Solubility and polarity parameters for pyridinecarboxamides and their complexes with copper(II) as determined by inverse gas chromatography

Voelkel, Adam; Borowiak‐Resterna, Aleksandra

doi:10.1016/0021-9673(96)00129-x

Cited by 9 publications

(4 citation statements)

References 29 publications

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“…Pyridinecarboxamides are more basic and stronger extractants [21][22][23] than pyridinecarboxylates. [24][25][26] As a result, some reagent protonation and a successive transfer of hydrochloric acid is observed. Thus, the protonated pyridinecarboxamide acts as a phase transfer catalyst and shortens the time necessary for attaining extraction equilibrium.…”

Section: Resultsmentioning

confidence: 99%

Palladium(II) Extraction and Extractant Adsorption at a Liquid/Liquid Interface

Wiśniewski

Szymanowski

1998

ANAL. SCI.

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Extraction has become a modern technique used to recover and separate noble metals, including palladium(II). Several reagents have been proposed, including hydroxyoximes, alkyl derivatives of 8-hydroxyquinoline, hydrophobic amines and esters of pyridine carboxylic acids. Some of them are used in industry. Usually, dihexyl sulfide or dioctyl sulfide are used. However, the extraction occurs very slowly, which is caused by the nature of hydrophobic extractant and symmetrical palladium chlorocomplex. The drawback can be overcome by the addition of thiocyanide ions, which disturb the symmetry of palladium(II) chlorocomplex 1,2 , the use of asymmetric dialkyl sulfides and/or containing a hydrophilic group 3,4 or the use of a phase transfer catalyst. 5-7 A similar effect is observed when other hydrophobic extractants are used, e.g. 2-hydroxy-5-nonylbenzophenone oxime (LIX65N) and 1-(2-pyridylazo)-2-naphthol (PAN). 1,8 Pyridine carbonates and carboxamides have been proposed by ICI 9-11 for copper extraction from chloride solutions, and the CUPREX Metal Extraction Process has been successfully used in a pilot plant for sulfidic copper ore concentrate processing. The commercial extractant Acorga CLX 50 has been used. It probably contains diisodecanyl pyridine-3,5-dicarboxylate as the active substance. The reagent seems to be an effective extractant for palladium(II) extraction.4-Alkylphenylamines are effective extractants of noble metals from acidic solutions.12,13 They extract selectively the group of noble metals in the presence of base metals. They are also successfully applied in analytical procedures used to determine the noble metals in various minerals, sludges and flotation concentrates.It is now commonly accepted that metal extraction with highly hydrophobic reagents occurs according to the interfacial mechanism with extractant preadsorption at the hydrocarbon/water interface. [14][15][16][17][18][19] The adsorption permits one to obtain an appropriate orientation and high concentration of extractant molecules at the interface needed for a quick extraction. This means that a relationship should be observed between the rate of extraction and the extractant interfacial activity.The aim of the work was to study the adsorption behavior at a hydrocarbon/water interface of welldefined palladium(II) extractants and effect of the adsorption on the rate of palladium(II) extraction. ExperimentalIndividual 4-alkylphenylamine (I) containing 6 to 14 carbon atoms in the alkyl group were used. The method of their synthesis and the analytical date were described previously. 19 Some other hydrophobic extractants were also considered: dihexyl sulfide (II), 2-hydroxyethyl decylsulfide (III) and its partly fluorinated analog (IV), decyl nicotiniate (V) and N,N-dihexylpyridine-3-carboxamide (VI). Palladium(II) extractionExtraction was carried out in dispersion at ambient temperature using equal volumes (5 cm 3 ) of the aqueous and organic phases. The concentrations of palladium(II) in 3 M HCl and of extractants in benzene or toluene ...

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Section: Resultsmentioning

confidence: 99%

Palladium(II) Extraction and Extractant Adsorption at a Liquid/Liquid Interface

Wiśniewski

Szymanowski

1998

ANAL. SCI.

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“…IGC is useful in studying IL thermodynamic properties. IGC has been used since 1969 in characterizing inorganic materials, polymers, carbon blacks, and other materials. − IGC underwent several improvements and is now used in characterizing ILs and IL blends. − When a liquid solute (probe) is injected into the column, the probe vaporizes and interacts with stationary-phase ILs; thus, retention time can then be determined. This method is directly applicable in analyzing mixtures.…”

Section: Introductionmentioning

confidence: 99%

Determination of Infinite Dilution Activity Coefficients of Several Organic Solutes in N-Butylpyridinium Nitrate/N-Octylpyridinium Nitrate by Blend Inverse Gas Chromatography

et al. 2017

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The miscibility behavior of N-butylpyridinium nitrate/ N-octylpyridinium blends with different compositions was studied using the inverse gas chromatography (IGC) technique. Twenty-one solvents, including alkanes, cycloalkane, aromatic hydrocarbons, alcohols, ethyl ether, acetone, and esters, with different chemical properties were studied to evaluate the interaction between N-alkylpyridinium nitrates and solvents. The interaction parameters of different ionic liquids [ILs] have been calculated. Results were consistent with the activity coefficients at infinite dilution and weight fraction activity coefficient. In addition, the miscibility term ΔH 1 S was significantly different in each obtained IL blend. The solubility parameters of N-butylpyridinium nitrate/N-octylpyridinium blends were derived using the calculation δ 1 2 /(RT) − χ 12 ∞ /V 1 versus δ 1 of probes. The altered values of the solubility parameters were consistent with those of the studied ILs based on the methylimidazolium cation.

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“…Furthermore, the thermodynamics of copper extraction was found to be strongly intluenced by the number [lor 2] and position of the ester group(s) in the pyridine ring. Finally, the extraction of copper was also studied with hydrophobic pyridine carboxamides (12)(13)(14)(15). All of these equilibrium studies demonstrate that ACORGA CLX-50 is a well designed extractant offering a good compromise between high efficiency of copper extraction from highly concentrated chloride media and easy stripping into water or dilute hydrochloric acid solutions.…”

Section: Introductionmentioning

confidence: 99%

Influence of Salting-Out Effects, Temperature and the Chemical Structure of the Extractant on the Rate of Copper(ii) Extraction From Chloride Media With Dialkyl Pyridine Dicarboxylates

Bouvier

Cote

Cierpiszewski

et al. 1998

Solvent Extraction and Ion Exchange

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ABS1RACTThe kinetics of copper(II) extraction from chloride solutions with ACORGA CLX-50 and three model dipentyl pyridine dicarboxylates having ester groups at various positions in the pyridine ring is investigated. It is shown that the extraction occurs in a diffusional regime and that both the ionic strength and temperature have a strong effect on the rate of copper extraction. Basically, the initial rate of copper extraction (denoted hereafter J0) increases as the ionic strength is increased, whereas J o increases or decreases versus temperature depending on the ionic strength. Such phenomena are explained in terms of salting-out effects and diffusion properties. Furthermore, ACORGA CLX·50 is shown to exhibit a good kinetic performance compared to the three model dipentyl pyridine dicarboxylates.

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Solubility and polarity parameters for pyridinecarboxamides and their complexes with copper(II) as determined by inverse gas chromatography

Cited by 9 publications

References 29 publications

Palladium(II) Extraction and Extractant Adsorption at a Liquid/Liquid Interface

Palladium(II) Extraction and Extractant Adsorption at a Liquid/Liquid Interface

Determination of Infinite Dilution Activity Coefficients of Several Organic Solutes in N-Butylpyridinium Nitrate/N-Octylpyridinium Nitrate by Blend Inverse Gas Chromatography

Influence of Salting-Out Effects, Temperature and the Chemical Structure of the Extractant on the Rate of Copper(ii) Extraction From Chloride Media With Dialkyl Pyridine Dicarboxylates

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