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7.6 References

  1. a) F.H. Hurley, U.S. Patent 1948, 2,446,331, [Chem. Abstr. 43, 1949, P7645b]; b) F.H. Hurley, T.P. Wier Jr., J. Electrochem. Soc. 98, 1951, 207–212.

    Google Scholar 

  2. a) H.L. Chum, V.R. Koch, L.L. Miller, R.A. Osteryoung, J. Am. Chem. Soc. 97, 1975, 3264–3265; b) J. Robinson, R.A. Osteryoung, J. Am. Chem. Soc. 101, 1979, 323–327.

    Article  CAS  Google Scholar 

  3. J.S. Wilkes, J.A. Levisky, R.A. Wilson, C.L. Hussey, Inorg. Chem. 21, 1982, 1263–1264.

    Article  CAS  Google Scholar 

  4. a) T.M. Laher, C.L. Hussey, Inorg. Chem. 22, 1983, 3247–3251; b) T.B. Scheffler, C.L. Hussey, Inorg. Chem. 23, 1984, 1926–1932; c) D. Appleby, C.L. Hussey, K.R. Seddon, J.E. Turp, Nature 323, 1986, 614–616.

    Article  CAS  Google Scholar 

  5. P.B. Hitchcock, T.J. Mohammed, K.R. Seddon, J.A. Zora, C.L. Hussey, E.H. Ward, Inorg. Chim. Acta 113, 1986, L25–L26.

    Article  CAS  Google Scholar 

  6. J.S. Wilkes, M.J.J. Zaworotko, J. Chem. Soc. Chem. Comm. 1992, 965–967.

    Google Scholar 

  7. J. Fuller, R.T. Carlin, H.C. deLong, D.J. Haworth, J. Chem. Soc. Chem. Comm. 1994, 299–300.

    Google Scholar 

  8. P. Bonhôte, A.-P. Dias, N. Papageorgiou, K. Kalyanasundaram, M. Grätzel, Inorg. Chem. 1996, 35, 1168–1178.

    Article  Google Scholar 

  9. P. Wasserscheid, A. Bösmann, unpublished results.

    Google Scholar 

  10. N. Karodia, S. Guise, C. Newlands, J.-A. Andersen, Chem. Comm. 1998, 2341–2342.

    Google Scholar 

  11. P. Wasserscheid, R. van Hal, A. Bösmann, Green Chem. 4, 2002, 400–404.

    Article  CAS  Google Scholar 

  12. a) J. Pernak, A. Czepukowicz, R. Pozniak, Ind. Eng. Chem. Res. 40, 2001, 2379–2383; b) B. Jastorff, R. Stoermann, J. Ranke, K. Moelter, F. Stock, B. Oberheitmann, W. Hoffmann, J. Hoffmann, M. Nüchter, B. Ondruschka, J. Filser, Green Chem. 5, 2003, 136–142.

    Article  CAS  Google Scholar 

  13. H. Waffenschmidt, PhD-thesis, RWTH Aachen, 2000.

    Google Scholar 

  14. a) P. Wasserscheid, M. Sesing, W. Korth, Green Chem. 4, 2002, 134–138; b) W. Keim, W. Korth, P. Wasserscheid, World Patent 2000 0016902 (to BP Chemicals Limited, UK; Akzo Nobel NV; Elementis UK Limited) 2000 [Chem. Abstr. 132, 2000, 238691].

    Article  CAS  Google Scholar 

  15. a) A.E. Visser, R.P. Swatlowski, M.W. Reichert, J.H. Davis, R.D. Rogers, R. Mayton, S. Sheff, A. Wiezbicki, Chem. Comm. 2001, 135–136; b) A.E. Visser, R.P. Swatloski, W.M. Reichert, R. Mayton, S. Sheff, A. Wierzbicki, J.H. Davis Jr., R.D. Rogers, Env. Sci. Techn. 36, 2002, 2523–2529; c) S. Anjaiah, S. Chandrasekhar, R. Gree, Tetrahedron Lett. 45, 2004, 569–571.

    Google Scholar 

  16. P. Wasserscheid, B. Drießen-Hölscher, R. van Hal, C.H. Steffens, J. Zimmermann Chem. Comm. 2003, 2038–2039.

    Google Scholar 

  17. T.L. Merrigan, E.D. Bates, S.C. Dorman, J.H. Davis Jr., Chem. Comm. 2000, 2051–2052.

    Google Scholar 

  18. C. Hardacre, J.D. Holbrey, S.E.J. McMath, Chem. Comm. 2001, 367–368.

    Google Scholar 

  19. a) P. Wasserscheid, A. Bösmann, C. Bolm, Chem. Comm. 2002, 200–2001; b) M.J. Earle, P.B. McCormac, K.R. Seddon, Green Chem. 1, 1999, 23–25.

    Google Scholar 

  20. a) Solvent Innovation (www.solvent-innovation.com); b) Fluka (www.fluka.com); c) Merck (www.merck.de); d) Acros Organics (www.acros.com); e) Wako (www.wako-chem.co.jp).

    Google Scholar 

  21. e.g. Solvent Innovation offers its ionic liquids routinely in 5 kg batches but some representatives are even commercialised on a ton-scale (for more details see www.solvent-innovation.com)

    Google Scholar 

  22. K.R. Seddon, A. Stark, M.J. Torres, Pure Appl. Chem. 72, 2000, 2275–2287.

    CAS  Google Scholar 

  23. Among the potential impurities in ionic liquids water, halide ions and organic starting material are of great importance for transition metal chemistry while the colour of an ionic liquid is not a critical parameter in most applications.

    Google Scholar 

  24. a) J.S. Wilkes, J.A. Levisky, R.A. Wilson, C.L. Hussey, Inorg. Chem. 21, 1982, 1263–1264; b) A.A. Fannin Jr., D.A. Floreani, L.A. King, J.S. Landers, B.J. Piersma, D.J. Stech, R.J. Vaughn, J.S. Wilkes, J.L. Williams, J. Phys. Chem. 88, 1984, 2614–2621.

    Article  CAS  Google Scholar 

  25. J. Fuller, R.T. Carlin, R.A. Osteryoung, J. Electrochem. Soc., 144, 1997, 3881–3886.

    Article  CAS  Google Scholar 

  26. A. Noda, K. Hayamizu, M. Watanabe, J. Phys. Chem. B, 105, 2001, 4603–4610.

    Article  CAS  Google Scholar 

  27. a) melting point: J.D. Holbrey, R.D. Rogers, Melting Points and Phase Diagrams in P. Wasserscheid, T. Welton (Eds.) Ionic Liquids in Synthesis, Wiley-VCH, Weinheim 2003, pp. 41–55; b) viscosity: S.N. Baker, G.A. Baker, G.A. Kane, F.V. Bright, J. Phys. Chem. B, 105, 2001, 9663–9668; c) density: S. Chun, S.V. Dzyuba, R.A. Bartsch, Anal. Chem. 73, 2001, 3737–3741.

    Google Scholar 

  28. P. Wasserscheid, T. Welton (Eds.) Ionic Liquids in Synthesis, Wiley-VCH, Weinheim, 2002.

    Google Scholar 

  29. G.W. Parshall, J. Am. Chem. Soc. 94, 1972, 8716–8719.

    Article  CAS  Google Scholar 

  30. J.F. Knifton, J. Mol. Catal. 43, 1987, 65–78.

    Article  CAS  Google Scholar 

  31. Y. Chauvin, B. Gilbert, I. Guibard, J. Chem. Soc. Chem. Comm. 1990, 1715–1716.

    Google Scholar 

  32. (a) P. Wasserscheid Transition Metal Catalysis in Ionic Liquids in P. Wasserscheid, T. Welton (Eds.) Ionic Liquids in Synthesis, Wiley-VCH, Weinheim 2003, pp. 213–257; (b) H. Olivier-Bourbigou, L. Magna, J. Mol. Catal. A (Chemical) 182–183, 2002, 419–437; (c) R. Sheldon, Chem. Comm. 2001, 2399–2407; (d) C.M. Gordon, Appl. Catal. A (General) 222, 2001, 101–117; (e) P. Wasserscheid, W. Keim, Angew. Chem. Int. Ed. 39, 2000, 3772–3789.

    Google Scholar 

  33. a) K.J. Baranyai, G.B. Deacon, D.R. MacFarlane, J.M. Pringle, J.L. Scott, Aust. J. Chem. 57, 2004, 145–147; b) M. Kosmulski, M; Gustafsson, J; Rosenholm, J.B., Thermochim. Acta 412, 2004, 47–53.

    Article  CAS  Google Scholar 

  34. J.D. Holbrey, A.E. Visser, R.D. Rogers, Solubility and Solvation in Ionic Liquids in P. Wasserscheid, T. Welton (Eds.) Ionic Liquids in Synthesis, Wiley-VCH, Weinheim 2003, pp. 68–81.

    Google Scholar 

  35. T. Welton, Polarity in P. Wasserscheid, T. Welton (Eds.) Ionic Liquids in Synthesis, Wiley-VCH, Weinheim 2003, pp. 94–103.

    Google Scholar 

  36. B. Drießen-Hölscher, P. Wasserscheid, W. Keim, CATTECH, 3, 1998, 47–52.

    Google Scholar 

  37. a) A.J. Arduengo, R.L. Harlow, M. Kline, J. Am. Chem. Soc. 113, 1991, 361–363; b) A.J. Arduengo, H.V.R. Dias, R.L. Harlow, J. Am. Chem. Soc. 114, 1992, 5530–5534; c) W.A. Herrmann, M. Elison, J. Fischer, C. Koecher, G.R.J. Artus, Angew. Chem. Int. Ed. 34, 1995, 2371–2374; d) D. Bourissou, O. Guerret, F.P. Gabba, Chem. Rev. 100, 2000, 39–91; e) L. Xu, W. Chen, J. Xiao, Organometallics 19, 2000, 1123–1127; f) C.J. Mathews, P.J. Smith; T. Welton, A.J.P. White, Organometallics, 20, 2001, 3848–3850; g) D.S. McGuinness, K.J. Cavell, B.F. Yates, Chem. Comm.s 2001, 355–356; h) M. Hasan, I.V. Kozhevnikow, MR.H. Siddiqui, C. Fermoni, A. Steiner, N. Winterton, Inorg. Chem. 40, 2001, 795–800.

    Article  CAS  Google Scholar 

  38. P. Wasserscheid, C.M. Gordon, C. Hilgers, M.J. Maldoon, I.R. Dunkin, Chem. Comm. 2001, 1186–1187.

    Google Scholar 

  39. a) R.T. Carlin, R.A. Osteryoung, J. Mol. Catal. 63, 1990, 125–129; b) Y. Chauvin, S. Einloft, H. Olivier, Ind. Eng. Chem. Res. 34, 1995, 1149–1155; c) H. Waffenschmidt, P. Wasserscheid, J. Mol. Catal. 164, 2001, 61–67.

    Article  CAS  Google Scholar 

  40. R.A. Mantz, P.C. Trulove, Viscosity and Density of Ionic Liquids in P. Wasserscheid, T. Welton (Eds.) Ionic Liquids in Synthesis, Wiley-VCH, Weinheim 2003, pp. 56–68.

    Google Scholar 

  41. H. Matsumoto, H. Kageyama, Y. Miyazaki, Chem. Comm. 16, 2002, 1726–1727.

    Article  Google Scholar 

  42. D.R. McFarlane, J. Golding, S. Forsyth, M. Forsyth, G.B. Deacon, Chem. Comm. 16, 2001, 1430–1431.

    Article  Google Scholar 

  43. P. Wasserscheid, C. Hilgers, W. Keim, J. Mol. Catal. A 214(1), 2004, 83–90.

    Article  CAS  Google Scholar 

  44. a) Y. Chauvin, L. Mussmann, H. Olivier, Angew. Chem. Int. Ed. 34, 1995, 1149–1153; b) Y. Chauvin, H. Olivier, L. Mußmann, Y. Chauvin, European Patent 1997 776880 (to Institut Francais Du Petrole, Fr.), [Chem. Abstr. 127, 1997, 65507].

    CAS  Google Scholar 

  45. C.C. Brasse, U. Englert, A. Salzer, H. Waffenschmidt, P. Wasserscheid, Organometallics 19, 2000, 3818–3823.

    Article  CAS  Google Scholar 

  46. P. Wasserscheid, H. Waffenschmidt, P. Machnitzki, K. Kottsieper, O. Stelzer, Chem. Comm. 5, 2001, 451–452.

    Article  Google Scholar 

  47. A. Heßler, O. Stelzer, H. Dibowski, K. Worm, F.P. Schmidtchen, J. Org. Chem. 1997, 62, 2362–2369.

    Article  Google Scholar 

  48. P. Machnitzki, M. Teppner, K. Wenz, O. Stelzer, E.J. Herdtweck, Organomet. Chem. 602, 2000, 158–169.

    Article  CAS  Google Scholar 

  49. H. Dibowski, F. P. Schmidtchen, Angew. Chem. Int. Ed. 37, 1998, 476–478.

    Article  CAS  Google Scholar 

  50. O. Stelzer, F.P. Schmidtchen, A. Heßler, M. Tepper, H. Dibowski, H. Bahrmann, M. Riedel, German Patent 1998 19701245 (to Celanese G.m.b.H., Germany), [Chem. Abstr. 129, 1998, 149094].

    Google Scholar 

  51. F. Favre, H. Olivier-Bourbigou, D. Commereuc, L. Saussine, Chem. Comm. 15, 2001, 1360–1361.

    Article  Google Scholar 

  52. J. Sirieix, M. Ossberger, B. Betzemeier, P. Knochel, Synlett. 11, 2000, 1613–1615.

    Google Scholar 

  53. a) K.W. Kottsieper, O. Stelzer, P. Wasserscheid, J. Mol. Catal. A: Chem. 175, 2001, 285–288; b) D. J. Brauer, K.W. Kottsieper, C. Liek, O. Stelzer, H. Waffenschmidt, P. Wasserscheid, J. Organomet. Chem. 630, 2001, 177–184.

    Article  CAS  Google Scholar 

  54. C.P. Casey, G.T. Whiteker, M.G. Melville, L.M. Petrovich, L.J.A. Gavey, D.R.J. Powell, J. Am. Chem. Soc. 114, 1992, 5535–5543.

    Article  CAS  Google Scholar 

  55. M. Kranenburg, Y.E.M. van der Burgt, P.C.J. Kamer, P.W.N.M van Leeuwen, K. Goubitz, J. Fraanje, Organometallics 14, 1995, 3081–3089.

    Article  CAS  Google Scholar 

  56. P.W.N.M. van Leeuwen, P.C.J. Kamer, J.N.H. Reek, P. Dierkes, Chem. Rev. 100, 2000, 2741–2770.

    Article  Google Scholar 

  57. P. Dierkes, S. Ramdeehul, L. Barloy, A. De Cian, J. Fischer, P.C.J. Kamer, P.W.N.M. van Leeuwen, Angew. Chem. Int. Ed. 37, 1998, 3116–3118.

    Article  CAS  Google Scholar 

  58. J. Dupont, S.M. Silva, R.F. de Souza, Catal. Lett. 77, 2001, 131–133.

    Article  CAS  Google Scholar 

  59. R.P.J. Bronger, S.M. Silva, P.C.J. Kamer, P.W.N.M. van Leeuwen, Chem. Comm. 24, 2002, 3044–3045.

    Article  Google Scholar 

  60. Experimental details available, see http://www.rsc.org/suppdata/cc/b2/b209486j/

    Google Scholar 

  61. A. Castellanos-Páez, S. Castillon, C. Claver, P.W.N.M. van Leeuwen, W.G.J. de Lange, Organometallics 17, 1998, 2543–2552.

    Article  Google Scholar 

  62. P. Wasserscheid, R. van Hal in R.D. Rogers, K.R. Seddon (Eds) “Ionic liquids as Green Solvents”, ACS Symposium Series 856, 2003, 57–70.

    Google Scholar 

  63. a) M.F. Sellin, P.B. Webb, D.J. Cole-Hamilton, Chem. Comm. 8, 2001, 781–782; b) D.J. Cole-Hamilton, M.F. Sellin, P.B. Webb World Patent 2002 0202218 (to the University of St. Andrews) [Chem. Abstr. 136, 2002, 104215]; c) D.J. Cole-Hamilton, Science 299, 2003, 1702–1706., d) P.B. Webb, M.F. Sellin, T.E. Kunene, S. Williamson, A.M.Z. Slawin, D.J. Cole-Hamilton, J. Am. Chem. Soc. 125, 2003, 15577–15588.

    Article  Google Scholar 

  64. P.G. Jessop, W. Leitner, (eds.), “Chemical Synthesis Using Supercritical Fluids”, Wiley-VCH, Weinheim, 1999.

    Google Scholar 

  65. L.A. Blanchard, D. Hancu, E.J. Beckman, J.F. Brennecke, Nature 299, 1999, 28–29.

    Article  Google Scholar 

  66. A. Bösmann, G. Franciò, E. Janssen, M. Solinas, W. Leitner, P. Wasserscheid, Angew. Chem. 113, 2001, 2769–2771.

    Article  Google Scholar 

  67. M.T. Reetz, W. Wiesenhoefer, G. Francio, W. Leitner, Adv. Synth & Catal. 345, 2003, 1221–1228.

    Article  CAS  Google Scholar 

  68. A. Riisager, P. Wasserscheid, R. van Hal, R. Fehrmann, J. Catal. 219, 2003, 452–455.

    Article  CAS  Google Scholar 

  69. a) L.A. Gerritsen, A. van Meerkerk, M.H. Vreugdenhil, J.J.F. Scholten, J. Mol. Catal.9, 1980, 139–155; b) L.A. Gerritsen, J.M. Herman, W. Klut, J.J.F. Scholten, J. Mol. Catal. 9, 1980, 157–168; c) L.A. Gerritsen, J.M. Herman, J.J.F. Scholten, J. Mol. Catal. 9, 1980, 241–256; d) L.A. Gerritsen, W. Klut, M.H. Vreugdenhil, J.J.F. Scholten, J. Mol. Catal. 9, 1980, 257–264; e) L.A. Gerritsen, W. Klut, M.H. Vreugdenhil, J.J.F. Scholten, J. Mol. Catal. 9, 1980, 265–274.

    Article  CAS  Google Scholar 

  70. J. Hjortkjær, M.S. Scurell, P. Simonsen, J. Mol. Catal. 6, 1979, 405–420.

    Article  Google Scholar 

  71. a) J.P. Arhancet, M.E. Davis, J.S. Merola, B.E. Hanson, Nature (London) 339, 1989 454–455; b) J.P. Arhancet, M.E. Davis, J.S. Merola, B.E. Hanson, Journal of Catalysis 121, 1990, 327–339; c) M.E. Davis CHEMTECH, 22, 1992, 498–502; d) I. Toth, I. Guo, B.E. Hanson, J. Mol. Catal. A 116, 1997, 217–229; e) H. Ding, J. Kang, B.E. Hanson, C.W. Kohlpaintner, J. Mol. Catal. A 124, 1997, 21–28.

    Article  CAS  Google Scholar 

  72. M.H. Valkenberg, C. de Castro, W.F. Hölderich, Appl. Catal. A General 215, 2001, 185–190.

    Article  CAS  Google Scholar 

  73. a) M.H. Valkenberg, C. deCastro, W.F. Hölderich, Topics in Catalysis 14, 2001, 139–144; b) M.H. Valkenberg, C. deCastro, W.F. Hölderich, Green Chem. 4, 2002, 88–93.

    Article  Google Scholar 

  74. C.P. Mehnert, R.A. Cook, N.C. Dispenziere, M. Afeworki, J. Am. Chem. Soc. 124, 2002, 12932–12933.

    Article  CAS  Google Scholar 

  75. W.A. Herrmann, C.W. Kohlpaintner, R.B. Manetsberger, H. Bahrmann, H. Kottmann, J. Mol. Catal. A 97, 1995, 65–72.

    Article  CAS  Google Scholar 

  76. a) B. Heinrich, Y. Chen, J. Hjortkjær, J. Mol. Catal. 80, 1993, 365–375; b) A. Riisager, K.M. Eriksen, J. Hjortkjær, R. Fehrmann, J.Mol. Catal. A 193, 2003, 259–272.

    Article  CAS  Google Scholar 

  77. A. Riisager, R. Fehrmann, P. Wasserscheid, R. Van Hal, unpublished results.

    Google Scholar 

  78. A. Riisager, K.M. Eriksen, P. Wasserscheid, R. Fehrmann, Catal. Lett. 90, 2003, 149–153.

    Article  CAS  Google Scholar 

  79. J.H. Davis Jr., P.A. Fox, Chem. Comm. 11, 2003, 1209–1212.

    Article  Google Scholar 

  80. S.M. Silva, R.P.J. Bronger, Z. Freixa, J. Dupont, P.W.N.M. van Leeuwen, New J. Chem. 27, 2003, 1294–1296.

    Article  CAS  Google Scholar 

  81. a) L.A. van der Veen, M.D.K. Boele, F.R. Bregman, P.C.J. Kamer, P.W.N.M. van Leeuwen, K. Goubitz, J. Fraanje, H. Schenk, C. Bo, J. Am. Chem. Soc. 120, 1998, 11616–11626; b) L.A. van der Veen, P.C.J. Kamer, P.W.N.M. van Leeuwen, Organometallics 18, 1999, 4765–4777; c) L.A. van der Veen, P.H. Keeven, G.C. Schoemaker, J.N.H. Reek, P.C.J. Kamer, P.W.N.M. van Leeuwen, M. Lutz, A.L. Spek, Organometallics 19, 2000, 872–883.

    Article  Google Scholar 

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Wasserscheid, P., Haumann, M. (2006). Catalyst Recycling Using Ionic Liquids. In: Cole-Hamilton, D.J., Tooze, R.P. (eds) Catalyst Separation, Recovery and Recycling. Catalysis by Metal Complexes, vol 30. Springer, Dordrecht . https://doi.org/10.1007/1-4020-4087-3_7

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