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A thin-gap cell for selective oxidation of 4-methylanisole to 4-methoxy-benzaldehyde-dimethylacetal

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Abstract

An electrochemical microreactor for organic electrosynthesis has been investigated for the anodic synthesis of 4-methylanisole to 4-methoxy-benzaldehyde-dimethylacetal in methanol solution. Selectivity and conversion in the single-pass thin-gap flow reactor were examined as a function of the composition of the electrolyte solution, the flow rate and the applied current. The experimental results indicate that potassium fluoride currently used for industrial synthesis and providing higher yields than sodium perchlorate, exerts an influence on the reaction mechanism: high KF concentrations facilitate the undesired oxidation of the diacetal. Nevertheless, a feed solution containing 0.1 M anisole in 0.01 M KF can be converted at 90% in the 100 μm thin-gap cell with acceptable voltages and a measured selectivity of nearly 87%. The selectivity observed substantially higher than that typically observed in conventional electrochemical cells.

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References

  1. Bersier BM, Carlsson L, Bersier J (1994) Topics in current chemistry. Springer-Verlag, Berlin, Heidelberg

    Google Scholar 

  2. Lund H, Hammerich O (2001) Organic electrochemistry, 4th edn. Marcel Dekker, New York

    Google Scholar 

  3. Pletcher D, Walsh FC (1990) Industrial electrochemistry, 2nd edn. Chapman-Hall, London–New York, 1990

    Google Scholar 

  4. Nishiguchi I, Hirashima T (1985) J Org Chem 50:539

    Article  CAS  Google Scholar 

  5. Degner D (1988) Organic electrochemistry in industry. In: Topics in current chemistry. Springer-Verlag, Berlin, Heidelberg

  6. Löwe H, Ehrfeld W (1999) Electrochim Acta 44:3679

    Article  Google Scholar 

  7. Rode S, Altmeyer S, Matlosz M (2004) J Appl Electrochem 34:671

    Article  CAS  Google Scholar 

  8. Wendt H, Bitterlich S (1992) Electrochim Acta 37:1951

    Article  CAS  Google Scholar 

  9. Wendt H, Bitterlich S, Lodowicks E, Liu Z (1992) Electrochim Acta 37:1959

    Article  CAS  Google Scholar 

  10. Lindermeir A, Horst C, Hoffmann U (2003) Ultrasonics Sonochem 10:223

    Article  CAS  Google Scholar 

  11. Bitterlich S (1990) PhD thesis, TH Darmstadt

  12. Venkatachalapathy MS, Ramaswamy R, Udupa HVK (1958) Bull Acad Polon Sci Ser Sci Chim 6:478

    Google Scholar 

  13. Wendt H, Schneider H (1986) J Appl Electrochem 16:134

    Article  CAS  Google Scholar 

  14. Attour A, Rode S, Bystron T, Matlosz M, Lapicque F (2007) J Appl Electrochem 37:861

    Article  CAS  Google Scholar 

  15. Beck F (1987) Organic electrosynthesis, Ullmann’s encyclopedia of industrial chemistry. VCH Verlagsgesellschaft mbH, Weinheim

    Google Scholar 

  16. Küpper M, Hessel V, Löwe H, Stark W, Jinkel J, Michel M, Schmidt-Traub H (2003) Electrochim Acta 48:2889

    Article  Google Scholar 

  17. Ziogas A, Löwe H, Küpper M, Ehrfeld W (2000) Electrochemical microreactors: a new approach for microreaction technology. In: Ehrfeld W (ed) Microreaction technology: industrial prospects, IMRET3: Proceedings of the 3rd international conference on microreaction technology, Frankfurt/Main. Springer-Verlag, Berlin, pp 136–156

  18. Cao E, Gavridilis A, Motherwell WB (2004) Chem Eng Sci 59:4803

    Article  CAS  Google Scholar 

  19. Ge H, Chen G, Yuan Q, Li H (2005) Catalysis Today 110:171

    Article  CAS  Google Scholar 

  20. Paddon CA, Pritchard GJ, Thiemann T, Marken F (2002) Electrochem Commun 4:825

    Article  CAS  Google Scholar 

  21. Horri D, Atobe M, Fuchigami T, Marken F (2005) Electrochem Commun 7:35

    Article  Google Scholar 

  22. He P, Watts P, Maken F, Haswell SJ (2005) Electrochem Commun 7:918

    Article  CAS  Google Scholar 

  23. Goodridge F, Scott K (1995) Electrochemical process engineering. Plenum Press, New York and London

    Google Scholar 

  24. Pickett DJ (1979) Electrochemical reactor design, 2nd edn. Elsevier, New York, 1979

    Google Scholar 

  25. Attour A (2007) Réacteur d’électrosynthèse microstructuré: conception, étude et développement appliqués à l’oxydation du 4-méthylanisole, PhD Dissertation, INPL, Nancy (in French)

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Acknowledgments

Financial support for this work was provided by the European Project Impulse (project reference ID NMP2-CT-2005-011816 of the 6th Framework Programme for Research and Technological Development of the European Union). The authors also thank the French Ministry of Research for the PhD grant allocated to A. Attour.

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Authors and Affiliations

  1. Laboratoire des Sciences du Génie Chimique, CNRS-ENSIC, BP 20451, 54001, Nancy, France

    Anis Attour, Sabine Rode, Michael Matlosz & François Lapicque

  2. Institut für Mikrotechnik Mainz (IMM) GmbH, Carl-Zeiss Strasse 18-20, 55129, Mainz, Germany

    Athanassios Ziogas

Authors
  1. Anis Attour
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  2. Sabine Rode
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  3. Athanassios Ziogas
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  4. Michael Matlosz
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  5. François Lapicque
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Correspondence to François Lapicque.

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Attour, A., Rode, S., Ziogas, A. et al. A thin-gap cell for selective oxidation of 4-methylanisole to 4-methoxy-benzaldehyde-dimethylacetal. J Appl Electrochem 38, 339–347 (2008). https://doi.org/10.1007/s10800-007-9444-8

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  • DOI: https://doi.org/10.1007/s10800-007-9444-8

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