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Selective Extraction with Chelates, Macrocycles and Calixarenes

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Extraction of Metals from Soils and Waters

Part of the book series: Modern Inorganic Chemistry ((MICE))

Abstract

When choosing a compound for use as an extractant for metal ions several factors must be considered. One is how strongly it binds to the metal, and although this stability constant of the metal complex is not the only factor, it is still an important consideration. Since it is likely that the in situ environment contains complexants such as chloride, nitrate or sulfate ions, possibly at high concentrations, it is necessary that the added extractant is a competitve complexant under such conditions. As a result, extractants are usually not simple monodentate complexants. Multidentate complexants such as chelates have higher metal ion stability constants than do monodentates, mainly because of entropic effects. They are therefore often chosen as extractants.

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References

  1. Y. A. Zolotov,“Extraction of Chelate Compounds” Ann Arbor-Humphrey Science Publishers, 1970.

    Google Scholar 

  2. P. Cazeneuve, C. R. Acad. Sci., 1900, 131, 346.

    CAS  Google Scholar 

  3. C. F. Bell, “Principles and Applications of Metal Chelation” Clarendon Press, Oxford, U.K., 1977

    Google Scholar 

  4. C. J. Pedersen, J. Am. Chem. Soc., 1967, 89, 2495.

    Google Scholar 

  5. B. P. Hay, Coord. Chem. Revs.,1993 126,177.

    Google Scholar 

  6. J. Gross, G. Harder, A. Siepen, J. Harren, F. Vögtle, H. Stephan, K. Gloe, B. Ahlers, K. Cammann, K. Rissanen, Chem. Eur. 1, 1996, 2, 1585.

    Article  Google Scholar 

  7. J. Rebek, Jr., Angew. Chem., Int. Ed. Engl., 1990, 29, 245.

    Article  Google Scholar 

  8. E. A. Wintner, M. M. Conn, J. Rebek, Jr., Accts. Chem. Res., 1994, 27, 198.

    Article  CAS  Google Scholar 

  9. F. C. J. M. van Veggel, W. VerJoom, D. N. Reinhoudt, Chem. Rev., 1994, 94, 279.

    Article  Google Scholar 

  10. H.-J. Schneider, Chem. Soc. Rev., 1994, 227.

    Google Scholar 

  11. A. Deratani, B. Sebille, Anal. Chem., 1981, 53, 1742.

    Article  CAS  Google Scholar 

  12. A. T. Yordanov, D. M. Roundhill, Coord. Chem. Rev., 1998, 170, 93.

    Article  CAS  Google Scholar 

  13. D. H. Busch, Chem. Rev., 1993, 93, 847.

    Article  CAS  Google Scholar 

  14. G. Drasch, L. V. Meyer, G. Kauert, Fresenius Z., Anal. Chem., 1982, 311, 571.

    Article  CAS  Google Scholar 

  15. J. M. Lo, Y. P. Lin, K. S. Lin, Anal. Sci., 1991, 7, 455.

    Article  CAS  Google Scholar 

  16. T. Yamane, T. Mukoyama, T. Sasamoto, Anal. Chim. Acta., 1974, 69, 347.

    Article  CAS  Google Scholar 

  17. A. Dornemann, H. Kleist, Analyst, 1979, 104, 1030.

    Article  CAS  Google Scholar 

  18. S. Ichinoki, T. Morita, M. Yamazaki, J. Liq. Chrom., 1983, 6, 2079.

    Google Scholar 

  19. S. Ichinoki, T. Morita, M. Yamazaki, J. Liq.Chrom., 1984, 7, 2467.

    Google Scholar 

  20. F. L. L. Muller, J. D. Burton, P. J. Statham, Anal. Chins. Acta.,1991 245,21.

    Google Scholar 

  21. G. Bozsai, M. Csanady, Fresenius Z. Anal. Chem., 1979, 297, 370.

    Article  CAS  Google Scholar 

  22. T. Hsieh, L. K. Liu, Anal. Chico. Acta., 1993, 282, 221.

    Article  CAS  Google Scholar 

  23. T. Honjo, Bull. Chem. Soc. Jpn., 1984, 57, 591.

    Article  CAS  Google Scholar 

  24. M. L. Lee, G. Tolg, E. Beinrohr, P. Tschopel, Anal. Chins. Acta., 1993, 272, 193.

    Article  CAS  Google Scholar 

  25. N. Wolf, D. M. Roundhill, Polyhedron, 1994, 13, 2801.

    Google Scholar 

  26. W. H. Chan, S. Y. Lam-Leung, K. W. Cheng, Y. C. Yip, Anal. Letts., 1992, 25, 305.

    Article  CAS  Google Scholar 

  27. Emerging Technologies in Hazardous Waste Management,A. P. Hong, T. Chen, R. Okey, ACS Symposium. Ser., No. 607, American Chemical Society. Washington, D.C., 1995.

    Google Scholar 

  28. T.-C. Chen, A. Hong, J. Hazard. Mater., 1995, 41, 147.

    Article  CAS  Google Scholar 

  29. A. P. Hong, T. Chen, R. W. Okey, Proc.WaterEnviron. Fed. Annu. Conf Expo.,1993, 66 Vol.5, p. 171.

    Google Scholar 

  30. R. L. Jenkins, B. J. Scheybeler, M. L. Smith, R. Baird, M. P. Lo, R. T. Haug, Journal WPCF, 1981, 53, 25.

    CAS  Google Scholar 

  31. J. L. Howard, J. Shu, Environ. Poll., 1996, 91, 89.

    Article  CAS  Google Scholar 

  32. J. Roca, F. Pomares, Commun. Soil Sci. Plant Anal., 1991, 22, 2119.

    Google Scholar 

  33. R. Kocjan, M. Garbacka, Sep. Sci. Technol., 1994, 29, 799.

    Article  CAS  Google Scholar 

  34. K. Garnett, P. W. W. Kirk, J. N. Lester, R. Perry, J. Environ. Qual., 1985, 14, 549.

    Article  CAS  Google Scholar 

  35. E. Schonberger, J. Kassovicz, A. Shenhar, Heavy Met. Environ., Int. Conf, 4 th 1983 vol. 1, 218.

    Google Scholar 

  36. W. P Miller, W. W. McFee, J. M. Kelly, J. Environ. Qual., 1983, 12, 579.

    Article  CAS  Google Scholar 

  37. A. K. Guha, P. V. Shanbhag, K. K. Sirkar, C. H. Yun, D. Trivedi, D. Vaccari, Waste Management, 1993, 13, 395.

    Article  CAS  Google Scholar 

  38. R. Kocjan, S. Przeszlakowski, Talanta, 1992, 39, 63.

    Article  CAS  Google Scholar 

  39. R. Kocjan, Analyst, 1992, 117, 741.

    Article  CAS  Google Scholar 

  40. K. Hiratani, K. Taguchi, Bull. Chem. Soc. Jpn., 1990, 63, 3331.

    Article  CAS  Google Scholar 

  41. M. Schuster, Nachr. Chem., Tech. Lab., 1992, 40, 682.

    CAS  Google Scholar 

  42. S. Inokuma, K. Hasegawa, S. Sakai, J. Nishimura, Chem. Lett., 1994, 1729.

    Google Scholar 

  43. P. M. van Berkel, W. L. Driessen, J. Reedijk, D.C. Sherrington, A. Zitsmanis, Reactive and Functional Polymers, 1995, 27, 15.

    Article  Google Scholar 

  44. P. Burla, Z. Fresenius, Anal. Chem., 1989, 306, 233.

    Google Scholar 

  45. I. P. Alimarin, V. M. Ivanov, T. A. Bolshova, E. M. Basova, Z. Fresenius, Anal. Chem., 1989, 335, 63.

    Article  CAS  Google Scholar 

  46. U. B. Talwar, B. C. Haldar, Indian J. Chem., 1969, 7, 803.

    CAS  Google Scholar 

  47. A. Miyazaki, A. Kimura, K. Bansho, Y. Umezaki, Anal. Chim. Acta, 1982, 14, 213.

    Article  Google Scholar 

  48. M. Garcia-Vargas, M. Belizon, M. P. Hernandez-Artiga, C. Martinez, J. A. Perez-Bustamante, Appl. Spectr., 1986, 40, 1058.

    Article  CAS  Google Scholar 

  49. S. Ide, Y. Katayama, H. Nakamura, M. Takagi, Solv. Extr. Ion Exch., 1987, 5, 853.

    Article  CAS  Google Scholar 

  50. T. Kitamori, K. Suzuki, T. Sawada, Y. Gohshi, K. Motojima, Anal. Chem., 1986, 58, 2275.

    Google Scholar 

  51. V. Leepipatpiboon, J. Chromar., 1995, A697, 137.

    Article  CAS  Google Scholar 

  52. K. Gloe, H. Stephan, T. Krüger, A. Möckel, N. Woller, G. Subkiew, M. J. Schwuger, R. Neumann, E. Weber, Progr. Colloid Polym. Sci., 1996, 101, 145.

    Article  CAS  Google Scholar 

  53. H. Stephan, K. Gloe, T. Krüger, C. Chartroux, R. Neumann, E. Weber, A. Möckel, N. Woher, G. Subklew, M. J. Schwuger, Solv. Extr. Res. andDev., Japan, 1996, 3, 43.

    CAS  Google Scholar 

  54. S. Prasad, D. C. Rupainwar, Poll. Res., 1990, 9, 15.

    CAS  Google Scholar 

  55. T. Hayashita, K. Yamasaki, K. Kunogi, K. Hiratani, X. Huang, Y. Jang, R. A. Bartsch, Abstr. XIX In Symp. Macrocycl. Chem. Lawrence, Kansas 1994, STS.

    Google Scholar 

  56. T. Nabeshima, T. Inaba, N. Furakawa, S. Ohshima, T. Hosoya, Y. Yano, Tet. Lett., 1990, 31, 6543.

    Article  CAS  Google Scholar 

  57. S. S. Lee, D. Y. Kim, J. H. Jung, I. Yoon, S-J. Kim, XXI Symp. on Macrocyclic Chem., Montecatini Terme, Italy, June 1996, Abstr. PB52.

    Google Scholar 

  58. G. G. Talanova, A. N. Kozachkova, K. B. Yatsimirskii, M. I. Kabachnik, T. A. Mastryukov, I. M. Aladzheva, O. V. Bikkovskaya, J. Coord. Chem., 1996, 39, 1.

    Article  CAS  Google Scholar 

  59. J. H. Van Zanten, D. S.-W. Chang, I. Stanish, H. G. Monbouquette, J. Membr. Sci., 1995, 99, 49.

    Article  Google Scholar 

  60. T. Krüger, K. Gloe, B. Habermann, M. Mühlstädt, K. Hohmann, Zeit. für Anorg. und Allg. Chem., 1997, 623, 340.

    Article  Google Scholar 

  61. K. Gloe, H. Stephan, O. Heitzsch, H. Braun, T. Kind in “HydrometallurgyFundamentals, Technology and Innovations”, J. B. Hiskey, G. W. Warren, Eds. Littleton, Colorado, 1993, Chapter 52, p. 845.

    Google Scholar 

  62. K. Gloe, H. Stephan, R. Jacobi, J. Beger, Solv. Extr. Res and Dev., Japan,1995 2, 18

    Google Scholar 

  63. Von E. Hoyer, W. Dietzsch, R. Heber, Wiss. Z., Karl-Marx-Univ., Leipzig, Math.-Naturwiss. Reihe, 1975, 24, 429.

    Google Scholar 

  64. R. W. Frei, G. H. Jamro, O. Navrath, Anal. Chim. Acta, 1971, 55, 125.

    Article  CAS  Google Scholar 

  65. A. V. Yazdi, T. A. Hoefling, E. J. Beckman, Proc. 87th Annu. Meeting of Air, Waste Management Assoc.,1994 (Vol. 13, hazard. Waste Management Control), 11, pp. 94-TA42.021.

    Google Scholar 

  66. D. E. Leyden, G. H. Luttrell, T. A. Patterson, Anal. Letts., 1975, 8, 51.

    Article  CAS  Google Scholar 

  67. H. Kawamoto, S. Yamazaki, E. Katoh, K-i. Tsunoda, H. Akaiwa, Anal. Sciences, 1992, 8, 265.

    Article  CAS  Google Scholar 

  68. A. V. Yazdi, E. J. Beckman, Met. Mater. Waste Product., Recovery Rem., Proc. Symp., 1994, 19.

    Google Scholar 

  69. J. S. Bradshaw, R. M. Izatt, Accts. Chem. Res., 1997, 30, 338.

    Article  CAS  Google Scholar 

  70. D. M. Roundhill, J. Shen, CALIX 2001, J. Vicens, V. Böhmer, J. Harrowfield, eds., Kluwer, Dordrecht, 2001.

    Google Scholar 

  71. T. Izumi, S. Oohashi, Y. Tate, J. Heterocycl. Chem., 1993, 30, 967.

    Article  CAS  Google Scholar 

  72. S. R. Cooper, “Crown Compounds: Toward Future Applications”, VCH Publishers, New York, 1992.

    Google Scholar 

  73. B. G. Cox, H. Schneider, “Coordination and Transport Properties of Macrocyclic Compounds in Solution”, Elsevier, 1992.

    Google Scholar 

  74. R. M. Izatt, J. S. Bradshaw, S. A. Nielsen, J. D. Lamb, J. J. Christensen, Chem. Rev., 1985, 85, 271.

    Article  CAS  Google Scholar 

  75. M. Kodama, E. Kimura, S. Yamaguchi, JCS, Dalton Trans., 1980, 2536.

    Google Scholar 

  76. A. Bencini, A. Bianchi, M. Micheloni, P. Paoletti, E. Garcia-Espana, M. A. Nino, JCS Dalton Trans., 1991, 1171.

    Google Scholar 

  77. L. Y. Martin, C. R. Sperati, D. H. Busch, J. Am. Chem. Soc., 1977, 99, 2968.

    Google Scholar 

  78. R. Nagai, M. Kodama, Inorg.Chem., 1984, 23, 4184.

    Google Scholar 

  79. M. Kato, T. Ito, Inorg. Chem., 1985, 24, 504.

    Article  CAS  Google Scholar 

  80. M. Kato, T. Ito, Inorg. Chem., 1985, 24, 509.

    Article  CAS  Google Scholar 

  81. H. Tsukube, JCS, Chem.Comm., 1983, 970.

    Google Scholar 

  82. H. Tsukube, K. Takagi, T. Higashiyama, T. Iwachido, N. Hayama, JCS, Perkin Trans. II, 1985, 1541.

    Google Scholar 

  83. H. Tsukube, J. Cord. Chem., 1987, 16, 101.

    Article  CAS  Google Scholar 

  84. R. M. Izatt, R. L. Bruening, B. J. Tarbet, M. L. Griffin, M. L. Bruening, K. E. Krakowiak, J. S. Bradshaw, Pure Appl. Chem., 1990, 62, 1115.

    Article  CAS  Google Scholar 

  85. D. Cordier, M. W. Hosseini, New J. Chem., 1990, 14, 611.

    CAS  Google Scholar 

  86. H. Tsukube, JCS, Perkin Trans. 1, 1985, 615.

    Article  Google Scholar 

  87. H. Tsukube, Y. Kubo, T. Toda, T. Araki, J. Polym. Sci.: Polym. Lett. Ed., 1985, 23, 517.

    Article  CAS  Google Scholar 

  88. Y. Inoue, M. Ouchi, T. Hakushi, Bull. Chem. Soc. Jpn., 1985, 58, 525.

    Article  CAS  Google Scholar 

  89. Y. Inoue, F. Amano, N. Okada, H. Inada, M. Ouchi, A. Tai, T. Hakushi, Y. Liu, L. Tong, JCS, Perkin Trans. II, 1990, 1239.

    Google Scholar 

  90. Y. Liu, L. Tong, Y. Inoue, T. Hakushi, JCS, Perkin Trans., 11, 1990, 1247.

    Article  Google Scholar 

  91. Y. Liu, Y. Inoue, T. Hakushi, Bull. Chem. Soc. Jpn.,1990 63, 3044.

    Google Scholar 

  92. S. Shinkai, T. Kouno, Y. Kusano, O. Manabe, JCS, Perkin Trans. 1, 1982, 2741.

    Google Scholar 

  93. S. Shinkai, T. Minami, T. Kouno, Y. Kusano, O. Manabe, Chem. Lett., 1982, 499.

    Google Scholar 

  94. S. Shinkai, Y. Honda, K. Ueda, O. Manabe, Bull. Chem. Soc. Jpn., 1984, 57, 2144.

    Google Scholar 

  95. S. Shinkai, K. Shigematsu, Y. Honda, O. Manabe, Bull. Chem. Soc. Jpn., 1984, 57, 2879.

    Google Scholar 

  96. H. Handel, F. R. Muller, R. Guglielmetti, Hely. Chim. Acta, 1983, 44, 514.

    Article  Google Scholar 

  97. M. Zhao, W. T. Ford, J. Incl. Phenom. Mol. Recogn. in Chem., 1994, 17, 53.

    Article  CAS  Google Scholar 

  98. S. Inokuma, S. Sakai, R. Katoh, J. Nishimura, Bull. Chem. Soc. Jpn., 1994, 67, 1462.

    Article  CAS  Google Scholar 

  99. B. Vaidya, J. Zak, G. Bastiaans, M. Porter, J. L. Hallman, N. A. R. Nabulsi, M. D. Utterback, B. Strzelbicka, R. A. Bartsch, Anal. Chem., 1995, 67, 4101.

    Article  CAS  Google Scholar 

  100. T. Kumagai, S. Akabori, Chem. Lett., 1989, 1667.

    Google Scholar 

  101. M-H Cho, H-S. Chun, J-H. Kim, C-H. Rhee, S-J. Kim, Bull. Korean Chem. Soc., 1991, 12, 474.

    CAS  Google Scholar 

  102. R. L. Bruening, B. J. Tarbet, K. E. Krakowiak, M. L. Bruening, R. M. Izatt, J. S. Bradshaw, Anal. Chem., 1991, 63, 1014.

    Article  CAS  Google Scholar 

  103. T. Nabeshima, K. Nishijima, N. Tsukada, H. Furusawa, T. Hosoya, Y. Yano, JCS, Chem. Comm., 1992, 1092.

    Google Scholar 

  104. T. Krueger, K. Gloe, H. Stephan, B. Habermann, K. Hollmann, XXI Symp. on Macrocyclic Chem.,Montecatini Terme, Italy, June 1996, Abst. PA 49

    Google Scholar 

  105. T. Nabeshima, N. Tsukada, K. Nishijima, H. Ohshiro, Y. Yano, J . Org. Chem., 1996, 61, 4342.

    Article  CAS  Google Scholar 

  106. H. Graubaum, F. Tittelbach, G. Lutze, K. Gloe, M. Mackrodt, J. Prakt. Chem. 1997, 339, 55.

    Article  CAS  Google Scholar 

  107. T. Krueger, K. Gloe, H. Stephan, B. Habermann, K. Holtman, E. Weber, J. Mol. Model., 1996, 2, 386.

    Article  CAS  Google Scholar 

  108. O. Heitzsch, K. Gloe, H. Stephan, E. Weber, Solv. Extr. Ion Exchange, 1994, 12, 475.

    Article  CAS  Google Scholar 

  109. K. Gloe, O. Heitzsch, H. Stephan, H.-J. Buschmann, R. Trülzsch, R. Jacobi, J. Beger, Solv. Extr. Res. Devel. (Japan), 1994, 1, 30.

    CAS  Google Scholar 

  110. T. Izumi, S. Ooohashi, Y. Tate, J. Heterocyclic Chem. 1993, 30, 967.

    Article  CAS  Google Scholar 

  111. M. D. Eley, R. A. Bartsch, M. D. Utterback, Abstr. XIX Int. Symp. Macrocycl. Chem. Lawrence, Kansas, 1994, A15.

    Google Scholar 

  112. R. Seangprasertkij, Z. Asfari, F. Arnaud, J. Vicens, J . Org. Chem., 1994, 59, 1741.

    Article  CAS  Google Scholar 

  113. K. M. O’Connor, G. Svehla, S. J. Harris, M. A. McKervey, Anal. Proc., 1993, 30, 137.

    Google Scholar 

  114. A. T. Yordanov, J. T. Mague, D. M. Roundhill, Inorg. Chem., 1995, 34, 5084.

    Article  CAS  Google Scholar 

  115. A. T. Yordanov, J. T. Mague, D. M. Roundhill, Inorg. Chim. Acta, 1995, 240, 441.

    Article  CAS  Google Scholar 

  116. A. T. Yordanov, J. T. Mague, D. M. Roundhill, Inorg. Chim. Acta, 1995, 250, 295.

    Article  Google Scholar 

  117. A. T. Yordanov, D. M. Roundhill, New J. Chem.1996, 20, 447.

    Google Scholar 

  118. F. Hamada, T. Fukugaki, K. Murai, G. W. Orr, J. L. Atwood, J. Incl. Phenom. Mol. Recogn. Chem., 1991, 10, 57.

    Article  CAS  Google Scholar 

  119. C. Canevet, J. Libman, A. Shanzer, Abstr. DC Int. Symp. Macrocycl. Chem. Jerusalem, Israel, 1995, 35.

    Google Scholar 

  120. E. M. Georgiev, N. Wolf, D. M. Roundhill, Polyhedron, 1997, 16, 1581.

    Article  CAS  Google Scholar 

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Roundhill, D.M. (2001). Selective Extraction with Chelates, Macrocycles and Calixarenes. In: Extraction of Metals from Soils and Waters. Modern Inorganic Chemistry. Springer, Boston, MA. https://doi.org/10.1007/978-1-4757-5204-5_5

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