Electrochemical Syntheses Involving Carbon Dioxide

  • Giuseppe Silvestri
  • Salvatore Gambino
  • Giuseppe Filardo
Part of the NATO ASI Series book series (ASIC, volume 314)

Abstract

The recent developments of electrosynthetic processes involving carbon dioxide are reviewed. Both processes involving carbon dioxide alone and electrocarboxylations are taken under consideration. The first of these two fields, mainly projected towards the production of basic chemicals such as methanol or carbon monoxide, is at present at a stage of fundamental research. Some interesting developments have recently appeared in the literature, concerning the use of electrode materials, or of transition metal complexes with particular catalytic activity. Electrocarboxylations are at a stage of more applicative development: some processes have reached the stage of pilot plant, and other have interesting, perspectives of application. A considerable effort has been devoted to the development of processes in undivided cells, with anodic reactions involving the oxidation of oxalates or formates, or the dissolution of sacrificial anodes. Specially designed electrochemical reactors have also been developed. The proper application field for electrocarboxylation processes appears to be the production of fine chemicals.

Keywords

Carbon Dioxide Cathodic Material Cathodic Potential Cathodic Current Density Sacrificial Anode 
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.

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References

  1. 1.
    Royer, M. E.; C. R. Hebd. Seances Acad. Sci. Fr.; 1870, 731, 70.Google Scholar
  2. 2.
    Haynes, L. V.; Sawyer, D. T.; Anal. Chem.; 1967, 332, 39.Google Scholar
  3. 3.
    Tyssee, D. A.; Wagenknecht, J. H.; Baizer, M. M.; Chruma, J. L.; Tetrahedron Lett.; 1972, 4809.Google Scholar
  4. 4.
    Vassiliev, Yu. B.; Bagotskii, V. S.; Osetrova, N. V.; Khazova, O. A.; Mayorova, N. A.; J. Electroanal. Chem. Interfacial Electrochem.; 1985, 271, 189 Google Scholar
  5. 5.
    Vassiliev, Yu. B.; Bagotskii, V. S.; Osetrova, N. V.; Mikhailova, A. A.; J. Electroanal. Chem. Interfacial Electrochem.; 1985, 311, 189.Google Scholar
  6. 6.
    Udupa, K. S.; Subramanian, G. S.; Udupa, H. V. K.; Electrochimica Acta; 1971, 1593, 16.Google Scholar
  7. 7.
    Ito, K.; Ikeda, S.; Okabe, M.; Denki Kagaku; 1980, 247, 48.Google Scholar
  8. 8.
    Ikeda, S.; Takagi, T.; Ito, K.; Bull. Chem. Soc. Jpn.; 1987, 2517, 60.Google Scholar
  9. 9.
    Hori, Y.; Suzuki, S.; Bull. Chem. Soc. Jpn.; 1982, 660, 55.Google Scholar
  10. 10.
    Mahmood, M. N.; Masheder, D.; Harty, C. J.; J. Appl. Electrochem.; 1987, 1159–70, 17.CrossRefGoogle Scholar
  11. 11.
    Furuya, N.; Matsui, K.; Motoo, S.; Denki Kagaku oyobi Kogyo Butsuri Kagaku; 1987, 787–8, 55.Google Scholar
  12. 12.
    Eggins, B. R.; Brown, E. M.; McNeill, E. A.; Grimshaw, J.; Tetrahedron Lett.; 1988, 945, 29.Google Scholar
  13. 13.
    Frese, K. W., Jr.; Leach, S. C.; Summers, D. P.; U.S. Pat. No.: 4609440 (1986). C.A. 105:199208Google Scholar
  14. 14.
    Summers, D. P.; Leach, S.; Frese, K. W., Jr.; J. Electroanal. Chem. Interfacial Electrochem.; 1986, 219–32, 205.CrossRefGoogle Scholar
  15. 15.
    Frese, K. W., Jr.; Leach, S.; J. Electrochem. Soc.; 1985, 259–60, 132 CrossRefGoogle Scholar
  16. 16.
    Frese, K. W., Jr.; Leach, S. C.; Summers, D. P.; U.S. Pat. No.: 4609441 (1986). C.A. 105:199209.Google Scholar
  17. 17.
    Hori, Y.; Kikuchi, K.; Suzuki, S.; Chem. Lett.; 1985, 1695.Google Scholar
  18. 18.
    Hori, Y.; Kikuchi, K.; Murata, A.; Suzuki, S.; Chem. Lett.; 1986, 897Google Scholar
  19. 19.
    Hori, Y.; Suzuki, S.; Kenkyu Hokoku - Asahi Garasu Kogyo Gijutsu Shoreikai; 1986, 213, 48.Google Scholar
  20. 20.
    Cook, R. L.; MacDuff, R. C.; Sammells, A. F.; J. Electrochem. Soc.; 1987, 1873, 134.Google Scholar
  21. 21.
    Cook, R. L.; MacDuff, R. C.; Sammells, A. F.; J. Electrochem. Soc.; 1987, 2375, 134.Google Scholar
  22. 22.
    Cook, R. L.; MacDuff, R. C.; Sammells, A. F.; J. Electrochem. Soc.; 1988, 1320–6, 135.CrossRefGoogle Scholar
  23. 23.
    Kim, J. J.; Summers, D. P.; Frese, K. W., Jr.; J. Electroanal. Chem. Interfacial Electrochem.; 1988, 223, 245.Google Scholar
  24. 24.
    Hori, Y.; Murata, A.; Kikuchi, K.; Suzuki, S.; J. Chem. Soc., Chem. Commun.; 1987, 728.Google Scholar
  25. 25.
    Alonso, C.; Gonzalez Velasco, J.; Arvia, A. J.; J. Electroanal. Chem. Interfacial Electrochem.; 1988, 183, 250.Google Scholar
  26. 26.
    Osetrova, N. V.; Vasiliev, Yu. B.; Bagotskii, V. S.; Sadkova, R.G.; Cherashev, A. F.; Khrushch, A. P.; Elektrokhimiya; 1984, 286, 20.Google Scholar
  27. 27.
    Lamy, E.; Nadjo, L., Saveant, J. M.; J. Electroanal. Chem. Interfacial Electrochem.; 1977, 403–07, 78.CrossRefGoogle Scholar
  28. 28.
    Vianello, E. et al, Communication at the VIIth Heyrowsky Discussion, Liblice (Prague), 1989.Google Scholar
  29. 29.
    Amatore, C.; Saveant, J. M.; J. Am. Chem. Soc.; 1981, 5021–23, 103.CrossRefGoogle Scholar
  30. 30.
    Vassiliev, Yu. B.; Bagotskii, V. S.; Khazova, O. A.; Mayorova, N. A.; J. Electroanal. Chem. Interfacial Electrochem.; 1985, 295, 189 Google Scholar
  31. 31.
    Ito, K.; Ikeda, S.; Iida, T.; Nomura, A.; Denki Kagaku; 1982, 463, 50.Google Scholar
  32. 32.
    Fisher, J.; Lehman, Th.; Heitz, E.; J. Appl. Electrochem.; 1981, 743–50, 11.CrossRefGoogle Scholar
  33. 33.a)
    Lamy, E.; Nadjo, L.; Saveant, J. M.; Nouv. J. Chim.; 1979, 21, 3 Google Scholar
  34. b).
    Kaiser, U; Heitz, E.;Ber. Bunsenges. Phys. Chem.; 1973, 818–23, 77.Google Scholar
  35. 34.
    Meshitsuka, S.; Ichikawa, M.; Tamaru, K.; J. Chem. Soc. Chem. Comm.; 1974, 158.Google Scholar
  36. 35.
    Hiratsuka, S.; Takahashi, H.; Sasaki, H.; Toshima, S; Chem. Lett.; 1917, 1137.Google Scholar
  37. 36.
    Kapusta, S.; Hackerman, N.; J. Electrochem. Soc.; 1984, 1511, 131.Google Scholar
  38. 37.
    Lieber, C. M.; Lewis, N. S.; J. Am. Chem. Soc.; 1984, 5033, 106 Google Scholar
  39. 38.
    Tanabe, H.; Ohno, K.; Electrochim. Acta; 1987, 1121, 32.Google Scholar
  40. 39.
    Masheder, D.; Williams, K. P. J.; J. Raman Spectrosc.; 1987, 391, 18 Google Scholar
  41. 40.
    Christensen, P. A.; Hamnett, A.; Muir, A. V. G.; J. Electroanal. Chem. Interfacial Electrochem.; 1988, 361, 241.Google Scholar
  42. 41.
    Mahmood, M. N.; Masheder, D.; Harty, C. J.; J. Appl. Electro chem.; 1987, 1223–7, 17.CrossRefGoogle Scholar
  43. 42.
    Cao, X.; Huang, C.; Wang, M.; Gaodeng Xuexiao Huaxue Xuebao; 1983, 549, 4. C.A. 100:058659.Google Scholar
  44. 43.
    Cao, X.; Mu, Y.; Wang, M.; Luan, L.; Huaxue Xuebao; 1986, 220 44. C.A. 104:195348.Google Scholar
  45. 44.
    Cao, X.; Mu, Y.; Wang, M.; Huang, C.; Gaodeng Xuexiao Huaxue Xuebao; 1986, 302, 7. C.A. 106:074777.Google Scholar
  46. 45.
    Cao, X.; Zheng, G.; Gaodeng Xuexiao Huaxue Xuebao; 1987, 686, 8. C.A. 108:194575Google Scholar
  47. 46.
    Cao, X.; Zheng, G.; Teng, Y.; Gaodeng Xuexiao Huaxue Xuebao; 1988, 861–3, 9. C.A. 110:30379Google Scholar
  48. 47.
    Hammouche, M.; Lexa, D.; Saveant, J. M.; Momenteau, M.; J. Electroanal. Chem. Interfacial Electrochem.; 1988, 347, 2494.Google Scholar
  49. 48.
    Becker, J. Y.; Vainas, B.; Eger, R.; Kaufman, L.; J. Chem. Soc., Chem. Commun.; 1985, 1471.Google Scholar
  50. 49.
    O’Connell, C.; Hommeltoft, S. I.; Eisenberg, R.; NATO ASI Ser., Ser. C; “Carbon Dioxide as a Source of Carbon: Biochem. Chem. Uses”, M. Aresta and G. Forti Eds., 1987, 33, 206.Google Scholar
  51. 50.
    Fisher, B.; Eisenberg, R.; J. Am. Chem. Soc.; 1980, 7361, 102.Google Scholar
  52. 51.
    Tinnemans, A. H. A.; Koster, T. P. M.; Thewissen, D. H. M. W.; Mackor, A.; Recl.: J. R. Neth. Chem. Soc.; 1984, 288, 103.Google Scholar
  53. 52.
    Pearce, D. J.; Pletcher, D.; J. Electroanal. Chem. Interfacial Electrochem.; 1986, 317, 197.Google Scholar
  54. 53.
    Bailey, C. L.; Bereman, R. D.; Rillema, D. P.; Nowak, R.; Inorg. Chim. Acta.; 1986, L45, 116.Google Scholar
  55. 54.
    Beley, M.; Collin, J. P.; Ruppert, R.; Sauvage, J. P.; J. Chem. Soc., Chem. Commun.; 1984, 1315.Google Scholar
  56. 55.
    Beley, M.; Collin, J.-P.; Ruppert, R.; Sauvage, J. P.; J. Am. Chem. Soc.; 1986, 7461, 108.Google Scholar
  57. 56.
    Collin, J.P.; Jouaiti, A.; Sauvage, J.P.; Inorg. Chem.; 1988, 1986–90, 27.CrossRefGoogle Scholar
  58. 57.
    Che, C. M.; Mak, S. T.; Lee, W. O.; Fung, K. W.; Mak, T. C. W.; J. Chem. Soc. Dalton Trans.; 1988, 2153.Google Scholar
  59. 58.
    Slater, S.; Wagenknecht, J. H.; J. Am. Chem. Soc.; 1984, 5367, 106.Google Scholar
  60. 59.
    DuBois, D. L.; Miedaner, A.; J. Am. Chem. Soc.; 1987, 113–17, 109.CrossRefGoogle Scholar
  61. 60.
    DuBois, D. L.; Miedaner, A.; ACS Symp. Ser.; 1988, 42, 363.Google Scholar
  62. 61.
    Gennaro, A.; Isse, A. A.; Vianello, E.; in “Recent Advances in Electroorganic Synthesis”, S. Torii Ed., Stud. Org. Chem. (Amsterdam); 1987, 321, 30.Google Scholar
  63. 62.
    Mitchell R. M.; O’Toole, T. R.; Bolinger, C. M.; Megehee, E.; Thorp, H.; Meyer, T. J.; ACS Symp. Ser.; 1988, 52, 363 Google Scholar
  64. 63.
    Ziessel, R.; NATO ASI Ser., Ser. C; “Carbon Dioxide as a Source of Carbon: Biochem. Chem. Uses”, M. Aresta and G. Forti Eds., 1987, 113, 206.Google Scholar
  65. 64.
    Cabrera, C. R.; Abruna, H. D.; J. Electroanal. Chem. Interfacial Electrochem.; 1986, 101, 209 Google Scholar
  66. 65.
    Meyer, T. J.; O’Toole, T. R.; Margerum, L. D.; Westmoreland, T. D.; Vining, W. J.; Murray, R. W.; Sullivan, B. P.; U.S. Pat. No.: 4711708; C.A. 109:013644.Google Scholar
  67. 66.
    Cosnier, S.; Deronzier, A.; Moutet, J. C.;J. Mol. Catal.; 1988, 381–91, 45 CrossRefGoogle Scholar
  68. 67.
    Cosnier, S.; Deronzier, A.; Moutet, J. C.; J. Electroanal. Chem. Interfacial Electrochem.; 1986, 315, 207.Google Scholar
  69. 68.
    Bolinger, C. M.; Sullivan, B. P.; Conrad, D.; Gilbert, J. A.; Story, N.; Meyer, T. J.; J. Chem. Soc., Chem. Commun.; 1985, 796.Google Scholar
  70. 69.
    Guadalupe, A. R.; Usifer, D. A.; Potts, K. T.; Hurrell, H. C.; Mogstad, A. E.; Abruna, H. D.; J. Am. Chem. Soc.; 1988, 3462, 110 Google Scholar
  71. 70.(a)
    Ogura, K.; Yoshida, I.; Electrochim. Acta; 1987, 1191–5, 32.CrossRefGoogle Scholar
  72. (b).
    Ogura, K.; J. Electrochem. Soc.; 1987, 2749, 134.Google Scholar
  73. 71.
    Ishida, H.; Tanaka, K.; Tanaka, T.; Chem. Lett.; 1985, 405.Google Scholar
  74. 72.
    Ishida, H.; Tanaka, K.; Tanaka, T.; Organometallics; 1987, 181, 6.Google Scholar
  75. 73.
    Ishida, H.; Tanaka, H.; Tanaka, K.; Tanaka, T.; J. Chem. Soc., Chem. Commun.; 1987, 131.Google Scholar
  76. 74.
    Ishida, H.; Tanaka, H.; Tanaka, K.; Tanaka, T.; Chem. Lett.; 1987, 597.Google Scholar
  77. 75.
    Tanaka, K.; Miyamoto, H.; Tanaka, T.; Chem. Lett.; 1988, 2033.Google Scholar
  78. 76.
    Silvestri, G.; NATO ASI Ser., Ser. C; “Carbon Dioxide as a Source of Carbon: Biochem. Chem. Uses”, M. Aresta and G. Forti Eds.,; 1987, 339, 206.Google Scholar
  79. 77.
    Gambino, S.; Gennaro, A.; Filardo, G.; Silvestri, G.; Vianello, E.; J. Electrochem. Soc.; 1987, 2172, 134.Google Scholar
  80. 78.
    Tkatchenko, I. B. M.; Ballivet-Tkatchenko, D. A.; El Murr, N.; Tanji, J.; Payne, J. D.; Fr. Pat. No.: 2542764; (1984). C.A. 102:069341Google Scholar
  81. 79.
    Pletcher, D.; Girault, J. Tietje; J. Appl. Electrochem.; 1986, 791–802, 16 CrossRefGoogle Scholar
  82. 80.
    Pletcher, D.; Girault, J. Tietje; Inst. Chem. Eng. Symp. Ser. Electrochem. Engineering; 1986, 13–21, 321–2, 98.Google Scholar
  83. 81.
    Wawzonek, S.; Wearring, D.; J. Am. Chem. Soc.; 1959, 2067 81.Google Scholar
  84. 82.
    Dunach, E.; Perichon, J.; J. Organomet. Chem.; 1988, 239–46, 352.CrossRefGoogle Scholar
  85. 83.
    Labbe, E.; Dunach, E.; Perichon, J.; J. Organomet. Chem.; 1988, C51–056, 353.CrossRefGoogle Scholar
  86. 84.
    Dunach, E.; Derien, S.; Perichon, J.; J. Organomet. Chem.; 1989, C33 - C36, 364.CrossRefGoogle Scholar
  87. 85.
    Daniele, S.; Ugo, P.; Bontempelli, G.; Fiorani, M.; J. Electroanal. Chem. Interfacial Elecrochem.; 1987, 259, 219.Google Scholar
  88. 86.
    Silvestri, G.; Gambino, S.; Filardo, G.; Tetrahedron Lett.; 1986, 3429–30, 27.CrossRefGoogle Scholar
  89. 87.a)
    Filardo, G.; Silvestri, G.; Gambino, S.; Eur. Pat. No.: 189120 (1986). C.A. 105:180522Google Scholar
  90. b).
    Maspero, F.; Piccolo, O.; Romano, U.; Gambino, S.; Eur. Pat. Appl. No.: 286944 (1988).Google Scholar
  91. 88.a)
    Wagenknecht, J. H.; U.S. Pat. No.: 4582577 (1986); C.A. 105:050861.Google Scholar
  92. b).
    Wagenknecht, J. H.; U. S. Pat. No.: 4601797 (1986); C.A. 106:024982.Google Scholar
  93. 89.
    Silvestri, G.; Gambino, S.; Filardo, G.; in“ Recent Advances in Electroorganic Synthesis”, S. Torii Ed. (Stud. Org. Chem.), Amsterdam; 1987, 287, 30.Google Scholar
  94. 90.
    Di Lorenzo, S.; Silvestri, G.; Filardo, G.; Gambino, S.;Chem. Eng. J.; 1989, 187, 40.Google Scholar
  95. 91.
    Bulhoes, L. O. de Sousa; Zara, A. J.; J. Electroanal. Chem. Interfacial Electrochem.; 1988, 159–65, 248.Google Scholar
  96. 92.
    Amatore, C.; Gareil, M.; Saveant, J. M.; J. Am. Chem. Soc.; 1988, 4120, 102.Google Scholar
  97. 93.
    Orliac Le Moing, A.; Delaunay, J.; Lebouc, A.; Simonet, J.; Tetrahedron; 1985, 4483, 41.Google Scholar
  98. 94.
    Hess, U.; Bluemcke, C. O.; Z. Chem.; 1988, 144, 28 Google Scholar
  99. 95.a)
    Komenda, J.; Hess, U.; Z. Phys. Chem. (Leipzig); 1984, 17, 265.Google Scholar
  100. b).
    Komenda, J.; Fiala, R.; Hess, U.; Z. Phys. Chem. (Leipzig); 1987, 48, 268.Google Scholar
  101. 96.
    Hess, U.; Granitza, D.; Thiele, R.; Z. Chem.; 1988, 188–9, 28.Google Scholar
  102. 97.
    Silvestri, G.; Gambino, S.; Filardo, G; Gazz. Chim. It.; 1988, 643, 118.Google Scholar
  103. 98.
    Baizer, M. M.; Chruma, J. L; J. Org. Chem.; 1972, 1951, 37.Google Scholar
  104. 99.
    Koch, D. A.; Henne, B. J.; Bartak, D. E.; J. Electrochem Soc.; 1987, 3062, 134.Google Scholar
  105. 100.
    Fauvarque, J. F.; Jutand, A.; Francois, M.; J. Appl. Electrochem.; 1988, 109–15, 18.CrossRefGoogle Scholar
  106. 101.
    Fauvarque, J. F.; Jutand, A.; Francois, M.; Petit, M. A.; J. Appl. Electrochem.; 1988, 116, 18 Google Scholar
  107. 102.a)
    Troupel,M.; Rollin, Y.; Sibille, S.; Fauvarque, J. F.; Perichon, J.; J. Chem. Res. Synop.; 1980, 26.Google Scholar
  108. b).
    Schiavon, G.; Bontempelli, G.; Corain, B.; J. Chem. Soc. Dalton Trans.; 1981, 1074Google Scholar
  109. 103.
    Amatore, C.; Jutand, A.; Organometallics; 1988, 2203, 7.Google Scholar
  110. 104.
    Amatore, C.; Jutand, A.; personal communication.Google Scholar
  111. 105.
    Heintz, M.; Sock, O.; Saboureau, C.; Perichon, J.; Troupel, M.; Tetrahedron; 1988, 1631, 44.Google Scholar
  112. 106.
    Maran, F.; Fabrizio, M.; D’Angeli, F.; Vianello, E.; Tetrahedron; 1988, 2351–8, 44.CrossRefGoogle Scholar
  113. 107.
    Casadei, M. A.; Moracci, F. M.; Inesi, A.; J. Chem. Soc., Perkin Trans. 2; 1986, 419.CrossRefGoogle Scholar
  114. 108.
    Ruettinger, H.H.; Rudorf, W. D.; Matschiner, H.; Electrochim. Acta; 1985, 155, 30.Google Scholar
  115. 109.
    Janietz, S.; Ruettinger, H. H.; Matschiner, H.; J. Prakt. Chem.; 1988, 147–53, 330.CrossRefGoogle Scholar
  116. 110.
    Ruettinger, H. H.; Matschiner, H.; Gollnow, W. D.; J. Prakt. Chem.; 1986, 539, 328.Google Scholar
  117. 111.
    Janietz, S.; Ruettinger, H. H.; Matschiner, H.; Z. Chem. 1987, 442, 27.Google Scholar
  118. 112.
    Schultz-von Itter, N.; Steckhan, E.; Tetrahedron; 1987, 2475, 43.Google Scholar
  119. 113.
    Cook, R. L.; Mc Duff, R. C.; Sammels, A. F.; J. Electrochem. Soc.; 1988, 1470, 135.Google Scholar
  120. 114.
    Brown, D. E.; Hall, S. M.; Mahmood, M. N.; Eur. Pat. No.: 81982; C.A. 99:060912.Google Scholar
  121. 115.
    Furuya, C.; Motoo, S.; Jpn.Pat. No.: 62280385; C.A. 108:228508.Google Scholar
  122. 116.
    Ang, P. G. P.; Sammells, A. F.; U.S. Pat. No.: 4673473; C.A. 107:105037.Google Scholar
  123. 117.
    Ang, P. G. P.; U.S. Pat. No.: 4620906; C.A. 106:035102.Google Scholar
  124. 118.
    Morduchowitz, A.; Ang, P. G. P.; U.S. Pat. No.: 4608133; C.A. 105:215761.Google Scholar
  125. 119.
    Sammells, A. F.; U.S. Pat. No.: 4608132; C.A. 105:160917.Google Scholar
  126. 120.
    Ang, P. G. P.; Sammells, A. F.; Morduchowitz, A.; U.S. Pat. No.: 4595465; C.A. 105:087537.Google Scholar
  127. 121.
    Chaussard, J.; Eur. Pat. No.: 219367.Google Scholar
  128. 122.
    Cohen, S.; Eur. Pat. No.: 13215.Google Scholar
  129. 123.
    Silvestri, G.; Filardo, G.; Gambino, S.; Eur. Pat. No.: 283796; (1988). C.A 110:065730.Google Scholar

Copyright information

© Kluwer Academic Publishers 1990

Authors and Affiliations

  • Giuseppe Silvestri
    • 1
  • Salvatore Gambino
    • 1
  • Giuseppe Filardo
    • 1
  1. 1.Dipartimento di Ingegneria Chimica dei Processi e dei MaterialiUniversità di PalermoPalermoItaly

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