Continuous-Flow Palladium-Catalyzed Synthesis of Cyclohexanones from Phenols using Sodium Formate as a Safe Hydrogen Source

被引:34
|
作者
Valentini, Federica [1 ]
Santillo, Niccolo [2 ]
Petrucci, Chiara [1 ]
Lanari, Daniela [1 ]
Petricci, Elena [2 ]
Taddei, Maurizio [2 ]
Vaccaro, Luigi [1 ]
机构
[1] Univ Perugia, Lab Green SOC, Dipartimento Chim Biol & Biotecnol, Via Elce Sotto 8, I-06123 Perugia, Italy
[2] Univ Siena, Dipartimento Biotecnol Chim & Farm, Via A Moro 2, I-53700 Siena, Italy
关键词
flow chemistry; hydrogenation; ketones; phenols; sustainable chemistry; HIGHLY SELECTIVE HYDROGENATION; C-O BOND; SUPPORTED PD; RHODIUM NANOPARTICLES; AQUEOUS-PHASE; BIO-OIL; LIGNIN; HYDRODEOXYGENATION; BIOMASS; DERIVATIVES;
D O I
10.1002/cctc.201701922
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
We report a procedure for the continuous-flow production of cyclohexanone from phenol on the basis of the use of sodium formate as a biomass-derived source of hydrogen and Pd/C as an easily accessible catalyst system. The reaction worked in water at pH 12.0 at 90 degrees C. By setting a packed reactor charged with the Pd/C catalyst (10 wt%) at a flow rate of 0.5 mL min(-1), we achieved continuous-flow production of cyclohexanone in high yield with high selectivity and productivity.
引用
收藏
页码:1277 / 1281
页数:5
相关论文
共 32 条
  • [21] Selective Hydrogenation of Phenol and Derivatives over Polymer-Functionalized Carbon-Nanofiber-Supported Palladium Using Sodium Formate as the Hydrogen Source
    Chen, Aibing
    Li, Yonglei
    Chen, Jinzhu
    Zhao, Guoying
    Ma, Longlong
    Yu, Yifeng
    CHEMPLUSCHEM, 2013, 78 (11): : 1370 - 1378
  • [22] An efficient and practical approach for the continuous-flow synthesis of 5-hydroxymethylfurfural from carbohydrates using an acidic ionic liquid
    Nguyen, Tan Van
    Nguyen, Trinh Hao
    Phan, Ha Bich
    Tran, Phuong Hoang
    JOURNAL OF CHEMICAL TECHNOLOGY AND BIOTECHNOLOGY, 2023, 98 (12) : 2876 - 2887
  • [23] Palladium-Catalyzed Synthesis of 1,2-Diketones from Aryl Halides and Organoaluminum Reagents Using tert-Butyl Isocyanide as the CO Source
    Chen, Bo
    Wu, Xiao-Feng
    ORGANIC LETTERS, 2020, 22 (02) : 636 - 641
  • [24] Palladium-Catalyzed Carbonylative Synthesis of 3-Methyleneisoindolin-1-ones from Ketimines with Hexacarbonylmolybdenum(0) as the Carbon Monoxide Source
    Wang, Zechao
    Zhu, Fengxiang
    Li, Yahui
    Wu, Xiao-Feng
    CHEMCATCHEM, 2017, 9 (01) : 94 - 98
  • [25] Hydrogen Generation from Organic Hydrides under Continuous-Flow Conditions Using Polymethylphenylsilane-Aluminum Immobilized Platinum Catalyst
    Miyamura, Hiroyuki
    Suzuki, Aya
    Zhu, Zhiyuan
    Kobayashi, Shu
    CHEMISTRY-AN ASIAN JOURNAL, 2022, 17 (17)
  • [26] Solvent-Free Hydrogenation of Squalene Using Parts per Million Levels of Palladium Supported on Carbon Nanotubes: Shift from Batch Reactor to Continuous-Flow System
    Guicheret, Boris
    Vanoye, Laurent
    Rivera-Carcamo, Camila
    de Bellefon, Claude
    Serp, Philippe
    Philippe, Regis
    Favre-Reguillon, Alain
    CHEMSUSCHEM, 2022, 15 (19)
  • [27] Direct Synthesis of Hydroquinones from Quinones through Sequential and Continuous-Flow Hydrogenation-Derivatization Using Heterogeneous Au-Pt Nanoparticles as Catalysts
    Miyamura, Hiroyuki
    Tobita, Fumiya
    Suzuki, Aya
    Kobayashi, Shu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (27) : 9220 - 9224
  • [28] Continuous-flow Fe-zeolite-catalyzed temperature-directed synthesis of bioactive tetraketones and xanthenes using epoxides and cyclic-1,3-diketones via a Meinwald rearrangement
    Mondal, Shankhajit
    Pandey, Akanksha M.
    Gnanaprakasam, Boopathy
    REACTION CHEMISTRY & ENGINEERING, 2023, 8 (04) : 855 - 862
  • [29] Experimental Evaluation of a Membrane Micro Channel Reactor for Liquid Phase Direct Synthesis of Hydrogen Peroxide in Continuous Flow Using Nafion® Membranes for Safe Utilization of Undiluted Reactants
    Selinsek, Manuel
    Kraut, Manfred
    Dittmeyer, Roland
    CATALYSTS, 2018, 8 (11):
  • [30] Highly efficient copper/palladium-catalyzed tandem Ullman reaction/arylation of azoles via C-H activation: synthesis of benzofuranyl and indolyl azoles from 2-(gem-dibromovinyl)phenols(anilines) with azoles
    Chen, Wei
    Wang, Min
    Li, Pinhua
    Wang, Lei
    TETRAHEDRON, 2011, 67 (33) : 5913 - 5919