Selective Extraction with Chelates, Macrocycles and Calixarenes

  • D. Max Roundhill
Chapter
Part of the Modern Inorganic Chemistry book series (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.

Keywords

Crown Ether Selective Extraction Sulfur Mustard High Coordination Number Transition Metal Salt 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    Y. A. Zolotov,“Extraction of Chelate Compounds” Ann Arbor-Humphrey Science Publishers, 1970.Google Scholar
  2. 2.
    P. Cazeneuve, C. R. Acad. Sci., 1900, 131, 346.Google Scholar
  3. 3.
    C. F. Bell, “Principles and Applications of Metal Chelation” Clarendon Press, Oxford, U.K., 1977Google Scholar
  4. 4.
    C. J. Pedersen, J. Am. Chem. Soc., 1967, 89, 2495.Google Scholar
  5. 5.
    B. P. Hay, Coord. Chem. Revs.,1993 126,177.Google Scholar
  6. 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.CrossRefGoogle Scholar
  7. 7.
    J. Rebek, Jr., Angew. Chem., Int. Ed. Engl., 1990, 29, 245.CrossRefGoogle Scholar
  8. 8.
    E. A. Wintner, M. M. Conn, J. Rebek, Jr., Accts. Chem. Res., 1994, 27, 198.CrossRefGoogle Scholar
  9. 9.
    F. C. J. M. van Veggel, W. VerJoom, D. N. Reinhoudt, Chem. Rev., 1994, 94, 279.CrossRefGoogle Scholar
  10. 10.
    H.-J. Schneider, Chem. Soc. Rev., 1994, 227.Google Scholar
  11. 11.
    A. Deratani, B. Sebille, Anal. Chem., 1981, 53, 1742.CrossRefGoogle Scholar
  12. 12.
    A. T. Yordanov, D. M. Roundhill, Coord. Chem. Rev., 1998, 170, 93.CrossRefGoogle Scholar
  13. 13.
    D. H. Busch, Chem. Rev., 1993, 93, 847.CrossRefGoogle Scholar
  14. 14.
    G. Drasch, L. V. Meyer, G. Kauert, Fresenius Z., Anal. Chem., 1982, 311, 571.CrossRefGoogle Scholar
  15. 15.
    J. M. Lo, Y. P. Lin, K. S. Lin, Anal. Sci., 1991, 7, 455.CrossRefGoogle Scholar
  16. 16.
    T. Yamane, T. Mukoyama, T. Sasamoto, Anal. Chim. Acta., 1974, 69, 347.CrossRefGoogle Scholar
  17. 17.
    A. Dornemann, H. Kleist, Analyst, 1979, 104, 1030.CrossRefGoogle Scholar
  18. 18.
    S. Ichinoki, T. Morita, M. Yamazaki, J. Liq. Chrom., 1983, 6, 2079.Google Scholar
  19. 19.
    S. Ichinoki, T. Morita, M. Yamazaki, J. Liq.Chrom., 1984, 7, 2467.Google Scholar
  20. 20.
    F. L. L. Muller, J. D. Burton, P. J. Statham, Anal. Chins. Acta.,1991 245,21.Google Scholar
  21. 21.
    G. Bozsai, M. Csanady, Fresenius Z. Anal. Chem., 1979, 297, 370.CrossRefGoogle Scholar
  22. 22.
    T. Hsieh, L. K. Liu, Anal. Chico. Acta., 1993, 282, 221.CrossRefGoogle Scholar
  23. 23.
    T. Honjo, Bull. Chem. Soc. Jpn., 1984, 57, 591.CrossRefGoogle Scholar
  24. 24.
    M. L. Lee, G. Tolg, E. Beinrohr, P. Tschopel, Anal. Chins. Acta., 1993, 272, 193.CrossRefGoogle Scholar
  25. 25.
    N. Wolf, D. M. Roundhill, Polyhedron, 1994, 13, 2801.Google Scholar
  26. 26.
    W. H. Chan, S. Y. Lam-Leung, K. W. Cheng, Y. C. Yip, Anal. Letts., 1992, 25, 305.CrossRefGoogle Scholar
  27. 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. 28.
    T.-C. Chen, A. Hong, J. Hazard. Mater., 1995, 41, 147.CrossRefGoogle 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. 30.
    R. L. Jenkins, B. J. Scheybeler, M. L. Smith, R. Baird, M. P. Lo, R. T. Haug, Journal WPCF, 1981, 53, 25.Google Scholar
  31. 31.
    J. L. Howard, J. Shu, Environ. Poll., 1996, 91, 89.CrossRefGoogle Scholar
  32. 32.
    J. Roca, F. Pomares, Commun. Soil Sci. Plant Anal., 1991, 22, 2119.Google Scholar
  33. 33.
    R. Kocjan, M. Garbacka, Sep. Sci. Technol., 1994, 29, 799.CrossRefGoogle Scholar
  34. 34.
    K. Garnett, P. W. W. Kirk, J. N. Lester, R. Perry, J. Environ. Qual., 1985, 14, 549.CrossRefGoogle Scholar
  35. 35.
    E. Schonberger, J. Kassovicz, A. Shenhar, Heavy Met. Environ., Int. Conf, 4 th 1983 vol. 1, 218.Google Scholar
  36. 36.
    W. P Miller, W. W. McFee, J. M. Kelly, J. Environ. Qual., 1983, 12, 579.CrossRefGoogle Scholar
  37. 37.
    A. K. Guha, P. V. Shanbhag, K. K. Sirkar, C. H. Yun, D. Trivedi, D. Vaccari, Waste Management, 1993, 13, 395.CrossRefGoogle Scholar
  38. 38.
    R. Kocjan, S. Przeszlakowski, Talanta, 1992, 39, 63.CrossRefGoogle Scholar
  39. 39.
    R. Kocjan, Analyst, 1992, 117, 741.CrossRefGoogle Scholar
  40. 40.
    K. Hiratani, K. Taguchi, Bull. Chem. Soc. Jpn., 1990, 63, 3331.CrossRefGoogle Scholar
  41. 41.
    M. Schuster, Nachr. Chem., Tech. Lab., 1992, 40, 682.Google Scholar
  42. 42.
    S. Inokuma, K. Hasegawa, S. Sakai, J. Nishimura, Chem. Lett., 1994, 1729.Google Scholar
  43. 43.
    P. M. van Berkel, W. L. Driessen, J. Reedijk, D.C. Sherrington, A. Zitsmanis, Reactive and Functional Polymers, 1995, 27, 15.CrossRefGoogle Scholar
  44. 44.
    P. Burla, Z. Fresenius, Anal. Chem., 1989, 306, 233.Google Scholar
  45. 45.
    I. P. Alimarin, V. M. Ivanov, T. A. Bolshova, E. M. Basova, Z. Fresenius, Anal. Chem., 1989, 335, 63.CrossRefGoogle Scholar
  46. 46.
    U. B. Talwar, B. C. Haldar, Indian J. Chem., 1969, 7, 803.Google Scholar
  47. 47.
    A. Miyazaki, A. Kimura, K. Bansho, Y. Umezaki, Anal. Chim. Acta, 1982, 14, 213.CrossRefGoogle Scholar
  48. 48.
    M. Garcia-Vargas, M. Belizon, M. P. Hernandez-Artiga, C. Martinez, J. A. Perez-Bustamante, Appl. Spectr., 1986, 40, 1058.CrossRefGoogle Scholar
  49. 49.
    S. Ide, Y. Katayama, H. Nakamura, M. Takagi, Solv. Extr. Ion Exch., 1987, 5, 853.CrossRefGoogle Scholar
  50. 50.
    T. Kitamori, K. Suzuki, T. Sawada, Y. Gohshi, K. Motojima, Anal. Chem., 1986, 58, 2275.Google Scholar
  51. 51.
    V. Leepipatpiboon, J. Chromar., 1995, A697, 137.CrossRefGoogle Scholar
  52. 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.CrossRefGoogle Scholar
  53. 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.Google Scholar
  54. 54.
    S. Prasad, D. C. Rupainwar, Poll. Res., 1990, 9, 15.Google Scholar
  55. 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. 56.
    T. Nabeshima, T. Inaba, N. Furakawa, S. Ohshima, T. Hosoya, Y. Yano, Tet. Lett., 1990, 31, 6543.CrossRefGoogle Scholar
  57. 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. 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.CrossRefGoogle Scholar
  59. 59.
    J. H. Van Zanten, D. S.-W. Chang, I. Stanish, H. G. Monbouquette, J. Membr. Sci., 1995, 99, 49.CrossRefGoogle Scholar
  60. 60.
    T. Krüger, K. Gloe, B. Habermann, M. Mühlstädt, K. Hohmann, Zeit. für Anorg. und Allg. Chem., 1997, 623, 340.CrossRefGoogle Scholar
  61. 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. 62.
    K. Gloe, H. Stephan, R. Jacobi, J. Beger, Solv. Extr. Res and Dev., Japan,1995 2, 18Google Scholar
  63. 63.
    Von E. Hoyer, W. Dietzsch, R. Heber, Wiss. Z., Karl-Marx-Univ., Leipzig, Math.-Naturwiss. Reihe, 1975, 24, 429.Google Scholar
  64. 64.
    R. W. Frei, G. H. Jamro, O. Navrath, Anal. Chim. Acta, 1971, 55, 125.CrossRefGoogle Scholar
  65. 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. 66.
    D. E. Leyden, G. H. Luttrell, T. A. Patterson, Anal. Letts., 1975, 8, 51.CrossRefGoogle Scholar
  67. 67.
    H. Kawamoto, S. Yamazaki, E. Katoh, K-i. Tsunoda, H. Akaiwa, Anal. Sciences, 1992, 8, 265.CrossRefGoogle Scholar
  68. 68.
    A. V. Yazdi, E. J. Beckman, Met. Mater. Waste Product., Recovery Rem., Proc. Symp., 1994, 19.Google Scholar
  69. 69.
    J. S. Bradshaw, R. M. Izatt, Accts. Chem. Res., 1997, 30, 338.CrossRefGoogle Scholar
  70. 70.
    D. M. Roundhill, J. Shen, CALIX 2001, J. Vicens, V. Böhmer, J. Harrowfield, eds., Kluwer, Dordrecht, 2001.Google Scholar
  71. 71.
    T. Izumi, S. Oohashi, Y. Tate, J. Heterocycl. Chem., 1993, 30, 967.CrossRefGoogle Scholar
  72. 72.
    S. R. Cooper, “Crown Compounds: Toward Future Applications”, VCH Publishers, New York, 1992.Google Scholar
  73. 73.
    B. G. Cox, H. Schneider, “Coordination and Transport Properties of Macrocyclic Compounds in Solution”, Elsevier, 1992.Google Scholar
  74. 74.
    R. M. Izatt, J. S. Bradshaw, S. A. Nielsen, J. D. Lamb, J. J. Christensen, Chem. Rev., 1985, 85, 271.CrossRefGoogle Scholar
  75. 75.
    M. Kodama, E. Kimura, S. Yamaguchi, JCS, Dalton Trans., 1980, 2536.Google Scholar
  76. 76.
    A. Bencini, A. Bianchi, M. Micheloni, P. Paoletti, E. Garcia-Espana, M. A. Nino, JCS Dalton Trans., 1991, 1171.Google Scholar
  77. 77.
    L. Y. Martin, C. R. Sperati, D. H. Busch, J. Am. Chem. Soc., 1977, 99, 2968.Google Scholar
  78. 78.
    R. Nagai, M. Kodama, Inorg.Chem., 1984, 23, 4184.Google Scholar
  79. 79.
    M. Kato, T. Ito, Inorg. Chem., 1985, 24, 504.CrossRefGoogle Scholar
  80. 80.
    M. Kato, T. Ito, Inorg. Chem., 1985, 24, 509.CrossRefGoogle Scholar
  81. 81.
    H. Tsukube, JCS, Chem.Comm., 1983, 970.Google Scholar
  82. 82.
    H. Tsukube, K. Takagi, T. Higashiyama, T. Iwachido, N. Hayama, JCS, Perkin Trans. II, 1985, 1541.Google Scholar
  83. 83.
    H. Tsukube, J. Cord. Chem., 1987, 16, 101.CrossRefGoogle Scholar
  84. 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.CrossRefGoogle Scholar
  85. 85.
    D. Cordier, M. W. Hosseini, New J. Chem., 1990, 14, 611.Google Scholar
  86. 86.
    H. Tsukube, JCS, Perkin Trans. 1, 1985, 615.CrossRefGoogle Scholar
  87. 87.
    H. Tsukube, Y. Kubo, T. Toda, T. Araki, J. Polym. Sci.: Polym. Lett. Ed., 1985, 23, 517.CrossRefGoogle Scholar
  88. 88.
    Y. Inoue, M. Ouchi, T. Hakushi, Bull. Chem. Soc. Jpn., 1985, 58, 525.CrossRefGoogle Scholar
  89. 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. 90.
    Y. Liu, L. Tong, Y. Inoue, T. Hakushi, JCS, Perkin Trans., 11, 1990, 1247.CrossRefGoogle Scholar
  91. Y. Liu, Y. Inoue, T. Hakushi, Bull. Chem. Soc. Jpn.,1990 63, 3044.Google Scholar
  92. 92.
    S. Shinkai, T. Kouno, Y. Kusano, O. Manabe, JCS, Perkin Trans. 1, 1982, 2741.Google Scholar
  93. 93.
    S. Shinkai, T. Minami, T. Kouno, Y. Kusano, O. Manabe, Chem. Lett., 1982, 499.Google Scholar
  94. 94.
    S. Shinkai, Y. Honda, K. Ueda, O. Manabe, Bull. Chem. Soc. Jpn., 1984, 57, 2144.Google Scholar
  95. 95.
    S. Shinkai, K. Shigematsu, Y. Honda, O. Manabe, Bull. Chem. Soc. Jpn., 1984, 57, 2879.Google Scholar
  96. 96.
    H. Handel, F. R. Muller, R. Guglielmetti, Hely. Chim. Acta, 1983, 44, 514.CrossRefGoogle Scholar
  97. 97.
    M. Zhao, W. T. Ford, J. Incl. Phenom. Mol. Recogn. in Chem., 1994, 17, 53.CrossRefGoogle Scholar
  98. 98.
    S. Inokuma, S. Sakai, R. Katoh, J. Nishimura, Bull. Chem. Soc. Jpn., 1994, 67, 1462.CrossRefGoogle Scholar
  99. 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.CrossRefGoogle Scholar
  100. 100.
    T. Kumagai, S. Akabori, Chem. Lett., 1989, 1667.Google Scholar
  101. 101.
    M-H Cho, H-S. Chun, J-H. Kim, C-H. Rhee, S-J. Kim, Bull. Korean Chem. Soc., 1991, 12, 474.Google Scholar
  102. 102.
    R. L. Bruening, B. J. Tarbet, K. E. Krakowiak, M. L. Bruening, R. M. Izatt, J. S. Bradshaw, Anal. Chem., 1991, 63, 1014.CrossRefGoogle Scholar
  103. 103.
    T. Nabeshima, K. Nishijima, N. Tsukada, H. Furusawa, T. Hosoya, Y. Yano, JCS, Chem. Comm., 1992, 1092.Google Scholar
  104. 104.
    T. Krueger, K. Gloe, H. Stephan, B. Habermann, K. Hollmann, XXI Symp. on Macrocyclic Chem.,Montecatini Terme, Italy, June 1996, Abst. PA 49Google Scholar
  105. 105.
    T. Nabeshima, N. Tsukada, K. Nishijima, H. Ohshiro, Y. Yano, J . Org. Chem., 1996, 61, 4342.CrossRefGoogle Scholar
  106. 106.
    H. Graubaum, F. Tittelbach, G. Lutze, K. Gloe, M. Mackrodt, J. Prakt. Chem. 1997, 339, 55.CrossRefGoogle Scholar
  107. 107.
    T. Krueger, K. Gloe, H. Stephan, B. Habermann, K. Holtman, E. Weber, J. Mol. Model., 1996, 2, 386.CrossRefGoogle Scholar
  108. 108.
    O. Heitzsch, K. Gloe, H. Stephan, E. Weber, Solv. Extr. Ion Exchange, 1994, 12, 475.CrossRefGoogle Scholar
  109. 109.
    K. Gloe, O. Heitzsch, H. Stephan, H.-J. Buschmann, R. Trülzsch, R. Jacobi, J. Beger, Solv. Extr. Res. Devel. (Japan), 1994, 1, 30.Google Scholar
  110. 110.
    T. Izumi, S. Ooohashi, Y. Tate, J. Heterocyclic Chem. 1993, 30, 967.CrossRefGoogle Scholar
  111. 111.
    M. D. Eley, R. A. Bartsch, M. D. Utterback, Abstr. XIX Int. Symp. Macrocycl. Chem. Lawrence, Kansas, 1994, A15.Google Scholar
  112. 112.
    R. Seangprasertkij, Z. Asfari, F. Arnaud, J. Vicens, J . Org. Chem., 1994, 59, 1741.CrossRefGoogle Scholar
  113. 113.
    K. M. O’Connor, G. Svehla, S. J. Harris, M. A. McKervey, Anal. Proc., 1993, 30, 137.Google Scholar
  114. 114.
    A. T. Yordanov, J. T. Mague, D. M. Roundhill, Inorg. Chem., 1995, 34, 5084.CrossRefGoogle Scholar
  115. 115.
    A. T. Yordanov, J. T. Mague, D. M. Roundhill, Inorg. Chim. Acta, 1995, 240, 441.CrossRefGoogle Scholar
  116. 116.
    A. T. Yordanov, J. T. Mague, D. M. Roundhill, Inorg. Chim. Acta, 1995, 250, 295.CrossRefGoogle Scholar
  117. 117.
    A. T. Yordanov, D. M. Roundhill, New J. Chem.1996, 20, 447.Google Scholar
  118. 118.
    F. Hamada, T. Fukugaki, K. Murai, G. W. Orr, J. L. Atwood, J. Incl. Phenom. Mol. Recogn. Chem., 1991, 10, 57.CrossRefGoogle Scholar
  119. 119.
    C. Canevet, J. Libman, A. Shanzer, Abstr. DC Int. Symp. Macrocycl. Chem. Jerusalem, Israel, 1995, 35.Google Scholar
  120. 120.
    E. M. Georgiev, N. Wolf, D. M. Roundhill, Polyhedron, 1997, 16, 1581.CrossRefGoogle Scholar

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© Springer Science+Business Media New York 2001

Authors and Affiliations

  • D. Max Roundhill
    • 1
  1. 1.Texas Tech UniversityLubbockUSA

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