Understanding Ketone Hydrodeoxygenation for the Production of Fuels and Feedstocks From Biomass

被引：46

作者：

King, Amanda E. ^{[1
]}

Brooks, Ty J. ^{[1
]}

Tian, Yong-Hui ^{[2
]}

Batista, Enrique R. ^{[2
]}

Sutton, Andrew D. ^{[1
]}

机构：

[1] Los Alamos Natl Lab, Chem Div C IIAC, Los Alamos, NM 87544 USA

[2] Los Alamos Natl Lab, Theoret Div T 1, Los Alamos, NM 87544 USA

来源：

ACS CATALYSIS | 2015年 / 5卷 / 02期

关键词：

hydrodeoxygenation; biomass; ketone reduction; dehydration; mechanism; COBALT-CATALYZED HYDROGENATION; ACID; ORGANOCATALYSIS; COMPLEXES; XYLOSE; MILD;

D O I：

10.1021/cs501965w

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：

Although we can efficiently convert bioderived furans into linear alkanes, the most energy-intensive step in this approach is the hydrodeoxygenation of the intermediate polyketone. To fully understand this process, we have examined the hydrodeoxygenation of a model compound, 3-pentanone, which allows us to follow this process stepwise using Pd/C, H-2 (200 psi), and La(OTf)(3) in acetic acid to remove the oxygen atom at temperatures between 25 and 200 degrees C. We have found that ketone reduction to an alcohol is followed by acetoxylation, which provides a more facile route to C-O bond cleavage relative to the parent alcohol.

引用

页码：1223 / 1226

页数：4

共 20 条

[1] Hydrogenation of Carboxylic Acids Catalyzed by Half-Sandwich Complexes of Iridium and Rhodium [J].

Brewster, Timothy P. ;

Miller, Alexander J. M. ;

Heinekey, D. Michael ;

Goldberg, Karen I. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (43) :16022-16025

[2] Production of High-Quality Diesel from Biomass Waste Products [J].

Corma, Avelino ;

de la Torre, Olalla ;

Renz, Michael ;

Villandier, Nicolas .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (10) :2375-2378

[3] Stainless Steel As a Catalyst for the Total Deoxygenation of Glycerol and Levulinic Acid in Aqueous Acidic Medium [J].

Di Mondo, Domenico ;

Ashok, Devipriya ;

Waldie, Fraser ;

Schrier, Nick ;

Morrison, Michael ;

Schlaf, Marcel .

ACS CATALYSIS, 2011, 1 (04) :355-364

[4] KETONES FROM MONOCARBOXYLIC ACIDS - CATALYTIC KETONIZATION OVER OXIDE SYSTEMS [J].

GLINSKI, M ;

KIJENSKI, J ;

JAKUBOWSKI, A .

APPLIED CATALYSIS A-GENERAL, 1995, 128 (02) :209-217

[5] Hydrolysis of cellulose to glucose by solid acid catalysts [J].

Huang, Yao-Bing ;

Fu, Yao .

GREEN CHEMISTRY, 2013, 15 (05) :1095-1111

[6] Synthesis of transportation fuels from biomass: Chemistry, catalysts, and engineering [J].

Huber, George W. ;

Iborra, Sara ;

Corma, Avelino .

CHEMICAL REVIEWS, 2006, 106 (09) :4044-4098

[7] Iron Borohydride Pincer Complexes for the Efficient Hydrogenation of Ketones under Mild, Base-Free Conditions: Synthesis and Mechanistic Insight [J].

Langer, Robert ;

Iron, Mark A. ;

Konstantinovski, Leonid ;

Diskin-Posner, Yael ;

Leitus, Gregory ;

Ben-David, Yehoshoa ;

Milstein, David .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (23) :7196-7209

[8] Efficient Hydrogenation of Ketones Catalyzed by an Iron Pincer Complex [J].

Langer, Robert ;

Leitus, Gregory ;

Ben-David, Yehoshoa ;

Milstein, David .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (09) :2120-2124

[9] Diesel and Alkane Fuels From Biomass by Organocatalysis and Metal-Acid Tandem Catalysis [J].

Liu, Dajiang ;

Chen, Eugene Y. -X. .

CHEMSUSCHEM, 2013, 6 (12) :2236-2239

[10] Integrated Catalytic Process for Biomass Conversion and Upgrading to C12 Furoin and Alkane Fuel [J].

Liu, Dajiang ;

Chen, Eugene Y. -X. .

ACS CATALYSIS, 2014, 4 (05) :1302-1310

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