Selective Photocatalytic Oxidation of Benzyl Amine by O2 into N-benzylidenebenzylamine on TiO2 Using Visible Light

被引：0
作者：
Higashimoto, Shinya [1 ]
Hatada, Yoshiaki [1 ]
Ishikawa, Ryo [1 ]
Azuma, Masashi [1 ]
Sakata, Yoshihisa [2 ]
Kobayashi, Hisayoshi [3 ]
机构：
[1] Osaka Inst Technol, Coll Engn, Asahi Ku, Osaka 5358585, Japan
[2] Yamaguchi Univ, Grad Sch Sci & Engn, Ube, Yamaguchi 7558611, Japan
[3] Kyoto Inst Technol, Dept Chem & Mat Technol, Sakyo Ku, Kyoto 6068585, Japan
来源：
CURRENT ORGANIC CHEMISTRY | 2013年 / 17卷 / 21期
关键词：
Apparent quantum yields; Benzyl amine; DFT calculation; N-benzylidenebenzylamine; Selective photocatalytic oxidation; Titanium dioxide; Visible light; ONE-POT SYNTHESIS; CORRESPONDING ALDEHYDES; AEROBIC OXIDATION; MOLECULAR-OXYGEN; ALCOHOLS; IMINES; IRRADIATION; DEHYDROGENATION; EFFICIENT; SECONDARY;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
This paper deals with the photocatalytic oxidation of benzyl amine by O-2 on TiO2 under visible light irradiation, and it was found that the benzyl amine is selectively converted into N-benzylidenebenzylamine with high conversion (>80 %). The origin of visible light response is not due to the band-gap transition of TiO2, but to the excitation of the charge transfer surface complex constructed by the interaction of benzyl amine with the TiO2 surface, as characterized by spectroscopic analysis such as UV-Vis, FT-IR and DFT calculations. Moreover, investigations of the role of the surface OH groups on TiO2, the electron-transfer from the surface complex as well as kinetic studies provided insight into the reaction mechanisms.
引用
收藏
页码：2374 / 2381
页数：8
相关论文
共 35 条
  • [1] Reaction Mechanism of Selective Photooxidation of Amines over Niobium Oxide: Visible-Light-Induced Electron Transfer between Adsorbed Amine and Nb2O5
    Furukawa, Shinya
    Ohno, Yasuhiro
    Shishido, Tetsuya
    Teramura, Kentaro
    Tanaka, Tsunehiro
    [J]. JOURNAL OF PHYSICAL CHEMISTRY C, 2013, 117 (01) : 442 - 450
  • [2] Pt-Sn/?-Al2O3-Catalyzed Highly Efficient Direct Synthesis of Secondary and Tertiary Amines and Imines
    He, Wei
    Wang, Liandi
    Sun, Chenglin
    Wu, Kaikai
    He, Songbo
    Chen, Jiping
    Wu, Ping
    Yu, Zhengkun
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (47) : 13308 - 13317
  • [3] Selective dehydrogenation of aromatic alcohols photocatalyzed by Pd-deposited CdS-TiO2 in aqueous solution using visible light
    Higashimoto, Shinya
    Tanaka, Yoshimi
    Ishikawa, Ryo
    Hasegawa, Shoko
    Azuma, Masashi
    Ohue, Hiroyoshi
    Sakata, Yoshihisa
    [J]. CATALYSIS SCIENCE & TECHNOLOGY, 2013, 3 (02) : 400 - 403
  • [4] Characteristics of the charge transfer surface complex on titanium(IV) dioxide for the visible light induced chemo-selective oxidation of benzyl alcohol
    Higashimoto, Shinya
    Okada, Kohei
    Azuma, Masashi
    Ohue, Hiroyoshi
    Terai, Tadamasa
    Sakata, Yoshihisa
    [J]. RSC ADVANCES, 2012, 2 (02) : 669 - 676
  • [5] Efficient and selective oxidation of benzylic alcohol by O2 into corresponding aldehydes on a TiO2 photocatalyst under visible light irradiation: Effect of phenyl-ring substitution on the photocatalytic activity
    Higashimoto, Shinya
    Suetsugu, Nobuaki
    Azuma, Masashi
    Ohue, Hiroyoshi
    Sakata, Yoshihisa
    [J]. JOURNAL OF CATALYSIS, 2010, 274 (01) : 76 - 83
  • [6] Effect of Surface Treatment on the Selective Photocatalytic Oxidation of Benzyl Alcohol into Benzaldehyde by O2 on TiO2 Under Visible Light
    Higashimoto, Shinya
    Okada, Kohei
    Morisugi, Tomoki
    Azuma, Masashi
    Ohue, Hiroyoshi
    Kim, Tae-Ho
    Matsuoka, Masaya
    Anpo, Masakazu
    [J]. TOPICS IN CATALYSIS, 2010, 53 (7-10) : 578 - 583
  • [7] Selective photocatalytic oxidation of benzyl alcohol and its derivatives into corresponding aldehydes by molecular oxygen on titanium dioxide under visible light irradiation
    Higashimoto, Shinya
    Kitao, Naoya
    Yoshida, Norio
    Sakura, Teruki
    Azuma, Masashi
    Ohue, Hiroyoshi
    Sakata, Yoshihisa
    [J]. JOURNAL OF CATALYSIS, 2009, 266 (02) : 279 - 285
  • [8] Charge separation and catalytic activity of Ag@TiO2 core-shell composite clusters under UV-irradiation
    Hirakawa, T
    Kamat, PV
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (11) : 3928 - 3934
  • [9] Heterogeneously Catalyzed One-pot Synthesis of Aldimines from Primary Alcohols and Amines by Supported Ruthenium Hydroxides
    Kim, Juno Won
    He, Jinling
    Yamaguchi, Kazuya
    Mizuno, Noritaka
    [J]. CHEMISTRY LETTERS, 2009, 38 (09) : 920 - 921
  • [10] One-Pot Synthesis of Imines and Secondary Amines by Pd-Catalyzed Coupling of Benzyl Alcohols and Primary Amines
    Kwon, Min Serk
    Kim, Sungjin
    Park, Sungho
    Bosco, William
    Chidrala, Ravi Kumar
    Park, Jaiwook
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (07) : 2877 - 2879
1234