Organocatalytic conversion of cellulose into a platform chemical

被引:74
作者
Caes, Benjamin R. [1 ]
Palte, Michael J. [2 ,3 ]
Raines, Ronald T. [1 ,4 ]
机构
[1] Univ Wisconsin, Dept Chem, Madison, WI 53706 USA
[2] Univ Wisconsin, Med Scientist Training Program, Madison, WI 53706 USA
[3] Univ Wisconsin, Mol & Cellular Pharmacol Grad Training Program, Madison, WI 53706 USA
[4] Univ Wisconsin, Dept Biochem, Madison, WI 53706 USA
关键词
ACID-CATALYZED CONVERSION; PHOSPHOGLUCOSE ISOMERASE; BORIC-ACID; BIOMASS; SUGARS; 2,5-DIMETHYLFURAN; CHEMISTRY; MECHANISM; CHROMIUM; GLUCOSE;
D O I
10.1039/c2sc21403b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The search for a source of fuels and chemicals that is both abundant and renewable has become of paramount importance. The polysaccharide cellulose meets both criteria, and methods have been developed for its transformation into the platform chemical 5-(hydroxymethyl)furfural (HMF). These methods typically employ harsh reaction conditions or toxic heavy metal catalysts, deterring large-scale implementation. Here, we describe a low-temperature, one-pot route that uses ortho-carboxyl-substituted phenylboronic acids as organocatalysts in conjunction with hydrated magnesium chloride and mineral acids to convert cellulose and cellulose-rich municipal waste to HMF in yields comparable to processes that use toxic heavy metal catalysts. Isotopic labeling studies indicate that the key aldose-to-ketose transformation occurs via an enediol intermediate. The route, which also allows for facile catalyst recovery and recycling, provides a green prototype for cellulose conversion.
引用
收藏
页码:196 / 199
页数:4
相关论文
共 44 条
  • [1] Benzoboroxoles as efficient glycopyranoside-binding agents in physiological conditions:: Structure and selectivity of complex formation
    Berube, Marie
    Dowlut, Meenakshi
    Hall, Dennis G.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (17) : 6471 - 6479
  • [2] Synthesis of Furfural from Xylose and Xylan
    Binder, Joseph B.
    Blank, Jacqueline J.
    Cefali, Anthony V.
    Raines, Ronald T.
    [J]. CHEMSUSCHEM, 2010, 3 (11) : 1268 - 1272
  • [3] Mechanistic insights on the conversion of sugars into 5-hydroxymethylfurfural
    Binder, Joseph B.
    Cefali, Anthony V.
    Blank, Jacqueline J.
    Raines, Ronald T.
    [J]. ENERGY & ENVIRONMENTAL SCIENCE, 2010, 3 (06) : 765 - 771
  • [4] Fermentable sugars by chemical hydrolysis of biomass
    Binder, Joseph B.
    Raines, Ronald T.
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2010, 107 (10) : 4516 - 4521
  • [5] Simple Chemical Transformation of Lignocellulosic Biomass into Furans for Fuels and Chemicals
    Binder, Joseph B.
    Raines, Ronald T.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (05) : 1979 - 1985
  • [6] Liquid-phase catalytic processing of biomass-derived oxygenated hydrocarbons to fuels and chemicals
    Chheda, Juben N.
    Huber, George W.
    Dumesic, James A.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (38) : 7164 - 7183
  • [7] Borinic Acids: A Neglected Class of Organoboron Compounds for Recognition of Diols in Aqueous Solution
    Chudzinski, Michael G.
    Chi, Yuechuan
    Taylor, Mark S.
    [J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 2011, 64 (11) : 1466 - 1469
  • [8] Effect of spark timing and load on a DISI engine fuelled with 2,5-dimethylfuran
    Daniel, Ritchie
    Tian, Guohong
    Xu, Hongming
    Wyszynski, Miroslaw L.
    Wu, Xuesong
    Huang, Zuohua
    [J]. FUEL, 2011, 90 (02) : 449 - 458
  • [9] Boronate-Mediated Biologic Delivery
    Ellis, Gregory A.
    Palte, Michael J.
    Raines, Ronald T.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (08) : 3631 - 3634
  • [10] Haxel G.B., 2002, US GEOLOGICAL SURVEY