Applicability of a Calixarene-Crown Compound for the Removal of Cesium from Alkaline Tank Waste

Haverlock, Tamara J.; Bonnesen, Peter V.; Sachleben, Richard A.; Moyer, Bruce A.

doi:10.1524/ract.1997.76.12.103

Cited by 79 publications

(55 citation statements)

References 13 publications

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“…[7] Calix[4]arene crown-6 ethers coordinate to cesium cations more strongly (by more than a factor of 100) and selectively than alkylated derivatives of dibenzo-21-crown-7, [8] previously considered to be the best crown ethers for cesium separations.…”

Section: Introductionmentioning

confidence: 99%

Rational Design of Cesium‐Selective Ionophores: Dihydrocalix[4]arene Crown‐6 Ethers

et al. 2003

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Molecular mechanics calculations performed on calix[4]arene crown‐6 ethers predict that the 1,3‐dihydro derivatives will exhibit greater complementarity for potassium and cesium ions than the parent 1,3‐bis(alkyloxy) calixcrowns. The X‐ray crystal structures of 1,3‐alt‐bis(octyloxy)calix[4]arene benzocrown‐6 ether, dihydrocalix[4]arene benzocrown‐6 ether, and the cesium nitrate complex of dihydrocalix[4]arene benzocrown‐6 ether were determined. The structure of the cesium complex corresponds closely to the structure predicted by molecular mechanics. The dihydrocalix[4]arene crown‐6 ethers exhibit enhanced cesium selectivity in the extraction of alkali‐metal salts. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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Section: Introductionmentioning

confidence: 99%

Rational Design of Cesium‐Selective Ionophores: Dihydrocalix[4]arene Crown‐6 Ethers

et al. 2003

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“…[6][7][8][9] The complementarity between the crown ether and Cs þ cation size as a guesthost system is an essential criterion for efficient extractant design. The performance of this system was first studied on simulated waste and confirmed on real high-activity liquid waste, in tests employing liquid-liquid extraction 10,11 and/ or supported liquid membranes. 12 Hence, these compounds were extensively studied in several experimental 13 and molecular modelling investigations.…”

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confidence: 96%

High‐performance liquid chromatography with electrospray ionisation mass spectrometry and diode array detection in the identification and quantification of the degradation products of calix[4]arene crown‐6 under radiolysis

Lamouroux

Aychet

Lelièvre

et al. 2004

Rapid Comm Mass Spectrometry

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The extraction of 135Cs from high-activity liquid waste, arising from reprocessing of spent nuclear fuel, can be achieved by using calix[4]arene crown-6 compounds. The radiolytic degradation of di(n-octyloxy)calix[4]arene crown-6 (octMC6), in aliphatic or aromatic solvent in contact with 3 M nitric acid, was studied by high-performance liquid chromatography directly coupled to electrospray ionisation mass spectrometry (LC/ESI-MS). More than 50 distinct degradation products were observed, and about 30 of these were identified. These compounds can be assigned to three categories, namely, products of reactions involving radical cleavage or addition, of oxidation reactions, or of aromatic substitution reactions. The major product, corresponding to substitution by an NO2 group, was quantified by external standard calibration using a purified synthetic sample. Despite the observation of all these degradation compounds, octMC6 appears to be remarkably stable under these drastic conditions, combining hydrolysis (HNO(3) 3 M) and an extreme exposure to radiolysis (10(6) Gy). Less than 35% degradation of octMC6 was observed in aromatic solvent under these conditions.

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“…Sr, which have fairly long half-lives of Ϸ30 years) from these wastes (24)(25)(26)(27). There have been extensive attempts to design and develop systems that can be used in nuclear waste separations as effective ionophores.…”

mentioning

confidence: 99%

“…There have been extensive attempts to design and develop systems that can be used in nuclear waste separations as effective ionophores. In this context the use of various types of ionophores has been reported (25)(26)(27), and there have been extensive attempts to explore new types of ionophores that have a high selectivity for these hazardous isotopes.…”

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confidence: 99%

Ionophores and receptors using cation-π interactions: Collarenes

Choi

Suh

Cho

et al. 1998

Proc. Natl. Acad. Sci. U.S.A.

153

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Cation-interactions are important forces in molecular recognition by biological receptors, enzyme catalysis, and crystal engineering. We have harnessed these interactions in designing molecular systems with circular arrangement of benzene units that are capable of acting as ionophores and models for biological receptors.[n]Collarenes are promising candidates with high selectivity for a specific cation, depending on n, because of their structural rigidity and well-defined cavity size. [12]Collarene exhibits a pronounced affinity for tetramethylammonium cation and acetylcholine, which implies that it could serve as a model for acetylcholinestrase. Thus, collarenes can prove to be novel and effective ionophores͞model-receptors capable of heralding a new direction in molecular recognition and host-guest chemistry.The design of novel ionophores and receptors has attracted considerable interest in the recent past (1-5). The cationinteraction discovered by Dougherty and coworkers (6, 7) has received much attention as a new type of binding force important in biological molecular recognition (8-15), enzyme catalysis (16, 17), and crystal engineering (3, 18). This cationinteraction is known to be responsible for the binding of acetylcholine (ACh) to its deactivating enzyme (8, 9), acetylcholinestrase (19,20), which has served as a target receptor in designing therapeutic agents against various ailments like myasthenia gravis, glaucoma, and Alzheimer's disease (21-23).A lot of effort and concern has been evinced on the disposal of nuclear wastes. A major bottleneck, however, stems from the effective separation of major hazardous isotopes (such as 137 Cs and 90 Sr, which have fairly long half-lives of Ϸ30 years) from these wastes (24-27). There have been extensive attempts to design and develop systems that can be used in nuclear waste separations as effective ionophores. In this context the use of various types of ionophores has been reported (25-27), and there have been extensive attempts to explore new types of ionophores that have a high selectivity for these hazardous isotopes.It therefore is appealing to investigate the possibility of designing novel ionophores and model receptors based on the principle of the cation-interaction. There have been reports of the systems in which -orbitals are oriented vertically to the plane of the rings, namely belt-shape carbocyclic-conjugated systems (such as annulenes, beltenes, cyclacenes, and collarenes) (28-37). The recent discoveries of fully conjugated systems with a curved surface like fullerenes and carbon nanotubes (38, 39) further adds fuel to such a kind of study. However, belt-shape carbocyclic-conjugated systems have hardly been studied apart from the synthetic study of cyclacene precursors and collarenes (32-37).Thus, it would be of importance to investigate whether cyclacenes (comprised of only benzene moieties) and collarenes (having CH 2 linkages between benzene units) can behave as ionophores and receptors. These molecular structures can be understood f...

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Applicability of a Calixarene-Crown Compound for the Removal of Cesium from Alkaline Tank Waste

Cited by 79 publications

References 13 publications

Rational Design of Cesium‐Selective Ionophores: Dihydrocalix[4]arene Crown‐6 Ethers

Rational Design of Cesium‐Selective Ionophores: Dihydrocalix[4]arene Crown‐6 Ethers

High‐performance liquid chromatography with electrospray ionisation mass spectrometry and diode array detection in the identification and quantification of the degradation products of calix[4]arene crown‐6 under radiolysis

Ionophores and receptors using cation-π interactions: Collarenes

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