Abstract
A prominent challenge in replacing petrochemical polymers with bioderived alternatives is the efficient transformation of biomass into useful monomers. In this work, we demonstrate a practical process for the synthesis of multifunctional alcohols from five- and six-carbon acids using heterogeneous catalysts in aqueous media. Design of this process was guided by thermodynamic calculations, which indicate the need for two sequential high-pressure hydrogenations: one, reduction of the acid to a lactone at high temperature; two, further reduction of the lactone to the corresponding diol or triol at low temperature. For example, the conversion of mesaconic acid into (α or β)-methyl-γ-butyrolactone was achieved with 95 % selectivity at a turnover frequency of 1.2 min−1 over Pd/C at 240 °C. Subsequent conversion of (α or β)-methyl-γ-butyrolactone into 2-methyl-1,4-butanediol was achieved with a yield of 80 % with Ru/C at 100 °C. This process is an efficient method for the production of lactones, diols, and triols, all valuable monomers for the synthesis of bioderived branched polyesters.
Original language | English (US) |
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Pages (from-to) | 3031-3035 |
Number of pages | 5 |
Journal | ChemCatChem |
Volume | 8 |
Issue number | 19 |
DOIs | |
State | Published - Oct 6 2016 |
Bibliographical note
Funding Information:This work was supported by the National Science Foundation through the University of Minnesota Center for Sustainable Polymers under award number CHE-1413862. D.K.S. acknowledges support from a doctoral fellowship awarded by the University of Minnesota Graduate School. We thank Ryan E. Patet for assistance with DFT calculations.
Publisher Copyright:
© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Keywords
- biomass
- diols
- heterogeneous catalysis
- polymers
- sustainable chemistry