An investigation of ester group steric effects on metal ion extraction by symmetrically substituted methylenediphosphonic acids

Solvent Extraction and Ion Exchange

Volumn 22, Issue 1, 2004, Pages 89-103

  Stepinski, D C ^a   McAlister, D R ^a   Zalupski, P R ^a   Chiarizia, R ^b   Herlinger, A W ^a  

^a LOYOLA UNIVERSITY CHICAGO   (United States)

^b ARGONNE NATIONAL LABORATORY   (United States)

Author keywords

Diphosphonic acids; Ester substituent; Metal ion extraction; Steric effects

Indexed keywords

ACTINIDES; AMERICIUM; BONDING; CALCIUM; ESTERS; OXIDATION; PHOSPHORS; SOLVENT EXTRACTION;

METAL ION EXTRACTION; STERIC EFFECT;

ION EXCHANGE;

ACTINIDE; AMERICIUM; CALCIUM; METAL EXTRACTION; PHOSPHONIC ACID ESTER; SOLVENT EXTRACTION;

EID: 1842832122     PISSN: 07366299     EISSN: None     Source Type: Journal    
DOI: 10.1081/SEI-120028004     Document Type: Article

References (23)

1. Chiarizia, R.; Horwitz, E.P.; Rickert, P.G.; Herlinger, A.W. Metal extraction by alkyl-substituted diphosphonic acids. I. P,P′-Di(2-Ethylhexyl) methanediphosphonic acid. Solvent Extr. Ion Exch. 1996, 14, 773-792.
2. Chiarizia, R.; Horwitz, E.P.; Alexandratos, S.D.; Gula, M.J. Diphonix resin: a review of its properties and applications. Sep. Sci. Technol. 1997, 32, 1-35.
3. Nash, K.L. Thermodynamics of formation of complexes between thorium(IV) and substituted methanediphosphonic acids in acidic solutions. Radiochim. Acta 1991, 54, 171-179.
4. Nash, K.L.; Horwitz, E.P. Stability constants for europium(III) complexes with substituted methane diphosphonic acids in acid solutions. Inorg. Chim. Acta 1990, 169, 245-252.
5. Rizkalla, E.N. Metal chelates of phosphonate-containing ligands. Rev. Inorg. Chem. 1983, 5, 223-304.
6. McAlister, D.R.; Dietz, M.L.; Chiarizia, R.; Barrans, R.E., Jr.; Herlinger, A.W. Metal ion extraction by silyl-substituted diphosphonic acids. Part I. P,P′-Di[3-Trimethylsilyl-1-Propylene] methylene- and ethylene-diphosphonic acids. Sep. Sci. Technol. 2001, 36, 3541-3562.
7. McAlister, D.R.; Dietz, M.L.; Chiarizia, R.; Zalupski, P.R.; Herlinger, A.W. Metal ion extraction by silyl-substituted diphosphonic acids. Part 2. Effect of alkylene bridge length on aggregation and metal ion extraction behavior. Sep. Sci. Technol. 2002, 37, 2289-2315.
8. Zalupski, P.R.; McAlister, D.R.; Stepinski, D.C.; Herlinger, A.W. Metal extraction by silyl-substituted diphosphonic acids. III. Ester group substituent effects on phosphoryl oxygen basicity. Solvent Extr. Ion Exch. 2003, 23, 331-345.
9. McAlister, D.R. Aggregation, Solvent Extraction, Metal Complexation and Supercritical Carbon Dioxide Solubility Properties of Symmetrically-Substituted Alkylenediphosphonic Acids; Loyola University Chicago: Chicago, IL, 2002; Ph.D. Dissertation.
10. Chiarizia, R.; Herlinger, A.W.; Horwitz, E.P. Metal extraction by alkyl-substituted diphosphonic acids. III. P,P′-Di(2-Ethylhexyl) ethanediphosphonic acid. Solvent Extr. Ion Exch. 1997, 15, 417-431.
11. Chiarizia, R.; Herlinger, A.W.; Cheng, Y.D.; Ferraro, J.R.; Rickert, P.G.; Horwitz, E.P. Metal extraction by alkyl-substituted diphosphonic acids. IV. P,P′-Di(2-Ethylhexyl) butanediphosphonic acid. Solvent Extr. Ion Exch. 1998, 16, 505-526.
12. Stepinski, D.C.; Nelson, D.W.; Zalupski, P.R.; Hettinger, A.W. Facile high yielding synthesis of symmetric esters of methylenebisphosphonic acid. Tetrahedron 2001, 57, 8637-8645.
13. Stepinski, D.C.; Herlinger, A.W. A facile and selective high yield synthesis of symmetric dialkyl-substituted methylenebisphosphonic acids. Synth. Commun. 2002, 32, 2683-2690.
14. Barrans, R.E., Jr.; McAlister, D.R.; Herlinger, A.W.; Chiarizia, R.; Ferraro, J.R. Hydrogen bonding in aggregates of dialkyl-substituted diphosphonic acids and monofunctional analogues. Solvent Extr. Ion Exch. 1999, 17, 1195-1217.
15. Chiarizia, R.; Barrans, R.E., Jr.; Ferraro, J.R.; Herlinger, A.W.; McAlister, D.R. Aggregation of dialkyl-substituted diphosphonic acids and its effect on metal ion extraction. Sep. Sci. Technol. 2001, 36, 687-708.
16. Herlinger, A.W.; Ferraro, J.R.; Chiarizia, R.; Horwitz, E.P. An investigation of P,P′-Di(2-Ethylhexyl) methanediphosphonic acid and some of its metal complexes. Polyhedron 1997, 16, 1843-1854.
17. Rozen, A.M.; Krupnov, B.V. Dependence of the extraction ability of organic compounds on their structure. Usp. Khim. 1996, 65, 1052-1079.
18. Turanov, A.N.; Karandashev, V.K.; Yarkevich, A.N.; Kharitonov, A.V. Effect of the structure of phosphorylated carboxylic acids on extraction of uranium and thorium from nitric acid solutions. Radiochemistry 2000, 42, 251-256.
19. Stepinski, D.C. Design, Synthesis and Evaluation of Symmetric Esters of Methylenebisphosphonic Acid and Methylenebisthiophosphonic Acid as Novel Metal Ion Extractants; Loyola University Chicago: Chicago, IL, 2003; Ph.D. Dissertation.
20. Horwitz, E.P.; Chiarizia, R. Liquid extraction, the TRUEX process-experimental studies. In Separation Techniques in Nuclear Waste Management; Carleson, T.E., Chipman, N.A., Wai, C.M., Eds.; CRC Press, Inc.: Boca Raton, FL, 1996; 3-33.
21. Danesi, P.R.; Reichley-Yinger, L.; Mason, G.; Kaplan, L.; Horwitz, E.P.; Diamond, H. Selectivity-structure trends in the extraction of Co(II) and Ni(II) by dialkyl phosphoric, alkyl alkylphosphonic, and dialkylphosphinic acids. Solvent Extr. Ion Exch. 1985, 3, 435-452.
22. Preston, J.S. The influence of extractant structure on the solvent extraction of zinc(II) and calcium(II) by carboxylic acids. Solvent Extr. Ion Exch. 1994, 12, 1-27.
23. Preston, J.S.; Preez, A.C. The influence of extractant structure on the solvent extraction of uranium(VI) and thorium(IV) from nitrate media by dialkyl sulphoxides. J. Chem. Tech. Biotechnol. 1997, 69, 86-92.