Molecular design of calixarene-based uranophiles which exhibit remarkably high stability and selectivity

Shinkai, Seiji; Koreishi, Hiroshi; Ueda, Kaori; Arimura, Takashi; Manabe, Osamu

doi:10.1021/ja00255a023

Cited by 247 publications

(203 citation statements)

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“…Hence, the design of effective host molecules for uranyl ions is related with the economic importance of selective extraction of uranium from water. [1][2][3] The process using adsorbents is thought to be the most effective method for recovery of uranium because of the high selectivity for uranium, the case of handling, the safety to the environment, etc. Examples of well-studied polymer ligands of uranyl ions are: carboxylate such as EDTA analogues, phenol, β-ketone, ammonium, sulfonic acid, and amidoxime.…”

Section: Introductionmentioning

confidence: 99%

Binding of Uranyl Ions by Water-Insoluble Polymers Containing Multiligand Groups

Rivas¹,

Peric²,

Villegas³

et al. 2008

J. Chil. Chem. Soc.

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ReagentsAcrylic acid (AA, Merck), 4-Acryloylmorpholine (AMo, 97% Aldrich), 4-vinyl pyridine (VPy, 95% Aldrich), 1,4-divinylbenzene (DVB, Fluka), N-(3-dimethylamino)propylmethacrylamide (NDAPA, Aldrich), 3-dimeth ylamino)propylacrylate (DAPA, Aldrich) were purified by distillation. 2,2'-Azoisobutyronitrile (AIBN, Merck) was recrystallized from methanol, N,N'-methylene-bis-acrylamide (MBA, 99% Aldrich) and ammonium persulfate (AP, 95% Aldrich) were used without further purification.The analytical grade, copper(II) nitrate, uranyl acetate, nitric acid, perchloric acid, sodium hydroxide and sodium carbonate were purchased from Merck.Synthesis of the resins P(NDAPA), P(DAPA), P(AMo-AA), P(NDAPA-AA), P(NDAPA-VPy), and P(DAPA-AA)The resins P(NDAPA), P(DAPA), P(AMo-AA), P(NDAPA-AA), P(NDAPA-VPy), and P(DAPA-AA) were synthesized by radical polymerization by mixing the corresponding reagents in a polymerization flask as follows:P ( BINDING OF URANYL IONS BY WATER-INSOLUBLE POLYMERS ABSTRACTThe crosslinked resins poly(N-(3-dimethylamino)propylmethacrylamide) P(NDAPA), poly((3-dimethylamino)propylacrylate)P(DAPA), poly(4-acryloylmorpholine-co-acrylic acid) P(AMo-AA), poly(N-(3-dimethylamino)propylmethacrylamide-co-4-vinyl pyridine) P(NDAPA-VPy) and poly((3-dimethyl amino)propylacrylate-co-acrylic acid) P(DAPA-AA), poly(N-(3-dimethylamino)propylmethacrylamide-co-acrylic acid) P(NDAPA-AA) were obtained by radical polymerization. These resins were completely insoluble in water. The uptake metal ion properties were studied by batch equilibrium procedure for copper(II) and uranyl ions. The polymerization mixtures were kept under nitrogen at 70ºC for 8 h (see Scheme 1). Then methanol was added and the resin was removed from the flask, filtered and washed with abundant water. The resin was dried under vacuum at 40ºC and then milled and sized by screening. The fraction with mesh size in the range of 250-500 mm was chosen.

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Section: Introductionmentioning

confidence: 99%

Binding of Uranyl Ions by Water-Insoluble Polymers Containing Multiligand Groups

Rivas¹,

Peric²,

Villegas³

et al. 2008

J. Chil. Chem. Soc.

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“…Correlation between ion-exchange properties and swelling/shrinking processes in hexasulfonated calix [6]arene doped polypyrrole films: ac-electrogravimetry and electrochemical atomic force microscopy investigations. Electrochimica Acta, Elsevier, 2011Elsevier, , 56 (10), pp.3516-3525.…”

mentioning

confidence: 99%

“…This electromechanical mechanism is amplified by the simultaneous exchange of free water molecules. Suggestions based on these observations, on structural characteristics of polypyrrole films, and on complexation ability of hexasulfonated calix [6]arenes incorporated in the films are discussed to explain i) the change of the identity of the exchanged cations as a function of the potential, ii) the exchange of free water molecules and, iii) the exchange of small amounts of nitrate ions. …”

mentioning

confidence: 99%

Correlation between ion-exchange properties and swelling/shrinking processes in hexasulfonated calix[6]arene doped polypyrrole films: ac-electrogravimetry and electrochemical atomic force microscopy investigations

Kim¹,

Gabrielli²,

Pailleret³

et al. 2011

Electrochimica Acta

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. Correlation between ion-exchange properties and swelling/shrinking processes in hexasulfonated calix [6]arene doped polypyrrole films: ac-electrogravimetry and electrochemical atomic force microscopy investigations. Electrochimica Acta, Elsevier, 2011Elsevier, , 56 (10), pp.3516-3525. <10.1016Elsevier, /j.electacta.2010 -00811845> 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 Unexpectedly, within the potential range encompassing this process, K + cations were found to be exchanged for more cathodic potentials whereas H 3 O + are exchanged for more anodic potentials. EC-AFM investigations revealed substantial shrinking and swelling during the oxidation (doping) and reduction (undoping) processes respectively. An obvious correlation can easily be built between these observations: the oxidation of the polymer films provokes an expulsion of the cations, as expected from cation exchanger polymer films, and therefore a decrease of the volume (and thickness) of these films whereas their reduction causes an insertion of cations and an increase of their volume (and thickness). This electromechanical mechanism is amplified by the simultaneous exchange of free water molecules. Suggestions based on these observations, on structural characteristics of polypyrrole films, and on complexation ability of hexasulfonated calix [6]arenes incorporated in the films are discussed to explain i) the change of the identity of the exchanged cations as a function of the potential, ii) the exchange of free water molecules and, iii) the exchange of small amounts of nitrate ions.

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“…Des études cristallographiques par diffraction des rayons X (Araki et al, 1993) ont établi que les complexes de l'ion uranyle adoptent une structure pseudoplanaire hexacoordonnée, ce qui n'est pas le cas des autres cations métal-liques. Ceci suggère l'utilisation d'un macrocycle hôte ayant un arrangement coplanaire de six groupes ligands spécifiques pour l'ion uranyle (Shinkai et al, 1986(Shinkai et al, ,1987. Toutefois, des travaux concernant le calix [o]arène substitué par six fonctions acide carboxylique ont montré une diminution de la sélectivité lorsque UO$+ se trouve en compétition avec d'autres cations métalliques lors de l'extraction (Nagaski et Shinkai, 1991).…”

Section: Various Wrocyclic Mobcuiesunclassified

Extraction sélective des actinides : application à l'analyse radiotoxicologique

et al. 1997

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Sur des solutions contenant en plus de l'uranium des ions sodium, marquées au 22Na euou du plutonium 239, l'extraction de l'uranium reste optimale. Sur des échantillons d'urine, après minéralisation, environ 100 % de l'uranium sont extraits par le calixarène. Ces premiers résultats montrent que le calixarène choisi présente une structure adéquate vis-à-vis de la structure de coordination de l'ion uranyle, permettant ainsi une extraction sélective de l'uranium. ABSTRACTSelective extraction of actinides: Application to radiotoxicological analysis. The extraction efficiency of uranium has heen studied in a two phases solventextraction system with a macrocyciic molecule, a calix[6]arene, bearing carboxy groups. The aqueous phase contained uranium in presence of sodium ions and the caiixarene was dissolved in benzene. The study of the extraction parameters allowed to propose an extraction mechanism. The extraction efficiency was found to increase with pH, with an optimal value around 100%. On synthetic solutions containing in addition to uranium sodium ions (spiked with 22Na) a n d or no decrease of uranium extraction was ohserved. When applied to urine samples, after organic digestion, about 100% of uranium have been extracted hy the caiixarene at pm3.7. These first results have shown that the caüxarene which has been selecteà has an adequate structure relative to the uranyl ion co-ordination structure, which permits a selective extraction of uranium.* service de dosimétrie, IPSN, B .P. no 6,

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Molecular design of calixarene-based uranophiles which exhibit remarkably high stability and selectivity

Cited by 247 publications

References 2 publications

Binding of Uranyl Ions by Water-Insoluble Polymers Containing Multiligand Groups

Binding of Uranyl Ions by Water-Insoluble Polymers Containing Multiligand Groups

Correlation between ion-exchange properties and swelling/shrinking processes in hexasulfonated calix[6]arene doped polypyrrole films: ac-electrogravimetry and electrochemical atomic force microscopy investigations

Extraction sélective des actinides : application à l'analyse radiotoxicologique

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