C3-symmetric tripodal thio/diglycolamide-based ligands for trivalent f-element separations

Separation Science and Technology

Volumn 41, Issue 10, 2006, Pages 2129-2146

  Matloka, Kornelia ^a   Gelis, Artem ^b   Regalbuto, Monica ^b   Vandegrift, George ^b   Scott, Michael J ^a  

^a UNIVERSITY OF FLORIDA   (United States)

^b ARGONNE NATIONAL LABORATORY   (United States)

Author keywords

C3 symmetric ligand; Diglycolamide; Extraction of lanthanides and actinides; Nuclear waste separations; Thiodiglycolamide

Indexed keywords

CHEMICAL BONDS; EXTRACTION; METHANE; OXYGEN; SYNTHESIS (CHEMICAL);

C3-SYMMETRIC LIGAND; DIGLYCOLAMIDE; EXTRACTION OF LANTHANIDES AND ACTINIDES; NUCLEAR WASTE SEPARATIONS; THIODIGLYCOLAMIDE;

NITROGEN COMPOUNDS;

CHEMICAL BONDS; EXTRACTION; METHANE; NITROGEN COMPOUNDS; OXYGEN; SYNTHESIS (CHEMICAL);

BINDING; COMPLEXING AGENT; EXTRACTION METHOD; FLUID; METAL; NITRIC ACID; SPECTROSCOPY; SYNTHESIS;

EID: 33746234873     PISSN: 01496395     EISSN: 15205754     Source Type: Journal    
DOI: 10.1080/01496390600745727     Document Type: Conference Paper

References (63)

1. Fritz, J.S. and Orf, G.M. (1975) Extraction of metal-ions with N,N-disubstituted amides. Anal. Chem., 47 (12): 2043-2045.
2. Thiollet, G. and Musikas, C. (1989) Synthesis and uses of the amides extractants. Solvent Extr. Ion Exch., 1 (5): 813-827.
3. Cuillerdier, C., Musikas, C., Hoel, P., Nigond, L., and Vitart, X. (1991) Malonamides as new extractants for nuclear waste solutions. Sep. Sci. Tech., 26 (9): 1229-1244.
4. Condamines, N. and Musikas, C. (1992) The Extraction by N,N-Dialkylamides.2. Extraction of actinide cations. Solvent Extr. Ion Exch., 10 (1): 69-100.
5. Nair, G.M., Prabhu, D.R., Mahajan, G.R., and Shukla, J.P. (1993) Tetra-butyl-mal-onamide and tetra-isobutyl-malonamide as extractants for uranium(VI) and plutonium(IV). Solvent Extr. Ion Exch., 11 (5): 831-847.
6. Prabhu, D.R., Mahajan, G.R., Nair, G.M., and Subramanian, M.S. (1993) Extraction of uranium(VI) and plutonium(IV) with unsymmetrical monoamides. Radiochim. Acta, 60 (2-3): 109-113.
7. Cuillerdier, C. and Musikas, C. (1993) Extraction of actinides from a chloride medium using pentaalkylpropanediamides. Sep. Sci. Tech., 28 (1-3): 115-126.
8. Nigond, L., Musikas, C., and Cuillerdier, C. (1994) Extraction by N,N,N',N'-tetra-alkyl-2-alkyl-propane-l,3-diamides 2. U(VI) and Pu(IV). Solvent Extr. Ion Exch., 12 (2): 297-323.
9. 4. Solvent Extr. Ion Exch., 12 (2): 261-296.
10. Nakamura, T. and Miyake, C. (1995) Extraction of lanthanide(III) and uranyl(VI) from nitric-acid solution by N, N'-dimethyl-N, N'-dibutylmalonamide. Solvent Extr. Ion Exch., 13 (2): 253-273.
11. Nigond, L., Condamines, N., Cordier, P.Y., Livet, J., Madic, C., Cuillerdier, C., Musikas, C., and Hudson, M.J. (1995) Recent advances in the treatment of nuclear wastes by the use of diamide and picolinamide extractants. Sep. Sci. Tech., 30 (7-9): 2075-2099.
12. Narita, H., Yaita, T., and Tachimori, S. (2004) Extraction of lanthanides with N,N'-dimethyl-N,N'-diphenyl-malonamide and -3,6-dioxaoctanediamide. Solvent Extr. Ion Exch., 22 (2): 135-145.
13. Manchanda, V. and Pathak, P. (2004) Amides and diamides as promising extractants in the back end of the nuclear fuel cycle: an overview. Sep. Purif. Technol., 35 (2): 85-103.
14. Stephan, H., Gloe, K., Beger, J., and Muhl, P. (1991) Liquid-liquid-extraction of strontium with amido podands. Solvent Extr. Ion Exch., 9 (3): 435-458.
15. Stephan, H., Gloe, K., Beger, J., and Muhl, P. (1991) Liquid-liquid-extraction of metal-ions with amido podands. Solvent Extr. Ion Exch., 9 (3): 459-469.
16. Yao, J., Wharf, R.M., and Choppin, G.R. (1995) Solvent extraction of Eu(III) and Am(III) with thio and amide extractants. In Separation of F-Elements; Nash, K.L. and Choppin, G.R. (eds.), Plenum Press: New York, 31-42.
17. Sasaki, Y. and Choppin, G.R. (1996) Extraction behaviors of Eu, Th, U and Am with diamides plus thenoyltrifluoroacetone. J. Radioanal. Nucl. Chem., 207 (2): 383-394.
18. Sasaki, Y.I. and Choppin, G.R. (1996) Solvent extraction of Eu, Th, U, Np and Am with N,N'-dimethyl-N,N'-dihexyl-3-oxapentanediamide and its analogous compounds. Anal. Sci., 12 (2): 225-230.
19. Narita, H., Yaita, T., Tamura, K., and Tachimori, S. (1998) Solvent extraction of trivalent lanthanoid ions with N,N '-dimethyl-N,N'-diphenyl-3-oxapentanediamide. Radiochim. Acta, 81 (4): 223-226.
20. Sasaki, Y. and Choppin, G. (1998) Extraction of Np(V) by N,N'-dimethyl-N,N'-dihexyl-3-oxapentanediamide. Radiochim. Acta, 80 (2): 85-88.
21. Narita, H., Yaita, T., and Tachimori, S. (1999) In Extraction Behavior for Trivalent Lanthanides with Amides and EXAFS Study on Their Complexes; ISEC'99, Barcelona, Spain, 693-696.
22. Narita, H., Yaita, T., Tamura, K., and Tachimori, S. (1999) Study on the extraction of trivalent lanthanide ions with N,N'-dimethyl-N,N'-diphenyl-malonamide and -diglycolamide. J. Radioanal. Nucl. Chem., 239 (2): 381-384.
23. Sasaki, Y., Sugo, Y., and Tachimori, S. (2000) In Actinide Separation with a Novel Tridentate Ligand, Diglycolic Amide for Application to Partitioning Process; International Conference ATALANTE 2000, Avignon, France.
24. Sasaki, Y. and Choppin, G.R. (2000) Extraction and mutual separation of actinide(III), (IV), (V) and (VI) ions by N,N '-dimethyl-N,N '-dihexyl-3-oxapentanediamide and thenoyltrifluoroacetone. J. Radioanal. Nucl. Chem., 246 (2): 267-273.
25. Tachimori, S., Suzuki, S., and Sasaki, Y. (2001) A process of spent nuclear fuel treatment with the interim storage of TRU by use of amidic extractants. J. Atom. Energ. Soc. Jpn.,43 (12): 1235-1241.
26. 3-n- dodecane system. Solvent Extr. Ion Exch., 19 (1): 91-103.
27. Sasaki, Y. and Tachimori, S. (2002) Extraction of actinides (III), (IV), (V), (VI), and lanthanides(III) by structurally tailored diamides. Solvent Extr. Ion Exch., 20(1): 21-34.
28. Yaita, T., Herlinger, A.W., Thiyagarajan, P., and Jensen, M.P. (2004) Influence of extractant aggregation on the extraction of trivalent f-element cations by a tetraalkyldiglycolamide. Solvent Extr. Ion Exch., 22 (4): 553-571.
29. Zhu, Z.X., Sasaki, Y., Suzuki, H., Suzuki, S., and Kimura, T. (2004) Cumulative study on solvent extraction of elements by N,N,N',N'-tetraoctyl-3-oxapentanediamide (TODGA) from nitric acid into n-dodecane. Anal. Chim. Acta, 527 (2): 163-168.
30. Cuillerdier, C., Musikas, C., and Nigond, L. (1993) Diamides as actinide extractants for various waste treatments. Sep. Sci. Tech., 28 (1-3): 155-175.
31. Madic, C., Blanc, P., Condamines, N., Baron, P., Berthon, L., Nicol, C., Pozo, C., Lecomte, M., Philippe, M., Masson, M., Hequet, C., and Hudson, M.J. (1994) In Actinide Partitioning from HLLW Using DIAMEX Process; Fourth International Conference of Nuclear Fuel Reprocessing and Waste Menagement, London, UK.
32. Nigond, L. (1994) Extraction properties of N,N,N',N'-tetraalkyl-alkyl-2 propane-diamides-1,3. Ph. D. Thesis. Univesite de Clermont-Ferrand II: Clermont-Ferrand, France.
33. Charbonnel, M.C., Nicol, C., Berthon, L., and Baron, P. (1997) In International Conference GLOBAL'97, Yokohama, Japan.
34. Bisel, I., Nicol, C., Charbonnel, M.C., Blanc, P., Baron, P., and Belnet, F. (1998) In Inactive Diamex Test with Theoptimized Extraction Agent DMDOHEMA, The Fifth Information Exchange Meeting on Actinides and Fission Products Partitioning and Transmutation, Mol, Belgium.
35. Satmark, B., Courson, O., Malmbeck, R., Pagliosa, G., Romer, K., and Glatz, J.P. (2000) In Separation of Minor Actinides from a Genuine Ma/Ln Fraction, Actinide and Fission Product Partitioning and Transmutation; The Sixth International Information Exchange Meeting on Actinide and Fission Product Partitioning and Transmutation, Madrid, Spain, 279-286.
36. Courson, O., Lebrun, M., Malmbeck, R., Pagliosa, G., Romer, K., Satmark, B., and Glatz, J.P. (2000) Partitioning of minor actinides from HLLW using the DIAMEX process. Part 1 - Demonstration of extraction performances and hydraulic behaviour of the solvent in a continuous process. Radiochim. Acta, 88 (12): 857-863.
37. Malmbeck, R., Courson, O., Pagliosa, G., Romer, K., Satmark, B., Glatz, J.P., and Baron, P. (2000) Partitioning of minor actinides from HLLW using the DIAMEX process. Part 2 - "Hot" continuous counter-current experiment. Radiochim. Acta, 88 (12): 865-871.
38. ArnaudNeu, F., Bohmer, V., Dozol, J.F., Gruttner, C., Jakobi, R.A., Kraft, D., Mauprivez, O., Rouquette, H., SchwingWeill, M.J., Simon, N., and Vogt, W. (1996) Calixarenes with diphenylphosphoryl acetamide functions at the upper rim. A new class of highly efficient extractants for lanthanides and actinides. J. Chem. Soc., Perkin Trans. 2, (6): 1175-1182.
39. Boerrigter, H., Verboom, W., and Reinhoudt, D.N. (1997) Novel resorcinarene cavitand-based CMP(O) cation ligands: Synthesis and extraction properties. J. Org. Chem., 62 (21): 7148-7155.
40. Barboso, S., Carrera, A.G., Matthews, S.E., Arnaud-Neu, F., Bohmer, V., Dozol, J.F., Rouquette, H., and Schwing-Weill, M.J. (1999) Calix-(4)-arenes with CMPO functions at the narrow-rim. Synthesis and extraction properties. J. Chem. Soc., Perkin Trans. 2, (4): 719-723.
41. Schmidt, C., Saadioui, M., Bohmer, V., Host, V., Spirlet, M.R., Desreux, J.F., Brisach, F., Arnaud-Neu, F., and Dozol, J.F. (2003) Modification of calix(4)arenes with CMPO-functions at the wide rim. Synthesis, solution behavior, and separation of actinides from lanthanides. Org. Biomol. Chem., 1 (22): 4089-4096.
42. Arduini, A., Bohmer, V., Delmau, L., Desreux, J.F., Dozol, J.F., Carrera, M.A.G., Lambert, B., Musigmann, C., Pochini, A., Shivanyuk, A., and Ugozzoli, F. (2000) Rigidified calixarenes bearing four carbamoylmethylphosphineoxide or carbamoylmethylphosphoryl functions at the wide rim. Chem. Eur. J., 6 (12): 2135-2144.
43. 2-II based on CMPO-functionalized resorcinarene cavitands; Synthesis and extraction. Liebigs Ann.-Recl, (11): 2247-2254.
44. Boerrigter, H., Verboom, W., de Jong, F., and Reinhoudt, D.N. (1998) Europium(III) extraction with new resorcinarene cavitand CMP(O) ligands: Solvent extraction and mechanistic study. Radiochim. Acta, 81 (1): 39-45.
45. 3-symmetric tripodal ligand containing diglycolamide arms. J. Chem. Soc., Dalton Trans., (23): 3719-3721.
46. 3-symmetric, conformational mimics of calix[n]arenes. Eur. J. Org. Chem., (13): 2467-2478.
47. Marczenko, Z. (1986) In Separation and Spectrophotometric Determination of Elements, Horwood, E. (ed.); Halsted Press: Chichester, New York, 678.
48. 3-symmetric triphenoxymethane platform. Inorg. Chem., 41 (7): 1707-1716.
49. 3-symmetric tripodal ligands for nitric acid liquid/liquid extraction system: highly selective recognition of Pu(IV) and low affinity for 3+ actinides and lanthanides. Manuscript in preparation.
50. Ping, Z., Jing, C., Chunyu, L., and Guoxin, T. (2003) Synthesis of N,N,N',N'-tetra-butyl-3-oxa-pentanediamide and its analogous compounds. Chem. J. on Internet, 5 (7): 52.
51. Spjuth, L., Liljenzin, J., Skalberg, M., Hudson, M., Chan, G., Drew, M., Feaviour, M., Iveson, P., and Madic, C. (1997) Extraction of actinides and lanthanides from nitric acid solution by malonamides. Radiochim, Acta, (78): 39-46.
52. Matloka, K. and Scott, M.J. unpublished data.
53. Bandurkin, G.A. and Dzhurinskii, B.F. (1997) Tricapped trigonal prism in crystal chemistry of oxygen lanthanide compounds. Zh. Neorg, Khim.,42 (7): 1143-1153 (and selected references therein).
54. Floris, P.M. and Tani, A. (2001) A study of aqueous solutions of lanthanide ions by molecular dynamics simulation with ab initio effective pair potentials. J, Chem. Phys., 115 (10): 4750-4765.
55. Abbasi, A., Lindqvist-Reis, P., Eriksson, L., Sandstrom, D., Lidin, S., Persson, I., and Sandstrom, M. (2005) Highly hydrated cations: Deficiency, mobility, and coordination of water in crystalline nonahydrated scandium(III), yttrium(III), and lanthanoid(III) trifluoromethanesulfonates. Chem. Eur. J., 11 (14): 4065-4077.
56. Shannon, R.D. (1976) Acta Crystallogr., Sect A, 32: 751-767.
57. Musicas, C. (1984) In Actinide-Lanthanide Group Separation Using Sulfur and Nitrogen Donor Extractants; The Actinide/Lanthanide Separation Conference, Honolulu, Hawaii, December 16-22, World Scientific Publishing: Honolulu, Hawaii, 1984, p. 19.
58. Ensor, D.D., Jarvinen, G.D., and Smith, B.F. (1988) The use of soft donor ligands, 4-benzoyl-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-thione and 4,7-diphenyl-1,10-phenanthroline, for improved separation of trivalent americium and europium. Solvent Extr. Ion Exch., 6 (3): 439-445.
59. Smith, B.F., Jarvinen, G.D., Jones, M.M., and Hay, P.J. (1989) The synthesis and actinide and lanthanide complexation of soft donor ligands-comparison between 4-benzoyl-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-thione (Hbmppt) and 4-thiobenzoyl-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one (Htbmpp) with tri-N-octylphosphine oxide (Topo) Synergist for Am(III) and Eu(III) extraction. Solvent Extr. Ion Exch., 7 (5): 749-765.
60. Chen, J., Zhu, Y.J., and Jiao, R.Z. (1996) The separation of Am from lanthanides by purified Cyanex 301 extraction. Sep. Sci. Tech., 31 (19): 2723-2731.
61. Sasaki, Y. and Choppin, G.R. (1997) Solvent extraction of Eu, Th, U and Am by N,N'-dimethyl-N,N'-dihexyl-3-thiopentanediamide and thenoyltrifluoroacetone. J. Radioanal. Nucl. Chem., 222 (1-2): 271-274.
62. Sasaki, Y., Adachi, T., and Choppin, G.R. (1998) Solvent extraction study of actinide elements by N,N'-dimethyl-N,N'-dihexyl-3-oxapentanediamide and thenoyltrifluoroacetone. J. Alloy. Compd, 271: 799-802.
63. Sasaki, Y. and Choppin, G. (2000) Extraction and mutual separation of actinide(III), (IV), (V) and (VI) ions by N,N'-dimethyl-N,N'-dihexyl-3-oxapentanediamide and thenoyltrifluoroacetone. J. Radioanal. Nucl. Chem., 246 (2): 267-273.