Waste-free electrochemical oxidation of alcohols in water

Advanced Synthesis and Catalysis

Volumn 348, Issue 15, 2006, Pages 2033-2037

  Palmisano, Giovanni ^a,c   Ciriminna, Rosaria ^a   Pagliaro, Mario ^a,b  

^a CNR   (Italy)

^b CNR   (Italy)

^c UNIVERSITY OF PALERMO   (Italy)

Author keywords

Alcohols; Carbonyl compounds; Electrochemistry; Green chemistry; Oxidation; TEMPO

Indexed keywords

EID: 33750511553     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200606199     Document Type: Article

References (28)

1. The potential waste coproduced with active pharmaceutical ingredients (APIs) is in the range of 500 million to 2 billion kg per year. Even at a nominal disposal cost of $1 per kg, the potential savings just in waste avoidance are significant faced to the pharmaceutical industry annual sales (almost $500 billion in 2003): B. W. Cue, Chem. Eng. News 2005, 83 (39), 46.
2. R. A. Sheldon, I. W. C. E. Arends, G. J. ten Brink, A. Dijksman, Acc. Chem. Res. 2002, 35, 774.
3. J. M. DeSimone, Science 2002, 297, 799.
4. S. J. Broadwater, S. L. Roth, K. E. Price, M. Kobašlija, D. Tyler McQuade, Org. Biomol. Chem. 2005, 3, 2899.
5. For carrying out reactions in aqueous suspension: S. Narayan, J. Muldoon, M. G. Finn, V. V. Fokin, H. C. Kolb, K. B. Sharpless, Angew. Chem. Int. Ed. 2005, 44, 3275.
6. For a recent review, see: S. Campestrini, R. Ciriminna, M. Pagliaro, Chem. Soc. Rev. 2005, 347, 825.
7. G. J. ten Brink, I. W. C. E. Arenas, R. A. Sheldon, Science 2000, 287, 1636.
8. D. I. Enache, J. K. Edwards, P. Landon, B. Solsona-Espriu, A. F. Carley, A. A. Herzing, M. Watanabe, C. J. Kiely, D. W. Knight, G. J. Hutchings, Science 2006, 311, 362.
9. B. M. Trost, Angew. Chem. Int. Ed. 1995, 34, 259.
10. A. E. J. de Nooy, A. C. Besemer, H. van Bekkum, Synthesis 1996, 1153.
11. 2 as primary oxidant: R. Ben-Daniel, P. Alsters, R. Neumann, J. Org. Chem. 2001, 66, 8650.
12. D. Liaigre, T. Breton, E. M. Belgsir, Electrochem. Commun. 2005, 7, 312.
13. a) Y. Kashiwagi, H. Ono, T. Osa, Chem. Lett. 1993, 257;
14. the method was recently extended to oxidative synthesis yields of enantiopure lactones from optically active diols by grafting of an optically active cyclic nitroxyl radical: b) Y. Kashiwagi, F. Kurashima, S. Chiba, J. Anzai, T. Osa, J. M. Bobbitt, Chem. Commun. 2003, 114.
15. H. Tanaka, Y. Kawakami, K. Goto, M. Kuroboshi, Tetrahedron Lett. 2001, 42, 445.
16. R. Shacham, D. Avnir, D. Mandler, Adv. Mater. 1999, 11, 384.
17. a) R. V. Chaudhari, V. H. Rane, A. A. Deshmukh, S. S. Divekar, US Patent Application 20050215827, 2005;
18. b) F. Wang, J. Xu, X. Li, J. Gao, L. Zhou, R. Ohnishi, Adv. Synth. Catal. 2005, 347, 1987.
19. Yet, as one referee rightly remarks, benzyl alcohol that is here proposed as the starting material for the production of benzaldehyde is still almost universally manufactured from toluene by chlorination/hydrolysis, with the usual environmental problems of traditional chemical processes that are being addressed by chemical research inspired by the "green chemistry" principles.
20. Organic Electrochemistry, Vol. 8 in the series: Encyclopaedia of Electrochemistry, (Eds.: A. Bard, M. Stratmann), Wiley-VCH, Weinheim, 2004.
21. H. Lund, J. Electrochem. Soc., 2002, 149, 21.
22. th edn., Marcel Dekker, New York, 2001.
23. A. Walcarius, D. Mandler, J. A. Cox, M. Collinson, O. Lev, J. Mater. Chem. 2005, 15, 3663.
24. A. Fidalgo, R. Ciriminna, L. M. Ilharco, M. Pagliaro, Chem. Mater. 2005, 17, 6686.
25. T. Fey, H. Fischer, S. Bachmann, K. Albert, C. Bolm, J. Org. Chem. 2001, 66, 8254.
26. Partly immobilized TEMPO in similar oxidations was described in: E. M. Belgsir, H. J. Schäfer, Electrochem. Commun. 2001, 3, 32.
27. In these oxidations, hydrogen carbonate buffer electrolyte can be completely removed by a cation-exchange resin membrane: M. Schämann, H. J. Schäfer, Eur. J. Org. Chem. 2003, 351.
28. R. Ciriminna, J. Blum, D. Avnir, M. Pagliaro, Chem. Commun. 2000, 1441.