(475f) Selective Catalytic Production of Polyols from Cellulose-Derived Levoglucosenone

Authors: 
Krishna, S. H., University of Wisconsin-Madison
Dumesic, J. A., University of Wisconsin-Madison
Huber, G. W., University of Wisconsin-Madison
Schmidt, Z. R., University of Wisconsin-Madison

Reduced C6 polyols
are valuable precursors to bio-based polymers. [1] Herein, we report a new
catalytic route to produce polyols in high yield from the cellulose-derived
platform molecule levoglucosenone (LGO). [2] We identify key reaction
intermediates and study the roles of the different catalyst active sites on product
selectivity, allowing us to propose a mechanism for this reaction which is
analogous to well-known sugar chemistry. We also investigate the correlation
between the stereochemistry of the reactant and product, explaining these
observations in terms of the proposed mechanism. Product stereochemistry could
have an impact on the physico-chemical properties of the resulting polymers. Our
high-yield route to produce polyols from biomass-derived LGO, as well as our
understanding of the underlying catalytic chemistry, open the door to new
biomass-based polymers from LGO.

References.

1.
Corma, A.; Iborra, S.; Velty, A., Chemical Routes for the Transformation of
Biomass into Chemicals. Chemical Reviews 2007, 107 (6),
2411-2502.

2. Krishna, S. H.; McClelland,
D. J.; Rashke, Q. A.; Dumesic, J. A.; Huber, G. W., Hydrogenation of
levoglucosenone to renewable chemicals. Green Chemistry 2017, 19
(5), 1278-1285.