Selective hydrogenation of 5-hydroxymethylfurfural to 2,5-bis-(hydroxymethyl)furan using Pt/MCM-41 in an aqueous medium: a simple approach

被引:159
作者
Chatterjee, Maya [1 ]
Ishizaka, Takayuki [1 ]
Kawanami, Hajime [1 ,2 ]
机构
[1] AIST, Res Ctr Compact Chem Syst, Organ Synth Team, Miyagino Ku, Sendai, Miyagi 9838551, Japan
[2] Japan Sci & Technol, CREST, Kawaguchi, Saitama 3320012, Japan
关键词
2,5-FURANDICARBOXYLIC ACID; OXIDATION; 2,5-DIFORMYLFURAN; CARBON; 2,5-DIMETHYLFURAN; DERIVATIVES; CONVERSION; AU;
D O I
10.1039/c4gc01127a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The hydrogenation of HMF has been conducted in a neutral aqueous medium. Without any additive, HMF was hydrogenated to 2,5-bis-(hydroxymethyl)furan (BHMF) with complete conversion and selectivity (98.9%) using Pt/MCM-41 as catalyst. A very low temperature of 35 degrees C and 0.8 MPa of hydrogen pressure was used to accomplish the highest selectivity of BHMF within a reaction time of 2 h. Different reaction parameters such as reaction time, hydrogen pressure and the amount of water was optimized to achieve the highest catalytic activity. In particular, the presence or absence of water and the amount of water played an important role to determine the conversion and product distribution of the reaction. For instance, in the absence of water or a large excess of water, the selectivity of BHMF was decreased. In addition, instead of water the influence of three different groups of organic solvent were also explored to obtain BHMF under the studied reaction conditions. It has been observed that the studied organic solvents strongly influenced the catalytic performance, such as solvents with a negative delta value, which followed a clear trend with the substrate conversion, whereas no impact was observed for solvents with a positive delta value. Catalyst recycling experiments revealed that the catalyst could be recycled several times without any significant loss of catalytic activity.
引用
收藏
页码:4734 / 4739
页数:6
相关论文
共 39 条
  • [1] Adams C. R., 1963, [No title captured], Patent No. [US3228966, 3228966]
  • [2] 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
  • [3] [Anonymous], DONOR ACCEPTOR APPRO
  • [4] 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
  • [5] Biomass into Chemicals: Aerobic Oxidation of 5-Hydroxymethyl-2-furfural into 2,5-Furandicarboxylic Acid with Gold Nanoparticle Catalysts
    Casanova, Onofre
    Iborra, Sara
    Corma, Avelino
    [J]. CHEMSUSCHEM, 2009, 2 (12) : 1138 - 1144
  • [6] Preparation and characterization of PdO nanoparticles on trivalent metal (B, Al and Ga) substituted MCM-41: Excellent catalytic activity in supercritical carbon dioxide
    Chatterjee, M.
    Ishizaka, T.
    Kawanami, H.
    [J]. JOURNAL OF COLLOID AND INTERFACE SCIENCE, 2014, 420 : 15 - 26
  • [7] Highly efficient hydrogenation of cinnamaldehyde catalyzed by Pt-MCM-48 in supercritical carbon dioxide
    Chatterjee, M
    Ikushima, Y
    Zhao, FY
    [J]. CATALYSIS LETTERS, 2002, 82 (1-2) : 141 - 144
  • [8] A two-step approach for the catalytic conversion of glucose to 2,5-dimethylfuran in ionic liquids
    Chidambaram, Mandan
    Bell, Alexis T.
    [J]. GREEN CHEMISTRY, 2010, 12 (07) : 1253 - 1262
  • [9] Efficient Synthesis of 8-Oxa-3-aza-bicyclo[3.2.1]octane Hydrochloride
    Connolly, Terrence J.
    Considine, John L.
    Ding, Zhixian
    Forsatz, Brian
    Jennings, Mellard N.
    MacEwan, Michael F.
    McCoy, Kevin M.
    Place, David W.
    Sharma, Archana
    Sutherland, Karen
    [J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2010, 14 (02) : 459 - 465
  • [10] Heteromacrocycles from ring-closing metathesis of unsaturated furanic ethers
    Cottier, L
    Descotes, GR
    Soro, Y
    [J]. SYNTHETIC COMMUNICATIONS, 2003, 33 (24) : 4285 - 4295