Cleaner Continuous Photo-Oxidation Using Singlet Oxygen in Supercritical Carbon Dioxide†
Richard A. Bourne Dr.
School of Chemistry, University Park, University of Nottingham, NG7 2RD (UK)
Search for more papers by this authorXue Han
School of Chemistry, University Park, University of Nottingham, NG7 2RD (UK)
Search for more papers by this authorMartyn Poliakoff Prof.
School of Chemistry, University Park, University of Nottingham, NG7 2RD (UK)
Search for more papers by this authorMichael W. George Prof.
School of Chemistry, University Park, University of Nottingham, NG7 2RD (UK)
Search for more papers by this authorRichard A. Bourne Dr.
School of Chemistry, University Park, University of Nottingham, NG7 2RD (UK)
Search for more papers by this authorXue Han
School of Chemistry, University Park, University of Nottingham, NG7 2RD (UK)
Search for more papers by this authorMartyn Poliakoff Prof.
School of Chemistry, University Park, University of Nottingham, NG7 2RD (UK)
Search for more papers by this authorMichael W. George Prof.
School of Chemistry, University Park, University of Nottingham, NG7 2RD (UK)
Search for more papers by this authorWe thank the EPSRC (EP/FO15275) for financial support and Prof. G. Pattenden, Dr. A. Wells, and Dr. S. K. Ross for helpful discussions. We also thank M. Dellar, M. Guyler, D. Lichfield, R. Wilson, and P.Fields for technical support. M.W.G. gratefully acknowledges receipt of a Wolfson Merit Award from The Royal Society.
Abstract
Hochdruck im Fokus: Ein Milliliter-Reaktor wurde entwickelt, um überkritisches CO2 für kontinuierliche Photooxidationen nutzen zu können. Der Wechsel von einer traditionellen Batch-Reaktion im Mikroliterbereich zu einer achtstündigen Reaktion im neuen Reaktor entsprach einer Ansatzvergrößerung um den Faktor 3000 bei der Oxidation von α-Terpinen (siehe Bild).
References
- 1E. L. Clennan, A. Pace, Tetrahedron 2005, 61, 6665–6691.
- 2I. Saito, T. Matsuura, K. Inoue, J. Am. Chem. Soc. 1983, 105, 3200–3206.
- 3T. Montagnon, M. Tofi, G. Vassilikogiannakis, Acc. Chem. Res. 2008, 41, 1001–1011.
- 4N. Hoffmann, Chem. Rev. 2008, 108, 1052–1103.
- 5N. Monnerie, J. Ortner, J. Sol. Energy Eng. 2001, 123, 171–174.
- 6M. C. DeRosa, R. J. Crutchley, Coord. Chem. Rev. 2002, 233, 351–371.
- 7C. S. Foote, S. Wexler, W. Ando, R. Higgins, J. Am. Chem. Soc. 1968, 90, 975–981.
- 8P. D. Bartlett, G. D. Mendenhall, D. L. Durham, J. Org. Chem. 1980, 45, 4269–4271.
- 9M. C. Carreño, M. Gonzalez-Lopez, A. Urbano, Angew. Chem. 2006, 118, 2803–2807;
10.1002/ange.200504605 Google ScholarAngew. Chem. Int. Ed. 2006, 45, 2737–2741.
- 10K. H. Pfoertner, J. Photochem. Photobiol. A 1990, 51, 81–86.
- 11M. Oelgemöller, N. Healy, L. de Oliveira, C. Jung, J. Mattay, Green Chem. 2006, 8, 831–834.
- 12M. Oelgemöller, C. Jung, J. Ortner, J. Mattay, E. Zimmermann, Green Chem. 2005, 7, 35–38.
- 13A. A. Abdel-Shafi, F. Wilkinson, D. R. Worrall, Chem. Phys. Lett. 2001, 343, 273–280.
- 14A. A. Abdel-Shafi, D. R. Worrall, J. Photochem. Photobiol. A 2007, 186, 263–269.
- 15M. Okamoto, T. Takagi, F. Tanaka, Chem. Lett. 2000, 1396–1397.
- 16D. R. Worrall, A. A. Abdel-Shafi, F. Wilkinson, J. Phys. Chem. A 2001, 105, 1270–1276.
- 17R. A. Bourne, X. Han, A. O. Chapman, N. J. Arrowsmith, H. Kawanami, M. Poliakoff, M. W. George, Chem. Commun. 2008, 4457–4459.
- 18J. A. Darr, M. Poliakoff, Chem. Rev. 1999, 99, 495–541.
- 19M. C. McHugh, V. J. Krukonis, Supercritical Fluid Extraction: Principles & Practice, Butterworth-Heinemann, Boston, 1994.
- 20E. J. Beckman, J. Supercrit. Fluids 2004, 28, 121–191.
- 21P. Licence, J. Ke, M. Sokolova, S. K. Ross, M. Poliakoff, Green Chem. 2003, 5, 99–104.
- 22A. A. Lapkin, V. M. Boddu, G. N. Aliev, B. Goller, S. Polisski, D. Kovalev, Chem. Eng. J. 2008, 136, 331–336.
- 23E. E. Coyle, M. Oelgemoller, Photochem. Photobiol. Sci. 2008, 7, 1313–1322.
- 24S. Meyer, D. Tietze, S. Rau, B. Schaefer, G. Kreisel, J. Photochem. Photobiol. A 2007, 186, 248–253.
- 25J. A. Banister, P. D. Lee, M. Poliakoff, Organometallics 1995, 14, 3876–3885.
- 26J. A. Banister, S. M. Howdle, M. Poliakoff, J. Chem. Soc. Chem. Commun. 1993, 1814–1815.
- 27P. Clark, M. Poliakoff, A. Wells, Adv. Synth. Catal. 2007, 349, 2655–2659.
- 28R. A. Bourne, J. G. Stevens, J. Ke, M. Poliakoff, Chem. Commun. 2007, 4632–4634.
- 29M. G. Hitzler, M. Poliakoff, Chem. Commun. 1997, 1667–1668.
- 30A. O’Neil, C. Wilson, J. M. Webster, F. J. Allison, J. A. K. Howard, M. Poliakoff, Angew. Chem. 2002, 114, 3950–3953;
10.1002/1521-3757(20021018)114:20<3950::AID-ANGE3950>3.0.CO;2-# Google ScholarAngew. Chem. Int. Ed. 2002, 41, 3796–3799.10.1002/1521-3773(20021018)41:20<3796::AID-ANIE3796>3.0.CO;2-T CAS PubMed Web of Science® Google Scholar
- 31C. N. Field, P. A. Hamley, J. M. Webster, D. H. Gregory, J. J. Titman, M. Poliakoff, J. Am. Chem. Soc. 2000, 122, 2480–2488.
- 32C. M. M. Duarte, M. Crew, T. Casimiro, A. Aguiar-Ricardo, M. N. da Ponte, J. Supercrit. Fluids 2002, 22, 87–92.
- 33A. M. Bruun, M. T. Muurette, E. Oliveros, Photochemical Technology, Wiley, Chichester, UK, 1991.
- 34P. N. Gooden, PhD thesis, University of Nottingham, UK, 2006.
- 35P. Licence, M. P. Dellar, R. G. M. Wilson, P. A. Fields, D. Litchfield, H. M. Woods, M. Poliakoff, S. M. Howdle, Rev. Sci. Instrum. 2004, 75, 3233–3236.
Citing Literature
This is the
German version
of Angewandte Chemie.
Note for articles published since 1962:
Do not cite this version alone.
Take me to the International Edition version with citable page numbers, DOI, and citation export.
We apologize for the inconvenience.
