Hydrogenation/Hydrolytic Ring Opening of 5-HMF by Cp*-Iridium(III) Half-Sandwich Complexes for Bioketones Synthesis

被引:60
作者
Xu, Zhanwei [1 ]
Yan, Peifang [1 ]
Xu, Wenjuan [1 ]
Liu, Xiumei [1 ]
Xia, Zhi [1 ]
Chung, Benjamin [1 ]
Jia, Songyan [1 ]
Zhang, Z. Conrad [1 ]
机构
[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian Natl Lab Clean Energy, State Key Lab Catalysis, Dalian 116023, Peoples R China
来源
ACS CATALYSIS | 2015年 / 5卷 / 02期
基金
中国博士后科学基金; 中国国家自然科学基金;
关键词
homogeneous catalysis; hydrogenation; iridium catalyst; 5-HMF; ketones; CATALYTIC CONVERSION; RENEWABLE RESOURCES; IRIDIUM COMPLEXES; LEVULINIC ACID; BIOMASS; FRUCTOSE; HYDRODEOXYGENATION; HYDROGENOLYSIS; DECOMPOSITION; REDUCTION;
D O I
10.1021/cs501874v
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
A new method for one-step synthesis of ketones from biobased 5-hydroxymethylfurfural (5-HMF) and its derivatives is reported. Bipyridine coordinated Cp*-Iridium(III) complexes (Cp*, 1,2,3,4,5-pentamethylcyclopenta-1,3-diene) exhibit highly efficient catalytic performance for hydrogenation/hydrolytic ring opening of 5-HMF and derivatives to produce ketones. The catalytic mechanism is proposed to proceed via carbonyl hydrogenation, hydroxyl group promoted and directed hydrolytic furan ring opening, followed by hydrogenation of a,fi-unsaturated carbonyl compound based on the experimental and independent events' statistical calculation results.
引用
收藏
页码:788 / 792
页数:5
相关论文
共 46 条
  • [1] The selective hydrogenation of biomass-derived 5-hydroxymethylfurfural using heterogeneous catalysts
    Alamillo, Ricardo
    Tucker, Mark
    Chia, Mei
    Pagan-Torres, Yomaira
    Dumesic, James
    [J]. GREEN CHEMISTRY, 2012, 14 (05) : 1413 - 1419
  • [2] Baird Jr W. C., 2002, [No title captured], Patent No. [WO 2002008157, 2002008157]
  • [3] Binder J. B., 2009, J AM CHEM SOC, V131, P1979
  • [4] Technology development for the production of biobased products from biorefinery carbohydrates-the US Department of Energy's "Top 10" revisited
    Bozell, Joseph J.
    Petersen, Gene R.
    [J]. GREEN CHEMISTRY, 2010, 12 (04) : 539 - 554
  • [5] Hydrogenation of Carboxylic Acids Catalyzed by Half-Sandwich Complexes of Iridium and Rhodium
    Brewster, Timothy P.
    Miller, Alexander J. M.
    Heinekey, D. Michael
    Goldberg, Karen I.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (43) : 16022 - 16025
  • [6] Caprolactam from Renewable Resources: Catalytic Conversion of 5-Hydroxymethylfurfural into Caprolactone
    Buntara, Teddy
    Noel, Sebastien
    Phua, Pim Huat
    Melian-Cabrera, Ignacio
    de Vries, Johannes G.
    Heeres, Hero J.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (31) : 7083 - 7087
  • [7] Upgrading of Levulinic Acid with Dimethylcarbonate as Solvent/Reagent
    Caretto, Alessio
    Perosa, Alvise
    [J]. ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2013, 1 (08): : 989 - 994
  • [8] Immobilized Ru Clusters in Nanosized Mesoporous Zirconium Silica for the Aqueous Hydrogenation of Furan Derivatives at Room Temperature
    Chen, Jiazhi
    Lu, Fang
    Zhang, Junjie
    Yu, Weiqiang
    Wang, Feng
    Gao, Jin
    Xu, Jie
    [J]. CHEMCATCHEM, 2013, 5 (10) : 2822 - 2826
  • [9] Selective Hydrogenolysis of Polyols and Cyclic Ethers over Bifunctional Surface Sites on Rhodium-Rhenium Catalysts
    Chia, Mei
    Pagan-Torres, Yomaira J.
    Hibbitts, David
    Tan, Qiaohua
    Pham, Hien N.
    Datye, Abhaya K.
    Neurock, Matthew
    Davis, Robert J.
    Dumesic, James A.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (32) : 12675 - 12689
  • [10] Chemical routes for the transformation of biomass into chemicals
    Corma, Avelino
    Iborra, Sara
    Velty, Alexandra
    [J]. CHEMICAL REVIEWS, 2007, 107 (06) : 2411 - 2502