Intramolecular synergism for group separation extraction of trivalent rare earths by a cross type calix[4]arene with phosphonic and carboxylic acid bifunctionality
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  • 作者:Anup Basnet Chetry (1)
    Takashi Matsufuji (1)
    Birendra Babu Adhikari (1)
    Shintaro Morisada (1)
    Hidetaka Kawakita (1)
    Keisuke Ohto (1)
    Tatsuya Oshima (2)
    Jumina (3)

    1. Department of Chemistry and Applied Chemistry
    ; Faculty of Science and Engineering ; Saga University ; 1-Honjo ; Saga ; 840-8502 ; Japan
    2. Department of Applied Chemistry
    ; Faculty of Engineering ; University of Miyazaki ; 1-1 Gakuen Kibanadai-nishi ; Miyazaki ; 889-2192 ; Japan
    3. Department of Chemistry
    ; Faculty of Mathematics and Natural Sciences ; Gadjah Mada University ; Sekip Utara Bis.21 ; Yogyakarta ; 55281 ; Indonesia
  • 关键词:Calix[4]arene ; Intramolecular synergistic extraction ; Rare earth elements ; Group separation
  • 刊名:Journal of Inclusion Phenomena and Macrocyclic Chemistry
  • 出版年:2015
  • 出版时间:April 2015
  • 年:2015
  • 卷:81
  • 期:3-4
  • 页码:301-310
  • 全文大小:618 KB
  • 参考文献:Gutsche, CD eds. (1996) Calixarenes Revisited. Royal society of chemistry, Cambridge
    Mandolini, L, Ungro, R eds. (2000) Calixarenes in Action. Imperial college press, London
    Lumetta, GJ, Rogers, RD, Gopalan, AS eds. (2000) Calixarenes for Separations. ACS, Washington DC
    1. Ludwig, R (2000) Calixarenes in analytical and separation chemistry. Fresenius J. Anal. Chem. 367: pp. 103-128 CrossRef
    2. Ohto, K (2013) Molecular design and metal extraction behavior of calixarene compounds as host extractants. Ion Exch. Solvent Extr. 21: pp. 8-127
    3. Ohto, K, Yano, M, Inoue, K, Yamamoto, T, Goto, M, Nakashio, F, Shinkai, S, Nagasaki, T (1995) Solvent extraction of trivalent rare earth metal ions with carboxylate derivatives of calixarenes. Anal. Sci. 11: pp. 893-902 CrossRef
    4. Ohto, K, Ishibashi, H, Kawakita, H, Inoue, K, Oshima, T (2009) Allosteric coextraction of sodium and metal ions with calix[4]arene derivatives 1. Role of the first-extracted sodium ion as an allosteric trigger for self-coextraction of sodium ions with calix[4]arene tetracarboxylic acid. J. Incl. Phenom. Macrocycl. Chem. 65: pp. 111-120 CrossRef
    5. Ohto, K, Matsufuji, T, Yoneyama, T, Tanaka, M, Kawakita, H, Oshima, T (2011) Preorganized, cone-conformational calix[4]arene possessing four propylenephosphonic acids with high extraction ability and separation efficiency for trivalent rare earth elements. J. Incl. Phenom. Macrocycl. Chem. 71: pp. 489-497 CrossRef
    6. Ohto, K, Takedomi, A, Chetry, AB, Morisada, S, Kawakita, H, Oshima, T (2013) The effect of phenoxy oxygen atoms on extremely high extraction ability and less separation efficiency of trivalent rare earth elements with tetraphosphonic acid derivative of calix[4]arene. J. Incl. Phenom. Macrocycl. Chem. 77: pp. 363-373 CrossRef
    7. Ohto, K, Shiratsuchi, K, Inoue, K, Goto, M, Nakashio, F, Shinkai, S, Nagasaki, T (1996) Extraction behavior of copper(II) ion by calixarene carboxylates derivatives preorganized by sodium ion. Solvent Extr. Ion Exch. 14: pp. 459-478 CrossRef
    8. Yoneyama, T, Sadamatsu, H, Kuwata, S, Kawakita, H, Ohto, K (2012) Allosteric coextraction of sodium and metal ions with calix[4]arene derivatives 2: first numerical evaluation for the allosteric effect on alkali metal extraction with crossed carboxylicacidtypecalix[4]arenes. Talanta 88: pp. 121-128 CrossRef
    9. Sadamatsu, H., Morisada, S., Kawakita, H., Ohto, K.: unpublished data
    10. Blake, CA, Baes, CF, Brown, KB, Coleman, CF, White, JC (1958) Solvent extraction of uranium and other metals by acidic and neutral organophosphorus compounds. Proceedings of the United Nations International Conference on the Peaceful Uses of Atomic Energy 28: pp. 289-298
    11. Irving, H, Edgington, DN (1960) Synergic effects in the solvent extraction of the actinides. I. Uranium(VI). J. Inorg. Nucl. Chem. 15: pp. 158-170 CrossRef
    12. Akaiwa, H, Kawamoto, H (1982) The application of synergistic extraction to analytical chemistry. Rev. Anal. Chem. 6: pp. 65-86 CrossRef
    13. Dukov, IL (1996) Synergistic solvent extraction of metals. Part 1. Chelating extractants plus amines or quaternary ammonium salts. Anal. Lab. 5: pp. 147-161
    14. Dukov, I. L.: Synergistic solvent extraction of metals. Part 2. Alkylphosphoric and carboxylic acids and neutral organophosphorus extractants plus amines or quaternary ammonium salts. Anal. Lab. 5(4), 219-161 (1996)
    15. Bond, AH, Dietz, ML, Chiarizia, R (2000) Incorporating size selectivity into synergistic solvent extraction: a review of crown ether-containing systems. Ind. Eng. Chem. Res. 39: pp. 3442-3464 CrossRef
    16. Nishihama, S, Hirai, T, Komasawa, I (2001) Review of advanced liquid-liquid extraction systems for the separation of metal ions by a combination of conversion of the metal species with chemical reaction. Ind. Eng. Chem. Res. 40: pp. 3085-3091 CrossRef
    17. Cox, M Liquid-liquid extraction and liquid membranes in the perspective of the twenty-first century. In: Aguilar, M, Cortina, JL eds. (2008) Solvent Extraction and Liquid Membranes. CRC Press, Boca Raton, pp. 1-19 CrossRef
    18. Strzelbicki, J, Bartsch, RA (1981) Extraction of alkali metal cations from aqueous solutions by a crown ether carboxylic acid. Anal. Chem. 53: pp. 1894-1899 CrossRef
    19. Strzelbicki, J, Bartsch, RA (1981) Solvent extraction of alkali metal cations from aqueous solutions by highly lipophilic crown ether carboxylic acids. Anal. Chem. 53: pp. 2247-2250 CrossRef
    20. Strzelbicki, J, Bartsch, RA (1981) Extraction of alkaline earth cations from aqueous solutions by crown ether carboxylic acids. Anal. Chem. 53: pp. 2251-2253 CrossRef
    21. Gokel, GW, Dishong, DM, Diamond, CJ (1980) Lariat ethers. Synthesis and cation binding of macrocyclic polyethers possessing axially disposed secondary donor groups. J. Chem. Soc., Chem. Commun. 22: pp. 1053-1054 CrossRef
    22. Umetani, S., Yamazaki, S., Ogura, K.: Solvent extraction of metal ions with novel 4-acyl-5-pyrazolones having crown ether moiety as intramolecular synergist. Proceedings of International Solvent Extraction Conference ISEC 2002, Cape Town, South Africa, 420鈥?24 (2002)
    23. Umetani, S, Ito, M, Shimojo, S, Kurahashi, K, Yamazaki, S, Ogura, K (2007) Solvent extraction of divalent transition metal ions with diaza-crown ethers having two acylpyrazolone moieties. Solvent Extr. Res. Dev., Jpn. 14: pp. 177-181
    24. Kurahashi, K, Umetani, S, Sohrin, Y (2008) Solvent extraction of divalent metal ions with azacrown ether substituted acylpyrazolones. Anal. Sci. 24: pp. 225-229 CrossRef
    25. Shimojo, K, Okamura, H, Hirayama, N, Umetani, S, Imura, H, Naganawa, H (2009) Cooperative intramolecular interaction of diazacrown ether bearing 尾-diketone fragments on an ionic liquid extraction system. Dalton Trans. 25: pp. 4850-4852 CrossRef
    26. Ogata, M, Fujimoto, K, Shinkai, S (1994) Molecular design of calix[4]arene-based extractants which show high Ca2聽+聽selectivity. J. Am. Chem. Soc. 116: pp. 4505-4506 CrossRef
    27. Casnati, A, Fischer, C, Guardigli, M, Isernia, A, Manet, I, Sabbatini, N, Ungaro, R (1996) Synthesis of calix[4]arene receptors incorporating (2,2鈥?bipyridin-6-yl)methyl and (9-methyl-1,10-phenanthrolin-2-yl)methyl chromophores and luminescence of their Eu3聽+聽and Tb3聽+聽complexes. J. Chem. Soc., Perkin Trans. 2: pp. 395-399 CrossRef
    28. Yaftian, MR, Burgard, M, Matt, D, Wieser, C (1997) Dieleman, C: multifunctional calix[4]arenes containing pendant amide and phosphoryl groups: their use as extracting agents and carriers for alkali cations. J. Incl. Phenom. Mol. Recog. Chem. 27: pp. 127-140 CrossRef
    29. Arnaud-Neu, F, Browne, JK, Byrne, D, Marrs, DJ, McKervey, MA, O鈥橦agan, P, Schwing-Weill, MJ, Walker, A (1999) Extraction and complexation of alkali, alkaline earth, and F-element cations by calixaryl phosphine oxides. Chem. Eur. J. 5: pp. 175-186 CrossRef
    30. Beer, PD, Drew, MGB, Hesek, D, Kan, M, Nicholson, G, Schmitt, P, Sheen, PD, Williams, G (1998) A neutral uranyl dimeric complex and remarkable extraction properties of a 1-acid 3-diethyl amide substituted calix[4]arene ligand. J. Chem. Soc., Dalton Trans. 17: pp. 2783-2786 CrossRef
    31. Mikulasek, L, Gruner, B, Dordea, C, Rudzevich, V, Boehmer, V, Haddaoui, J, Hubscher-Bruder, V, Arnaud-Nue, F, Caslavsky, J, Selucky, P (2007) Tert-butyl-calix[4]arenes substituted at the narrow rim with cobalt bis(dicarbollide)(1-) and CMPO groups - new and efficient extractants for lanthanides and actinides. Eur. J. Org. Chem. 28: pp. 4772-4783 CrossRef
    32. Casnati, A, Ungaro, R, Asfari, Z, Vicens, J Crown ethers derived from calix[4]arenes. In: Asfari, Z, Boehmer, V, Harrowfield, JM, Vicens, J eds. (2001) Calixarenes 2001. Kluwer, Netherlands, pp. 365-384
    33. Alfieri, C, Dradi, E, Pochini, A, Ungaro, R, Andreetti, GD (1983) Synthesis and x-ray crystal and molecular structure of a novel macrobicyclic ligand: crowned p-tert-butylcalix[4]arene. J. Chem. Soc., Chem. Commun. 19: pp. 1075-1077 CrossRef
    34. Ungaro, R, Pochini, A, Andreetti, GD (1984) New ionizable ligands from p-tert-butylcalix[4]arene. J. Incl. Phenom. Macrocycl. Chem. 2: pp. 199-206 CrossRef
    35. Casnati, A, Pochini, A, Ungaro, R, Ugozzoli, F, Arnaud, F, Fanni, S, Schwing, M-J, Egberink, RJM, Jong, F, Reinhoudt, DN (1995) Synthesis, complexation, and membrane transport studies of 1,3-alternate calix[4]arene-crown-6 conformers: a new class of cesium selective ionophores. J. Am. Chem. Soc. 117: pp. 2767-2777 CrossRef
    36. Thuery, P, Nierlich, M, Lamare, V, Dozol, J-F, Asfari, Z, Vicens, J (2000) Bis(crown ether) and azobenzocrown derivatives of calix[4]arene. A review of structural information from crystallographic and modelling studies. J. Incl. Phenom. Macrocycl. Chem. 36: pp. 375-408 CrossRef
    37. Haverlock, TJ, Bonnesen, PV, Sachleben, RA, Moyer, BA (2000) Analysis of equilibria in the extraction of cesium nitrate by calix[4]arene-bis(t-octylbenzo-crown-6) in 1,2-dichloroethane. J. Incl. Phenom. Macrocycl. Chem. 36: pp. 21-37 CrossRef
    38. Ramachandran, BR, Baker, SD, Suravajhula, G, Derosa, PA (2013) Selective complexation of alkali metal ions using crown ethers derived from calix[4]arenes: a computational investigation of the structural and energetic factors. J. Incl. Phenom. Macrocycl. Chem. 75: pp. 185-195 CrossRef
    39. Ohto, K, Fujimoto, Y, Inoue, K (1999) Stepwise extraction of two lead ions with a single molecule of calix[4]arene tetracarboxylic acid. Anal. Chim. Acta 387: pp. 61-69 CrossRef
  • 刊物类别:Chemistry and Materials Science
  • 刊物主题:Chemistry
    Organic Chemistry
    Food Science
    Crystallography
  • 出版者:Springer Netherlands
  • ISSN:1573-1111
文摘
A well organized calix[4]arene derivative in the cone configuration with carboxylic and phosphonic acid groups positioned at distal pairs has been prepared in order to investigate the extraction behavior of trivalent rare earths together with selected divalent metals. This product exhibited high extraction ability for the rare earths over the divalent metals investigated due to the complementarity of these trivalent ions with the above two functional groups without chelation to the phenoxy oxygen atoms. The extraction of the rare earths takes place by one of ion-exchange, where three protons are replaced by one Ln(III) cation. The stoichiometry of rare earth complexation was also determined by slope analysis, loading test and the continuous variation procedures. The extraction ability of the above reagent towards the respective rare earth ions was constant and their group separation over other metal ions proved possible. It was concluded that the presence of the two different functional groups on the calixarene structure results in a favorable synergistic interaction with the lanthanides. The results of stripping experiments for the loaded metals are also reported.

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