Acetate induced enhancement of photocatalytic hydrogen peroxide production from oxalic acid and dioxygen

Journal of Physical Chemistry A

Volumn 117, Issue 18, 2013, Pages 3751-3760

  Yamada, Yusuke ^a   Nomura, Akifumi ^a   Miyahigashi, Takamitsu ^a   Ohkubo, Kei ^a   Fukuzumi, Shunichi ^a,b  

^a OSAKA UNIVERSITY   (Japan)

^b Ewha Womans University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

DISPROPORTIONATIONS; EFFECT OF SOLVENTS; NANOSECOND LASERS; PHOTO-CATALYTIC; PHOTO-IRRADIATION; PHOTOCATALYTIC HYDROGEN; REACTION MECHANISM; REACTION SOLUTIONS;

ACETONITRILE; CHEMICAL PLANTS; HYDROGEN PEROXIDE; IONS; ORGANIC ACIDS; PEROXIDES; QUANTUM YIELD; VOLATILE FATTY ACIDS;

OXALIC ACID;

ACETIC ACID; ACETONITRILE; ACETONITRILE DERIVATIVE; HYDROGEN PEROXIDE; OXALIC ACID; OXYGEN; QUINOLINE DERIVATIVE; SINGLET OXYGEN; SOLUTION AND SOLUBILITY; WATER;

CATALYSIS; CHEMISTRY; LIGHT; PHOTOLYSIS; SOLUTION AND SOLUBILITY;

ACETIC ACID; ACETONITRILES; CATALYSIS; HYDROGEN PEROXIDE; LIGHT; OXALIC ACID; OXYGEN; PHOTOLYSIS; QUINOLINIUM COMPOUNDS; SINGLET OXYGEN; SOLUTIONS; WATER;

EID: 84877692952     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp312795f     Document Type: Article

References (69)

1. Gray, H. B. Powering the Planet with Solar Fuel Nat. Chem. 2009, 1, 7-7
2. Lewis, N. S.; Nocera, D. G. Powering the Planet: Chemical Challenges in Solar Energy Utilization Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 15729-15735
3. Nocera, D. G. Living Healthy on a Dying Planet Chem. Soc. Rev. 2009, 38, 13-15
4. Fukuzumi, S.; Yamada, Y.; Suenobu, T.; Ohkubo, K.; Kotani, H. Catalytic Mechanisms of Hydrogen Evolution with Homogeneous and Heterogeneous Catalysts Energy Environ. Sci. 2011, 4, 2754-2766
5. Fukuzumi, S. Development of Bioinspired Artificial Photosynthetic Systems Phys. Chem. Chem. Phys. 2008, 10, 2283-2297
6. Fukuzumi, S. In Handbook of Porphyrin Science; Kadish, K. M.; Smith, K. M.; Guilard, R., Eds.; World Scientific: New Jersy, 2010; Vol. 10, p 183.
7. Fukuzumi, S.; Ohkubo, K. Assemblies of Artificial Photosynthetic Reaction Centres J. Mater. Chem. 2012, 22, 4575-4587
8. Amunts, A.; Drory, O.; Nelson, N. The Structure of a Plant Photosystem I Supercomplex at 3.4 Å Resolution Nature 2007, 447, 58-63
9. Umena, Y.; Kawakami, K.; Shen, J.-R.; Kamiya, N. Crystal Structure of Oxygen-Evolving Photosystem II at a Resolution of 1.9 Å Nature 2011, 473, 55
10. Magnuson, A.; Anderlund, M.; Johansson, O.; Lindblad, P.; Lomoth, R.; Polivka, T.; Ott, S.; Stensjo, K.; Styring, S.; Sundstrom, V.; Hammarstrom, L. Biomimetic and Microbial Approaches to Solar Fuel Generation Acc. Chem. Res. 2009, 42, 1899-1909
11. Disselkamp, R. S. Energy Storage Using Aqueous Hydrogen Peroxide Energy Fuels 2008, 22, 2771-2774
12. Disselkamp, R. S. Can Aqueous Hydrogen Peroxide Be Used as a Stand-Alone Energy Source? Int. J. Hydrogen Energy 2010, 35, 1049-1053
13. Fukuzumi, S.; Yamada, Y.; Karlin, K. D. Hydrogen Peroxide as a Sustainable Energy Carrier: Electrocatalytic Production of Hydrogen Peroxide and the Fuel Cell Electrochim. Acta 2012, 82, 493-511
14. Yamada, Y.; Fukunishi, Y.; Yamazaki, S.; Fukuzumi, S. Hydrogen Peroxide as Sustainable Fuel: Electrocatalysts for Production with a Solar Cell and Decomposition with a Fuel Cell Chem. Commun. 2010, 46, 7334-7336
15. Yamazaki, S.; Siroma, Z.; Senoh, H.; Ioroi, T.; Fujiwara, N.; Yasuda, K. A Fuel Cell with Selective Electrocatalysts Using Hydrogen Peroxide as Both an Electron Acceptor and a Fuel J. Power Sources 2008, 178, 20-25
16. Sanli, A. E.; Aytac, A. Response to Disselkamp: Direct Peroxide/Peroxide Fuel Cell as a Novel Type Fuel Cell Int. J. Hydrogen Energy 2011, 36, 869-875
17. Yamada, Y.; Yoshida, S.; Honda, T.; Fukuzumi, S. Protonated Iron-Phthalocyanine Complex Used for Cathode Material of a Hydrogen Peroxide Fuel Cell Operated under Acidic Conditions Energy Environ. Sci. 2011, 4, 2822-2825
18. Shaegh, S. A. M.; Nguyen, N.-T.; Ehteshami, S. M. M.; Chan, S. H. A Membraneless Hydrogen Peroxide Fuel Cell Using Prussian Blue as Cathode Material Energy Environ. Sci. 2012, 5, 8225-8228
19. Yamada, Y.; Nomura, A.; Miyahigashi, T.; Fukuzumi, S. Photocatalytic Production of Hydrogen Peroxide by Two-Electron Reduction of Dioxygen with Carbon-Neutral Oxalate Using a 2-Phenyl-4-(1-Naphthyl)Quinolinium Ion as a Robust Photocatalyst Chem. Commun. 2012, 48, 8329-8331
20. Santacesaria, E.; Serio, M. D.; Veloti, R.; Leone, U. Kinetics, Mass Transfer, and Palladium Catalyst Deactivation in the Hydrogenation Step of the Hydrogen Peroxide Synthesis via Anthraquinone Ind. Eng. Chem. Res. 1994, 33, 277-284
21. 2-Philic Anthraquinones Ind. Eng. Chem. Res. 1999, 38, 2833-2841
22. 2-Philic Anthrahydroquinones Ind. Eng. Chem. Res. 2000, 39, 2843-2848
23. Herrmann, J.-M.; Mozzanega, M.-N.; Pichat, P. Oxidation of Oxalic Acid in Aqueous Suspensions of Semiconductors Illuminated with UV or Visible Light J. Photochem. 1983, 22, 333-343
24. Aguilar, C.; Urzua, U.; Koenig, C.; Vicuna, R. Oxalate Oxidase from Ceriporiopsis Subvermispora: Biochemical and Cytochemical Studies Arch. Biochem. Biophys. 1999, 366, 275-282
25. Opaleye, O.; Rose, R.-S.; Whittaker, M. M.; Woo, E.-J.; Whittaker, J. W.; Pickersgill, R. W. Structural and Spectroscopic Studies Shed Light on the Mechanism of Oxalate Oxidase J. Biol. Chem. 2006, 281, 6428-6435
26. Woo, E.-J.; Dunwell, J. M.; Goodenough, P. W.; Marvier, A. C.; Pickersgill, R. W. Germin Is a Manganese Containing Homohexamer with Oxalate Oxidase and Superoxide Dismutase Activities Nat. Struct. Biol. 2000, 7, 1036-1040
27. Yamazaki, S.; Yamada, Y.; Fujiwara, N.; Ioroi, T.; Shiroma, Z.; Senoh, H.; Yasuda, K. Electrochemical Oxidation of Oxalic Acid by Rh Octaethylporphyrin Adsorbed on Carbon Black at Low Overpotential J. Electroanal. Chem. 2007, 602, 96-102
28. Shimada, M.; Akamatsu, Y.; Tokimatsu, T.; Mii, K.; Hattori, T. Possible Biochemical Roles of Oxalic Acid as a Low Molecular Weight Compound Involved in Brown-Rot and White-Rot Wood Decays J. Biotechnol. 1997, 53, 103-113
29. 2, Part II: Catalytic Activities and Mechanism Chem.-Eur. J. 2006, 16, 1875-1888
30. Catalytic Oxidations with Hydrogen Peroxide as Oxidant; Strukul, G., Ed.; Kluwer Academic: Dordrecht, The Netherlands, 1992.
31. Teranishi, M.; Naya, S.; Tada, H. In Situ Liquid Phase Synthesis of Hydrogen Peroxide from Molecular Oxygen Using Gold Nanoparticle-Loaded Titanium(IV) Dioxide Photocatalyst J. Am. Chem. Soc. 2010, 132, 7850-7851
32. Ilisz, I.; Foglein, K.; Dombi, A. The Photochemical Behavior of Hydrogen Peroxide in near UV-Irradiated Aqueous TiO Suspensions J. Mol. Cat. A 1998, 135, 55-61
33. 2 Formation from Photocatalytic Processes at the ZnO/Water Interface Environ. Sci. Pollut. Res. 2001, 8, 285-287
34. 2 Loaded with Au-Ag Bimetallic Alloy Nanoparticles ACS Catal. 2012, 2, 599-603
35. Cai, R.; Kubota, Y.; Fujishima, A. Effect of Copper Ions on the Formation of Hydrogen Peroxide from Photocatalytic Titanium Dioxide Particles J. Catal. 2003, 219, 214-218
36. 2-Fluoride Systems Chem. Commun. 2005, 2627-2629
37. 2 Photocatalysts with Visible Light in Aqueous Suspension Systems J. Phys. Chem. C 2008, 112, 15818-15823
38. Bakac, A.; Espenson, J. H.; Creaser, I. I.; Sargesont, A. M. Kinetics of the Superoxide Radical Oxidation of [Cobalt Sepulchrate](2+). A Flash Photolytic Study J. Am. Chem. Soc. 1983, 105, 7624-7628
39. Foyle, V. P.; Takahiashi, Y.; Guillet, J. E. Photocatalytic Production of Hydrogen Peroxide Using Polymer Bound Anthraquinone. 1. Photoproducts in 2-Hydroxyethyl Methacrylate Hydrogels Swollen with Water and 2-Propanol J. Polymer Sci. A 1992, 257-269
40. Hong, A. P.; Bahnemann, D. W.; Hoffmann, M. R. Cobalt(II) Tetrasulfophthalocyanine on Titanium Dioxide: A New Efficient Electron Relay for the Photocatalytic Formation and Depletion of Hydrogen Peroxide in Aqueous Suspensions J. Phys. Chem. 1987, 91, 2109-2117
41. Rao, M. V.; Rajeshwar, K.; PaiVerneker, V. R.; DuBow, J. Photosynthetic Production of Hydrogen and Hydrogen Peroxide on Semiconducting Oxide Grains in Aqueous Solutions J. Phys. Chem. 1980, 84, 1987-1991
42. Shiraishi, F.; Kawanishi, C. Effect of Diffusional Film on Formation of Hydrogen Peroxide in Photocatalytic Reactions J. Phys. Chem. A 2004, 108, 10491-10496
43. Fukushima, M.; Tatsumi, K.; Tanaka, S.; Nakamura, H. Photocatalytic Production of Hydrogen Peroxide by Tris(2,2′-Bipyridine) Ruthenium(II) Using Humic Acids as Electron Donor Environ. Sci. Technol. 1998, 32, 3948-3953
44. Fukuzumi, S.; Yasui, K.; Suenobu, T.; Ohkubo, K.; Fujitsuka, M.; Ito, O. Efficient Catalysis of Rare-Earth Metal Ions in Photoinduced Electron-Transfer Oxidation of Benzyl Alcohols by a Flavin Analogue J. Phys. Chem. A 2001, 105, 10501-10510
45. Ohkubo, K.; Suga, K.; Fukuzumi, S. Solvent-Free Selective Photocatalytic Oxidation of Benzyl Alcohol to Benzaldehyde by Molecular Oxygen Using 9-Phenyl-10-Methylacridinium Chem. Commun. 2006, 2018-2020
46. Fukuzumi, S.; Kuroda, S.; Tanaka, T. Flavin Analog-Metal Ion Complexes Acting as Efficient Photocatalysts in the Oxidation of p -Methylbenzyl Alcohol by Oxygen under Irradiation with Visible Light J. Am. Chem. Soc. 1985, 107, 3020-3027
47. Fukuzumi, S.; Itoh, S.; Komori, T.; Suenobu, T.; Ishida, A.; Fujitsuka, M.; Ito, O. Photochemical Reactions of Coenzyme PQQ (Pyrroloquinolinequinone) and Analogues with Benzyl Alcohol Derivatives via Photoinduced Electron Transfer J. Am. Chem. Soc. 2000, 122, 8435-8443
48. Rubin, T. R.; Calvert, J. G.; Rankin, G. T.; MacNevin, W. Photochemical Synthesis of Hydrogen Peroxide at Zinc Oxide Surfaces J. Am. Chem. Soc. 1953, 75, 2850-2853
49. 2 and Organic Peroxides on Quantum-Sized Semiconductor Collolds Environ. Sci. Technol. 1994, 28, 776-785
50. Fukuzumi, S.; Ohkubo, K. Selective Photocatalytic Reactions with Organic Photocatalysts Chem. Sci. 2013, 4, 561-574
51. Kotani, H.; Ohkubo, K.; Fukuzumi, S. Photocatalytic Oxygenation of Anthracenes and Olefins with Dioxygen via Selective Radical Coupling Using 9-Mesityl-10-Methylacridinium Ion as an Effective Electron-Transfer Photocatalyst J. Am. Chem. Soc. 2004, 126, 15999-16006
52. Kotani, H.; Ohkubo, K.; Fukuzumi, S. Formation of Hydrogen Peroxide from Coal Tar as Hydrogen Sources Using 9-Mesityl-10-Methylacridinium Ion as an Effective Photocatalyst Appl. Catal., B 2008, 77, 317-324
53. Ohkubo, K.; Iwata, R.; Mizushima, K.; Souma, K.; Yamamoto, Y.; Suzuki, N.; Fukuzumi, S. Efficient Aerobic Photocatalytic Oxygenation of Toluene Derivatives and Production of Hydrogen Peroxide with Electron-Transfer States of 9-Mesityl-10-Methylacridinium Ion Derivatives Chem. Commun. 2010, 46, 601-603
54. Kotani, H.; Ohkubo, K.; Fukuzumi, S. Formation of a Long-Lived Electron-Transfer State of a Naphthalene-Quinolinium Ion Dyad and the π-Dimer Radical Cation Faraday Discuss. 2012, 155, 89-102
55. Yamada, Y.; Miyahigashi, T.; Ohkubo, K.; Fukuzumi, S. Photocatalytic Hydrogen Evolution from Carbon-Neutral Oxalate with 2-Phenyl-4-(1-Naphthyl) quinolinium Ion and Metal Nanoparticles Phys. Chem. Chem. Phys. 2012, 14, 10564-10571
56. Chang, M.-M.; Saji, T.; Bard, A. J. Electrogenerated Chemiluminescence. 30. Electrochemical Oxidation of Oxalate Ion in the Presence of Luminescers in Acetonitrile Solutions J. Am. Chem. Soc. 1977, 99, 5399-5403
57. Fukuzumi, S.; Ishikawa, M.; Tanaka, T. Mechanisms of Photo-Oxidation of NADH Model Compounds by Oxygen J. Chem. Soc., Perkin Trans. 2 1989, 1037-1045
58. Matsubara, C.; Kawamoto, N.; Takamura, K. Oxo[5,10,15,20-Tetra(4-Pyridyl) Porphyrinato]Titanium(IV)-An Ultra-high Sensitivity Spectrophotometric Reagent for Hydrogen-Peroxide Analyst 1992, 117, 1781-1784
59. Hatchard, C. G.; Parker, C. A. A New Sensitive Chemical Actinometer. II. Potassium Ferrioxalate as a Standard Chemical Actinometer Proc. R. Soc. London, Ser. A 1956, 235, 518-536
60. Calvert, J. C.; Pitts, J. N. In Photochemistry; Wiley: New York, 1966; p 783.
61. Weast, R. C. Handbook of Chemistry and Physics, 56th ed.; CRC: Cleveland, OH, 1975.
62. Espinosa, S.; Bosch, E.; Rosés, M. Retention of Ionizable Compounds in High-Performance Liquid Chromatography: 14. Acid-Base p K Values in Acetonitrile-Water Mobile Phases J. Chromatogr., A 2002, 964, 55-66
63. Izutsu, K. IUPAC: Acid-Base Dissociation Constants in Dipolar Aprotic Solvents; Blackwell: Oxford, 1990.
64. Yamada, Y.; Miyahigashi, T.; Kotani, H.; Ohkubo, K.; Fukuzumi, S. Photocatalytic Hydrogen Evolution under Highly Basic Conditions by Using Ru Nanoparticles and 2-Phenyl-4-(1-Naphthyl)quinolinium Ion J. Am. Chem. Soc. 2011, 133, 16136-16145
65. Fukuzumi, S.; Kotani, H.; Ohkubo, K. Response: Why Had Long-Lived Electron-Transfer States of Donor-Substituted 10-Methylacridinium Ions Been Overlooked? Formation of the Dimer Radical Cations Detected in the near-IR Region Phys. Chem. Chem. Phys. 2008, 10, 5159-5162
66. Fukuzumi, S.; Miyao, H.; Ohkubo, K.; Suenobu, T. Electron-Transfer Oxidation Properties of DNA Bases and DNA Oligomers J. Phys. Chem. A 2005, 109, 3285-3294
67. Fukuzumi, S.; Kuroda, S. Photooxidation of Benzyl Alcohol Derivatives by Oxygen, Catalyzed by Protonated Flavin Analogs Res. Chem. Intermed. 1999, 25, 789-811
68. Mulazzani, Q. G.; D'Angelantonio, M.; Venturi, M.; Hoffman, M. Z.; Rodgers, M. A. J. Interaction of Formate and Oxalate Ions with Radiation-Generated Radicals in Aqueous Solution. Methylviologen as a Mechanistic Probe J. Phys. Chem. 1986, 90, 5347-5352
69. - Radicals in Aqueous Solution J. Phys. Chem. Ref. Data 1985, 14, 1041-1101