclusion in SAFs. Our data also indicate that polysubstituted cycloalkanes have higher YSI values.

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Solid−Liquid Equilibria under High Pressure of Eight Puren-Alkylcyclohexanes

Cited by 6 publications

References 40 publications

Solid-liquid equilibrium of binary and ternary systems formed by ethyl laurate, ethyl palmitate and dodecylcylohexane: Experimental data and thermodynamic modeling

Solid-liquid equilibrium of binary and ternary systems formed by ethyl laurate, ethyl palmitate and dodecylcylohexane: Experimental data and thermodynamic modeling

Supramolecular packing of alkyl substituted Janus face all-cis 2,3,4,5,6-pentafluorocyclohexyl motifs

Building Structure-Property Relationships of Cycloalkanes in Support of Their Use in Sustainable Aviation Fuels

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