Industrial preparation of phosphonium ionic liquids

Green Chemistry

Volumn 5, Issue 2, 2003, Pages 143-152

  Bradaric, Christine J ^a   Downard, Andrew ^a   Kennedy, Christine ^a   Robertson, Allan J ^a   Zhou, Yuehui ^a  

^a Cytec Canada Inc   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

IONIC LIQUID; N,N DIMETHYLIMIDAZOLIUM DIMETHYLPHOSPHATE; PHOSPHONIUM DERIVATIVE; TRIHEXYL(TETRADECYL)PHOSPHONIUM BIS(2,4,4 TRIMETHYLPENTYL)PHOSPHINATE; TRIHEXYL(TETRADECYL)PHOSPHONIUM CHLORIDE; TRIHEXYL(TETRADECYL)PHOSPHONIUM TETRAFLUOROBORATE; TRIISOBUTYL(METHYL)PHOSPHONIUM DIMETHYLPHOSPHATE; TRIISOBUTYL(METHYL)PHOSPHONIUM TOSYLATE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL INDUSTRY; PATENT; PHYSICAL CHEMISTRY; SYNTHESIS;

EID: 0242481657     PISSN: 14639262     EISSN: None     Source Type: Journal    
DOI: 10.1039/b209734f     Document Type: Article

References (112)

1. The terms 'ionic liquid' and 'room-temperature ionic liquid' are used here, interchangeably, to described ionic salts with melting points < ∼ 100°C. Many systems of interest have melting points around or below room temperature.
2. C. M. Gordon, Appl. Catal. A, 2001, 222, 101.
3. J. G. Huddleston, A. E. Visser, W. M. Reichert, H. D. Willauer, G. A. Broker and R. D. Rogers, Green Chem., 2001, 3, 156.
4. (a) K. R. Seddon, J. Chem. Tech. Biotech., 1997, 68, 351;
5. (b) J. D. Holbrey and K. R. Seddon, Clean Products Proc., 1999, 1, 223;
6. (c) K. R. Seddon, A. Stark and M. J. Torres, Pure Appl. Chem., 2000, 72, 2275.
7. R. Sheldon, Chem. Commun., 2001, 2399.
8. T. Welton, Chem. Rev., 1999, 99, 2071.
9. P. Wasserscheid and W. Keim, Angew. Chem., Int. Ed., 2000, 39, 3772.
10. (a) D. Zhao, M. Wu, Y. Kou and E. Min, Catal. Today C., 2002, 74, 157;
11. (b) Y. S. Vygodskii, E. I. Lozinskaya and A. S. Shaplov, Polym. Sci. Ser. C, 2001, 34, 236;
12. (c) J. Dupont, C. S. Consorti and J. Spencer, J. Braz. Chem. Soc., 2000, 11, 337.
13. For example, see: N. Karodia, S. Guise, C. Newlands and J. Andersen, Chem. Commun., 1998, 2341.
14. Cytec phosphonium salts are, in general, sold under the CYPHOS® trade name. Those specifically designated as ionic liquids will heretofore be known as CYPHOS IL phosphonium ionic liquids.
15. J. S. Wilkes, Green Chem., 2002, 73.
16. P. Walden, Bull. Acad. Imp. Sci. St. Petersbourg, 1914, 1800.
17. R. M. Pagni, in Advances in Molten Salt Chemistry, 1987, ed. G. Mamantov, C.B. Mamantov and J. Braunstein, Elsevier, New York, 1987, vol. 6, pp. 211-346.
18. (a) H. L. Chum, V. R. Koch, L. L. Miller and R. A. Osteryoung, J. Am. Chem. Soc., 1975, 97, 3264;
19. (b) J. Robinson and R. A. Osteryoung, J. Am. Chem. Soc., 1979, 101, 323.
20. J. S. Wilkes, J. A. Levisky, R. A. Wilson and C. L. Hussey, Inorg. Chem., 1982, 21, 1263.
21. T. B. Scheffler, C. L. Hussey, K. R. Seddon, C. M. Kear and P. D. Armitage, Inorg. Chem., 1983, 22, 2099.
22. D. Appleby, C. L. Hussey, K. R. Seddon and J. E. Turp, Nature, 1986, 323, 614.
23. J. A. Boon, J. A. Levisky, J. L. Pflug and J. S. Wilkes, J. Org. Chem., 1986, 51, 480.
24. (a) Y. Chauvin, B. Gilbert and I. Guibard, J. Chem. Soc., Chem. Commun., 1990, 1715;
25. (b) R. T. Carlin and R. A. Osteryoung, J. Mol. Catal., 1990, 63, 125.
26. J. S. Wilkes and M. J. Zaworotko, J. Chem. Soc., Chem. Commun., 1992, 965.
27. K. R. Seddon, Green Chem., 2002, G25.
28. A. E. Visser, R. P. Swatloski and R. D. Rogers, Green Chem., 2001, 2, 1.
29. B. M. Quinn, Z. Ding, R. Moulton and A. J. Bard, Langmuir, 2002, 18, 1734.
30. F. Endres, Chem. Phys. Chem., 2002, 3, 144.
31. C. M. Gordon and A. J. McLean, Chem. Commun., 2000, 1395.
32. C. M. Gordon, J. D. Holbrey, A. R. Kennedy and K. R. Seddon, J. Mater. Chem., 1998, 8, 2627.
33. E. D. Bates, R. D. Mayton, I. Ntai and J. H. Davis, J. Am. Chem. Soc., 2002, 6, 926.
34. A. Bösmann, L. Datsevich, A. Jess, A. Lauter, C. Schmitz and P. Wasserscheid, Chem. Commun., 2001, 2494.
35. (a) C. Ye, W. Liu, Y. Chen and L. Yu, Chem. Commun., 2001, 2244;
36. (b) W. Liu, C. Ye, H. Wang and L. Yu, Tribology, 2001, 21, 482.
37. G. Gamero-Castaño and V. Hruby, J. Propulsion Power, 2001, 5, 977.
38. B. Wu, R. G. Reddy and R. D. Rogers, Sol. Eng., 2001, 445.
39. M. R. Netherton and G. C. Fu, Org. Lett., 2001, 26, 4295.
40. D. E. Kaufmann, M. Nouroozian and H. Henze, Synlett, 1996, 1091.
41. J. McNulty, A. Capretta, J. Wilson, J. Dyck, G. Adjabeng and A. Robertson, Chem. Commun., 2002, 1986.
42. (a) A. E. Visser, R. P. Swatloski, W. M. Reichart, R. Mayton, S. Sheff, A. Wierzbicki, J. H. Davis and R. D. Rogers, Chem. Commun., 2001, 135;
43. (b) A. E. Visser, R. P. Swatloski, W. M. Reichart, R. Mayton, S. Sheff, A. Wierzbicki, J. H. Davis and R. D. Rogers, Environ. Sci. Technol., 2002, 36, 2523.
44. J. H. Davis, Jr., personal communication, November 27, 2001.
45. (a) A. W. Herriott and D. Picker, J. Am. Chem. Soc., 1975, 97, 2345;
46. (b) C. M. Starks and C. Liotta, Phase Transfer Catalysis, Academic Press, Inc., New York, 1978;
47. (c) M. O. Wolff, K. M. Alexander and G. Belder, Chim. Oggi, 2000, January/February, 29.
48. (a) W. A. Johnson, Ylids and Imines of Phosphorus, John Wiley and Sons, Inc., New York, USA, 1993;
49. (b) The Chemistry of Organophosphorus Compounds Vol. 3: Phosphonium Salts, Ylids and Phosphoranes, ed. F. R. Hartley, John Wiley and Sons, Inc., New York, USA, 1994.
50. For example, see: V. P. Balema, J. W. Wiench, M. Pruski and V. K. Pecharsky, Chem. Commun., 2002, 724.
51. S. A. Buckler and W. A. Henderson, J. Am. Chem. Soc., 1960, 82, 5791.
52. W. A. Henderson and C. J. Schultz, J. Am. Chem. Soc., 1960, 82, 5759.
53. We note that phosphine gas is highly toxic and pyrophoric, necessitating dedicated equipment and special handling techniques. The same is true, to a lesser extent, of many tertiary phosphines. Reactions involving these reagents should only be attempted by appropriately trained personnel.
54. M. M. Rahut, H. A. Currier, A. M. Semsel and V. P. Wystrach, J. Org. Chem., 1961, 26, 5138.
55. See http://www.dupont.com/vazo/.
56. A. J. Robertson, WO 01/87900, 2001 (Cytec Industries).
57. A. Downard and K. R. Seddon, unpublished results.
58. K. R. Seddon and A. J. Robertson, patent pending.
59. (a) P. C. Mørk and D. Norgård, 8th Scandinavian Symposium on Lipids, Helsinki, Proceedings, 1975, 339;
60. (b) P. C. Mørk and D. Norgård, J. Am. Oil Chem. Soc., 1976, 53, 506;
61. (c) A. Menzel, K. Swamy, R. Beer, P. Hanesch, E. Bertel and U. Birkenheuer, Surf. Sci., 2000, 454, 88.
62. M. O. Wolff, K. M. Alexander and G. Belder, Chim. Oggi, 2000, 29.
63. (a) C. K. Ingold and O. Schumacher, J. Chem. Soc., 1928, 3125;
64. (b) W. Hanhart and C. K. Ingold, J. Chem. Soc., 1927, 999;
65. (c) J. March, Advanced Organic Chemistry, John Wiley and Sons, Inc., New York, USA, 4th edn., 1992.
66. M. Zanger, C. A. VanderWerf and W. E. McEwen, J. Am. Chem. Soc., 1959, 81, 3806.
67. J. B. Campbell, US Pat., 3,639,493, 1972 (DuPont).
68. We note that dynamic thermal stabilities normally reported for ionic liquids are typically much higher than static thermal stabilities. Thus, most ionic liquids are not stable for extended periods of time at, or even well below, the 'onset of decomposition' temperature typically measured by TGA. We are currently in the process of investigating static stabilities of several phosphonium ionic liquids, and will report the results on these investigations in due course.
69. -1; temp, control: Peltier plate (±1°C).
70. (a) K. R. Seddon, A. Stark and M. J. Torres, Pure Appl. Chem., 2000, 72, 2275;
71. (b) K. R. Seddon, A. Stark and M. J. Torres, in Clean Solvents: Alternative Media for Chemical Reactions and Processing, ACS Symp. Ser. 819, ed. M. Abraham and L. Moens, American Chemical Society, Washington, DC, 2002, vol. 819.
72. -1). Each vial was immediately tightly capped then shaken for 1 h using a moderate speed wrist-shaker. A spatula was used to give a final gentle mixing before making the viscosity measurements. Samples containing other solvents were prepared similarly.
73. A. G. Avent, P. A. Chaloner, M. P. Day, K. R. Seddon and T. Welton, J. Chem. Soc., Dalton Trans., 1994, 3405.
74. (a) D. Jerchel, Chem. Ber., 1943, 76B, 600;
75. (b) D. Jerchel and J. Kimmig, Chem. Ber., 1950, 83, 277;
76. (c) K. P. Davis and R. E. Talbot, US Pat., 4,673,509 (Albright and Wilson, Ltd.);
77. (d) R. E. Talbot, Eur. Pat., EP 275207A2 (Albright and Wilson, Ltd.)
78. (e) Tolcide PS 72A Product Brochure, Albright and Wilson Biocides, Oldbury, Worley, West Midlands, UK;
79. (f) W. Wehner and R. Grade, Eur. Pat., EU0549006, 1993 (FMC Corp. (UK) Ltd.).
80. (a) W. A. Rickelton and D. Nucciarone, The Treatment of Cobalt/ Nickel Solutions Using CYANEX Extractants, in Proceedings of the Nickel-Cobalt 97 International Symposium - Hydrometallurgy and Refining of Nickel and Cobalt, ed. W.C. Cooper and I. Mihaylov, Canadian Institute of Mining, Metallurgy and Petroleum, Montreal, 1997, pp. 275-292;
81. (b) P. R. Danesi, L. Reichley-Yinger, G. Mason, L. Kaplan, E. P. Horwitz and H. Diamond, Solvent Extr. Ion Exch., 1985, 4, 435.
82. (a) W. A. Rickelton and A. J. Robertson, US Pat., 4,353,883, 1982 (Cytec Technology Corp.);
83. (b) A. J. Roberston, US Pat., 4,374,780, 1983 (Cytec Technology Corp.);
84. (c) W. A. Rickelton, D. S. Flett and D. W. West, Solv. Extr. Ion. Exch., 1984, 2, 815.
85. A. J. Carmichael, M. J. Earle, J. D. Holbrey, P. B. McCormac and K. R. Seddon, Org. Lett., 1999, 1, 997.
86. For proprietary reasons, quantities of reagents in this section have been scaled.
87. Sodium tetrafluoroborate can be extremely toxic and corrosive (due to liberated HF) in the presence of moisture. It should be handled with extreme care, and special safety considerations should be reviewed before its use. In particular, it is recommended that calcium gluconate gel be kept on hand when working with this reagent.
88. H. Bayer, W. Fischer, W. Hekele and E. Wipfelder, US Pat., 6,160,077, 2000 (A. G. Siemens).
89. M. Yokoyama, J. Takano, M. Hasegawa and Y. Tatsukawa, US Pat., 5,578,694, 1996 (Mitsubishi).
90. S. Mori, K. Ida and M. Ue, US Pat., 4,892,944, 1990 (Mitsubishi).
91. Chem. Eng. News, 2002 (April 22), 32.
92. I. Hechenbleikner and K. R. Molt, US Pat., 3,652,735, 1972 (Carlisle Chemical Works, Inc.).
93. Searches for this information can be conducted using free resources available on the Internet. For example, see: (a) http://ep.espacenet.com/; (b) http://www.uspto.gov/. Reflecting the use of these methods, the survey presented here is intended to be informal and representative rather than exhaustive.
94. Searches for this information can be conducted using free resources available on the Internet. For example, see: (a) http://ep.espacenet.com/; (b) http://www.uspto.gov/. Reflecting the use of these methods, the survey presented here is intended to be informal and representative rather than exhaustive.
95. K. R. Seddon, A. J. Carmichael and M. J. Earle, World Pat., WO 01/40146A1, 2000.
96. J. A. King, Jr., US Pat., 5,705,696, 1998 (General Electric Company).
97. T. Kitazume, US Pat., 2,001,0031,875A1 2001 (Crowell & Moring LLP Intellectual Property Group).
98. W. Keim, A. Boesmann and P. Wasserscheid, World Pat., WO 01/55060, DE10003708, 2001 (Solvent Innovation GmbH).
99. W. Keim, W. Korth and P. Wasserscheid, World Pat., WO 00/16902, 2000 (BP Chemicals Ltd., Akzo Nobel NV, Elementis UK Ltd.).
100. B. Ellis, World Pat., WO 96/18459, 1996 (BP Chemicals Ltd.).
101. A. A. K. Abdul-Sada, K. R. Seddon and N. J. Stewart, World Pat., WO 95/21872, 1995 (BP Chemicals Ltd.).
102. H. Bahrmann and M. Schulte, US Pat., 6,103,908, 2000 (Celanese GmbH).
103. H. Bohnen and H. Bahrmann, World Pat.,, WO 00/66597, DE19919494, 2000 (Celanese GmbH).
104. (a) W. R. Pitner, D. W. Rooney and K. R. Seddon, World Pat., WO 99/41752, 1999 (British Nuclear Fuels Plc)
105. (b) C. G. Mackintosh, M. Fields, G. V. Hutson and K. R. Seddon, TW420809, 2001 (British Nuclear Fuels Plc)
106. (c) R. C. Thied, A. J. Jeapes, W. R. Pitner, D. W. Rooney, T. Welton, J. E. Hatter and K. R. Seddon, World Pat., WO 01/15175, 2001 (British Nuclear Fuels Plc)
107. (d) W. R. Pitner, D. Hebditch, J. Hatter D. W. Rooney, K. R. Seddon and R. C. Thied, World Pat., WO 01/13379, 2001 (British Nuclear Fuels Plc)
108. (e) C. G. McIntosh, M. Fields, G. V. Hutson and K. R. Seddon, World Pat., WO 98/06106, 1988 (British Nuclear Fuels Plc).
109. W. M. Schwarz, US Pat., 6,048,388, 2000 (Xerox).
110. B. J. Palmer, D. Fu, R. J. Card and M. J. Miller, World Pat., WO 01/77486A1, 2001 (Schlumberger).
111. Y. Chauvin, D. Commereuc, I. Guibard, A. Hirschauer, H. Olivier and L. Saussine, US Pat., 5,104,840, 1992 (Institut Français du Petrole).
112. B. Ellis, F. Hubert and P. Wasserscheid, World Pat., WO 00/41809, 2000 (BP Chemicals Ltd.).