Abstract
TiO2 and related photocatalysts can promote productive reactions for organic syntheses, e.g., selective partial oxidation of hydrocarbons by molecular oxygen or water, hydrogenation with water, decarboxylation, C–C bond formation, C–N bond formation, isomerization, and so on. Various kinds of TiO2 photocatalysts were employed for each reaction, such as anatase and rutile TiO2, mesoporous TiO2, platinum-loaded TiO2, and highly dispersed titanium oxide species on supports. In this chapter, representative photocatalytic systems for organic syntheses are reviewed briefly.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsReferences
Al-Ekabi H, Mayo PD (1984) Surface photochemistry: photocatalysed olefin cis–trans equilibrium mediated by CdS. J Chem Soc Chem Commun 1231–1232
Amano F, Tanaka T, Funabiki T (2004) Steady-state photocatalytic epoxidation of propene by O2 over V2O5/SiO2 photocatalysts. Langmuir 20:4236–4240
Amano F, Yamaguchi T, Tanaka T (2006) Photocatalytic oxidation of propylene with molecular oxygen over highly dispersed titanium, vanadium, and chromium oxides on silica. J Phys Chem 110:281–288
Amano F, Tanaka T (2006) Prolylene oxide synthesis and selective oxidation over supported metal oxide photocatalysts with molecular oxygen. Chem Lett 35:468–473
Anpo M, Aikawa N, Kodama S, Yutaka Kubokawa Y (1984a) Photocatalytic hydrogenation of alkynes and alkenes with water over titanium dioxide. Hydrogenation accompanied by bond fission. J Phys Chem 88:2569–2572
Anpo M, Aikawa N, Kubokawa Y (1984b) Photocatalytic hydrogenation of alkynes and alkenes with water over titanium dioxide. Platinum loading effect on the primary processes. J Phys Chem 88:3998–4000
Anpo M, Aikawa N, Kubokawa Y, Che M, Louis C, Giamello E (1985) Photoluminescence and photocatalytic activity of highly dispersed titanium oxide anchored onto porous Vycor glass. J Phys Chem 89:5017–5021
Anpo M, Nakaya H, Kodama S, Kubokawa Y, Domen K, Onishi T (1986a) Photocatalysis over binary metal oxides. Enhancement of the photocatalytic activity of titanium dioxide in titanium-silicon oxides. J Phys Chem 90:1633–1636
Anpo M, Yabuta M, Kodama S, Kubokawa Y (1986b) Photocatalytic isomerization of butenes over TiO2. Photo-formed active species and characteristics of reaction. Bull Chem Soc Jpn 59:259–264
Anpo M, Shima T, Kodama S, Kubokawa Y (1987) Photocatalytic hydrogenation of propyne with water on small-particle titania: size quantization effects and reaction intermediates. J Phys Chem 91:4305–4310
Anpo M, Che M (2000) Application of photoluminesccence techniques to the characterization of solid surface in relation to adsorption, catalysis, and photocatalysis. Adv Catal 44:119–257
Boarini P, Carassiti V, Maldotti A, Amadelli R (1998) Photocatalytic oxygenation of cyclohexane on titanium dioxide suspensions: effect of the solvent and of oxygen. Langmuir 14:2080–2085
Boonstra AH, Mutsaers CAHA (1975) Photohydrogenation of ethyne and ethene on the surface of titanium dioxide. J Phys Chem 79:2025–2072
Fox MA, Dulay MT (1993) Heterogeneous photocatalysis. Chem Rev 93:341–357
Fujihira M, Satoh Y, Osa T (1981a) Heterogeneous photocatalytic oxidation of aromatic compounds on TiO2. Nature 293:206–208
Fujihira M, Satoh Y, Osa T (1981b) Heterogeneous photocatalytic oxidation of aromatic compounds on semiconductor materials: the photo-Fenton type reaction. Chem Lett 10:1053–1056
Fujihira M, Satoh Y, Osa T (1982) Heterogeneous photocatalytic reactions on semiconductor materials. III. Effect of pH and Cu2+ ions on the photo-Fenton type reaction. Bull Chem Soc Jpn 55:666–671
Giannotti C, Le Greneur S, Watts O (1983) Photo-oxidation of alkanes by metal oxide semiconductors. Tertahedron Lett 24:5071–5072
Hashimoto K, Kawai T, Sakata T (1984) Photocatalytic reactions of hydrocarbons and fossil fuels with water. Hydrogen production and oxidation. J Phys Chem 88:4083–4088
Izumi I, Dunn WW, Wilbourn KO, Fan FF, Bard AJ (1980) Heterogeneous photocatalytic oxidation of hydrocarbons on platinized titanium dioxide powders. J Phys Chem 84:3207–3210
Izumi I, Fan FF, Bard AJ (1981) Heterogeneous photocatalytic decomposition of benzoic acid and adipic acid on platinized titanium dioxide powder. The photo-Kolbe decarboxylative route to the breakdown of the benzene ring and to the production of butane. J Phys Chem 85:218–223
Kaise M, Kondoh H, Nishihara C, Nozoye H, Shindo H, Nimura S, Kikuchi O (1993) Photocatalytic reactions of acetic acid on platinum-loaded TiO2: ESR evidence of radical intermediates in the photo-Kolbe reaction. J Chem Soc Chem Commun 395–396
Kato Y, Yoshida H, Hattori T (1998) Photoinduced non-oxidative coupling of methane over silica-alumina and alumina around room temperature. Chem Commun 2389–2390
Kato Y, Yoshida H, Hattori T (2002) Photo-induced non-oxidative coupling of methane over H-zeolite around room temperature. Micropor Mesopor Mater 51:223–231
Kawai T, Sakata T (19269) Hydrogen evolution from water using solid carbon and light energy. Nature 282:283–284
Kawai T, Sakata T (1980) Photocatalytic hydrogen production from liquid methanol and water. J Chem Soc Chem Commun 694–695
Kawai T, Sakata T (1980b) Conversion of carbohydrate into hydrogen fuel by a photocatalytic process. Nature 286:474–476
Kisch H (1994) Preparative photoreactions catalyzed by semiconductor powders. J Prakt Chem 336:635–648
Kodama S, Yabuta M, Kubokawa Y (1982) Photocatalytic isomerization of butenes over TiO2 and ZnO. Chem Lett 11:1671–1674
Kraeutler B, Bard AJ (1977) Photoelectrosynthesis of ethane from acetate ion at an n-type titanium dioxide electrode. The photo-Kolbe reaction. J Am Chem Soc 99:7729–7731
Kraeutler B, Bard AJ (1978a) Heterogeneous photocatalytic synthesis of methane from acetic acid – new Kolbe reaction pathway. J Am Chem Soc 100:2239–2240
Kraeutler B, Bard AJ (19786) Heterogeneous photocatalytic decomposition of saturated carboxylic acids on titanium dioxide powder. Decarboxylative route to alkanes. J Am Chem Soc 100:5985–5992
Maldotti A, Molinari A, Amadelli R (2002) Photocatalysis with organized systems for the oxofunctionalization of hydrocarbons by O2. Chem Rev 102:3811–3836
Morikawa A, Hattori M, Yagi K, Otsuka K (1977) Photocatalytic isomerization of butene-2 on porous silica glass. Z Phys Chem 104:309–320
Mu W, Herrmann J-M, Pichat P (1989) Room temperature photocatalytic oxidation of liquid cyclohexane into cyclohexanone over neat and modified TiO2. Catal Lett 3:73–84
Murata C, Yoshida H, Hattori T (2001) Visible-light-induced epoxidation of propene by molecular oxygen over chromia-silica catalysts. Chem Commun 2412–2413
Murata C, Yoshida H, Hattori T (2002) Titania-silica catalysts prepared by sol–gel method for photoepoxidation of propene with molecular oxygen. Stud Surf Sci Catal 143:845–853
Murata C, Yoshida H, Kumagai J, Hattori T (2003) Active sites and active oxygen species for photocatalytic epoxidation of propene by molecular oxygen over TiO2–SiO2 binary oxides. J Phys Chem B 107:4364–4373
Murata C, Hattori T, Yoshida H (2005) Electrophilic property of O −3 photoformed on isolated Ti species in silica promoting alkene epoxidation. J Catal 231:292–299
Nishimoto S, Ohtani B, Yoshikawa T, Kagiya T (1983) Photocatalytic conversion of primary amines to secondary amines and cyclization of polymethylene-alpha, omega-diamines by an aqueous suspension of TiO2/Pt. J Am Chem Soc 105:7180–7182
Ohno T, Nakabeya K, Matsumura M (1998) Epoxidation of olefins on photoirradiated titanium dioxide powder using molecular oxygen as an oxidant. J Catal 176:76–81
Ohno T, Mitsui T, Matsumura M (2003) TiO2-photocatalyzed oxidation of adamantane in solutions containing oxygen or hydrogen peroxide. J Photochem Photobio A 160:3–9
Ohtani B, Osaki H, Nishimoto S, Kagiya T (1986a) A novel photocatalytic process of amine N-alkylation by platinized semiconductor particles suspended in alcohols. J Am Chem Soc 108:308–310
Ohtani B, Osaki H, Nishimoto S, Kagiya T (1986b) A redox combined photocatalysis: New method of N-alkylation of ammonia by TiO2/Pt suspended in alcohols. Tetrahedron Lett 27:2019–2022
Ohtani B, Tsuru S, Nishimoto S, Kagiya T, Izawa K (1990) Photocatalytic one-step syntheses of cyclic imino acids by aqueous semiconductor suspensions. J Org Chem 55:5551–5553
Ohtani B, Kusakabe S, Okada K, Tsuru S, Izawa K, Amino Y, Nishimoto S (1995) Stereoselective synthesis of piperidine-2, 6-dicarboxylic acids by photocatalytic reaction of aqueous cadmium(II) sulfide dispersion. Tetrahedron Lett 36:3189–3192
Ohtani B, Pal B, Ikeda S (2003) Photocatalytic organic syntheses: selective cyclization of amino acids in aqueous suspensions. Catal Surv Asia 7:165–176
Palmisano G, Augugliaro V, Pagliaro M, Palmisano L (2007) Photocatalysis: a promising route for 21st century organic chemistry. Chem Commun 3425–3437
Pichat P (1994) Partial or complete heterogeneous photocatalytic oxidation of organic compounds in liquid organic or aqueous phases. Catal Today 19:313–333
Reiche H, Bard AJ (1979) Heterogeneous photosynthetic production of amino acid from methane-ammonia-water at Pt/TiO2. Implications in chemical evolution. J Am Chem Soc 101:3127–3128
Sakata T, Kawai T (1981) Heterogeneous photocatalytic production of hydrogen and methane from ethanol and water. Chem Phys Lett 80:341–344
Sakata T, Kawai T, Hashimoto K (1984) Heterogeneous photocatalytic reactions of organic acids and water. New reaction paths besides the photo-Kolbe reaction. J Phys Chem 88:2344–2350
Sato S, White JM (1980a) Photoassisted water-gas shift reaction over platinized titanium dioxide catalysts. J Am Chem Soc 102:7206–7210
Sato S, White JM (1980b) Reactions of water with carbon and ethylene over illuminated Pt/TiO2. Chem Phys Lett 70:131–134
Shiraishi Y, Morishita M, Hirai T (2005) Acetonitril-assisted highly selective photocatalytic epoxidation of olefins on Ti-containing silica with molecular oxygen. Chem Commun 5977–5979
Shiraishi Y, Saito N, Hirai T (2005b) Adsorption-driven photocatalytic activity of mesoporous titanium dioxide. J Am Chem Soc 127:12820–12822
Shiraishi Y, Hirai T (2008) Selective organic transformation on titanium oxide-based photocatalysts. J Photochem Photobio C 9:157–170
Shimamura Y, Misawa H, Oguchi T, Kanno T, Sakuragi H, Tokumaru K (1983) Titanium dioxide photocatalyzed oxidation of aromatic hydrocarbons: the role of water and oxygen to induce aromatic hydroxylation. Chem Lett 12:1691–1694
Takagi K, Fujioka T, Sawaki Y, Iwamura H (1985) An 18O-tracer study on the TiO2-sensitized photooxidation of aromatic compounds. Chem Lett 14:913–916
Tanaka T, Nojima H, Yoshida H, Nakagawa H, Funabiki T, Yoshida S (1993) Preparation of highly dispersed niobium oxide on silica by equilibrium adsorption method. Catal Today 16:297–307
Tanaka T, Teramura K, Yamamoto T, Takenaka S, Yoshida S, Funabiki T (2002) TiO2/SiO2 photocatalysts at low levels of loading: preparation, structure and photocatalysis. J Photochem Photobio A: Chem 148:277–281
Teratani S, Takagi Y, Takahashi M, Noda H, Ikuo A, Tanaka K (1984) Photocatalyzed hydroxylation of benzene in the presence of semiconductors. Nihon Kagakukaishi 283–291
Yoneyama H, Takao Y, Tamura H, Bard AJ (1983) Factors influencing product distribution in photocatalytic decomposition of aqueous acetic acid on platinized titania. J Phys Chem 87:1417–1422
Yoshida H, Tanaka T, Yamamoto M, Yoshida T, Funabiki T, Yoshida S (19926) Epoxidation of propene by gaseous oxygen over silica and Mg-loaded silica under photoirradiation. J Catal 171:351–357
Yoshida H, Murata C, Hattori T (1999) Photocatalytic epoxidation of propene by molecular oxygen over highly dispersed titanium oxide species on silica. Chem Commun 1551–1552
Yoshida H, Kato Y, Hattori T (2000a) Photoinduced non-oxidative methane coupling over silica-alumina. Stud Surf Sci Catal 130:659–664
Yoshida H, Murata C, Hattori T (2000b) Screening study of silica-supported catalysts for photoepoxidation of propene by molecular oxygen. J Catal 194:364–372
Yoshida H, Matsushita N, Kato Y, Hattori T (2002) Active sites in sol–gel prepared silica-alumina for photoinduced non-oxidative methane coupling. Phys Chem Chem Phys 4:2459–2465
Yoshida H, Shimizu T, Murata C, Hattori T (2003a) Highly dispersed zinc oxide species on silica as active sites for photoepoxidation of propene by molecular oxygen. J Catal 220:226–232
Yoshida H, Chaskar MG, Kato Y, Hattori T (2003b) Active sites on silica-supported zirconium oxide for photoinduced direct methane conversion and photoluminescence. J Photochem Photobio A 160:47–53
Yoshida H, Matsushita N, Kato Y, Hattori T (2003c) Synergistic active sites on SiO2–Al2O3–TiO2 photocatalysts for direct methane coupling. J Phys Chem B 107:8355–8362
Yoshida H (2003) Silica-based quantum photocatalysts for selective reactions. Curr Opinion Solid Mater Sci 7:435–442
Yoshida H (2005) Active sites of silica-based quantum photocatalysts for non-oxidative reactions. Catal Surv Asia 9:1–9
Yoshida H, Yuzawa H, Aoki M, Otake K, Itoh H and Hattori T (2008) Photocatalytic hydroxylation of aromatic ring by using water as an oxidant. Chem Commun 4634–4636
Yoshida H, Hirao K, Nishimoto J, Shimura K, Kato S, Itoh H, Hattori T (2008) Hydrogen production from methane and water on platinum loaded titanium oxide photocatalysts. J Phys Chem C 112:5542–5551.
Yoshida S, Takenaka S, Tanaka T, Hirano H, Hayashi H (1996) Highly dispersed titanium oxide on silica: preparation, characterization by XAFS, and photocatalysis. Stud Surf Sci Catal 40:871–880
Yoshida S, Takenaka S, Tanaka T, Funabiki T (1997) Ultrahighly dispersed titanium oxide on silica: Effect of precursors on the structure and photocatalysis. J Phys IV France 7, C2-859-861
Yuliati L, Hattori T, Yoshida H (2005a) Highly dispersed magnesium oxide species on silica as photoactive sites for photoinduced direct methane coupling and photoluminescence. Phys Chem Chem Phys 7:195–201
Yuliati L, Hamajima T, Hattori T, Yoshida H (2005) Highly dispersed Ce(III) species on silica and alumina as new photocatalysts for non-oxidative direct methane coupling. Chem Commun 4824–4826
Yuliati L, Tsubota M, Satsuma A, Itoh H, Yoshida H (2006a) Photoactive sites on pure silica materials for non-oxidative direct methane coupling. J Catal 238:214–220
Yuliati L, Itoh H, Yoshida H (2006b) Modification of highly dispersed cerium oxides on silica with highly dispersed titanium oxides as a new photocatalyst design for nonoxidative direct methane coupling. Chem Lett 35:932–933
Yuliati L, Itoh H, Yoshida H (2006c) Preparation of isolated highly dispersed titanium oxides on silica by sol–gel method for photocatalytically non-oxidative direct methane coupling. Stud Surf Sci Catal 162:961–968
Yuliati L, Yoshida H (2008) Photocatalytic conversion of methane. Chem Soc Rev 37:1592–1602
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2010 Springer Science+Business Media LLC
About this chapter
Cite this chapter
Yoshida, H. (2010). Photocatalytic Organic Syntheses. In: Anpo, M., Kamat, P. (eds) Environmentally Benign Photocatalysts. Nanostructure Science and Technology. Springer, New York, NY. https://doi.org/10.1007/978-0-387-48444-0_27
Download citation
DOI: https://doi.org/10.1007/978-0-387-48444-0_27
Published:
Publisher Name: Springer, New York, NY
Print ISBN: 978-0-387-48441-9
Online ISBN: 978-0-387-48444-0
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)