Metal extraction by sulfur-containing symmetrically-substituted bisphosphonic acids. Part I. P,P′-di(2-ethylhexyl) methylenebisthio-phosphonic acid

Solvent Extraction and Ion Exchange

Volumn 24, Issue 3, 2006, Pages 331-346

  Zalupski, P R ^a   Chiarizia, R ^b   Jensen, M P ^b   Herlinger, A ^a  

^a LOYOLA UNIVERSITY CHICAGO   (United States)

^b ARGONNE NATIONAL LABORATORY   (United States)

Author keywords

Aggregation; Bisphosphonates; Bisthiophosphonic acids; Lanthanide actinide separations; Metal extraction; Partial esters

Indexed keywords

ACIDS; ACTINIDES; AGENTS; IONS; MIXTURES; PH EFFECTS; RARE EARTH ELEMENTS; SOLUTIONS; STOICHIOMETRY; SYNTHESIS (CHEMICAL);

ACTINIDE SEPARATION; BISPHOSPHONATES; BISTHIOPHOSPHONIC ACIDS; LANTHANIDE SEPARATION; METAL EXTRACTION; METAL EXTRACTION REAGENTS; METAL IONS; PARTIAL ESTERS;

SOLVENT EXTRACTION;

ACIDS; ACTINIDES; AGENTS; IONS; MIXTURES; PH EFFECTS; RARE EARTH ELEMENTS; SOLUTIONS; SOLVENT EXTRACTION; STOICHIOMETRY; SYNTHESIS (CHEMICAL);

EID: 33646832383     PISSN: 07366299     EISSN: 15322262     Source Type: Journal    
DOI: 10.1080/07366290600646988     Document Type: Article

References (30)

1. Chiarizia, R. and Herlinger, A. (2004) Symmetrical P,P' -disubstituted esters of alkylenedi-phosphonic acids as reagents for metal solvent extraction. In Ion Exchange and Solvent Extraction. (pp. 85-164). New York: Marcel Dekker, Inc.
2. Chiarizia, R. and McAlister, D. and Herlinger, A. (2005) Trivalent actinide and lanthanide separations by dialkyl-substituted diphosphonic acids Sep. Sci. Technol., 40, pp. 69-90.
3. Zhu, Y. and Chen, J. and Jiao, R. (1996) Extraction of Am(III) and Eu(III) from nitrate solution with purified Cyanex 301 Solvent Extr. Ion Exch., 14, pp. 61-68.
4. Nash, K. (1999) Aqueous complexes in f-element separation science. In Metal-Ion Separation and Preconcentration, Progress and Opportunities. (pp. 52-78). Washington, DC: American Chemical Society.
5. Nash, K. (1994) Separation chemistry for lanthanides and trivalent actinides. In Lanthanides/Actinides: Chemistry. (pp. 197-238). New York: Elsevier Science., Chapter 121
6. Modolo, G. and Odoj, R. (1999) Synergistic selective extraction of actinides(III) over lanthanides from nitric acid using new aromatic diorganyldithiophosphinic acids and neutral organophosphorus compounds Solvent Extr. Ion Exch., 17, pp. 33-53.
7. Zalupski, P. and Jensen, M. and Herlinger, A. (2005) Investigation of acid-base equilibria for symmetrically substituted P,P' -dialkyl partial esters of bisphosphonic acids J. Soln. Chem., 34, pp. 871-883.
8. Zalupski, P. and Jensen, M. and Chiarizia, R. and Chiarelli, M. and Herlinger, A. (2006) Investigation of acid-base and phase distribution equilibria for symmetrically substituted P,P' -dialkyl partial esters of bisphosphonic acids Solvent Extr. Ion Exch., 24, pp. 177-195.
9. Jensen, M. and Bond, A. (2002) Influence of aggregation on the extraction of trivalent lanthanide and actinide cations by purified Cyanex 272, Cyanex 301, and Cyanex 302. Radiochim. Acta, 90, pp. 205-209.
10. Stepinski, D. (2003) Synthesis, characterization and evaluation of P,P' -dialkyl alkylenebisphosphonic acids and P,P' -dialkyl alkylenebisthiophosphonic acids as solvent extraction reagents. Chicago: Loyola University Chicago. PhD Dissertation
11. Burgers, P. and Eckstein, F. (1978) Synthesis of dinucleoside monophosphorothiolates via addition of sulfur to phosphite triesters Tetrahedron Lett., 40, pp. 3835-3838.
12. Stepinski, D. and Nelson, D. and Zalupski, P. and Herlinger, A. (2001) Facile high yielding synthesis of symmetric esters of methylenebisphosphonic acid Tetrahedron, 57, pp. 8637-8645.
13. Stepinski, D. and Herlinger, A. (2002) A facile and selective high yield synthesis of symmetric dialkyl-substituted methylenebisphosphonic acids Synthetic Commun., 32, pp. 2683-2690.
14. Socrates, G. (1994) Infrared Characteristic Group Frequencies 2nd ed. New York N.Y.: John Wiley & Sons.
15. Alimarin, I. and Rodionova, T. and Ivanov, V. (1989) Extraction with thio and dithio phosphorus acids. Russian Chem. Rev., pp. 863-878.
16. Chiarizia, R. and Horwitz, E. and Rickert, P. and Herlinger, A. (1996) Metal extraction by alkyl-substituted diphosphonic acids Part 1. P,P' -Di(2-ethylhexyl) methanediphosphonic acid. Solvent Extr. Ion Exch., 14, pp. 773-792.
17. Barakat, T. and Nelson, M. and Nelson, S. and Pullin, A. (1966) Spectra and hydrogen-bonding characteristics of thiocyanic acid, part 3, thermodynamics of hydrogen-bonding with ethers Trans. Faraday Soc., 62, pp. 2674-2684.
18. Barakat, T. and Nelson, J. and Nelson, S. and Pullin, A. (1969) Spectra and hydrogen-bonding characteristics of thiocyanic acid, part 4, association with weak proton acceptors Trans. Faraday Soc., 65, pp. 41-51.
19. West, R. and Powell, D. and Lee, M. and Whatley, L. (1964) Hydrogen bonding studies. IX. The thermodynamics of hydrogen bonding of phenol to ethers and related compounds J. Am. Chem. Soc., 86, pp. 3227-3229.
20. Krebs, B. (1983) Thio- and seleno-compounds of main group elements - Novel inorganic oligomers and polymers Angew. Chem. Int. Ed. Engl., 22, pp. 113-134.
21. Van Wazer, J. (1958) Phosphorus and Its Compounds. New York: Interscience Publishers.
22. Almela, A. and Elizalde, M. and Menoyo, B. (1994) The interactions of metal extractant reagents: VI. Aggregation equilibria of Cyanex 302 and Span 80 in toluene solutions. J. Solution Chem., 23, pp. 685-696.
23. Sella, C. and Bauer, D. (1988) Diphasic acido-basic properties of organophosphorus acids. Solvent Extr. Ion Exch., 6, pp. 819-833.
24. Orth, D. and Wallace, R. and Karraker, D. (1984) Solvent extraction reactions and mechanisms. In Science and Technology of Tributyl Phosphate, Volume I: Synthesis, Properties, Reactions and Analysis. (pp. 169). Boca Raton: CRC Press.
25. McAlister, D. and Dietz, M. and Chiarizia, R. and Herlinger, A. (2001) Metal ion extraction by silyl-substituted diphosphonic acids. Part 1. P,P' -di-[3-(trimethylsilyl)-1-propylene] methylene- and ethylenediphosphonic acids. Sep. Sci. Technol., 36, pp. 3541-3562.
26. Kabachnik, M. (1956) Application of the Hammett formula to elementoorganic compounds Ionization constants of phosphorus acids. Proc. Acad. Sci. U.S.S.R., Sect. Chem., 110, pp. 577-581.
27. Kabachnik, M. and Ioffe, S. and Mastryukova, T. (1955) On the theory of tautomeric equilibrium in solutions. Tautomerism of the dialkylthiophosphates. J. Gen. Chem. USSR Eng. Transl., 25, pp. 653-660.
28. Jencks, W. and Salvesen, K. (1971) Equilibrium deuterium isotope effects on the ionization of thiol acids. J. Am. Chem. Soc., 93, pp. 4433-4436.
29. Xun, F. and Yahong, X. and Shuyun, X. and Shaona, Z. and Zhengshui, H. (2002) Study on the thiophosphinic extractants I. The basic properties of the extractants and the phase behavior in their saponified systems Solvent Extr. Ion Exch., 20, pp. 331-344.
30. Chmutova, M. and Litvina, M. and Nesterova, N. and Kochetkova, N. and Myasoedov, B. and Kabachnik, M. (1990) Extraction of americium(III) by dialkyl(diaryl)[carbamoylmethyl] phosphine oxides from HClO4 solutions Radiokhimiya (Eng. Transl.), 32, pp. 88-95.