Skip to main content
SpringerLink
Log in
Book cover

Electrochemistry for the Environment pp 125–141Cite as

Green Electroorganic Synthesis Using BDD Electrodes

  • Chapter
  • First Online:

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.

This is a preview of subscription content, log in via an institution.

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   139.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   179.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD   219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

References

  • 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 

  • Bäumer, U.-St. and Schäfer, H.-J. (2005) Cleavage of alkenes by anodic oxidation. J. Appl. Electrochem. 35, 1283–1292.

    Google Scholar 

  • 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.

    CAS  Google Scholar 

  • 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.

    CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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 

  • 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.

    Article  CAS  Google Scholar 

  • 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 

  • 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.

    Article  CAS  Google Scholar 

  • Fardel, R., Griesbach, U., Pütter, H. and Comninellis, Ch. (2006) Electrosynthesis of trimethylorthoformate on BDD electrodes. J. Appl. Electrochem. 36, 249–253.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • Haenni, W., Perret, A. and Richen, P. (2002) Large-sized electrode. PCT patent WO 2002061181.

    Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • Jörissen, J. (1996) Ion-exchange membranes as solid polymer electrolytes (SPE) in electroorganic synthesis without supporting electrolytes. Electrochim. Acta 41, 553–562.

    Article  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    CAS  Google Scholar 

  • 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 

  • 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.

    Chapter  Google Scholar 

  • 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.

    Article  Google Scholar 

  • 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 

  • 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.

    CAS  Google Scholar 

  • 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.

    Article  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • Nad, S. and Breinbauer, R. (2004) Electroorganic synthesis on the solid phase using polymer beads as supports. Angew. Chem. Int. Ed. 43, 2297–2299.

    Article  CAS  Google Scholar 

  • 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.

    Article  Google Scholar 

  • 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.

    CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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 

  • 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 

  • 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 

  • 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 

  • 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 

  • 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.

    Article  CAS  Google Scholar 

  • 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 

  • 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.

    Article  Google Scholar 

  • Spataru, N., Spataru, T. and Fujishima, A. (2005) Voltammetric determination of thiourea at conductive diamond electrodes. Electroanalysis 17, 800–805.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • Weissermel, K. and Arpe, H.-J. (1997) Industrial organic chemistry, 3rd ed., VCH, Weinheim.

    Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. BASF SE, Care Chemicals, Ludwigshafen, Germany

    Ulrich Griesbach

Authors
  1. Ulrich Griesbach
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Itamar M. Malkowsky
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Siegfried R. Waldvogel
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ulrich Griesbach .

Editor information

Editors and Affiliations

  1. Dept. Chemical Engineering, Ecole Polytech. Fed. Lausanne, Lausanne, 1015, Switzerland

    Christos Comninellis

  2. Science and Technology, Hong Kong University of, Clear Water Bay, Kowloon, Hong Kong/PR China

    Guohua Chen

Rights and permissions

Reprints and permissions

Copyright information

© 2010 Springer Science+Business Media, LLC

About this chapter

Cite this chapter

Griesbach, U., Malkowsky, I.M., Waldvogel, S.R. (2010). Green Electroorganic Synthesis Using BDD Electrodes. In: Comninellis, C., Chen, G. (eds) Electrochemistry for the Environment. Springer, New York, NY. https://doi.org/10.1007/978-0-387-68318-8_5

Download citation

Publish with us

Policies and ethics

Search

Navigation