Effect of sidearm length upon competitive alkali metal solvent extraction into chloroform by lipophilic crown phosphonic acid monoalkyl esters

Pugia, Michael J.; Ndip, Grace; Lee, Han Koo.; Yang, Il Woo; Bartsch, Richard A.

doi:10.1021/ac00126a031

Cited by 34 publications

(21 citation statements)

References 17 publications

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“…In earlier work, we prepared lariat ether derivatives based upon a dibenzo-16-crown-5 scaffold in which oxyacetic acid [3][4][5][6][7][8], oxyacetohydroxamic acid [7], monoethyl oxymethylphosphonic ester [9], or N-(X)sulfonyl oxyacetamide groups [10] were attached to the central carbon of the three-carbon bridge in the polyether ring. In their ionized forms, such proton-ionizable lariat ethers are efficient and selective agents for the solvent extraction of alkali metal, alkaline earth metal, and lanthanide ions and for their transport across liquid membranes [7,[9][10][11][12][13][14][15][16][17][18][19][20][21][22][23].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of dibenzo‐16‐crown‐5 compounds with pendant ester and ether groups

Babb¹,

Bartsch²,

Collier³

et al. 2004

Journal of Heterocyclic Chem

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Structurally related dibenzo-16-crown-5 lariat ethers with pendant ester and ether groups are prepared. Structural variations within the series of alkyl lariat ether esters include changes in the O-alkyl group, attachment site and nature of the lipophilic group, and length of the spacer, which connects the ester group to the polyether framework. Also synthesized are bis(crown ether) diesters with two dibenzo-16-crown-5 or two dicyclohexano-16-crown-5 units and two ester groups connected to each other by a linker of varying length. Synthetic strategies for the preparation of these lariat ethers with pendant ester-and ether-containing side arms are described.

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Section: Introductionmentioning

confidence: 99%

“…In their ionized forms, such proton-ionizable lariat ethers are efficient and selective agents for the solvent extraction of alkali metal, alkaline earth metal, and lanthanide ions and for their transport across liquid membranes [7,[9][10][11][12][13][14][15][16][17][18][19][20][21][22][23].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of dibenzo‐16‐crown‐5 compounds with pendant ester and ether groups

Babb¹,

Bartsch²,

Collier³

et al. 2004

Journal of Heterocyclic Chem

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“…This property has been used to separate certain metal ions from matrices containing other ions, either by selective transport through a membrane containing the crown ether [6, 7 1 or by solvent extraction into an organic phase [8][9][10][11][12][13].…”

Section: Introductionmentioning

confidence: 99%

“…The solvent extraction and the potentiometric selectivities of the crown ether for one ion over another depend on many factors, such as the ion size [2j, the ring and cavity sizes of the crown ether [2, 24,331, the stability constant [ 11 j and the extractability of the complex into the organic phase [5,31 j, the stoichiometry of the complex [23], the lipophilicity, the nature and the position of the side arm [ 13,30,321, the number and coplanarity of the coordinating sites [23 1, the flexibility of the molecule's skeleton to attain the conformational position necessary for complex formal To whom correspondence should be addressed.…”

Section: Introductionmentioning

confidence: 99%

Potentiometric selectivity study of crown ethers containing four ring oxygen atoms and benzoxymethyl or carboxylic acid side chains as ionophores for lithium and potassium

1989

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Five crown ethers with four ring oxygen atoms and different types of pendant groups were used t o prepare ion-selective electrodes by coating a membrane containing the crown ether on the tip o f a silver wire incorporated in a flow cell. A flow injection analysis study was conducted to determine the potentiometric selectivities of the crown ethers for lithium, sodium, potassium, magnesium, and calcium ions. It was found that crown ethers with neutral side arms show selectivities for lithium over other ions, while those of acidic side arms show selectivities for potassium over the other ions. The effect of the addition of trioctylphosphine oxide to the electrode matrix was also investigated. A comparison is made between the potentiometric selectivities of the crown ethers for certain metal ions and tlieir selectivities in extracting the ions into an organic phase.

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“…The following procedures were similar to the method used for preparing 36; white powder, mp 246 -247° C, yield 93%, TLC (Si02 This preparation was based on a paper by Bartsch et a1. 13 Under a nitrogen atmosphere to sodium hydride (10.01 g, 95%, 396 mmol) was added dropwise 100 cm3 of dry tetrahydrofuran; the solution was then stirred for half an hour at room temperature. To the solution was added dropwise 300 cm3 of tetrahydrofuran containing p-(1,1,3,3-tetramethylbutyl)phenol (40.22 g, 195 mmol) for 5.5 h; the solution was then stirred for 1 h at room temperature.…”

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Solvent Extraction of Trivalent Rare Earth Metal Ions with Carboxylate Derivatives of Calixarenes

et al. 1995

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As novel calixarene or macrocyclic types of extractants, 37,38,39,40,41,42-hexakis(carboxymethoxy)-5,11,17,23,29,35-hexakis(1,1,3,3-tetramethylbutyl)calix [6]arene and 25,26,27,28-tetrakis(carboxymethoxy)-5,11,17,23-tetrakis(1,1,3,3-tetramethylbutyl)calix [4]arene as well asp-(1,1,3,3-tetramethylbutyl)phenoxy acetic acid, as their monomeric analog, and 2,6-bis[2-carboxymethoxy-5-(1,1,3,3-tetramethylbutyl}benzyl]-4-(1,1,3,3-tetramethylbutyl)phenoxyacetic acid as a linear trimer analog, have been synthesized in order to investigate their extraction abilities of rare earth metal ions, RE3+ (RE=Y, La, Pr, Nd, Sm, Eu, Gd, Ho, Er), from an aqueous nitrate solution. It was found that the calixarene derivatives provide much higher extractability and greater separation efficiency than do the monomeric analog and the other acidic carboxylate extractants. The selectivity for rare earth elements in this system is not affected by the ring size. In extraction from an aqueous mixture of nitric acid-glycine, the stoichiometry of the extracted species was determined and the extraction equilibrium constants as well as the separation factors were evaluated for each extractant. A stripping test was also performed and the stripping of rare earths was found to be successfully achieved with diluted hydrochloric acid. Calixarenepolyols and their derivatives have been attracting much attention as novel types of interesting host compounds.l-3 Their recognition ability for metal ions can be one of the remarkable features as a specific receptor.They have plural phenolic hydroxyl groups which can be relatively easily chemically modified. It is expected that the introduction of ion-exchangeable functional groups into them will make them effective extractants, due to a chelating effect, and also that the cyclic structures and their rigid skeletons contribute to a high selectivity, owing to their size-discriminating ability for metal ions with different ionic radii.A number of studies have been conducted on calixarenes or their derivatives as receptors for metal ions. Izatt et al. carried out extraction of alkali metal ions with 5, 1 1 , 17,23-tetra-t-butylcalix 26,27,11,17,23,29,38,39,40,41,38, 39,40,41,11,17,23,29,38,39,40,41,11,17,23,29,arene extract uranyl ion (U022+) efficiently and selectively as a complex with a pseudo planar penta-or hexacoordinate geometry.5 Yoshida et al. reported that 5,11,17, 23,29,38,39,40,41,hexol can extract copper(II) ions from an alkaline ammoniacal solution.6 Masuda et al. reported on the extraction of silver(I), palladium(II), and nickel(II) ion with 5, 1 1 , 1 7,23,29,35-hexa-t-butylcalix[6]arene-37,38, 39,40,41,42-hexol 37,38,39,40,41,42-hexakis(carboxymethoxy)-5,11,17,23,29,35-hexa-t-butylcalix[6]arene and 25,26,27, 28-tetrakis(carboxymethoxy)-5,11,17,23-tetra-t-butylcalix[4]arene.9However, the calixarene derivatives with t-butyl groups as alkyl radicals so far investigated have poor solubility in ordinary organic diluents, such as kerosene, benzene or toluene, and, consequently, are not necessarily...

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Effect of sidearm length upon competitive alkali metal solvent extraction into chloroform by lipophilic crown phosphonic acid monoalkyl esters

Abstract: A homologous serles of sym -bl~4(5)-terl-butylbenzo~16-

Cited by 34 publications

References 17 publications

Synthesis of dibenzo‐16‐crown‐5 compounds with pendant ester and ether groups

Synthesis of dibenzo‐16‐crown‐5 compounds with pendant ester and ether groups

Potentiometric selectivity study of crown ethers containing four ring oxygen atoms and benzoxymethyl or carboxylic acid side chains as ionophores for lithium and potassium

Solvent Extraction of Trivalent Rare Earth Metal Ions with Carboxylate Derivatives of Calixarenes

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