Doubly Crowned Calix[4]arenes in the 1,3-Alternate Conformation as Cesium-Selective Carriers in Supported Liquid Membranes

Asfari, Zouhair; Bressot, Christophe; Vicens, Jacques; Hill, C.; Dozol, Jean‐François; Rouquette, H.; Eymard, S.; Lamare, V.; Tournois, B.

doi:10.1021/ac00114a006

Cited by 198 publications

(118 citation statements)

References 39 publications

Supporting

Mentioning

115

Contrasting

Order By: Relevance

“…[1][2][3] Calixarene has plural phenolic hydroxyl groups, and various derivatives are readily synthesized by introducing a suitable functional group. To date, some investigators have synthesized attractive calixarene derivatives as a novel cyclic receptor for a target material: it had a remarkable selectivity to the target material based on the cavity size and the rigid molecular structure.…”

mentioning

confidence: 99%

Liquid-Liquid Extraction of Metal Ions with a Cyclic Ligand Calixarene Carboxyl Derivative

et al. 1998

View full text Add to dashboard Cite

Numerous studies have been performed to develop efficient separation and concentration processes of metals with a solvent-extraction technique, which is well known to be one of the promising techniques to separate and concentrate metals on an industrial scale. The extractant is known to have a crucial effect on the separation and extraction efficiency in the solvent-extraction process. Therefore, it is very important to develop an efficient extractant for a target metal ion. Thus, the choice of the extractant often determines the success of the metal-separation process.Recently, a cyclic ligand calixarene derivative has been noted to be a novel host compound of metal ions.1-3 Calixarene has plural phenolic hydroxyl groups, and various derivatives are readily synthesized by introducing a suitable functional group. To date, some investigators have synthesized attractive calixarene derivatives as a novel cyclic receptor for a target material: it had a remarkable selectivity to the target material based on the cavity size and the rigid molecular structure. However, apart from a large number of studies concerning the synthesis of novel calixarene compounds, its application to metal extraction is still limited. Izatt et al. 4 first reported on the extraction of alkaline metal ions with a calixarene; then, novel calixarene ligands have been synthesized for the extraction of several metal ions. 5-9In a previous paper we reported on the extraction behavior of rare-earth metals with a calixarene derivative functionalized by carboxyl groups. 10 In the present study, we investigated the extraction behavior of twelve kinds of metal ions, such as alkaline (Li, Na, K, Cs), alkaline-earth (Mg, Ca, Sr, Ba) and transition-metal ions (Cu, Zn, Co, Ni) with two cyclic compound calixarenes (o-carboxylate derivatives of p-toctylcalix[n]arene (n=4,6)) along with the monomer analog (n=1). The relationship between the cyclic structure of the calixarene and the extraction behavior of the metal ions was discussed. In particular, we focused on the ring-size effect of the cyclic ligands and the stability constants between the functional carboxyl group and the metal ions. ExperimentalReagents Figure 1 shows the structures and abbreviations of the extractants used in the present study. The extraction behavior of alkaline, alkaline-earth, and transition metals in liquid-liquid extraction was systematically investigated with a cyclic host compound calixarene carboxyl derivative. Using a novel host ligand, an extraction equilibrium experiment was carried out and the complexation mechanism between the metal ions and the cyclic ligand was investigated. Calixarene carboxyl derivatives showed high extractability for all of the metal ions compared to that of the monomer analog. The extraction behavior of alkaline and alkaline-earth metals is closely related to the cavity size of the cyclic ligands; thus, the tetramer selectively extracted sodium and calcium ions, while the hexamer did so for cesium and barium ions. On the other hand, the extractabilit...

show abstract

mentioning

confidence: 99%

Liquid-Liquid Extraction of Metal Ions with a Cyclic Ligand Calixarene Carboxyl Derivative

et al. 1998

View full text Add to dashboard Cite

show abstract

“…In an effort to find better cesium extractants, a Commission of the European Communities study performed at Cadarache, France, looked at functionalized calixarenes and, particularly, dialkyl calyx [4]arenas-crowns [82][83][84]. Numerous calixarene-crown extractants were developed, synthesized, and lab-scale tested during this project.…”

Section: Calixarenes/calixarene-crown Ethersmentioning

confidence: 99%

Cesium and Strontium Separation Technologies Literature Review

Todd¹,

Law²,

Herbst³

2004

View full text Add to dashboard Cite

“…Then 300 cm 3 chloroform was added to the acidic solution in order to extract the product. The mixed liquor containing chloroform was stirred for 2 h. The organic phase was separated, washed twice with 250 cm 3 hydrochloric acid (1 M), and dried with anhydrous magnesium sulfate. After the organic phase was evaporated, the final product was obtained.…”

Section: Synthesis Of Mono-functional Extractant 2ehpamentioning

confidence: 99%

“…To date, a lot of extractants have been developed and their extraction properties have been evaluated for a variety of metal ions. [1][2][3][4][5][6][7][8][9][10][11] In a previous study, we have developed novel bi-functional organophosphorus extractants in which two phosphonic acids were introduced as functional groups in the molecular structure for the separation of rare earth metals. 12 The result indicated that extraction performance of bi-functional extractants is very sensitive to the molecular structure of the spacer which connects the two functional moieties.…”

mentioning

confidence: 99%

Bi-Functional Organophosphorus Extractants and Computational Modeling for Copper(II) and Zinc(II) Extraction

et al. 1999

View full text Add to dashboard Cite

In the liquid-liquid extraction technology, the extractant is well-known to play a key role for separating target metal ions. The selection of appropriate extractant often decides the success of the extraction process. To date, a lot of extractants have been developed and their extraction properties have been evaluated for a variety of metal ions. [1][2][3][4][5][6][7][8][9][10][11] In a previous study, we have developed novel bi-functional organophosphorus extractants in which two phosphonic acids were introduced as functional groups in the molecular structure for the separation of rare earth metals. 12 The result indicated that extraction performance of bi-functional extractants is very sensitive to the molecular structure of the spacer which connects the two functional moieties. In the present study, we applied this novel type of bi-functional extractants to the separation of Cu(II) and Zn(II). Since the structures of Cu(II) and Zn(II) complexes with a ligand are different from each other, an interesting extraction behavior is expected for the bi-functional extractants. We focused on the difference in the length of the spacer because the spacer length was considered to affect the complex formation of Cu(II) (square planar) and Zn(II) (tetrahedral). In this work, three bifunctional organophosphorus extractants which have a different spacer length were prepared, and their extraction performance for Cu(II) and Zn(II) was investigated compared to that of a monomeric extractant as an analog.Recently, computational chemistry attracted much attention for the design of novel extractants. [12][13][14][15][16] In the field of solvent extraction, interfacial properties of extractants at the oil-water interfaces were discussed on the extraction rate using MD method. 17 In our study, extraction behavior of the bi-functional extractants for Cu(II) and Zn(II) is discussed with computational modeling. Calculated results support the conclusion that the bi-functional organophosphorus extractants show a high selectivity towards Zn(II) over Cu(II) compared to that of mono-functional analog. We also demonstrate that the computational modeling is very helpful for predicting extraction behavior and designing new extractants for a target metal ion. ExperimentalReagents 1,4-Butanediol-O,O′-diphenyl phosphonic acid (abbreviated as BDPA), 1,8-octanediol-O,O′-diphenyl phosphonic acid (abbreviated as ODPA) and 1,12-dodecanediol-O,O′-diphenyl phosphonic acid (abbreviated as DDDPA) were synthesized by the procedures described in the following section. A mono-functional extractant, phenyl phosphonic acid mono-2-ethylhexyl ester (abbreviated as 2EHPA), was also synthesized as the analog to discuss the bi-functional effect. Figure 1 shows the molecular structures of the newly developed extractants applied in this study. Novel bi-functional extractants, which possess two phosphonic groups on both sides of the extractants, have been synthesized for the separation of Zn(II) and Cu(II). The separation properties and extractability of the novel ex...

show abstract

Doubly Crowned Calix[4]arenes in the 1,3-Alternate Conformation as Cesium-Selective Carriers in Supported Liquid Membranes

Cited by 198 publications

References 39 publications

Liquid-Liquid Extraction of Metal Ions with a Cyclic Ligand Calixarene Carboxyl Derivative

Liquid-Liquid Extraction of Metal Ions with a Cyclic Ligand Calixarene Carboxyl Derivative

Cesium and Strontium Separation Technologies Literature Review

Bi-Functional Organophosphorus Extractants and Computational Modeling for Copper(II) and Zinc(II) Extraction

Contact Info

Product

Resources

About