Deoxygenation of Biomass-Derived Feedstocks: Oxorhenium-Catalyzed Deoxydehydration of Sugars and Sugar Alcohols

被引:220
作者
Shiramizu, Mika [1 ]
Toste, F. Dean [1 ]
机构
[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
关键词
biomass; deoxydehydration; deoxygenation; rhenium; sustainable chemistry; ENANTIOSELECTIVE REDUCTION; RHENIUM; CHEMICALS; CONVERSION; PYROLYSIS; ALKENES; ROUTES; DIOLS; BOND; OIL;
D O I
10.1002/anie.201203877
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Turn sugar into oil: The deoxygenation reaction of sugar moieties is important for the conversion of biomass into chemicals and fuels. The methyltrioxorhenium-catalyzed deoxydehydration reaction was successfully applied to this purpose using another alcohol as solvent/reductant. The reaction was highly stereospecific, affording linear polyene products from C 4-C6 sugar alcohols and aromatic compounds from C 4-C6 sugars. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:8082 / 8086
页数:5
相关论文
共 43 条
[1]   Sulfite-Driven, Oxorhenium-Catalyzed Deoxydehydration of Glycols [J].
Ahmad, Irshad ;
Chapman, Garry ;
Nicholas, Kenneth M. .
ORGANOMETALLICS, 2011, 30 (10) :2810-2818
[2]   Catalytic conversion of biomass to biofuels [J].
Alonso, David Martin ;
Bond, Jesse Q. ;
Dumesic, James A. .
GREEN CHEMISTRY, 2010, 12 (09) :1493-1513
[3]   Rhenium-Catalyzed Didehydroxylation of Vicinal Dials to Alkenes Using a Simple Alcohol as a Reducing Agent [J].
Arceo, Elena ;
Ellman, Jonathan A. ;
Bergman, Robert G. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (33) :11408-11409
[4]   A Direct, Biomass-Based Synthesis of Benzoic Acid: Formic Acid-Mediated Deoxygenation of the Glucose-Derived Materials Quinic Acid and Shikimic Acid [J].
Arceo, Elena ;
Ellman, Jonathan A. ;
Bergman, Robert G. .
CHEMSUSCHEM, 2010, 3 (07) :811-813
[5]   An efficient didehydroxylation method for the biomass-derived polyols glycerol and erythritol. Mechanistic studies of a formic acid-mediated deoxygenation [J].
Arceo, Elena ;
Marsden, Peter ;
Bergman, Robert G. ;
Ellman, Jonathan A. .
CHEMICAL COMMUNICATIONS, 2009, (23) :3357-3359
[6]   POLYMERIZATION OF CONJUGATED TRIENES [J].
BELL, VL .
JOURNAL OF POLYMER SCIENCE PART A-GENERAL PAPERS, 1964, 2 (12PA) :5291-&
[7]   Technology development for the production of biobased products from biorefinery carbohydrates-the US Department of Energy's "Top 10" revisited [J].
Bozell, Joseph J. ;
Petersen, Gene R. .
GREEN CHEMISTRY, 2010, 12 (04) :539-554
[8]   Pentanol isomer synthesis in engineered microorganisms [J].
Cann, Anthony F. ;
Liao, James C. .
APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 2010, 85 (04) :893-899
[9]   Transformations of biomass-derived platform molecules: from high added-value chemicals to fuels via aqueous-phase processing [J].
Carlos Serrano-Ruiz, Juan ;
Luque, Rafael ;
Sepulveda-Escribano, Antonio .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (11) :5266-5281
[10]   Toward nonoxidative routes to oxygenated organics: Stereospecific deoxydehydration of diols and polyols to alkenes and allylic alcohols catalyzed by the metal oxo complex (C(5)Me(5))ReO3 [J].
Cook, GK ;
Andrews, MA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (39) :9448-9449