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Original Articles

Carbon Dioxide Solubility Enhancement through Silicone Functionalization: “CO2-philic” Oligo(dimethylsiloxane)-substituted Diphosphonates∗

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Pages 2520-2536 | Received 25 Oct 2007, Accepted 12 Mar 2008, Published online: 06 Aug 2008

REFERENCES

  • McHugh , M.A. ; Krukonis , V.J. ( 1986 ) Supercritical Fluid Extraction: Principles and Practice ; Butterworths : London .
  • Jessop , P.G. ; Leitner , W. ( 1999 ) Chemical Synthesis Using Supercritical Fluids ; Wiley-VCH : Weinheim , Germany .
  • Nelson , W.M. ( 2003 ) Green Solvents for Chemistry ; Oxford University Press : New York .
  • Afonso , C.A.M. ; Crespo , J.G. ( 2005 ) Green Separation Processes ; Wiley-VCH : Weinheim , Germany .
  • Phelps , C.L. ; Smart , N.G. ; Wai , C.M. ( 1996 ) Past, present, and possible future applications of supercritical fluid extraction technology . J. Chem. Educ. , 73 : 1163 .
  • Clifford , T. ( 1999 ) Fundamentals of Supercritical Fluids ; Oxford University Press : New York .
  • Gopalan , A.S. ; Wai , C.M. ; Jacobs , H.K. ( 2003 ) Supercritical Carbon Dioxide: Separations and Processes ; American Chemical Society : Washington , DC .
  • Laintz , K.E. ; Hale , C.D. ; Stark , P. ; Pouquette , C. L. ; Wilkinson , J. ( 1998 ) A comparison of liquid and supercritical carbon dioxide as an extraction solvent for plating bath treatment . Anal. Chem. , 70 : 400 .
  • Hyatt , J.A. (1984). Liquid and supercritical carbon dioxide as organic-solvents. J. Org. Chem. , 49: 5097.
  • Yazdi , A. ; Beckman , E.J. ( 1994 ) Highly CO2-soluble chelating agents for supercritical extraction and recovery of heavy metals . MRS Symposium Proceedings. 344 : 211 .
  • DeSimone , J.M. ; Maury , E.E. ; Menceloglu , Y.Z. ; McClain , J.B. ; Romack , T.J. ; Combes , J.R. ( 1994 ) Dispersion polymerizations in supercritical carbon-dioxide . Science. , 265 : 356 .
  • Wai , C.M. ; Wang , S.F. ( 1997 ) Supercritical fluid extraction: metals as complexes . J. Chromatogr. A. , 785 : 369 .
  • Smart , N.G. ; Carleson , T. ; Kast , T. ; Clifford , A.A. ; Burford , M.D. ; Wai , C.M. ( 1997 ) Solubility of chelating agents and metal-containing compounds in supercritical fluid carbon dioxide . Talanta. , 44 : 137 .
  • Fink , R. ; Hancu , D. ; Valentine , R. ; Beckman , E.J. ( 1999 ) Toward the development of “CO2-philic” hydrocarbons. 1. Use of side-chain functionalization to lower the miscibility pressure of polydimethylsiloxanes in CO2 . J. Phys. Chem. B. , 103 : 6441 .
  • Fink , R. ; Beckman , E.J. ( 2000 ) Phase behavior of siloxane-based amphiphiles in supercritical carbon dioxide . J. Supercrit. Fluids. , 18 : 101 .
  • Yazdi , A.V. ; Beckman , E.J. ( 1996 ) Design, synthesis, and evaluation of novel, highly CO2-soluble chelating agents for removal of metals . Ind. Eng. Chem. Res. , 35 : 3644 .
  • Hoefling , T.A. ; Newman , D.A. ; Enick , R.M. ; Beckman , E.J. ( 1993 ) Effect of structure on the cloud-point curves of silicone-based amphiphiles in supercritical carbon-dioxide . J. Supercrit. Fluids. , 6 : 165 .
  • Nash , K.L. ( 1997 ) f-Element complexation by diphosphonate ligands . J. Alloys Compd. , 249 : 33 .
  • Chiarizia , R. ; Horwitz , E.P. ; Alexandratos , S.D. ; Gula , M.J. ( 1997 ) Diphonix® resin: a review of its properties and applications . Sep. Sci. Technol. , 32 : 1 .
  • Horwitz , E.P. ; Chiarizia , R. ; Dietz , M.L. ( 1997 ) DIPEX: a new extraction chromatographic material for the separation and preconcentration of actinides from aqueous solution . React. Funct. Polym. , 22 : 25 .
  • McAlister , D.R. ; Dietz , M.L. ; Chiarizia , R. ; Herlinger , A.W. ( 2001 ) Metal ion extraction by silyl-substituted diphosphonic acids. I. P, P'-Di-[3-(trimethylsilyl)-1-propylene] methylene and ethylenediphosphonic acids . Sep. Sci. Technol. , 36 : 3541 .
  • McAlister , D.R. ; Herlinger , A.W. ; Ferraro , J.R. ; Dietz , M.L. ( 2002 ) Synthesis and characterization of metal complexes of P, P′-Di-[3-trimethylsilyl)-1-propyl]methylenediphosphonic acid.Synth . React. Inorg. Met.-Org. Chem. , 32 : 277 .
  • McAlister , D.R. ; Dietz , M.L. ; Chiarizia , R. ; Herlinger , A.W. ( 2002 ) Aggregation and metal ion extraction properties of novel, silicon-substituted alkylenediphosphonic acids . Proceedings of the International Solvent Extraction Conference , 1 : 390 .
  • McAlister , D.R. ; Chiarizia , R. ; Dietz , M.L. ; Herlinger , A.W. ; Zalupski , P.R. ( 2002 ) Extraction of alkaline earth and actinide cations by mixtures of di-(2-ethylhexyl)alkylenediphosphonic acids and neutral synergists . Solvent Extr. Ion Exch. , 20 : 447 .
  • McAlister , D.R. ; Dietz , M.L. ; Chiarizia , R. ; Zalupski , P.R. ; Herlinger , A.W. (2002) Metal extraction by silyl-substituted diphosphonic acids. II. Effect of alkylene bridge length on aggregation and metal ion extraction behavior. Sep. Sci. Technol. , 37: 2289.
  • Smart , N.G. ; Carleson , T.E. ; Elshani , S. ; Wang , S. ; and Wai , C.M. ( 1997 ) Dioxide containing organophosphorus reagents . Ind. Eng. Chem. Res. , 36 : 1819 .
  • Meguro , Y. ; Iso , S. ; Sasaki , T. ; Yoshida , Z. ( 1998 ) Solubility of organophosphorus metal extractants in supercritical carbon dioxide . Anal. Chem. , 70 : 774 .
  • Carrott , M.J. ; Waller , B.E. ; Smart , N.S. ; Wai , C.M. ( 1998 ) High solubility of UO2(NO3)2·2TBP complex in supercritical CO2 . Chem. Commun. , 373 .
  • Herlinger , A.W. ; McAlister , D.R. ; Chiarizia , R. ; Dietz , M.L. ( 2003 ) Aggregation, metal ion extraction, and solubility properties of silyl-substituted alkylenediphosphonic acids . Sep. Sci. Technol. , 38 : 2741 .
  • McAlister , D.R. ; Dietz , M.L. ; Stepinski , D. ; Zalupski , P.R. ; Dzielawa , J.A. ; Barrans , R.E. , Jr.; Hess , J.N. ; Herlinger , A.W. ( 2004 ) Application of molecular connectivity indices to the design of supercritical carbon dioxide-soluble metal ion extractants: SC-CO2 solubilities of symmetrically substituted alkylenediphosphonic acids . Sep. Sci. Technol. , 39 : 761 .
  • Stepinski , D.C. ; Herlinger , A.W. ( 2002 ) A facile and selective high-yield synthesis of symmetric dialkyl-substituted methylenebisphosphonic acids . Synth. Comm. , 32 : 2683 .
  • Zhao , K. ; Landry , D.W. ( 1993 ) Tetrazole catalyzed synthesis of phosphonate esters . Tetrahedron. , 49 : 363 .
  • Lesiak , K. ; Watanabe , K.A. ; George , J. ; Pankewicz , K.W.J. ( 1998 ) Org. Chem. , 63 : 1906 .
  • Speier , J.L. ; Webster , J.A. ; Barnes , G.H. ( 1957 ) J. Am. Chem. Soc. , 79 : 974 .
  • Lee , K.H. ; Kohn , J.P. ( 1969 ) Heterogeneous phase equilibrium in the ethane-n-dodecane system . J. Chem. Eng. Data. , 14 : 292 .
  • Eastoe , J. ; Paul , A. ; Nave , S. ; Steyler , D.C. ; Robinson , B.H. ; Rumsoy , E. ; Thorpe , M. ; Heenan , R.K. ( 2001 ) J. Am. Chem. Soc. , 123 : 988 .
  • Andersen , W.C. ; Sievers , R.E. ; Lagalante , A.F. ; Bruno , T.J.J. ( 2001 ) Chem. Eng. Data. , 46 : 1045 .

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