Advertisement

Green Electroorganic Synthesis Using BDD Electrodes

  • Ulrich Griesbach
  • Itamar M. Malkowsky
  • Siegfried R. Waldvogel
Chapter

Abstract

A survey of recent results of preparative organic electrochemistry using boron-doped diamond electrodes is given. The focus is on the non-destructive conversion of organic substrates including anodic and cathodic transformations on this novel electrode material.

Keywords

Current Efficiency Spin Centre Sacrificial Anode Electrochemical Conversion Reductive Carboxylation 
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.

References

  1. Bartsch, M., Baumann, R., Haderlein, G., Flores M.A., Jungkamp, T., Luyken, H., Scheidel, J. and Siegel, W. (2005) Method for the production of adipodinitrile by hydrocyanation of 1,3-butadiene. PCT patent WO20055073167 A1. BASF Aktiengesellschaft, Germany.Google Scholar
  2. Bäumer, U.-St. and Schäfer, H.-J. (2005) Cleavage of alkenes by anodic oxidation. J. Appl. Electrochem. 35, 1283–1292.Google Scholar
  3. Bosma, C, Gouws, S., Loyson, P. and Zeelie, B. (1999) Anodic oxidation of 4-tert-butyltoluene to 4-tert-butylbenzaldehyde dimethyl acetal: optimisation and scale-up. S. Afr. J. Chem. 52, 133–144.Google Scholar
  4. Boye, B., Michaud, P.A., Marselli, B., Dieng, M.M., Brillas, E. and Comninellis, Ch. (2002) Anodic oxidation of 4-chlorophenoxyacetic acid on synthetic boron-doped diamond electrodes. New Diam. Front. Carbon Technol. 12, 63–72.Google Scholar
  5. Boye, B., Brillas, E., Michaud, P.A., Comninellis, Ch., Farnia, G. and Sandonà, G. (2006) Electrochemical incineration of chloromethylphenoxy herbicides in acid medium by anodic oxidation with boron-doped diamond electrode. Electrochim. Acta. 51, 2872–2880.CrossRefGoogle Scholar
  6. Bringmann, G., Günther, C., Ochse, M., Schupp, M. and Tasler, S. (2001) Biaryls in nature: A multi-facetted class of stereochemically, biosynthetically, and pharmacologically intriguing secondary metabolites. In: Herz, W., Falk, H., Kirby, G.W. and Moore, R.E. (Eds.) Progress in the chemistry of organic natural products, vol. 82, Springer, New York, NY.Google Scholar
  7. DeClements, R. and Swain, G.M. (1997) The formation and electrochemical activity of microporous diamond thin film electrodes in concentrated KOH. J. Electrochem. Soc. 144, 856–866.CrossRefGoogle Scholar
  8. Degner, D., Nohe H. and Hannebaum, H. (1978) Verfahren zur elektrolytischen Herstellung von 2,5-Dialkoxy-2,5-dihydrofuranen. German patent DE 2710420 B1. BASF Aktiengesellschaft, Germany.Google Scholar
  9. Duo, I., Levy-Clement, C., Fujishima, A. and Comninellis, Ch. (2004) Electron transfer kinetics on boron-doped diamond Part 1: Influence of anodic treatment. J. Appl. Electrochem. 34, 935–943.CrossRefGoogle Scholar
  10. Fardel, R., Griesbach, U., Pütter, H. and Comninellis, Ch. (2006) Electrosynthesis of trimethylorthoformate on BDD electrodes. J. Appl. Electrochem. 36, 249–253.CrossRefGoogle Scholar
  11. Griesbach, U., Zollinger, D., Pütter, H. and Comninellis, Ch. (2005) Evaluation of boron doped diamond electrodes for organic electrosynthesis on a preparative scale. J. Appl. Electrochem. 35, 1265–1270.CrossRefGoogle Scholar
  12. Haenni, W., Perret, A. and Richen, P. (2002) Large-sized electrode. PCT patent WO 2002061181.Google Scholar
  13. Iniesta, J., Michaud, P.A., Panizza, M. and Commninellis, Ch. (2001a) Electrochemical oxidation of 3-methylpyridine at a boron-doped diamond electrode: applications to electroorganic synthesis and waste water treatment. Electrochem. Commun. 3, 346–351.CrossRefGoogle Scholar
  14. Iniesta, J., Michaud, P.A., Panizza, M., Cerisola, G., Aldaz, A. and Commninellis, Ch. (2001b) Electrochemical oxidation of phenol at boron-doped diamond electrode. Electrochim. Acta 46, 3573–3578.CrossRefGoogle Scholar
  15. Jörissen, J. (1996) Ion-exchange membranes as solid polymer electrolytes (SPE) in electroorganic synthesis without supporting electrolytes. Electrochim. Acta 41, 553–562.CrossRefGoogle Scholar
  16. Kondo, T., Honda, K., Tryk, D.A. and Fujishima, A. (2005) Covalent modification of single-crystal diamond electrode surfaces. J. Electrochem. Soc. 152, E18–E23.CrossRefGoogle Scholar
  17. Lehmann, Th., Schneider, R., Reufer, C. and Sanzenbacher, R. (2001) Elektrochemische Carboxylierung zur Synthese von α-Hydroxycarbon-Säuren. Elektronenübertragung in Chemie und Biochemie, Russow, J., Schäfer, H. J. (Eds.), GDCh-Monographie 23, 251–258.Google Scholar
  18. Lehmann, Th., Schneider, R., Weckbecker, Ch., Dunach, E. and Oliviero, S. (2002) Process for the production of 2-hydroxy-4-methylmercaptobutyric acid. International patent WO 02/16671 A1. Degussa AG, Germany.Google Scholar
  19. Lessene, G. and Feldman, K.S. (2002) Oxidative aryl-coupling reactions in synthesis. In: Astruc, D. (Ed.) Modern arene chemistry, Wiley-VCH, Weinheim, 479–538.CrossRefGoogle Scholar
  20. Malkowsky, I.M., Rommel, C.E., Wedeking, K., Fröhlich, R., Bergander, K., Nieger, M., Quaiser, C., Griesbach, U., Pütter, H. and Waldvogel, S.R. (2006a) Facile and highly diastereoselective formation of a novel pentacyclic scaffold by direct anodic oxidation of 2,4-dimethylphenol. Eur. J. Org. Chem. 2006, 241–245.CrossRefGoogle Scholar
  21. Malkowsky, I.M., Fröhlich, R., Griesbach, U., Pütter, H. and Waldvogel, S.R. (2006b) Facile synthesis and properties of tetraphenoxy borates. Eur. J. Inorg. Chem. 1690–1697.Google Scholar
  22. Malkowsky, I.M., Griesbach, U., Pütter, H. and Waldvogel, S.R. (2006c) Novel template-directed anodic phenol coupling reaction. Chem.-Eur. J. 12, 7482–7488.Google Scholar
  23. Malkowsky, I.M., Griesbach, U., Pütter, H. and Waldvogel, S.R. (2006d) Unexpected highly chemoselective anodic ortho-coupling reaction of 2,4-dimethylphenol on boron-doped diamond electrodes. Eur. J. Org. Chem. 2006, 4569–4572.CrossRefGoogle Scholar
  24. Marselli, B., Garcia-Gomez, J., Michaud, P.A., Rodrigo, M.A. and Comninellis, Ch. (2003) Electrogeneration of hydroxyl radicals on boron-doped diamond electrodes. J. Electrochem. Soc. 150, D79–D83.CrossRefGoogle Scholar
  25. Martin, H.B., Argoita, A, Landau, U., Anderson, A.B. and Angus, J.C. (1996) Hydrogen and oxygen evolution on boron-doped diamond electrodes. J. Electrochem. Soc. 143, L133–L136.CrossRefGoogle Scholar
  26. Nad, S. and Breinbauer, R. (2004) Electroorganic synthesis on the solid phase using polymer beads as supports. Angew. Chem. Int. Ed. 43, 2297–2299.CrossRefGoogle Scholar
  27. Nad, S. and Breinbauer, R. (2005) Electroorganic synthesis of 2,5-dialkoxydihydrofurans and pyridazines on solid phase using polymer beads as supports. Synthesis 2005, 3654–3665.CrossRefGoogle Scholar
  28. Ouattara, L., Duo, I., Diaco, T., Ivandini, A., Honda, K., Rao, T., Fujishima, A. and Comninellis, Ch. (2003) Electrochemical oxidation of ethylenediaminetetraacetic acid (EDTA) on BDD electrodes: Application to wastewater treatment. New Diam. Front. Carbon Technol. 13, 97–108.Google Scholar
  29. Panizza, M., Michaud, P.A., Cerisola, G. and Comninellis, Ch. (2001) Anodic oxidation of 2-naphthol at boron-doped diamond electrodes. J. Electroanal. Chem. 507, 206–214.CrossRefGoogle Scholar
  30. Pleskov, Y.V., Evstefeeva, Y.E., Krotova, M.D., Mishuk, V.Y., Laptev, V.A., Palyanov, Y.N. and Borzdov, Y.M. (2002) Effect of crystal structure on the behavior of diamond electrodes. J. Electrochem. Soc. 149, E260–E264.CrossRefGoogle Scholar
  31. Pütter, H. (2001) Industrial electroorganic chemistry. In: Lund, H., Hammerich, O. (Eds) Organic electrochemistry, 4th ed., Marcel Dekker, New York, NY, 1259–1307.Google Scholar
  32. Pütter, H., Weiper-Idelmann, A., Merk, C., Fryda, M., Klages, C.-P., Schäfer, L. and Hampel, A. (2003) Process for the electrochemical conversion of organic compounds on diamond coated electrodes. European patent EP 1 036 861 B1. BASF Aktiengesellschaft, Fraunhofer Gesellschaft, Germany.Google Scholar
  33. Rao, N., Lütz, S., Seelbach, K. and Liese, A. (2006) Basics of bioreaction engineering. In: Liese, A., Seelbach, K. Wandrey, Ch. (Eds.) Industrial biotransfromations, 2nd ed., Wiley-VCH, Weinheim, 115–145.Google Scholar
  34. Reufer, Ch., Lehmann, Th., Sanzenbacher, R. and Weckbecker, Ch. (2004) Verfahren zur anodischen Alkoxylierung von organischen Substraten. German patent DE 10313169 A1. Degussa AG, Germany.Google Scholar
  35. Reufer Ch., Hateley, M., Lehmann, Th., Weckbecker, Ch., Sanzenbacher R. and Bilz, J. (2006) Process for the preparation of α-substituted carboxylic acids from the series comprising α-hydroxycarboxylic acids and N-substituted α-aminocarboxylic acids. European patent EP 1 631 702 B1, Degussa AG, Germany.Google Scholar
  36. Rodrigo, M.A., Michaud, P.A., Duo, I., Panizza, M., Cerisola, G. and Comninellis, Ch. (2001) Oxidation of 4-chlorophenol at boron-doped diamond electrode for wastewater treatment. J. Electrochem. Soc. 148, D60–D64.CrossRefGoogle Scholar
  37. Rommel, E., Malkowsky, I.M., Waldvogel, S.R., Pütter, H. and Griesbach, U. (2005) Anodic dimerization of substituted benzenes. PCT patent WO 2005075709 A2, BASF Aktiengesellschaft, Germany.Google Scholar
  38. Sopchak, D., Miller, B., Avyigal, Y. and Kalish, R. (2002) Rotating ring-disk electrode studies of the oxidation of p-methoxyphenol and hydroquinone at boron-doped diamond electrodes. J. Electroanal. Chem. 538, 39–45.CrossRefGoogle Scholar
  39. Spataru, N., Spataru, T. and Fujishima, A. (2005) Voltammetric determination of thiourea at conductive diamond electrodes. Electroanalysis 17, 800–805.CrossRefGoogle Scholar
  40. Steckhan, E., Arns, Th., Heinemann, W.R., Hilt, G., Hoormann, D., Kröner, L., Lewall, B. and Pütter, H. (2001) Environmental protection and economization of resources by electroorganic and electroenzymatic synthesis. Chemosphere 43, 63–73.CrossRefGoogle Scholar
  41. Weissermel, K. and Arpe, H.-J. (1997) Industrial organic chemistry, 3rd ed., VCH, Weinheim.Google Scholar
  42. Wilson, N.R., Clewes, S.L., Newton, M.E., Unwin, P.R. and Macpherson, J.V. (2006) Impact of grain-dependent boron uptake on the electrochemical and electrical properties of polycrystalline boron doped diamond electrodes. J. Phys. Chem. B 110, 5639–5646.CrossRefGoogle Scholar
  43. Zhi, J.-F., Wang, H.-B., Nakashima, T., Rao, T.N. and Fujishima, A. (2003) Electrochemical incineration of organic pollutants on boron-doped diamond electrode. Evidence for direct electrochemical oxidation pathway. J. Phys. Chem. B 107, 13389–13395.Google Scholar
  44. Zollinger, D., Griesbach, U., Pütter, H. and Comninellis, Ch. (2004a) Methoxylation of p-tert-butyltoluene on boron-doped diamond electrodes. Electrochem. Commun. 6, 600–604.CrossRefGoogle Scholar
  45. Zollinger, D., Griesbach, U., Pütter, H. and Comninellis, Ch. (2004b) Electrochemical cleavage of 1,2-diphenylethanes at boron-doped diamond electrodes. Electrochem. Commun. 6, 605–608.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2010

Authors and Affiliations

  • Ulrich Griesbach
    • 1
  • Itamar M. Malkowsky
  • Siegfried R. Waldvogel
  1. 1.BASF SE, Care ChemicalsLudwigshafenGermany

Personalised recommendations