Liquid–Liquid Equilibria for Systems Containing 4-Phenylbutan-2-one or Benzyl Ethanoate and Selected Alkanes

Abstract

Liquid-liquid equilibrium (LLE) phase diagrams have been determined, by means of the critical opalescence method with a laser scattering technique, for the mixtures 4phenylbutan-2-one + CH (CH) n CH (n = 10,12,14) and for benzyl ethanoate + CH 3 (CH 2) n CH 3 (n = 12,14). The systems are characterized by having an upper critical solution temperature (UCST), which increases with n. The corresponding LLE curves show a rather horizontal top and become skewed towards higher mole fractions of the polar compound when n is increased. Calorimetric and LLE measurements show that, for mixtures with molecules with a given functional group, interactions between aromatic molecules are stronger than those between homomorphic linear molecules (aromaticity effect). This has been ascribed to proximity effects arising from the presence of the polar group and the aromatic ring within the same molecule. Proximity effects become weaker in the sequence: 1-phenylpropan-2-one > 4-phenylbutan-2one > 1-phenylethanone, and are more important in benzyl ethanoate than in ethyl benzoate molecules. Values of the critical compositions and temperatures calculated with the DISQUAC group contribution model are in good agreement with the experimental results. Accordingly, the shape of the LLE curves is also correctly described by DISQUAC.

Liquid–Liquid Equilibria for 2-Phenylethan-1-ol + Alkane Systems

“…Experimental results determined in this work, the directly measured liquid–liquid equilibrium temperatures, T , versus x 1 , the mole fraction of 2-PhEtOH, for the systems with n -C 8 , n -C 10 , n -C 12 , n -C 14 , or 2,2,4,-trimethylpentane, are collected in Table (Figure ). As in many systems previously investigated, ,− ,,− the LLE curves of the present mixtures are characterized by some typical features: (i) they show a rather flat maximum (Figure ); (ii) the curves become progressively skewed toward higher x 1 values when the chain length of the alkane is increased (Figure ); (iii) the upper critical solution temperature, UCST increases with the number of C atoms of the n -alkane (Table ).…”

“…Lines are only for the aid of the eye. For experimental data, see 3-phenylpropionitrile, 2-phenylethanol (this work), 1-phenylpropan-2-one (phenylacetone), benzylethanoate, , 2-phenoxyethanol …”

“…These effects are intramolecular effects and lead to interactions between the phenyl ring and the X group which are substantially different from those between the mentioned groups when they belong to different molecules . In this framework, we have investigated mixtures including aromatic amines − (anilines, 2-amino-1-methylbenzene, 1-phenylmethanamine (benzylamine), 1 H -pyrrole, quinoline or imizadoles), aromatic alkanals, ketones, or alkanoates, ,− and aromatic nitriles, 2-phenoxyethanol, or aromatic alkanols (phenol or phenylmethanol). , As continuation, we provide now liquid–liquid (LLE) measurements for binary systems formed by 2-phenylethan-1-ol (2-phenylethanol, 2PhEtOH) and octane, decane, dodecane, tetradecane, or 2,2,4-trimethylpentane.…”

Thermodynamics of mixtures containing aromatic nitriles

“…We are engaged in a systematic research on proximity effects between the phenyl group C 6 H 5 − and a polar group as carbonyl, aldehyde, alkanoate, amine, alkanol or oxygen. At this end, we have provided LLE measurements for systems formed by one alkane and a polar aromatic compound such as: C 6 H 5 − (CH 2 ) n-1 COCH 3 (n =1,2,3) [8][9][10]; C 6 H 5 − CHO [11]; C 6 H 5 − CH 2 COOCH 3 [9,10] C 6 H 5 − CH 2 NH 2 [12]; C 6 H 5 − CH 2 OH [13], or C 6 H 5 − O − CH 2 CH 2 OH [14]. These data together with measurements available in the literature on VLE or E m H for these or related compounds, aniline or phenol, e.g., have been employed for the characterization of aromatic polar compound + organic solvent mixtures [8][9][10][11][12][13][14][15][16] in terms of the DISQUAC group contribution model [17].…”