Association and vapor pressure isotope effect of variously deuterated methanols in n-hexane

Wolff, H.; Bauer, Oliver; Goetz, R.; Landeck, Heiner; Schiller, Otto; Schimpf, L.

doi:10.1021/j100543a010

Cited by 26 publications

(4 citation statements)

References 3 publications

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“…The 1-decene/DEA VLE was measured at 25 kPa in the temperature range from 300.5 to 309.4 K and at 30 kPa in the temperature range from 296.8 to 301.6 K (Table ). Again, the determined vapor pressure of pure DEA (30 kPa at 296.8 K) perfectly agrees with available literature data, as can be seen in Figure S8 in the Supporting Information. Using the same temperature-independent k ij (Table ) for both pressures allows a very accurate description of the experimental data with an ARD of 0.36% (Figure ).…”

Section: Resultssupporting

confidence: 87%

Phase Equilibria for the Hydroaminomethylation of 1-Decene

et al. 2021

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This work focuses on the measuring and modeling of phase equilibria of interest for the hydroaminomethylation of 1-decene with syngas (CO/H2) and diethylamine to N,N-diethylundecan-1-amine and water in a solvent system of methanol and n-dodecane. H2 solubilities were measured in undecanal and N,N-dimethyldodecan-1-amine at 343 and 363 K between 2 and 4 MPa via the isochoric saturation method. Vapor–Liquid equilibrium data were measured for the binary systems methanol/N,N-diethylundecan-1-amine, 1-decene/diethylamine, and 1-decene/N,N-diethylundecan-1-amine at temperatures between 299 and 372 K and at pressures of 0.005, 0.018, 0.025, or 0.030 MPa. Liquid–Liquid equilibria were measured in the ternary systems methanol/n-dodecane/diethylamine, methanol/n-dodecane/undecanal, and methanol/n-dodecane/N,N-diethylundecan-1-amine at 0.1 MPa and at temperatures ranging from 278.15 to 308.15 K. Measured and available phase-equilibrium data from literature were modeled using perturbed-chain polar statistical associating fluid theory. This then allowed for modeling the Henry’s law constant for H2 and CO in the liquid components (methanol, n-dodecane, 1-decene, diethylamine, undecanal, N,N-diethylundecan-1-amine, and water) at 373.15 and 393.15 K.

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Section: Resultssupporting

confidence: 87%

Phase Equilibria for the Hydroaminomethylation of 1-Decene

et al. 2021

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“…Using their results, we previously confirmed the validity of our results for the Kd's of carboxylic acids9 by using the equations of Schrier et al20 It should be mentioned here that the isotope effects on hydrogen bonding are usually quite small, probably because of the compensation of lowering stretching frequencies on formation of hydrogen bonds by an increase in resistance to bending motion, leading to a near equivalence of binding at the hydrogenic site between hydrogen-bonded and free species. 21,22 Similar to the results in Figure 3, Kd values of GAD and PTC AD in D20 were smaller than those of acetic acid-di and propionic acid-di, and Kd values for polymers did not depend much on molecular weights (Afw = 1000, 2000, (•) propionic acid-di (data from ref 9), (©) glutaric acid-d2, (O) 1,3,5-pentanetricarboxylic acid, ( ) polyacrylic acid (Af, = 1000), ( ) polyacrylic acid (Afw = 2000), (o) polyacrylic acid (Afw = 90 000). The abscissa shows the molar fraction of the carboxylic group of each acid and not that of the molecules.…”

Section: Resultsmentioning

confidence: 99%

Raman spectroscopic study of hydrogen bonding in aqueous carboxylic acid solutions. 3. Polyacrylic acid

Tanaka¹,

Kitano²,

Ise³

1991

Macromolecules

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“…The isotope effect on thermodynamic properties has been well-known for a long time. [28][29][30][31][32][33][34][35][36] For example, Jancso and Van Hook 32 reviewed vapor pressure isotope effects in 1974. A simple momentum effect due to the mass differences predicts that the light isotope should always have the higher vapor pressure.…”

Section: Discussionmentioning

confidence: 99%

“…The isotope effect on thermodynamic properties has been well-known for a long time. − For example, Jancso and Van Hook 32 reviewed vapor pressure isotope effects in 1974. A simple momentum effect due to the mass differences predicts that the light isotope should always have the higher vapor pressure. , However, numerous cases of polyatomic molecules are known to be opposite or to have crossover phenomena at certain temperatures .…”

Section: Discussionmentioning

confidence: 99%

Phase Equilibria of Hydrofluorocarbon-4310mee Mixtures with Ionic Liquids: Miscibility of threo- and erythro-Diastereomers in Ionic Liquids

Shiflett

Yokozeki

2008

Ind. Eng. Chem. Res.

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Solubilities of hydrofluorocarbon-4310mee (threo-2,3-dihydrodecafluoropentane and erythro-2,3-dihydrodecafluoropentane) as well as their deuterated species in room-temperature ionic liquids (RTILs) have been studied. RTILs used here are 1-butyl-3-methylimidazolium hexafluorophosphate, [bmim][PF6], 1-butyl-3-methylimidazolium tetrafluoroborate, [bmim][BF4], and 1-ethyl-3-methylimidazolium tetrafluoroborate, [emim][BF4]. All systems showed limited miscibility, and the liquid−liquid phase equilibria (LLE) have been investigated with the volumetric and cloud-point methods. It was found that the threo-isomer is more soluble than the erythro-isomer in the present RTILs, and the LLE curves of the threo-isomers in the RTILs possess lower critical solution temperatures (LCSTs). The deuterated isotope effect on the solubility was found to be minor, but the deuterated isomers did show slightly better miscibility than the nondeuterated isomers. This trend of the isotope effect is qualitatively consistent with the case of alcohol + RTIL mixtures in the literature, although the LLE behavior is different (LCSTs vs upper critical solution temperatures (UCSTs)).

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Association and vapor pressure isotope effect of variously deuterated methanols in n-hexane

Cited by 26 publications

References 3 publications

Phase Equilibria for the Hydroaminomethylation of 1-Decene

Phase Equilibria for the Hydroaminomethylation of 1-Decene

Raman spectroscopic study of hydrogen bonding in aqueous carboxylic acid solutions. 3. Polyacrylic acid

Phase Equilibria of Hydrofluorocarbon-4310mee Mixtures with Ionic Liquids: Miscibility of threo- and erythro-Diastereomers in Ionic Liquids

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