Production of 5-hydroxy-4-keto-2-pentenoic acid by photo-oxidation of 5-hydroxymethylfurfural with singlet oxygen: A kinetic investigation

Journal of Photochemistry and Photobiology A: Chemistry

Volumn 210, Issue 1, 2010, Pages 69-76

  Marisa, Canterino ^a   Ilaria, Di Somma ^a   Marotta, Raffaele ^a   Roberto, Andreozzi ^a   Vincenzo, Caprio ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

5 Hydroxymethylfurfural; Methylene blue; Photo oxidation; Photosensitizer; Singlet oxygen

Indexed keywords

EID: 75249092005     PISSN: 10106030     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotochem.2009.12.003     Document Type: Article

References (20)

1. Hamelinck C.N., and Faaij A.P.C. Future prospects for production of methanol and hydrogen from biomass. J. Power Sources 111 (2002) 1-22
2. Corma A., Iborra S., and Velty A. Chemical routes for the transformation of biomass into chemicals. Chem. Rev. 107 (2007) 2411-2502
3. Gallezot P. Catalytic routes from renewables to fine chemicals. Catal. Today 121 (2007) 76-91
4. Huber G.W., Chheda J.N., Barrett C.J., and Dumesic J.A. Production of liquid alkanes by aqueous-phase processing of biomass-derived carbohydrates. Science 308 (2005) 1446-1450
5. Kuster B.F.M. 5-Hydroxymethylfurfural (HMF): a review focusing on its manufacture. Starch/Staerke 42 (1990) 314-321
6. Carlini C., Patrono P., Raspolli Galletti A.M., and Sbrana G. Heterogeneous catalysts based on vanadyl phosphate for saccharides dehydration to 5-hydroxymethyl-2-furaldehyde. Appl. Catal. A: Gen. 275 (2004) 111-118
7. Roman-Leshkov Y., Chheda J.N., and Dumesic J.A. Phase modifiers promote efficient production of hydroxymethylfurfural from fructose. Science 312 (2006) 1933-1937
8. Moreau C., Belgacem M.N., and Gandini A. Recent catalytic advances in the chemistry of substituted furans from carbohydrates and in the ensuing polymers. Top. Catal. 27 (2004) 11-30
9. Bernasconi C., Cottier L., Descotes G., Nigay H., Pardon J.C., and Wisniewski A. B. Soc. Chim. Fr. 7-8 (1984) II-323-II-328
10. Zepp R.G., Gumz M.M., Miller W.L., and Gao H. Photoreaction of valerophenone in aqueous solution. J. Phys. Chem. A 102 (1998) 5716-5723
11. Kuhn H.J., Braslavsky S.E., and Schmidt R. Chemical actinometry (Iupac Technical Report). Pure Appl. Chem. 76 (2004) 2105-2146
12. Llano J., Raber J., and Eriksson L.A. Theoretical study of phototoxic reactions of psoralens. J. Photochem. Photobiol. A 154 (2003) 235-243
13. Yamamoto Y., Niki E., Shiokawa H., and Kamiya Y. Ozonation of organic compounds. 4. Ozonolysis of alfa,beta unsaturated carbonyl compounds in protic solvents. J. Org. Chem. 46 (1981) 250-254
14. Gollnick K., and Griesbeck A. Singlet oxygen photooxygenation of furans. Isolation and reaction of (4+2)-cycloaddition products (unsaturated sec. -ozonides). Tetrahedron 41 (1985) 2057-2068
15. De Rosa M.C., and Crutchley R.J. Photosensitized singlet oxygen and its applications. Coordin. Chem. Rev. 233/234 (2002) 351-371
16. Wilkinson F., Helman W.P., and Ross A.B. Quantum yields for the photosensitized formation of the lowest electrochemically excited singlet state of molecular oxygen in solution. J. Phys. Chem. Ref. Data 22 (1993) 113-262
17. De Moyer C.D., Schierholz E.L., Gulliver J.S., and Wilhelms S.C. Impact of bubble and free surface oxygen transfer on diffused aeration systems. Water Res. 37 (2003) 1890-1904
18. Perry R.H., and Green D.W. Perry's Chemical Engineers' Handbook. 7th Ed. (1997), McGraw-Hill, New York
19. Schmidt H., Al-Ibrahim A., Dietzel U., and Bieker L. On the acridine and thiazine dye sensitized photodynamic inactivation of lysozyme-singlet oxygen self-quenching by the sensitizers. Photochem. Photobiol. 33 (1981) 127-130
20. Usui Y., and Kamogawa K. A standard system to determine the quantum yield of singlet oxygen formation in aqueous solution. Photochem. Photobiol. 19 (1974) 245-247