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(682i) Controlling Reactivity in Levoglucosenone Conversion to Renewable Chemicals over Metal and Acid Catalysts

Krishna, S. H., University of Wisconsin-Madison
Assary, R., Argonne National Laboratory
McClelland, D. J., University of Wisconsin-Madison
Rashke, Q. A., University of Wisconsin-Madison
Schmidt, Z. R., University of Wisconsin-Madison
Curtiss, L. A., Argonne National Laboratory
Weckhuysen, B. M., Utrecht University
Dumesic, J. A., University of Wisconsin-Madison
Huber, G. W., University of Wisconsin-Madison
De bruyn, M., Utrecht University

line-height:107%;font-family:" times new roman>Title: Controlling
Reactivity in Levoglucosenone Conversion to Renewable Chemicals over Metal and
Acid Catalysts

line-height:107%;font-family:" times new roman>Abstract: Lignocellulosic
biomass is an abundant, renewable source of carbon which could be used to
produce a variety of oxygenated chemicals, forming the basis for a sustainable
chemical industry. Levoglucosenone (LGO) can be produced from cellulose in 50%
yield using a polar aprotic solvent and acid catalyst [1]. In this work, we
investigate the catalytic conversion of LGO to molecules with applications as
green solvents and polymer precursors (Figure 1). Relevant reactions include hydrogenation
over metal catalysts [2], and hydrogenolysis over bifunctional metal-acid
catalysts [3,4]. Reaction pathways are elucidated using a combination of techniques
including analysis of selectivity versus conversion, reaction kinetics,
considerations of stereochemistry, isotopic labeling, variation of catalyst properties,
and quantum chemical calculations. Our mechanistic understanding of the
catalytic chemistry of LGO conversion provides directions for the rational
design of processes to produce valuable chemicals from biomass.

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12.0pt;line-height:107%;font-family:" times new roman>Figure 1.
Reaction pathways for conversion of levoglucosenone over metal and acid

line-height:107%;font-family:" times new roman>References:

line-height:107%;font-family:" times new roman>[1] F. Cao, T. J.
Schwartz, D. J. McClelland, S. H. Krishna, J. A. Dumesic and G. W. Huber,
"Dehydration of cellulose to levoglucosenone using polar aprotic solvents,"
Energy & Environmental Science, 2015, 8, 1808-1815.

line-height:107%;font-family:" times new roman>[2] S. H. Krishna, D. J.
McClelland, Q. A. Rashke, J. A. Dumesic and G. W. Huber, "Hydrogenation of
levoglucosenone to renewable chemicals," Green Chemistry, 2017, 19,

line-height:107%;font-family:" times new roman>[3] S. H. Krishna, R. S.
Assary, Q. A. Rashke, Z. R. Schmidt, L. A. Curtiss, J. A. Dumesic and G. W.
Huber, "Mechanistic Insights into the Hydrogenolysis of Levoglucosanol
over Bifunctional Platinum Silica–Alumina Catalysts," ACS Catalysis,
2018, 3743-3753.

S. H. Krishna, M. De bruyn, Z. R. Schmidt, B. M. Weckhuysen, J. A. Dumesic and
G. W. Huber, "Catalytic production of hexane-1,2,5,6-tetrol from
bio-renewable levoglucosanol in water: effect of metal and acid sites on
(stereo)-selectivity," Green Chemistry, 2018, 20, 4557-4565.

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