非均相催化剂在光催化苯羟基化反应中的应用及机理研究进展
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摘要
本文综述了光催化苯羟基化反应中的一元和多元一元和多元非均相催化剂。如石墨烯、金系催化剂、铜系催化剂、铁系催化剂等。简要介绍了光催化苯转化为苯酚可能存在的机理,并对非均相催化剂的发展方向及应用前景进行展望。
This paper reviews the mono-and multi-component mono-and multi-component heterogeneous catalysts in photocatalytic benzene hydroxylation. For example, graphene, a gold-based catalyst, a copper-based catalyst, an iron-based catalyst, and the like. The possible mechanism of photocatalytic conversion of benzene to phenol is briefly introduced, and the development direction and application prospect of heterogeneous catalyst are prospected.
This paper reviews the mono-and multi-component mono-and multi-component heterogeneous catalysts in photocatalytic benzene hydroxylation. For example, graphene, a gold-based catalyst, a copper-based catalyst, an iron-based catalyst, and the like. The possible mechanism of photocatalytic conversion of benzene to phenol is briefly introduced, and the development direction and application prospect of heterogeneous catalyst are prospected.
引文
[1]Zhang G,Yi J,Shim J,et al.Photocatalytic hydroxylation of benzene to phenol over titanium oxide entrapped into hydrophobically modified siliceous foam[J].Appl Cata B:Environ,2011,102:132-139.
[2]Li Y,Wang Z,Chen R Z,et al.The hydroxylation of benzene to phenol over heteropolyacid encapsulated in silica[J].Catal Commun,2014,55:34-37.
[3]Antonyraj C A,Kannan S.Influence of co-bivalent ions in Cu-containing LDHs and solvent on hydroxylation of benzene to phenol[J].Appl Clay Sci,2011,53:297-304.
[4]Hu L Y,Yue B,Wang C,et al.Enhanced catalytic activity over vanadium-containing silylated SBA-15 catalysts for styrene epoxidation and benzene hydroxylation[J].Appl Catal A:Gen,2014,477:141-146.
[5]Hu L Y,Yue B,Wang C,et al.Direct hydroxylation of benzene to phenol on Cu-V bimetal modified HMS catalysts[J].Catal Commun,2014,43:179-183.
[6]Kharat A N,Moosavikia S,Jahromi B T,et al.Liquid phase hydroxylation of benzene to phenol over vanadium substituted Keggin anion supported on amine functionalized SBA-15[J].J Mol Catal A:Chem,2011,348:14-19.
[7]Jourshabani M,Badiei A,Shariatinia Z,et al.Fe-supported SBA-16 type cage-like mesoporous silca with enhanced catalytic activity for direct hydroxylation of benzene to phenol[J].Ind Eng Chem Res,2016,55:3900-3908.
[8]Tian K,Liu W J,Zhang S,et al.One-pot synthesis of a carbon supported bimetallic Cu-Ag NPs catalyst for robust catalytic hydroxylation of benzene to phenol by fast pyrolysis of biomass wastes[J].Green Chem,2016,18:5643-5650.
[9]王旭,萨嘎拉,照日格图.光催化苯羟基化制苯酚研究进展[J].工业催化,2015,4:251-257.
[10]Ohkubo K, Kobayashi T, Fukuzumi S. Mesoporous Graphitic CarbonNitride as a Heterogeneous Visible Light Photoinitiator for Radical Polymerization[J].Chem Int Ed,2011,50:8652-8655.
[11]Ohkubo K,Fujimoto A,Fukuzumi S.Visible-Light-Induced Oxygenation of Benzene by the Triplet Excited State of 2,3-Dichloro-5,6-dicyano-p-benzoquinone[J].J Am Chem Soc,2013,135:5368-5371.
[12]Devaraji P,Sathu N K,Gopinath C S.Toward a Quantitative Correlation between Microstructure and DSSC Efficiency:A Case Study of TiO-xNx Nanoparticles in a Disordered Mesoporous Framework[J].ACS Catal,2014,4:2844-2853.
[13]Wang D K,Wang M T,Li Z H.Fe-Based Metal-Organic Frameworks for Highly Selective Photocatalytic Benzene Hydroxylation to Phenol[J].ACS Catal,2015,5:6852-6857.
[14]Yusuke Ide, Mizuki Matsuoka, and Makoto Ogawa. Controlled Photocatalytic Oxidation of Benzene in Aqueous Clay Suspension[J].Chem Cat Chem,2012,4:628-630.
[15]Bui T D,Kimura A,Higashida S,et al.Two routes for mineralizing benzene by TiO2-photocatalyzed reaction[J]. Applied Catalysis B:Enxironmental,2011,107(1/2):119-127.
[16]Cai J Y,Zhang M,Wang D K,et al.Engineering Surface Wettability of Reduced Graphene Oxide(RGO)to Realize Efficient Interfacial Photocatalytic Benzene Hydroxylation in Water[J].ACS Sustainable Chem Eng,2018,6(11):15682-15687.
[17]Tiziana Marino,Raffaele Molinari,Hermenegildo García.Selectivity of gold nanoparticles on the photocatalytic activity of TiO2 for the hydroxylation of benzene by water[J].Catalysis Today,2013,206:40-45.
[18]Hyunwoong Park,Wonyong Choi.Photocatalytic conversion of benzene to phenol using modified TiO2 and polyoxometalates[J].Catalysis Today,2005,101(3/4):291-297.
[19]Yusuke Ide, Mizuki Matsuoka, Makoto Ogawa. Efficient visible-light-induced photocatalytic activity on gold-nanoparticle-supported layered titanate[J].Journal of the American Chemical Society,2010,132:16762-16764.
[20]Keiko Fujishima, Atsushi Fukuoka, Akihiko Yamagishi, et al.Photooxidation of benzene to phenol by ruthenium bipyridime complexes grafted on mesoporosus silica FSM-16[J].2001,166(2):211-218.
[21]Xu B,Chen Z M,Han B,et al.Glycol assisted synthesis of MIL-100(Fe)nanospheres for photocatalytic oxidation of benzene to phenol[J].Catalysis Communications,2017,98:112-115.
[22]Ye X J,Cui Y J,Qiu X Q,et al.Selective oxidation of benzene to phenol by Fe-CN/TS-1 catalysts under visible light irradiation[J].Applied Catalysis B:Environmental,2014,152-153:383-389.
[23]Ghasem SHIRAVAND,Alireza BADIEI,Ghodsi Mohammadi ZIARANI,et al.Photocatalytic Synthesis of Phenol by Direct Hydroxylation of Benzene by a Modified Nanoporous Silica(LUS-1)under Sunlight[J].Chin J Catal,2012,33:1347-1353.
[24]Bishal Bhuyan,Meghali Devi,Debashree Bora,et al.Design of a Photoactive Bimetallic Cu-Au@g-C3N4 Catalyst for Visible Light Driven Hydroxylation of the Benzene Reaction through C–H Activation[J].Eur J Inorg Chem,2018,34:3849-3858.
[25]Venkata D B C Dasireddy,Bla?Likozar.Selective photocatalytic oxidation of benzene to phenol using carbon nanotube(CNT)-supported Cu and TiO2 heterogeneous catalysts[J].Journal of the Taiwan Institute of Chemical Engineers,2018,82:331-341.
[26]Perumal Devaraji, Wan-Kuen Jo. Natural leaf-assisted dual-phase two-dimensional leaf TiO2 and Cu(OH)2 cocatalyst for photocatalytic conversion of benzene to phenol[J].Materials Research Bulletin,2019,110:67–75.
[27]陈福山,杨涛,胡华南.VO@g-C3N4-T高效可见光催化苯羟基化制苯酚[J].精细化工,2018,35(9):1535-1541.
[28]Guan Zhang, Jaeseon Yi, Jongmin Shim, et al. Photocatalytic hydroxylation of benzene to phenol over titanium oxide entrapped into hydrophobically modified siliceous foam[J]. Applied Catalysis B:Environmental,2011,102(1/2):132-139.
[29]Wang B,Masakazu Anpo,Lin J,et al.Direct Hydroxylation of Benzene to Phenol on h-BCN Nanosheets in the Presence of FeCl3 and H2O2 under Visible Light[J].Catalysis Today,2019,324:73-82.
[30]Three-dimension hierarchical heterostructure of CdWO4 microrods decorated with Bi2WO6 nanoplates for high-selectivity photocatalytic benzene hydroxylation to phenol[J].Applied Catalysis B:Environmental,2018,234:311-317.
[2]Li Y,Wang Z,Chen R Z,et al.The hydroxylation of benzene to phenol over heteropolyacid encapsulated in silica[J].Catal Commun,2014,55:34-37.
[3]Antonyraj C A,Kannan S.Influence of co-bivalent ions in Cu-containing LDHs and solvent on hydroxylation of benzene to phenol[J].Appl Clay Sci,2011,53:297-304.
[4]Hu L Y,Yue B,Wang C,et al.Enhanced catalytic activity over vanadium-containing silylated SBA-15 catalysts for styrene epoxidation and benzene hydroxylation[J].Appl Catal A:Gen,2014,477:141-146.
[5]Hu L Y,Yue B,Wang C,et al.Direct hydroxylation of benzene to phenol on Cu-V bimetal modified HMS catalysts[J].Catal Commun,2014,43:179-183.
[6]Kharat A N,Moosavikia S,Jahromi B T,et al.Liquid phase hydroxylation of benzene to phenol over vanadium substituted Keggin anion supported on amine functionalized SBA-15[J].J Mol Catal A:Chem,2011,348:14-19.
[7]Jourshabani M,Badiei A,Shariatinia Z,et al.Fe-supported SBA-16 type cage-like mesoporous silca with enhanced catalytic activity for direct hydroxylation of benzene to phenol[J].Ind Eng Chem Res,2016,55:3900-3908.
[8]Tian K,Liu W J,Zhang S,et al.One-pot synthesis of a carbon supported bimetallic Cu-Ag NPs catalyst for robust catalytic hydroxylation of benzene to phenol by fast pyrolysis of biomass wastes[J].Green Chem,2016,18:5643-5650.
[9]王旭,萨嘎拉,照日格图.光催化苯羟基化制苯酚研究进展[J].工业催化,2015,4:251-257.
[10]Ohkubo K, Kobayashi T, Fukuzumi S. Mesoporous Graphitic CarbonNitride as a Heterogeneous Visible Light Photoinitiator for Radical Polymerization[J].Chem Int Ed,2011,50:8652-8655.
[11]Ohkubo K,Fujimoto A,Fukuzumi S.Visible-Light-Induced Oxygenation of Benzene by the Triplet Excited State of 2,3-Dichloro-5,6-dicyano-p-benzoquinone[J].J Am Chem Soc,2013,135:5368-5371.
[12]Devaraji P,Sathu N K,Gopinath C S.Toward a Quantitative Correlation between Microstructure and DSSC Efficiency:A Case Study of TiO-xNx Nanoparticles in a Disordered Mesoporous Framework[J].ACS Catal,2014,4:2844-2853.
[13]Wang D K,Wang M T,Li Z H.Fe-Based Metal-Organic Frameworks for Highly Selective Photocatalytic Benzene Hydroxylation to Phenol[J].ACS Catal,2015,5:6852-6857.
[14]Yusuke Ide, Mizuki Matsuoka, and Makoto Ogawa. Controlled Photocatalytic Oxidation of Benzene in Aqueous Clay Suspension[J].Chem Cat Chem,2012,4:628-630.
[15]Bui T D,Kimura A,Higashida S,et al.Two routes for mineralizing benzene by TiO2-photocatalyzed reaction[J]. Applied Catalysis B:Enxironmental,2011,107(1/2):119-127.
[16]Cai J Y,Zhang M,Wang D K,et al.Engineering Surface Wettability of Reduced Graphene Oxide(RGO)to Realize Efficient Interfacial Photocatalytic Benzene Hydroxylation in Water[J].ACS Sustainable Chem Eng,2018,6(11):15682-15687.
[17]Tiziana Marino,Raffaele Molinari,Hermenegildo García.Selectivity of gold nanoparticles on the photocatalytic activity of TiO2 for the hydroxylation of benzene by water[J].Catalysis Today,2013,206:40-45.
[18]Hyunwoong Park,Wonyong Choi.Photocatalytic conversion of benzene to phenol using modified TiO2 and polyoxometalates[J].Catalysis Today,2005,101(3/4):291-297.
[19]Yusuke Ide, Mizuki Matsuoka, Makoto Ogawa. Efficient visible-light-induced photocatalytic activity on gold-nanoparticle-supported layered titanate[J].Journal of the American Chemical Society,2010,132:16762-16764.
[20]Keiko Fujishima, Atsushi Fukuoka, Akihiko Yamagishi, et al.Photooxidation of benzene to phenol by ruthenium bipyridime complexes grafted on mesoporosus silica FSM-16[J].2001,166(2):211-218.
[21]Xu B,Chen Z M,Han B,et al.Glycol assisted synthesis of MIL-100(Fe)nanospheres for photocatalytic oxidation of benzene to phenol[J].Catalysis Communications,2017,98:112-115.
[22]Ye X J,Cui Y J,Qiu X Q,et al.Selective oxidation of benzene to phenol by Fe-CN/TS-1 catalysts under visible light irradiation[J].Applied Catalysis B:Environmental,2014,152-153:383-389.
[23]Ghasem SHIRAVAND,Alireza BADIEI,Ghodsi Mohammadi ZIARANI,et al.Photocatalytic Synthesis of Phenol by Direct Hydroxylation of Benzene by a Modified Nanoporous Silica(LUS-1)under Sunlight[J].Chin J Catal,2012,33:1347-1353.
[24]Bishal Bhuyan,Meghali Devi,Debashree Bora,et al.Design of a Photoactive Bimetallic Cu-Au@g-C3N4 Catalyst for Visible Light Driven Hydroxylation of the Benzene Reaction through C–H Activation[J].Eur J Inorg Chem,2018,34:3849-3858.
[25]Venkata D B C Dasireddy,Bla?Likozar.Selective photocatalytic oxidation of benzene to phenol using carbon nanotube(CNT)-supported Cu and TiO2 heterogeneous catalysts[J].Journal of the Taiwan Institute of Chemical Engineers,2018,82:331-341.
[26]Perumal Devaraji, Wan-Kuen Jo. Natural leaf-assisted dual-phase two-dimensional leaf TiO2 and Cu(OH)2 cocatalyst for photocatalytic conversion of benzene to phenol[J].Materials Research Bulletin,2019,110:67–75.
[27]陈福山,杨涛,胡华南.VO@g-C3N4-T高效可见光催化苯羟基化制苯酚[J].精细化工,2018,35(9):1535-1541.
[28]Guan Zhang, Jaeseon Yi, Jongmin Shim, et al. Photocatalytic hydroxylation of benzene to phenol over titanium oxide entrapped into hydrophobically modified siliceous foam[J]. Applied Catalysis B:Environmental,2011,102(1/2):132-139.
[29]Wang B,Masakazu Anpo,Lin J,et al.Direct Hydroxylation of Benzene to Phenol on h-BCN Nanosheets in the Presence of FeCl3 and H2O2 under Visible Light[J].Catalysis Today,2019,324:73-82.
[30]Three-dimension hierarchical heterostructure of CdWO4 microrods decorated with Bi2WO6 nanoplates for high-selectivity photocatalytic benzene hydroxylation to phenol[J].Applied Catalysis B:Environmental,2018,234:311-317.