Cleaner continuous photo-oxidation using singlet oxygen in supercritical carbon dioxide.

High pressure under the spotlight: A new milliliter-scale reactor is developed for using supercritical CO(2) to perform continuous photo-oxidation reactions. Changing from a traditional microliter-scale batch reaction to 8 hours of reaction using the new reactor gives a 3000-fold scale-up of the oxidation of alpha-terpinene (see picture).

[1]  J. Mattay,et al.  Green photochemistry: solar photooxygenations with medium concentrated sunlight , 2005 .

[2]  Peter Licence,et al.  Chemical reactions in supercritical carbon dioxide: from laboratory to commercial plantThis work was presented at the Green Solvents for Catalysis Meeting held in Bruchsal, Germany, 13–16th October 2002. , 2003 .

[3]  N. Hoffmann,et al.  Photochemical reactions as key steps in organic synthesis. , 2008, Chemical reviews.

[4]  G. Kreisel,et al.  Photosensitized oxidation of citronellol in microreactors , 2007 .

[5]  J. M. Webster,et al.  The supercritical fluid antisolvent synthesis of C60(C2Hx) (x=4 or 6); the crystal structures of two materials which were thought unlikely to exist. , 2002, Angewandte Chemie.

[6]  J. M. Webster,et al.  Precipitation of Solvent-Free C60(CO2)0.95 from Conventional Solvents: A New Antisolvent Approach to Controlled Crystal Growth Using Supercritical Carbon Dioxide , 2000 .

[7]  Michael Oelgemöller,et al.  Micro-photochemistry: photochemistry in microstructured reactors. The new photochemistry of the future? , 2008, Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology.

[8]  F. Wilkinson,et al.  Factors Affecting the Rate of Decay of the First Excited Singlet State of Molecular Oxygen O2(a1Δg) in Supercritical Fluid Carbon Dioxide , 2001 .

[9]  Nathalie Monnerie,et al.  Economic Evaluation of the Industrial Photosynthesis of Rose Oxide via Lamp or Solar Operated Photooxidation of Citronellol , 2001 .

[10]  M. Poliakoff,et al.  Homogeneous photochemical oxidation via singlet O2 in supercritical CO2. , 2008, Chemical communications.

[11]  Martyn Poliakoff,et al.  Continuous hydrogenation of organic compounds in supercriticalfluids , 1997 .

[12]  M. Poliakoff,et al.  Continuous Flow Hydrogenation of a Pharmaceutical Intermediate, [4-(3,4-Dichlorophenyl)-3,4-dihydro-2H-naphthalenyidene]-methylamine, in Supercritical Carbon Dioxide , 2007 .

[13]  S. Howdle,et al.  Preparative-scale organometallic chemistry in supercritical fluids; isolation of [Cr(CO)5(C2H4)] as a stable solid at room temperature , 1993 .

[14]  TanakaFujio,et al.  Lifetime of Singlet Oxygen (1Δg) in Liquid and Supercritical Carbon Dioxide , 2000 .

[15]  D. R. Worrall,et al.  Photosensitized production of singlet oxygen and factors governing its decay in xenon and carbon dioxide supercritical fluids , 2007 .

[16]  James G. Stevens,et al.  Maximising opportunities in supercritical chemistry: the continuous conversion of levulinic acid to gamma-valerolactone in CO(2). , 2007, Chemical communications.

[17]  T. Montagnon,et al.  Using singlet oxygen to synthesize polyoxygenated natural products from furans. , 2008, Accounts of chemical research.

[18]  M. Okamoto,et al.  Lifetime of Singlet Oxygen (1.DELTA.g) in Liquid and Supercritical Carbon Dioxide. , 2000 .

[19]  Bernhard Goller,et al.  Photo-oxidation by singlet oxygen generated on nanoporous silicon in a LED-powered reactor , 2008 .

[20]  F. Wilkinson,et al.  Photosensitised production of singlet oxygen, O2*(a1Δg), in the unique 'heavy-atom' solvent, supercritical fluid xenon. pressure dependence of electronic to vibrational energy conversion during quenching of O2*(a1Δg) by xenon and by ground state oxygen , 2001 .

[21]  Jawwad A. Darr,et al.  New Directions in Inorganic and Metal-Organic Coordination Chemistry in Supercritical Fluids. , 1999, Chemical reviews.

[22]  Eric J. Beckman,et al.  Supercritical and near-critical CO2 in green chemical synthesis and processing , 2004 .

[23]  Formation of superoxide ion via one-electron transfer from electron donors to singlet oxygen , 1983 .

[24]  A. Aguiar-Ricardo,et al.  Phase equilibrium for capsaicin + water + ethanol + supercritical carbon dioxide , 2002 .

[25]  K. Pfoertner Photochemistry in industrial synthesis , 1990 .

[26]  Martin P. Dellar,et al.  Large-aperture variable-volume view cell for the determination of phase-equilibria in high pressure systems and supercritical fluids , 2004 .

[27]  M. C. Carreño,et al.  Oxidative de-aromatization of para-alkyl phenols into para-peroxyquinols and para-quinols mediated by oxone as a source of singlet oxygen. , 2006, Angewandte Chemie.

[28]  C. Foote,et al.  Chemistry of singlet oxygen. IV. Oxygenations with hypochlorite-hydrogen peroxide , 1968 .

[29]  M. DeRosa Photosensitized singlet oxygen and its applications , 2002 .

[30]  L. Oliveira,et al.  Green photochemistry: solar-chemical synthesis of Juglone with medium concentrated sunlight , 2006 .

[31]  A. Pace,et al.  Advances in Singlet Oxygen Chemistry , 2005 .