Advertisement

Organic Sonoelectrochemistry

  • David J. Walton
  • Timothy J. Mason

Abstract

Electrosynthesis has a respected tradition in organic chemistry, and the Kolbe electrooxidation of aqueous acetate solutions is one of the oldest known organic reactions.1 Since then there have been reports at intervals until the development of high-dielectric organic solvents for routine use in the 1960s, which vastly increased the scope of systems that could be studied.2 Despite this, exploitation of organic electrosynthesis has lagged behind expectations,3 and it is an aim of workers in the field to redress this situation.

Keywords

Ultra Sound Silent System Butyl Xanthate Cleaning Bath Potentiostatic Control 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Kolbe, W. Ann.1849, 69, 257.Google Scholar
  2. 2.
    Organic Electrochemistry (Baizer, M. M.; Lund, H. Eds.), Marcel Dekker, New York, 3rd Ed., 1991. Google Scholar
  3. 3.
    See various industrial reports, for instance: (a) Atkinson, N. Process Engineering, Nov. 1988 p. 44; (b) Dotson, R.L. Interface 1994, 3, 95.Google Scholar
  4. 4.
    Moriguchi N. J. Chem. Soc. Jpn.1934, 55, 751–754.Google Scholar
  5. 5.
    Yeager, E.; Hovorka, F. J. Acoust. Soc. Am.1953, 25, 443–455.Google Scholar
  6. 6.
    Walker, R. in Advances in Sonochemistry (Mason, T.J. Ed.), JAI Press, London, 1993, Vol. 3, 125–144.Google Scholar
  7. 7.
    (a) Compton, R.G. Electrochimica Acta 1997, 42, 2919–2927; (b) Compton, R. G.; Marken, F.; Eklund, J. Electroanalysis 1997, 9, 509–522.Google Scholar
  8. 8.
    Walton, D.J.; Phull, S.S. in Advances in Sonochemistry (Mason, T.J. Ed.) JAI Press, London, 1996, Vol. 4, pp. 205–284.Google Scholar
  9. 9.
    9 (a) Southampton Electrochemistry Group Instrumental Methods in Electrochemistry Ellis Horwood, 1985; (b) Laboratory Techniques in Electroanalytical Chemistry (Kissinger, P.T.; Heineman, W.R. Eds.), Marcel Dekker, New York, 1984; (c) Bockris, J.O.M.; Reddy, A.K.M. Modern Electrochemistry Plenum, Rosetta, 1970, Vols. 1 and 2.Google Scholar
  10. 10.
    (a) Christensen, P.A.; Hamnett, A. Techniques and Mechanisms in Electrochemistry Blackie Academic and Professional, London, 1994 Google Scholar
  11. (b).
    Brett, C.M.A.; Oliviera Brett, A.M. Electrochemistry, Principles, Methods and Applications Oxford University Press, Oxford, 1993 Google Scholar
  12. (c).
    Compton, R.G.; Sanders, G.H.W. Electrode Potentials Oxford Chemistry Primers, 1996 Google Scholar
  13. (d).
    Fisher, A.C. Electrode Dynamics Oxford Chemistry Primers, 1996 Google Scholar
  14. (e).
    Pletcher, D. A First Course in Electrode Processes The Electrochemical Consultancy, New York, 1991.Google Scholar
  15. 11.
    For example, Modern Aspects of Electrochemistry, N°27 (Bockris, J.O.M.; Conway, B.E.; White, R.E. Series Eds.), Plenum, New York, 1995.Google Scholar
  16. 12.
    Fry, A.J. Synthetic Organic Electrochemistry Harper and Row, New York, 1972.Google Scholar
  17. 13.
    (a) Kyriacou, D. Modern Electroorganic Chemistry Springer-Verlag, 1994 Google Scholar
  18. (b).
    Shono, T. Electroorganic Synthesis in Best Synthetic Methods, Academic Press, 1991 Google Scholar
  19. (c).
    Torii, S. Electroorganic Syntheses, Part I, Electrooxidations, 1995; Part 2, Electroreductions, 1996 VCH, Dearfield Beach, Florida, USA; (d) Techniques of Electroorganic Synthesis (Weinberg, N.L. Ed.), Part 3, Wiley, 1982.Google Scholar
  20. 14.
    Walsh, F. A First Course in Electrochemical Engineering Electrochemical Consultancy, Romsey, 1993.Google Scholar
  21. 15.
    Pletcher, D.; Walsh F. Industrial Electrochemistry Chapman and Hall, 2 Edn., 1990.Google Scholar
  22. 16.
    Albery, W. J. Electrode Kinetics Clarendon Press, 1975.Google Scholar
  23. 17.
    Physical Electrochemistry, Principles, Methods and Applications (Rubenstein, I. Ed.), Marcel Dekker, New York, 1995.Google Scholar
  24. 18.
    (a) Mason, T.J.; Lorimer, J.P. Sonochemistry Ellis Horwood, Chichester, 1988 Google Scholar
  25. (b).
    Margulis, M.A.; Maltsev, A.N. Zh. Fiz. Khim.1969, 43, 1055–1059Google Scholar
  26. (c).
    Mason, T.J.; Lorimer, J.P.; Bates, D.M. Ultrasonics 1992, 30, 40–42.Google Scholar
  27. 19.
    Marken, F.; Compton, R.G. Ultrasonics Sonochemistry 1996, 3, S131–S134.Google Scholar
  28. 20.
    Compton, R.G.; Eklund, J.C.; Page, S.D.; Sanders, G. H.W.; Booth, J. J. Phys. Chem.1994, 98, 12410–12414.Google Scholar
  29. 21.
    Eklund, J.C.; Marken, F.; Waller, D.N.; Compton, R.G. Electrochemica Acta, 1996 42, 1541–1547.Google Scholar
  30. 22.
    Walton, D.J.; Phull, S.S.; Chyla, A.; Lorimer, J.P.; Mason, T.J.; Burke, L.D.; Murphy, M.; Compton, R.G.; Eklund, J.C.; Page, S.D. J. Appl. Electrochem.1995, 25, 1083–1090.Google Scholar
  31. 23.
    (a) Lorimer, J.P.; Pollet, B.; Phull, S.S.; Mason, T.J.; Walton, D.J.; Geissler, U. Electrochim Acta 1996, 41, 2737–2746Google Scholar
  32. (b).
    Klima, J.; Bernard, C.; Degrand, C. J. Electroanal. Chem.1994, 367, 297–300Google Scholar
  33. (c).
    Hagan, C.R.S.; Coury, L.A. Anal. Chem.1994, 66, 399–405Google Scholar
  34. (d).
    Jung, C.G.; Chapelle, F.; Fontana, A. ISE 47 th Meeting, Balatonfured, Hungary, 1996.Google Scholar
  35. 24.
    Compton, R.G.; Eklund, J.C.; Page, S. D.; Mason, T. J.; Walton, D.J. J. Appl. Electrochem.1996, 26, 775–784.Google Scholar
  36. 25.
    Compton, R.G.; Marken, F.; Rebbit T.O. J. Chem. Soc. Chem. Commun.1996, 1017–1018.Google Scholar
  37. 26.
    Compton, R. G.; Eklund, J.C.; Page, S.D.; Rebbit, T.O. J. Chem. Soc. Dalton Trans.1995, 389–393 1.Google Scholar
  38. 27.
    Compton, R. G.; Eklund, J. G; Page, S. D. J. Phys. Chem.1995, 99, 4211–4214.Google Scholar
  39. 28.
    Eklund, J. G; Waller, D. N.; Rebbit, T.O.; Marken, F.; Compton, R.G J. Chem. Soc. Perkin Trans. 2 1995, 1981–1984.Google Scholar
  40. 29.
    Lee, C.W.; Compton, R.G.; Eklund, J.G.; Waller, D.N. Ultrasonics Sonochemistry 1995, 2, S59–S62.Google Scholar
  41. 30.
    Marken, F.; Eklund, S.G.; Compton, R.G. J. Electroanal. Chem.1995, 395, 335–339.Google Scholar
  42. 31.
    Neppiras, A.E. Phys. Rep. Sect. Phys. Lett.1980, 61, 159–163.Google Scholar
  43. 32.
    Birkin, P. R.; Silva-Martinez, S. J. Chem. Soc. Chem. Commun.1995, 1807–1808.Google Scholar
  44. 33.
    Leighton, T.G. The Acoustic Bubble Academic Press, 1994.Google Scholar
  45. 34.
    Benahcene, A.; Labbe, P.; Pétrier, C.; Reverdy, G. New J. Chem.1995, 19, 989–995.Google Scholar
  46. 35.
    Walton, D.J.; Murphy, M.; Burke, L.D. Electrochimica Acta 1996, 41, 2747–2751.Google Scholar
  47. 36.
    Wilis, B.A. Mineral Processing Technology, 5th Ed., Pergamon, New York, 1992.Google Scholar
  48. 37.
    Zholshibekova, M.R.; Ischenko, V.V.; Baishulakov, A.A.; Malakhov, Y.A. Komplenskn Ispol’z Miner. Syr’ya 1983, 2, 7–9; Chem. Abstr. 1983, 99, 74461.Google Scholar
  49. 38.
    Chanturiya, V.A.; Zholshibekova, M.R.; Malakhov, Y.V. Elektron. Obrab. Mater.1983, 2, 76–77.Google Scholar
  50. 39.
    Chanturiya, V.A.; Dimitrieva, L.L.; Zholshibekova, M.R.; Malakhov, Y.V. Vestn. Akad. Nauk Kaz. SSR 1984, 9, 47–52; Chem. Abstr.1985, 102, 49131g.Google Scholar
  51. 40.
    Shautenov, M.R., Malakhov, Y.V. Kompleksn. Ispol’z Miner. Syr’ya.1988, 3, 24–26; Chem. Abstr.1988, 109, 25658c.Google Scholar
  52. 41.
    Chanturiya, V.A.; Dimitrieva, L.L. in Flotatsionnye Reagenty (Gol’man, A.M.; Dimitrieva, L.L. Eds.) Nauka, Moscow, 1986.Google Scholar
  53. 42.
    Tsonkov, T.; Paulapanski, M.; Djendova, S. Oxid. Commun.1994, 17, 321–325.Google Scholar
  54. 43.
    Connors, T.F.; Rusling, J.F. Chemosphere 1984, 13, 415–420.Google Scholar
  55. 44.
    Schweizer, S.; Rusling, J.F.; Huang, G. Chemosphere 1994, 28, 961–970.Google Scholar
  56. 45.
    Zhang, S.; Rusling, J.F. Environ. Sci. Technol.1993, 27, 1375–1380.Google Scholar
  57. 46 (a).
    Rusling, J.F. Acc. Chem. Res.1991, 24, 75–81Google Scholar
  58. (b).
    id. in Electroanalytical Chemistry (Bard, A.J. Ed.), Marcel Dekker, New York, 1994, Vol. 19, pp. 1–88; (c) id. in Modern Aspects of Electrochemistry (Conway, B.E.; Bockris, J.O.M. Eds.), Plenum Press, New York 1994, 26, pp. 49–104.Google Scholar
  59. 47.
    Franklin, T.C.; Darlington, J.; Solouki, T. J. Electrochem. Soc. 1991, 138, 747–750. Google Scholar
  60. 48.
    Franklin, C.; Darlington, J.; Adeniyl, W.K. J. Electrochem. Soc.1990, 137, 2124–2126.Google Scholar
  61. 49.
    Mizera, J. Waste Treatment and Disposal 1982, Pol 2.Google Scholar
  62. 50.
    Matschiner, H.; Wildner, K.; Thiele, W. German Patent DE 4430391 1994; Chem. Abstr.1996, 124, 21091z.Google Scholar
  63. 51.
    Gindre, M.; Josiane, E. French Patent 2724163 1994; Chem. Abstr.1996, 124, 32489j.Google Scholar
  64. 52.
    Eberson, L.; Utley, J.H.P. in Organic Electrochemistry (Baizer, M.M.; Lund, H. Eds.), Marcel Dekker, New York, 2 Ed., 1982.Google Scholar
  65. 53.
    Vassiliev, Y.B.; Grinberg, V.A. J. Electroanal. Chem. 1991, 308, 1–16, and papers cited.Google Scholar
  66. 54.
    Hawkes, G.E.; Utley, J.H.P.; Yates, G.B. J. Chem. Soc. Perkin Trans. 21976, 1709–1716.Google Scholar
  67. 55.
    Walton, D.J.; Chyla, A.; Lorimer, J.P.; Mason, T.J.; Smith, G. J. Chem. Soc. Chem. Commun.1989, 603–604 1.Google Scholar
  68. 56.
    Luche, J.L.; Cintas, P. in Active Metals: Preparation, Characterisation, Applications (Fürstner, A. Ed.), VCH, Weinheim, 1996, pp. 133–190.Google Scholar
  69. 57.
    Walton, D.J.; Chyla, A.; Lorimer, J.P.; Mason, T.J. Ultrasonics Conference 1989, 1241.Google Scholar
  70. 58.
    Walton, D.J.; Chyla, A.; Lorimer, J.P.; Mason, T.J. Synth. Commun.1990, 20, 1843–1852.Google Scholar
  71. 59.
    Coleman, J.P.; Lines, R.; Utley, J.H.P.; Weedon, B.C.L. J. Chem. Soc. Perkin Trans. 21974, 1064–1069.Google Scholar
  72. 60.
    Koehl, W.J. J. Org. Chem.1967, 32, 614–618.Google Scholar
  73. 61.
    Bonner, W.A.; Mango, F.D. J. Org. Chem.1964, 29, 430–435.Google Scholar
  74. 62.
    Tashino, M.; Tsuzuki, W.; Goto, H.; Ogashasa, S.; Mataka, S. J. Labelled Comp.; Radiopharmaceuticals 1991, 29, 475–484.Google Scholar
  75. 63.
    Tashiro, M.; Tsuzuki, H.; Goto, H.; Makata, S. Chemistry Express 1991, 6, 403–406.Google Scholar
  76. 64.
    Walton, D.J.; Phull, S.S.; Mason, T.J.; Lorimer, J.P.; Geissler, D. J. to be published. Google Scholar
  77. 65.
    Walton, D. J.; Geissler, U.; Durham, A. Proc. World Congress on Ultrasonics, Berlin, 1995 p 659.Google Scholar
  78. 66.
    Gigi, S.; Paucescu, V.; Jurth, S. Romanian Patent 1980 RO 72382; Chem. Abstr.1982, 96, 151408x.Google Scholar
  79. 67.
    Ono, Y.; Mishiki, Y.; Nonaka, T. Chem. Lett.1994, 1623–1626 1.Google Scholar
  80. 68.
    Cheng, P.C.; Nonaka, T.; Chou, T.C. Bull Chem. Soc. Jpn.1991, 64, 1911–1915.Google Scholar
  81. 69.
    Atobe, M.; Matsuda, K.; Nonaka, T. Electroanalysis 1996, 8, 784–788.Google Scholar
  82. 70.
    Sunashima, K. T.; Nonaka, T. Chem. Lett.1995, 862 1.Google Scholar
  83. 71.
    Durrant, A.; François, W.; Reisse, J.; Kirsch-De Mesmaeker, A. Electrochimica Acta 1996, 41, 277–284.Google Scholar
  84. 72.
    Atobe, M.; Nonaka, T. Chem. Lett.1995, 669–670 4.Google Scholar
  85. 73.
    Atobe, M.; Matsuda, K.; Nonaka, T. Denki Kagaku Oyobi Kogyo Butsuri Kagaku 1994, 62, 1298–1299; Chem. Abstr. 1995, 122, 117297f.Google Scholar
  86. 74.
    Fry, A.J.; Touster, J.; Sirisoma, N.U.; Raimundo, B. Electroorganic Synthesis M.M. Baizer Memorial Symposium (Little, D.R.; Weinberg, N.L. Eds.), Marcel Dekker, New York, 1991 pp. 99–104.Google Scholar
  87. 75.
    Touster, J. PhD Thesis, Wesleyan University, 1991.Google Scholar
  88. 76.
    Fry, A.J.; Bujanauskas, P. J. Org. Chem.1978, 43, 3157–3163.Google Scholar
  89. 77.
    Fry, A.J.; O’Dea, J. J. Org. Chem.1975, 40, 3625–3631.Google Scholar
  90. 78.
    Fry, A.J.; Herr, D. Tetrahedron Lett 1978, 20, 1721–1724.Google Scholar
  91. 79.
    Fry, A.J.; Lefor, A.T. J. Org. Chem.1979, 44, 1270–1273.Google Scholar
  92. 80.
    Gautheron, B.; Tainturier, G.; Degrand, C. J. Am. Chem. Soc.1985, 107, 5579–5581.Google Scholar
  93. 81.
    Gautheron, B.; Tainturier, G.; Degrand, C. Organometallics 1986, 5, 942–944.Google Scholar
  94. 82.
    Degrand, C. J. Chem. Soc. Chem. Commun.1986, 1113–1115 1.Google Scholar
  95. 83.
    Degrand, C.; Prest, R.; Compagnon, P.L. J. Org. Chem.1987, 52, 5229–5233.Google Scholar
  96. 84.
    Degrand, C.; Prest, R.; Nour, M. Phosphorus Sulfur 1987, 38, 201–209.Google Scholar
  97. 85.
    Shono, T.; Kashimura, S.; Ishifune, M.; Nishida, R. J. Chem. Soc. Chem. Commun.1990, 1160–1161.Google Scholar
  98. 86.
    Hengge, E.; Firgo, H. J. Organomet. Chem.1981, 212, 155–161.Google Scholar
  99. 87.
    Hengge, E.; Latscher, G. Monatsh. Chem.1978, 109, 1217–1225.Google Scholar
  100. 88.
    Shono, T.; Kashiwamura, S.; Nishida, P. Jpn. Kokai Tokkyo Koho JP326 4683 1991; Chem. Abstr. 1992, 116, 161234h.Google Scholar
  101. 89.
    Shono, T.; Kashiwamura, S.; Nishida, P.; Murase, H. Jpn. Kokai Tokkyo Koho JP 05306483 1993; Chem. Abstr. 1994, 120, 17 6388t.Google Scholar
  102. 90.
    Shono, T.; Kashiwamura, S.; Nishida, P.; Kawasaki, S. Eur. Pat. App. EP446578 1991; Chem. Abstr.1992, 116, 21 727w.Google Scholar
  103. 91.
    Shono, T.; Kashiwamura, S.; Nishida, P.; Murase, H. Jpn. Kokai Tokkyo Koho JP 05306340 1993; Chem. Abstr. 1994, 120, 299615x.Google Scholar
  104. 92.
    Shono, T.; Kashiwamura, S.; Nishida, P.; Murase, H. Jpn. Kokai Tokkyo Koho JP 05306342 1993; Chem. Abstr. 1994, 120, 194194f.Google Scholar
  105. 93.
    Shono, T.; Kashiwamura, S.; Nishida, P.; Kawasaki, S. Jpn. Kokai Tokkyo Koho JP 05230317/8 1993; PCT Int. Appl. W09306152 1993; Chem. Abstr.1994, 120, 56009y.Google Scholar
  106. 94.
    Akbulut, U.; Toppare, L.; Yurttas, B. Polymer 1986, 27, 803–806.Google Scholar
  107. 95.
    Akbulut, U.; Fernandez, J.E.; Birke, R.L. J. Polym. Sci. Chem.1975, 13, 133–149.Google Scholar
  108. 96.
    Akbulut, U.; Toppare, L.; Yurttas, B. Brit. Polym. J.1986, 18, 273–276.Google Scholar
  109. 97.
    Eren, S.; Toppare, L.; Akbulut, U. Polymer Commun.1987, 28, 36–38.Google Scholar
  110. 98.
    Akbulut, U.; Eren, S.; Toppare, L.K. J. Macromol. Sci. Chem.1984, A21, 335–342.Google Scholar
  111. 99.
    Aybar, S.P.; Hacioglu, B.; Akbulut, U. J. Poly. Sci. Part A, Polym. Chem.1991, 29, 1971–1976.Google Scholar
  112. 100.
    The Handbook of Conducting Polymers (Skotheim, T.A. Ed.), Marcel Dekker, New York 1986, Vols. 1 and 2. Google Scholar
  113. 101.
    Walton, D.J. in Electronic Materials, from Silicon to Organics (Miller, L. S.; Mullin, J. B. Eds.), Plenum Press, 1991.Google Scholar
  114. 102.
    Walton, D.J.; Hall, C.E.; Chyla, A. The Analyst 1992, 117, 1305–1311.Google Scholar
  115. 103.
    Osawa, S.; Ito, M.; Tanaka, K.; Kuwano, J. Synthetic Metals 1987, 18, 145–150.Google Scholar
  116. 104.
    Osawa, S.; Ito, M; Tanaka, K.; Kuwano, J. J. Polym. Sci. Part B, Polym. Physics 1992, 30, 19–24.Google Scholar
  117. 105.
    Walton, D. J.; Geissler, U.; Ryley, S.; Campbell, C.; Evans, J. ISE 47 th Meeting, Balatonfured, Hungary, 1996.Google Scholar
  118. 106.
    Faulkner, L.R.; Bard, A.J. in Creation and Detection of the Excited State (Ware, W.R. Ed.) Marcel Dekker, New York, 1976.Google Scholar
  119. 107.
    Phull, S.S. Ph.D Thesis University of Warwick, UK, 1990 and references therein.Google Scholar
  120. 108.
    Walton, D.J.; Phull, S.S.; Lorimer, J.P.; Mason, T.J. Ultrasonics 1992, 30, 186–191.Google Scholar
  121. 109.
    Walton, D.J.; Phull, S.S.; Bates, D.M.; Lorimer, J.P.; Mason, T.J. Electrochimica Acta 1993, 38, 307–310.Google Scholar
  122. 110.
    Burgess, A.E.; Feigneux, M.; Hapher, M.J. 4 th Meeting, European Society of Sonochemistry Blankenberge, Belgium 1994.Google Scholar
  123. 111.
    Zhivnov, V.A.; Rumyantsev, I.Y.; Tomin, V.I.; Dezhkunov, N.V.; Prokhorenko, P.P. Vesti Akad. Navuk SSR Ser. Fiz.-Tekh. Navuk 1976, 3, 86–88; Chem. Abstr.1977, 86, 10234u.Google Scholar
  124. 112.
    Zhivnov, V.A.; Rumyantsev, I.Y.; Tomin, V.I. Spectrosc. Lett.1977, 10, 763–770; Chem. Abstr.1978, 88, 43149q.Google Scholar
  125. 113.
    Walton, D.J.; Phull, S.S.; Colton, C.; Richards, P.; Chyla, A.; Javed, T.; Clarke, L.; Lorimer, J.P.; Mason, T.J. Ultrasonics Sonochemistry 1994, 1, S23-S26.Google Scholar
  126. 114.
    Dincturk, S.; Jackson, R. J. Chem. Soc. Perkin Trans. 2 1981, 1127–1131.Google Scholar
  127. 115.
    Fisher, T.H.; Dersheim, S.M.; Crewitt, M.I. J. Org. Chem. 1990, 55, 1040 4043.Google Scholar

Copyright information

© Springer Science+Business Media New York 1998

Authors and Affiliations

  • David J. Walton
  • Timothy J. Mason

There are no affiliations available

Personalised recommendations