Maciej Zawadzki - Academia.edu (original) (raw)
Papers by Maciej Zawadzki
Journal of Solution Chemistry, 2021
In recent years, many compounds have been proposed as additives to conventional working fluids to... more In recent years, many compounds have been proposed as additives to conventional working fluids to improve the performance of the absorption refrigeration system. The main aim of this research is to show the influence of ionic liquid based additives on thermodynamic and physicochemical properties of {LiBr + water} solutions. The following additives: 3-(1-methyl-morpholinium)propane-1-sulfonate,N,N-di(2-hydroxyethyl)-N,N-dimethylammonium bromide, andN,N,N-tri(2-hydroxy-ethyl)-N-methylammonium bromide have been added to aqueous lithium bromide solutions (IL to LiBr mass fraction,w2 = 0.3). The physicochemical and thermodynamic properties of {LiBr (1) + additive (2) + water (3)} and {LiBr + water} systems including (vapor + liquid) phase equilibria (VLE), density (ρ) and dynamic viscosity (η) were determined over wide temperature and composition ranges. The conductor-like screening model for real solvents (COSMO-RS) was used for the VLE data prediction. For the density and dynamic visco...
The Journal of Chemical Thermodynamics, 2020
Abstract This work is an attempt to determine appropriate solvents for extractive desulfurization... more Abstract This work is an attempt to determine appropriate solvents for extractive desulfurization, which is the dominant alternative to the risky and expensive solution, which is hydrodesulfurization (HDS). The main part of this research is the study on (liquid + liquid) phase equilibria in {IL (1) + heptane, or thiophene, or 2-methylthiophene, or benzothiophene (2) binary systems and {IL (1) + thiophene/2-methylthiophene/benzothiophene (2) + heptane (3)} ternary system. In this work, five new synthesized tricyanomethanide – based ILs that is: N-(3-cyanopropyl)-N-methylmorpholinium tricyanomethanide, [Mo1,3CN][TCM], N-(3-hydroxypropyl)-N-methylmorpholinium tricyanomethanide, [Mo1,3OH][TCM], N-(3-cyanopropyl)pyridinium tricyanomethanide, [Py3CN][TCM], N-(3-hydroxypropyl)pyridinium tricyanomethanide, [Py3OH][TCM], N-(2-hydroxyethyl)pyridinium tricyanomethanide, [Py2OH][TCM] are analyzed as an extractant in desulfurization of model fuel. Based on the experimental ternary LLE data, the selectivity and solute distribution ratio are calculated and used to determine the efficiency of the tested ILs as solvents for the extraction of sulfur compounds from model fuel. The experimental results have been compared to literature data for other tricyanomethanide-based ILs and were discussed in terms of the selectivity and solute distribution ratio of separation of related systems. The NRTL equation was successfully used to correlate the LLE in binary systems as well as the experimental tie-lines.
Fluid Phase Equilibria, 2018
In this work a series of ammonium-and phosphonium-based zwitterions (ZIs) namely: 3-(triethylammo... more In this work a series of ammonium-and phosphonium-based zwitterions (ZIs) namely: 3-(triethylammonio)propane-1-sulfonate, N 222 C3S, 4-(triethylammonio)butane-1-sulfonate, N 222 C4S, 3-(tributylammonio)propane-1-sulfonate, N 444 C3S, 4-(tributylammonio)butane-1-sulfonate, N 444 C4S, 3-(trihexylammonio)propane-1-sulfonate, N 666 C3S, 4-(trihexyl-ammonio)butane-1-sulfonate, N 666 C4S, 3-(tributylphosphonio)propane-1-sulfonate, P 444 C3S and 4-(tributyl-phosphonio)butane-1-sulfonate, P 444 C4S have been synthesized. The structure and purity of these compounds were confirmed by 1 H NMR. The thermal properties such as temperature and enthalpy of (solid þ solid) phase transition as well as the melting temperature of pure ZIs were evaluated by DSC technique. The (solid þ liquid) and (liquid þ liquid) phase equilibria measurements have been performed for eight binary systems of synthesized ZIs and one purchased 3-(1-pyridinio)-1-propanesulfonate [PyC3S] using the dynamic method and the experimental results were correlated using NRTL equation. Additionally, ternary system of {N 666 C3S (1) þ N 444 C3S (2) þ water (3)} with three different N 666 C3S to N 444 C3S initial molar fractions was determined.
Fluid Phase Equilibria, 2019
In this work, thermodynamic and physicochemical properties including (vapor + liquid) equilibria ... more In this work, thermodynamic and physicochemical properties including (vapor + liquid) equilibria (VLE), density and dynamic viscosity of binary mixtures composed of bromidebased ionic liquid (IL) and water were measured as a function of IL mole fraction in a wide range of temperature. The aqueous solution of the following ILs: 1-ethyl-1methylpiperidinium bromide, ethylpyridinium bromide, 1-(2-hydroxyethyl)pyridinium bromide, 1-ethyl-1-methyl-morpholinium bromide, 1-hydroxyethyl-1-methylmorpholinium bromide, and N-ethyl-N,N-diN -hydroxyethylammonium bromide have been tested for potential applications as working fluids in absorption refrigeration technology. The isothermal VLE has been measured by an ebulliometric method within a temperature range from T = (338.15 to 368.15) K and pressure up to 85 kPa and correlated using Redlich-Kwong equation of state. This work is a continuation of our systematic investigation of an aqueous solution of ionic liquids as a potential working fluid in absorption refrigeration technology. The summary of this research is the modeling of the theoretical cycles using working fluids proposed in this paper. The calculated values of the coefficient of performance (COP) were compared to other ILs from available literature and {LiBr + water} system, conventionally used on the industrial scale in absorption refrigeration technology.
The Journal of Chemical Thermodynamics, 2018
The activity coefficients (c 1 13) at infinite dilution for 65 solutes and the effect of interact... more The activity coefficients (c 1 13) at infinite dilution for 65 solutes and the effect of interaction between organic solvents or water on the interfacial and bulk properties of 1,3-didecyl-2-methylimidazolium dicyanamide, [D 2 MIM][DCA] were detected by the gas-liquid chromatography at six temperatures in range of (358.15-408.15) K. The data are provided for polar and non-polar solutes as alkanes, alkenes and alkynes, aromatic hydrocarbons, alcohols, ethers, ketones, acetonitrile, pyridine, 1-nitropropane, thiophene, esters as well as for water. The synthesis and the thermal properties of [D 2 MIM][DCA] are presented. The fundamental thermodynamic functions, the partial molar excess Gibbs energy, enthalpy and entropy at infinite dilution were calculated and discussed. The values of selectivity and capacity for the separation problem water/butan-1-ol were calculated from c 1 13 and compared to literature values for imidazolium-based, or dicyanamide-based ionic liquids (ILs) for the same separation problem. The data presented here shows that [D 2 MIM][DCA] reveals attractive selectivity and capacity in the comparison to measured earlier ILs in the chosen separation problem. These findings seem useful for future applications of this IL in projects of new technologies for water/butan-1-ol separation process.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, Jan 3, 2017
Synthesis of three mefenamic acid (MEF) derivatives - ionic liquid compounds composed of MEF in a... more Synthesis of three mefenamic acid (MEF) derivatives - ionic liquid compounds composed of MEF in an anionic form and ammonium cation (choline, MEF1), or {di(2-hydroxyethyl)dimethyl ammonium (MEF2)}, or {tri(2-hydroxyethyl)methyl ammonium compound (MEF3)} is presented. The basic thermal properties of pure compounds i.e. fusion temperatures, and the enthalpy of fusion of these compounds have been measured with differential scanning microcalorimetry technique (DSC). Molar volumes have been calculated with the Barton group contribution method. The solubilities of MEF1, MEF2 and MEF3 using the dynamic method were measured at constant pH in a range of temperature from (290 to 370) K in three solvents: water, ethanol and 1-octanol. The experimental solubility data have been correlated by means of three commonly known G(E) equations: the Wilson, NRTL and UNIQUAC with the assumption that the systems studied here present simple eutectic behaviour. The activity coefficients of pharmaceuticals a...
The Journal of Physical Chemistry B, 2017
2-Phenylethanol (PEA) is an important alcohol involved in aroma and flavour of food, soft drinks,... more 2-Phenylethanol (PEA) is an important alcohol involved in aroma and flavour of food, soft drinks, candy, ice cream, pudding, chewing gum and cookies. This study investigates the ability of three tetracyanoborate-based ionic liquids (ILs) for the extraction of PEA from aqueous phases. In this regard, experimental measurements of liquid-liquid equilibria (LLE) in the binary systems {IL (1) + PEA or water (2)} and ternary systems of {IL (1) + PEA (2) + water (3)} at temperature T = 308.15 K and ambient pressure were undertaken. The ILs investigated were 1-hexyl-3-methylimidazolium tetracyanoborate [HMIM][TCB], 1-decyl-3-methylimidazolium tetracyanoborate [DMIM][TCB], and 1-butyl-1-methylpyrrolidinium tetracyanoborate [BMPYR][TCB]. The suitability of the ILs for use as entrainers for the extraction of PEA from water has been evaluated in terms of the selectivity and solute distribution ratio. An immiscibility gap was observed in the binary systems of (IL + water). All ILs showed complete miscibility with PEA in the liquid phase at a temperature T = 308.15 K. The average selectivity of the extraction of PEA from water increases in the following order: [HMIM][TCB] (S av = 408) b [BMPYR][TCB] (S av = 509) b [DMIM][TCB] (S av = 577). The solute distribution ratio increases in the following order: [HMIM][TCB] (β av = 178) b [DMIM][TCB] (β av = 198) b [BMPYR][TCB] (β av = 241). The best IL with the highest selectivity and acceptable distribution ratio is [DMIM][TCB]. The LLE data for the systems were correlated with the NRTL model. The model satisfactorily describes the solubility of the ternary systems with an average root mean square deviation of σ x = 0.005.
The Journal of Chemical Thermodynamics, 2017
The measurements of a limiting activity coefficients, ∞ 13 γ at infinite dilution for 63 solutes ... more The measurements of a limiting activity coefficients, ∞ 13 γ at infinite dilution for 63 solutes including wide spectra of alkanes, alkenes and alkynes as well as aromatic hydrocarbons, alcohols, water, ethers, ketones, acetonitrile, pyridine, 1-nitropropane, thiophene, and esters in the 1-(3-hydroxypropyl)pyridinium dicyanamide, [N-C 3 OHPY][DCA], determined by gasliquid chromatography at temperature range of (298.15 to 368.15) K are developed. The synthesis and thermochemical characteristic of the ionic liquid (IL) is described. The density and viscosity of the IL was measured as a function of temperature in a range of (298.15 to 368.15) K. The comparison of ∞ 13 γ for selected solutes in ionic liquids (ILs) with [N-C 3 OHPY] + cation and [TCM] − , [DCA] − , [TCB] − and [SCN] −-anions at one temperature, T = 328.15 K is shown. The gas-liquid partition coefficients, L K at infinite dilution and the limiting fundamental thermodynamic functions, the partial molar excess Gibbs energy, enthalpy and entropy were calculated for all solutes. The values of selectivity and capacity for three separation problems hexane/hex-1-ene, cyclohexane/cyclohexene and methylbenzene/styrene were calculated from ∞ 13 γ and compared to literature values for [N-C 3 OHPY]-based or [DCA]-based ILs for the same separation problems. The data presented here shows that [N-C 3 OHPY][DCA] reveals large selectivity 2.34, 2.79 and 2.27 in three of discussed separation problems. However, the comparison to the measured earlier [DCA]based ILs shows the low capacity for the hex-1-ene and cyclohexene. The Abraham solvation parameter model was also presented for all solutes. On the bases of the results the intermolecular interactions of the chosen IL and solutes was discussed.
The Journal of Chemical Thermodynamics, 2016
This work presents some important issues and topics related to possible extraction of 2-phenyleth... more This work presents some important issues and topics related to possible extraction of 2-phenylethanol (PEA) from aqueous phase ''in situ" during the biosynthesis with ionic liquids (ILs). It consists of a series of experimental phase equilibrium measurements in binary and ternary systems. Three ILs as extraction media are proposed for the extraction process based on phase equilibria in ternary systems {IL (1) + PEA (2) + water (3)} at temperature T = 308.15 K and ambient pressure. The systems are composed of the following ILs: 1-hexyl-1-methylmorpholinium bis{(trifluoromethyl)sulfonyl}imide, [HMMOR][NTf 2 ], 1-allyl-3-methylimidazolium bis{(trifluoromethyl)sulfonyl}imide, [AMIM][NTf 2 ], and diethylmethylsulfonium bis{(trifluoromethyl)sulfonyl}imide, [S 221 ][NTf 2 ]. A differential scanning calorimetry (DSC) was used to determine the thermal properties of the ILs. The synthesis of new [HMMOR][NTf 2 ] IL and its thermal and physicochemical properties as density, viscosity, surface tension were presented. The volume expansivity, as well as the surface thermodynamic functions, such as surface entropy and enthalpy have been derived from the temperature dependence of the surface tension values, as well as the critical temperature, parachor and speed of sound for all ILs were presented. The correlation of the liquidus curves in binary systems and tie-lines in ternary systems was undertaken with the NRTL equation. These results of solubility can be used to design future alternative technological processes of the extraction of PEA from fermentation broth.
Green Chemistry, 2016
This study is aimed at developing a sustainable process for the recovery of valuable drugs from p... more This study is aimed at developing a sustainable process for the recovery of valuable drugs from pharmaceutical wastes using ionic liquid (IL)-based aqueous biphasic systems (ABS).
The Journal of Chemical Thermodynamics, 2011
The Journal of Chemical Thermodynamics, 2010
ABSTRACT Quinolinium ionic liquid has been prepared from 1-butylquinolinium bromide as a substrat... more ABSTRACT Quinolinium ionic liquid has been prepared from 1-butylquinolinium bromide as a substrate. The work includes specific basic characterization of synthesized compound by NMR spectra, elementary analysis and water content. The basic thermal properties of the pure IL, i.e. melting and glass-transition temperatures, as well as the enthalpy of fusion have been measured using a differential scanning microcalorimetry technique (DSC). (Solid + liquid) phase equilibria (SLE) and (liquid + liquid) phase equilibria (LLE) for the binary systems: ionic liquid (IL) N-butylquinolinium bis{(trifluoromethyl)sulfonyl}imide, {([BQuin] [NTf2]) + aromatic hydrocarbon (benzene, or toluene, or methylbenzene, or propylbenzene, or thiophene), or an alcohol (ethanol, or 1-butanol, or 1-hexanol, or 1-octanol, or 1-dodecanol)} have been determined at ambient pressure. A dynamic method was used over a broad range of mole fractions and temperatures from (260 to 330) K. For the binary systems, the simple eutectic diagrams were observed with immiscibility in the liquid phase with an upper critical solution temperature (UCST). For mixtures with alcohols, it was observed that with increasing chain length of an alcohol the solubility decreases and the UCST increases. In the case of mixture (IL + benzene, or alkylbenzene, or thiophene) the eutectic systems with mutual immiscibility in the liquid phase with very high UCSTs were observed. These points were not detectable with our method and they were observed at low ionic liquid mole fraction. Densities at high temperatures were determined and extrapolated to T = 298.15 K. Well-known UNIQUAC, and NRTL equations have been used to correlate experimental SLE data sets. For the systems containing immiscibility gaps {IL + an alcohol} parameters of the LLE correlation equation have been derived using only the NRTL equation.
The Journal of Chemical Thermodynamics, 2011
ABSTRACT A new isoquinolinium ionic liquid (IL) has been synthesised as a continuation of our wor... more ABSTRACT A new isoquinolinium ionic liquid (IL) has been synthesised as a continuation of our work with quinolinium-based ionic liquids (ILs). The work includes specific basic characterization of synthesized compounds: N-isobutylquinolinium bromide, [BiQuin][Br] and N-isobutylquinolinium bis{(trifluoromethyl) sulfonyl}imide [BiQuin][NTf2] by NMR spectra, elementary analysis and water content. The basic thermal properties of the pure [BiQuin][NTf2], i.e. melting and glass-transition temperatures, the enthalpy of fusion as well as heat capacity at glass transition have been measured using a differential scanning microcalorimetry technique (DSC). Densities and viscosities were determined as a function of temperature. The temperature-composition phase diagrams of 8 binary mixtures composed of organic solvent dissolved in the IL: {[BiQuin][NTf2] + aromatic hydrocarbon (benzene, or toluene, or ethylbenzene, or n-propylbenzene), or an alcohol (1-butanol, or 1-hexanol, or 1-octanol, or 1-decanol)} were measured at ambient pressure. A dynamic method was used over a broad range of mole fraction and temperature from (270 to 320) K. For all the binary systems with benzene and alkylbenzenes, the eutectic diagrams were observed with an immiscibility gap in the liquid phase existing at low mole fraction of the IL with a very high upper critical solution temperature (UCST). For mixtures with alcohols, complete miscibility was observed for 1-butanol and also an immiscibility gap with UCST in the liquid phase for the remaining alcohols. The typical dependence was observed that with increasing chain length of an alcohol, the solubility decreases. The well-known NRTL equation was used to correlate experimental (solid + liquid), SLE and (liquid + liquid), LLE phase equilibrium data sets.
Journal of Molecular Liquids, 2008
ABSTRACT The DISQUAC group contribution model has been applied to the study of mixtures containin... more ABSTRACT The DISQUAC group contribution model has been applied to the study of mixtures containing a polycyclic aromatic compound, naphthalene, phenanthrene, anthracene or pyrene, and an organic solvent, n-alkane, cyclohexane or 1-alkanol. The corresponding interaction parameters are reported. Systems with alkanes are characterized by dispersive parameters only. For naphthalene +1-alkanol mixtures, the aromatic/OH contacts are represented by dispersive and quasichemical parameters. The latter are equal to those encountered in 1-alkanol +benzene, or +alkylbenzene mixtures for such contacts. DISQUAC provides good results on molar excess enthalpies, HE, solid–liquid equilibria, SLE, and vapor–liquid equilibria over a wide range of temperature for the investigated mixtures. In PAH+ n-alkane systems, there is an enthalpy-entropy compensation effect in solutions with long alkanes, and no Patterson's effect is observed. Solubility of naphthalene in hexane or 1-hexanol is similar, and lower than that of 1-alkanol in alkane. This seems to indicate that interactions between unlike molecules are not so relevant as in 1-alkanol +benzene mixtures.
![Research paper thumbnail of Measurements of activity coefficients at infinite dilution for organic solutes and water in the ionic liquid 1-butyl-1-methylpyrrolidinium tris(pentafluoroethyl)trifluorophosphate ([BMPYR][FAP])](https://attachments.academia-assets.com/96895734/thumbnails/1.jpg)
](Chemical Engineering Journal, 2012
Measurements of activity coefficients at infinite dilution for organic solutes and water in the i... more Measurements of activity coefficients at infinite dilution for organic solutes and water in the ionic liquid 1-butyl-1-methylpyrrolidinium tris(pentafluoroethyl)trifluorophosphate ([BMPYR][FAP]
Chemical Engineering Journal, 2012
Isoquinolinium ionic liquid has been studied as the temperature-composition phase diagrams of 13 ... more Isoquinolinium ionic liquid has been studied as the temperature-composition phase diagrams of 13 binary mixtures composed of the ionic liquid (IL) N-octylisoquinolinium bis{(trifluoromethyl)sulfonyl}imide, ([C 8 iQuin][NTf 2 ]) and an aliphatic hydrocarbon (n-hexane, or n-heptane), or cyclic hydrocarbons (cyclohexane, or cycloheptane), or an aromatic hydrocarbon (toluene, or ethylbenzene, or n-propylbenzene, or thiophene), or an alcohol (1-butanol, or 1-hexanol, or 1-octanol, or 1-decanol, or 1-dodecanol, or 2-phenylethanol), or water have been determined from ambient temperature to the boiling point temperature of the solvent at ambient pressure. A dynamic method was used over a broad range of mole fractions and temperatures from 270 to 360 K. For the binary systems the immiscibility in the liquid phase with an upper critical solution temperature (UCST) was observed in all mixtures. In the case of the mixture of {IL + alkylbenzene} only one experimental point of immiscibility was observed because of the very high UCSTs. Complete solubility in the liquid phase was observed for 1-butanol and 2-phenylethanol. In the mixtures with alcohols the typical dependence was observed that with an increasing chain length of an alcohol the solubility decreases and the UCST increases. The coexistence curves corresponding to liquid-liquid phase equilibrium (LLE) boundaries have been correlated using the well-known NRTL model. The ternary system of {[C 8 iQuin][NTf 2 ] (1) + 2-phenylethanol (2) + water (3)} was studied at 298.15 K to analyze the performance of the ([C 8 iQuin][NTf 2 ]) in the extractive selectivity of 2-phenylethanol from medium of biosynthesis. From the ternary LLE experiments, it was found that the selectivities and the distribution coefficients of the 2-phenylethanol were as high as 1539 and 1214. The experimental results were correlated using the NRTL model. The root mean square deviation (RMSD) of mole fraction in ternary system was 0.003.
Canadian Journal of Chemistry, 2005
Binary mixtures of aniline with benzene, toluene, alkane, alkanol, or N,N-dialkylamide have been ... more Binary mixtures of aniline with benzene, toluene, alkane, alkanol, or N,N-dialkylamide have been investigated in the framework of the DISQUAC model. The reported interaction parameters change regularly with the molecular structure of the mixture components. The model consistently describes a set of thermodynamic properties including liquidliquid equilibria, vaporliquid equilibria, and molar excess enthalpies. The two latter properties for ternary systems are well-represented by DISQUAC using binary parameters only (i.e., neglecting ternary interactions). A comparison of DISQUAC results and those obtained from the UNIFAC (Dortmund version) and ERAS models is also shown. The experimental molar excess enthalpies for binary and ternary mixtures are better described by DISQUAC than by UNIFAC. ERAS fails when representing molar excess enthalpies of those binary systems including methanol or ethanol. This may be due to the existence of strong dipolar interactions among aniline molecules ...
RSC Advances
In flight coalescence of polyurea inks in different volume ratios produces materials with varied ... more In flight coalescence of polyurea inks in different volume ratios produces materials with varied degrees of elasticity.
The Journal of Chemical Thermodynamics, 2016
The Journal of Chemical Thermodynamics
In this work, we studied the applicability of new 1-alkyl-cyanopyridinium-based ionic liquids (IL... more In this work, we studied the applicability of new 1-alkyl-cyanopyridinium-based ionic liquids (ILs) in the extraction of aromatic-sulfur compounds from aliphatic mixtures. The synthesis of new 1-alkyl-cyanopyridinium-based ionic liquids is presented. Experimental data for (liquid + liquid) equilibrium (LLE) were obtained for various binary and ternary mixtures of {IL (1) + thiophene, or benzothiophene (2) + heptane (3)} at T = 308.15 K and ambient pressure. Three ILs have been studied: 1-butyl-3-cyanopyridinium bis{(trifluoromethyl)sulfonyl}imide [BCN3Py][NTf2], 1-butyl-4-cyanopyridinium bis{(trifluoromethyl)sulfonyl}imide [BCN4Py][NTf2] and 1-hexyl-4-cyanopyridinium bis{(trifluoromethyl)sulfonyl}imide, [HCN4Py][NTf2]. One of the IL showed excellent results in terms of sulfur compounds selectivity and solute distribution ratio compared to what is currently used in industry. Chromatography analysis showed that the IL used as an entrainer was not present in the alkane layer. This elim...
Journal of Solution Chemistry, 2021
In recent years, many compounds have been proposed as additives to conventional working fluids to... more In recent years, many compounds have been proposed as additives to conventional working fluids to improve the performance of the absorption refrigeration system. The main aim of this research is to show the influence of ionic liquid based additives on thermodynamic and physicochemical properties of {LiBr + water} solutions. The following additives: 3-(1-methyl-morpholinium)propane-1-sulfonate,N,N-di(2-hydroxyethyl)-N,N-dimethylammonium bromide, andN,N,N-tri(2-hydroxy-ethyl)-N-methylammonium bromide have been added to aqueous lithium bromide solutions (IL to LiBr mass fraction,w2 = 0.3). The physicochemical and thermodynamic properties of {LiBr (1) + additive (2) + water (3)} and {LiBr + water} systems including (vapor + liquid) phase equilibria (VLE), density (ρ) and dynamic viscosity (η) were determined over wide temperature and composition ranges. The conductor-like screening model for real solvents (COSMO-RS) was used for the VLE data prediction. For the density and dynamic visco...
The Journal of Chemical Thermodynamics, 2020
Abstract This work is an attempt to determine appropriate solvents for extractive desulfurization... more Abstract This work is an attempt to determine appropriate solvents for extractive desulfurization, which is the dominant alternative to the risky and expensive solution, which is hydrodesulfurization (HDS). The main part of this research is the study on (liquid + liquid) phase equilibria in {IL (1) + heptane, or thiophene, or 2-methylthiophene, or benzothiophene (2) binary systems and {IL (1) + thiophene/2-methylthiophene/benzothiophene (2) + heptane (3)} ternary system. In this work, five new synthesized tricyanomethanide – based ILs that is: N-(3-cyanopropyl)-N-methylmorpholinium tricyanomethanide, [Mo1,3CN][TCM], N-(3-hydroxypropyl)-N-methylmorpholinium tricyanomethanide, [Mo1,3OH][TCM], N-(3-cyanopropyl)pyridinium tricyanomethanide, [Py3CN][TCM], N-(3-hydroxypropyl)pyridinium tricyanomethanide, [Py3OH][TCM], N-(2-hydroxyethyl)pyridinium tricyanomethanide, [Py2OH][TCM] are analyzed as an extractant in desulfurization of model fuel. Based on the experimental ternary LLE data, the selectivity and solute distribution ratio are calculated and used to determine the efficiency of the tested ILs as solvents for the extraction of sulfur compounds from model fuel. The experimental results have been compared to literature data for other tricyanomethanide-based ILs and were discussed in terms of the selectivity and solute distribution ratio of separation of related systems. The NRTL equation was successfully used to correlate the LLE in binary systems as well as the experimental tie-lines.
Fluid Phase Equilibria, 2018
In this work a series of ammonium-and phosphonium-based zwitterions (ZIs) namely: 3-(triethylammo... more In this work a series of ammonium-and phosphonium-based zwitterions (ZIs) namely: 3-(triethylammonio)propane-1-sulfonate, N 222 C3S, 4-(triethylammonio)butane-1-sulfonate, N 222 C4S, 3-(tributylammonio)propane-1-sulfonate, N 444 C3S, 4-(tributylammonio)butane-1-sulfonate, N 444 C4S, 3-(trihexylammonio)propane-1-sulfonate, N 666 C3S, 4-(trihexyl-ammonio)butane-1-sulfonate, N 666 C4S, 3-(tributylphosphonio)propane-1-sulfonate, P 444 C3S and 4-(tributyl-phosphonio)butane-1-sulfonate, P 444 C4S have been synthesized. The structure and purity of these compounds were confirmed by 1 H NMR. The thermal properties such as temperature and enthalpy of (solid þ solid) phase transition as well as the melting temperature of pure ZIs were evaluated by DSC technique. The (solid þ liquid) and (liquid þ liquid) phase equilibria measurements have been performed for eight binary systems of synthesized ZIs and one purchased 3-(1-pyridinio)-1-propanesulfonate [PyC3S] using the dynamic method and the experimental results were correlated using NRTL equation. Additionally, ternary system of {N 666 C3S (1) þ N 444 C3S (2) þ water (3)} with three different N 666 C3S to N 444 C3S initial molar fractions was determined.
Fluid Phase Equilibria, 2019
In this work, thermodynamic and physicochemical properties including (vapor + liquid) equilibria ... more In this work, thermodynamic and physicochemical properties including (vapor + liquid) equilibria (VLE), density and dynamic viscosity of binary mixtures composed of bromidebased ionic liquid (IL) and water were measured as a function of IL mole fraction in a wide range of temperature. The aqueous solution of the following ILs: 1-ethyl-1methylpiperidinium bromide, ethylpyridinium bromide, 1-(2-hydroxyethyl)pyridinium bromide, 1-ethyl-1-methyl-morpholinium bromide, 1-hydroxyethyl-1-methylmorpholinium bromide, and N-ethyl-N,N-diN -hydroxyethylammonium bromide have been tested for potential applications as working fluids in absorption refrigeration technology. The isothermal VLE has been measured by an ebulliometric method within a temperature range from T = (338.15 to 368.15) K and pressure up to 85 kPa and correlated using Redlich-Kwong equation of state. This work is a continuation of our systematic investigation of an aqueous solution of ionic liquids as a potential working fluid in absorption refrigeration technology. The summary of this research is the modeling of the theoretical cycles using working fluids proposed in this paper. The calculated values of the coefficient of performance (COP) were compared to other ILs from available literature and {LiBr + water} system, conventionally used on the industrial scale in absorption refrigeration technology.
The Journal of Chemical Thermodynamics, 2018
The activity coefficients (c 1 13) at infinite dilution for 65 solutes and the effect of interact... more The activity coefficients (c 1 13) at infinite dilution for 65 solutes and the effect of interaction between organic solvents or water on the interfacial and bulk properties of 1,3-didecyl-2-methylimidazolium dicyanamide, [D 2 MIM][DCA] were detected by the gas-liquid chromatography at six temperatures in range of (358.15-408.15) K. The data are provided for polar and non-polar solutes as alkanes, alkenes and alkynes, aromatic hydrocarbons, alcohols, ethers, ketones, acetonitrile, pyridine, 1-nitropropane, thiophene, esters as well as for water. The synthesis and the thermal properties of [D 2 MIM][DCA] are presented. The fundamental thermodynamic functions, the partial molar excess Gibbs energy, enthalpy and entropy at infinite dilution were calculated and discussed. The values of selectivity and capacity for the separation problem water/butan-1-ol were calculated from c 1 13 and compared to literature values for imidazolium-based, or dicyanamide-based ionic liquids (ILs) for the same separation problem. The data presented here shows that [D 2 MIM][DCA] reveals attractive selectivity and capacity in the comparison to measured earlier ILs in the chosen separation problem. These findings seem useful for future applications of this IL in projects of new technologies for water/butan-1-ol separation process.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, Jan 3, 2017
Synthesis of three mefenamic acid (MEF) derivatives - ionic liquid compounds composed of MEF in a... more Synthesis of three mefenamic acid (MEF) derivatives - ionic liquid compounds composed of MEF in an anionic form and ammonium cation (choline, MEF1), or {di(2-hydroxyethyl)dimethyl ammonium (MEF2)}, or {tri(2-hydroxyethyl)methyl ammonium compound (MEF3)} is presented. The basic thermal properties of pure compounds i.e. fusion temperatures, and the enthalpy of fusion of these compounds have been measured with differential scanning microcalorimetry technique (DSC). Molar volumes have been calculated with the Barton group contribution method. The solubilities of MEF1, MEF2 and MEF3 using the dynamic method were measured at constant pH in a range of temperature from (290 to 370) K in three solvents: water, ethanol and 1-octanol. The experimental solubility data have been correlated by means of three commonly known G(E) equations: the Wilson, NRTL and UNIQUAC with the assumption that the systems studied here present simple eutectic behaviour. The activity coefficients of pharmaceuticals a...
The Journal of Physical Chemistry B, 2017
2-Phenylethanol (PEA) is an important alcohol involved in aroma and flavour of food, soft drinks,... more 2-Phenylethanol (PEA) is an important alcohol involved in aroma and flavour of food, soft drinks, candy, ice cream, pudding, chewing gum and cookies. This study investigates the ability of three tetracyanoborate-based ionic liquids (ILs) for the extraction of PEA from aqueous phases. In this regard, experimental measurements of liquid-liquid equilibria (LLE) in the binary systems {IL (1) + PEA or water (2)} and ternary systems of {IL (1) + PEA (2) + water (3)} at temperature T = 308.15 K and ambient pressure were undertaken. The ILs investigated were 1-hexyl-3-methylimidazolium tetracyanoborate [HMIM][TCB], 1-decyl-3-methylimidazolium tetracyanoborate [DMIM][TCB], and 1-butyl-1-methylpyrrolidinium tetracyanoborate [BMPYR][TCB]. The suitability of the ILs for use as entrainers for the extraction of PEA from water has been evaluated in terms of the selectivity and solute distribution ratio. An immiscibility gap was observed in the binary systems of (IL + water). All ILs showed complete miscibility with PEA in the liquid phase at a temperature T = 308.15 K. The average selectivity of the extraction of PEA from water increases in the following order: [HMIM][TCB] (S av = 408) b [BMPYR][TCB] (S av = 509) b [DMIM][TCB] (S av = 577). The solute distribution ratio increases in the following order: [HMIM][TCB] (β av = 178) b [DMIM][TCB] (β av = 198) b [BMPYR][TCB] (β av = 241). The best IL with the highest selectivity and acceptable distribution ratio is [DMIM][TCB]. The LLE data for the systems were correlated with the NRTL model. The model satisfactorily describes the solubility of the ternary systems with an average root mean square deviation of σ x = 0.005.
The Journal of Chemical Thermodynamics, 2017
The measurements of a limiting activity coefficients, ∞ 13 γ at infinite dilution for 63 solutes ... more The measurements of a limiting activity coefficients, ∞ 13 γ at infinite dilution for 63 solutes including wide spectra of alkanes, alkenes and alkynes as well as aromatic hydrocarbons, alcohols, water, ethers, ketones, acetonitrile, pyridine, 1-nitropropane, thiophene, and esters in the 1-(3-hydroxypropyl)pyridinium dicyanamide, [N-C 3 OHPY][DCA], determined by gasliquid chromatography at temperature range of (298.15 to 368.15) K are developed. The synthesis and thermochemical characteristic of the ionic liquid (IL) is described. The density and viscosity of the IL was measured as a function of temperature in a range of (298.15 to 368.15) K. The comparison of ∞ 13 γ for selected solutes in ionic liquids (ILs) with [N-C 3 OHPY] + cation and [TCM] − , [DCA] − , [TCB] − and [SCN] −-anions at one temperature, T = 328.15 K is shown. The gas-liquid partition coefficients, L K at infinite dilution and the limiting fundamental thermodynamic functions, the partial molar excess Gibbs energy, enthalpy and entropy were calculated for all solutes. The values of selectivity and capacity for three separation problems hexane/hex-1-ene, cyclohexane/cyclohexene and methylbenzene/styrene were calculated from ∞ 13 γ and compared to literature values for [N-C 3 OHPY]-based or [DCA]-based ILs for the same separation problems. The data presented here shows that [N-C 3 OHPY][DCA] reveals large selectivity 2.34, 2.79 and 2.27 in three of discussed separation problems. However, the comparison to the measured earlier [DCA]based ILs shows the low capacity for the hex-1-ene and cyclohexene. The Abraham solvation parameter model was also presented for all solutes. On the bases of the results the intermolecular interactions of the chosen IL and solutes was discussed.
The Journal of Chemical Thermodynamics, 2016
This work presents some important issues and topics related to possible extraction of 2-phenyleth... more This work presents some important issues and topics related to possible extraction of 2-phenylethanol (PEA) from aqueous phase ''in situ" during the biosynthesis with ionic liquids (ILs). It consists of a series of experimental phase equilibrium measurements in binary and ternary systems. Three ILs as extraction media are proposed for the extraction process based on phase equilibria in ternary systems {IL (1) + PEA (2) + water (3)} at temperature T = 308.15 K and ambient pressure. The systems are composed of the following ILs: 1-hexyl-1-methylmorpholinium bis{(trifluoromethyl)sulfonyl}imide, [HMMOR][NTf 2 ], 1-allyl-3-methylimidazolium bis{(trifluoromethyl)sulfonyl}imide, [AMIM][NTf 2 ], and diethylmethylsulfonium bis{(trifluoromethyl)sulfonyl}imide, [S 221 ][NTf 2 ]. A differential scanning calorimetry (DSC) was used to determine the thermal properties of the ILs. The synthesis of new [HMMOR][NTf 2 ] IL and its thermal and physicochemical properties as density, viscosity, surface tension were presented. The volume expansivity, as well as the surface thermodynamic functions, such as surface entropy and enthalpy have been derived from the temperature dependence of the surface tension values, as well as the critical temperature, parachor and speed of sound for all ILs were presented. The correlation of the liquidus curves in binary systems and tie-lines in ternary systems was undertaken with the NRTL equation. These results of solubility can be used to design future alternative technological processes of the extraction of PEA from fermentation broth.
Green Chemistry, 2016
This study is aimed at developing a sustainable process for the recovery of valuable drugs from p... more This study is aimed at developing a sustainable process for the recovery of valuable drugs from pharmaceutical wastes using ionic liquid (IL)-based aqueous biphasic systems (ABS).
The Journal of Chemical Thermodynamics, 2011
The Journal of Chemical Thermodynamics, 2010
ABSTRACT Quinolinium ionic liquid has been prepared from 1-butylquinolinium bromide as a substrat... more ABSTRACT Quinolinium ionic liquid has been prepared from 1-butylquinolinium bromide as a substrate. The work includes specific basic characterization of synthesized compound by NMR spectra, elementary analysis and water content. The basic thermal properties of the pure IL, i.e. melting and glass-transition temperatures, as well as the enthalpy of fusion have been measured using a differential scanning microcalorimetry technique (DSC). (Solid + liquid) phase equilibria (SLE) and (liquid + liquid) phase equilibria (LLE) for the binary systems: ionic liquid (IL) N-butylquinolinium bis{(trifluoromethyl)sulfonyl}imide, {([BQuin] [NTf2]) + aromatic hydrocarbon (benzene, or toluene, or methylbenzene, or propylbenzene, or thiophene), or an alcohol (ethanol, or 1-butanol, or 1-hexanol, or 1-octanol, or 1-dodecanol)} have been determined at ambient pressure. A dynamic method was used over a broad range of mole fractions and temperatures from (260 to 330) K. For the binary systems, the simple eutectic diagrams were observed with immiscibility in the liquid phase with an upper critical solution temperature (UCST). For mixtures with alcohols, it was observed that with increasing chain length of an alcohol the solubility decreases and the UCST increases. In the case of mixture (IL + benzene, or alkylbenzene, or thiophene) the eutectic systems with mutual immiscibility in the liquid phase with very high UCSTs were observed. These points were not detectable with our method and they were observed at low ionic liquid mole fraction. Densities at high temperatures were determined and extrapolated to T = 298.15 K. Well-known UNIQUAC, and NRTL equations have been used to correlate experimental SLE data sets. For the systems containing immiscibility gaps {IL + an alcohol} parameters of the LLE correlation equation have been derived using only the NRTL equation.
The Journal of Chemical Thermodynamics, 2011
ABSTRACT A new isoquinolinium ionic liquid (IL) has been synthesised as a continuation of our wor... more ABSTRACT A new isoquinolinium ionic liquid (IL) has been synthesised as a continuation of our work with quinolinium-based ionic liquids (ILs). The work includes specific basic characterization of synthesized compounds: N-isobutylquinolinium bromide, [BiQuin][Br] and N-isobutylquinolinium bis{(trifluoromethyl) sulfonyl}imide [BiQuin][NTf2] by NMR spectra, elementary analysis and water content. The basic thermal properties of the pure [BiQuin][NTf2], i.e. melting and glass-transition temperatures, the enthalpy of fusion as well as heat capacity at glass transition have been measured using a differential scanning microcalorimetry technique (DSC). Densities and viscosities were determined as a function of temperature. The temperature-composition phase diagrams of 8 binary mixtures composed of organic solvent dissolved in the IL: {[BiQuin][NTf2] + aromatic hydrocarbon (benzene, or toluene, or ethylbenzene, or n-propylbenzene), or an alcohol (1-butanol, or 1-hexanol, or 1-octanol, or 1-decanol)} were measured at ambient pressure. A dynamic method was used over a broad range of mole fraction and temperature from (270 to 320) K. For all the binary systems with benzene and alkylbenzenes, the eutectic diagrams were observed with an immiscibility gap in the liquid phase existing at low mole fraction of the IL with a very high upper critical solution temperature (UCST). For mixtures with alcohols, complete miscibility was observed for 1-butanol and also an immiscibility gap with UCST in the liquid phase for the remaining alcohols. The typical dependence was observed that with increasing chain length of an alcohol, the solubility decreases. The well-known NRTL equation was used to correlate experimental (solid + liquid), SLE and (liquid + liquid), LLE phase equilibrium data sets.
Journal of Molecular Liquids, 2008
ABSTRACT The DISQUAC group contribution model has been applied to the study of mixtures containin... more ABSTRACT The DISQUAC group contribution model has been applied to the study of mixtures containing a polycyclic aromatic compound, naphthalene, phenanthrene, anthracene or pyrene, and an organic solvent, n-alkane, cyclohexane or 1-alkanol. The corresponding interaction parameters are reported. Systems with alkanes are characterized by dispersive parameters only. For naphthalene +1-alkanol mixtures, the aromatic/OH contacts are represented by dispersive and quasichemical parameters. The latter are equal to those encountered in 1-alkanol +benzene, or +alkylbenzene mixtures for such contacts. DISQUAC provides good results on molar excess enthalpies, HE, solid–liquid equilibria, SLE, and vapor–liquid equilibria over a wide range of temperature for the investigated mixtures. In PAH+ n-alkane systems, there is an enthalpy-entropy compensation effect in solutions with long alkanes, and no Patterson's effect is observed. Solubility of naphthalene in hexane or 1-hexanol is similar, and lower than that of 1-alkanol in alkane. This seems to indicate that interactions between unlike molecules are not so relevant as in 1-alkanol +benzene mixtures.
Chemical Engineering Journal, 2012
Measurements of activity coefficients at infinite dilution for organic solutes and water in the i... more Measurements of activity coefficients at infinite dilution for organic solutes and water in the ionic liquid 1-butyl-1-methylpyrrolidinium tris(pentafluoroethyl)trifluorophosphate ([BMPYR][FAP]
Chemical Engineering Journal, 2012
Isoquinolinium ionic liquid has been studied as the temperature-composition phase diagrams of 13 ... more Isoquinolinium ionic liquid has been studied as the temperature-composition phase diagrams of 13 binary mixtures composed of the ionic liquid (IL) N-octylisoquinolinium bis{(trifluoromethyl)sulfonyl}imide, ([C 8 iQuin][NTf 2 ]) and an aliphatic hydrocarbon (n-hexane, or n-heptane), or cyclic hydrocarbons (cyclohexane, or cycloheptane), or an aromatic hydrocarbon (toluene, or ethylbenzene, or n-propylbenzene, or thiophene), or an alcohol (1-butanol, or 1-hexanol, or 1-octanol, or 1-decanol, or 1-dodecanol, or 2-phenylethanol), or water have been determined from ambient temperature to the boiling point temperature of the solvent at ambient pressure. A dynamic method was used over a broad range of mole fractions and temperatures from 270 to 360 K. For the binary systems the immiscibility in the liquid phase with an upper critical solution temperature (UCST) was observed in all mixtures. In the case of the mixture of {IL + alkylbenzene} only one experimental point of immiscibility was observed because of the very high UCSTs. Complete solubility in the liquid phase was observed for 1-butanol and 2-phenylethanol. In the mixtures with alcohols the typical dependence was observed that with an increasing chain length of an alcohol the solubility decreases and the UCST increases. The coexistence curves corresponding to liquid-liquid phase equilibrium (LLE) boundaries have been correlated using the well-known NRTL model. The ternary system of {[C 8 iQuin][NTf 2 ] (1) + 2-phenylethanol (2) + water (3)} was studied at 298.15 K to analyze the performance of the ([C 8 iQuin][NTf 2 ]) in the extractive selectivity of 2-phenylethanol from medium of biosynthesis. From the ternary LLE experiments, it was found that the selectivities and the distribution coefficients of the 2-phenylethanol were as high as 1539 and 1214. The experimental results were correlated using the NRTL model. The root mean square deviation (RMSD) of mole fraction in ternary system was 0.003.
Canadian Journal of Chemistry, 2005
Binary mixtures of aniline with benzene, toluene, alkane, alkanol, or N,N-dialkylamide have been ... more Binary mixtures of aniline with benzene, toluene, alkane, alkanol, or N,N-dialkylamide have been investigated in the framework of the DISQUAC model. The reported interaction parameters change regularly with the molecular structure of the mixture components. The model consistently describes a set of thermodynamic properties including liquidliquid equilibria, vaporliquid equilibria, and molar excess enthalpies. The two latter properties for ternary systems are well-represented by DISQUAC using binary parameters only (i.e., neglecting ternary interactions). A comparison of DISQUAC results and those obtained from the UNIFAC (Dortmund version) and ERAS models is also shown. The experimental molar excess enthalpies for binary and ternary mixtures are better described by DISQUAC than by UNIFAC. ERAS fails when representing molar excess enthalpies of those binary systems including methanol or ethanol. This may be due to the existence of strong dipolar interactions among aniline molecules ...
RSC Advances
In flight coalescence of polyurea inks in different volume ratios produces materials with varied ... more In flight coalescence of polyurea inks in different volume ratios produces materials with varied degrees of elasticity.
The Journal of Chemical Thermodynamics, 2016
The Journal of Chemical Thermodynamics
In this work, we studied the applicability of new 1-alkyl-cyanopyridinium-based ionic liquids (IL... more In this work, we studied the applicability of new 1-alkyl-cyanopyridinium-based ionic liquids (ILs) in the extraction of aromatic-sulfur compounds from aliphatic mixtures. The synthesis of new 1-alkyl-cyanopyridinium-based ionic liquids is presented. Experimental data for (liquid + liquid) equilibrium (LLE) were obtained for various binary and ternary mixtures of {IL (1) + thiophene, or benzothiophene (2) + heptane (3)} at T = 308.15 K and ambient pressure. Three ILs have been studied: 1-butyl-3-cyanopyridinium bis{(trifluoromethyl)sulfonyl}imide [BCN3Py][NTf2], 1-butyl-4-cyanopyridinium bis{(trifluoromethyl)sulfonyl}imide [BCN4Py][NTf2] and 1-hexyl-4-cyanopyridinium bis{(trifluoromethyl)sulfonyl}imide, [HCN4Py][NTf2]. One of the IL showed excellent results in terms of sulfur compounds selectivity and solute distribution ratio compared to what is currently used in industry. Chromatography analysis showed that the IL used as an entrainer was not present in the alkane layer. This elim...