Journal
ACS CATALYSIS
Volume 10, Issue 4, Pages 2667-2683Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.9b05055
Keywords
biomass; homogeneous catalysis; hydrodeoxygenation; hydrogenation; diols; Piancatelli rearrangement
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Funding
- Canadian Natural Sciences and Engineering Research Council (NSERC)
- Ontario Ministry of Agriculture, Food and Rural Affairs (OMAFRA) Bioeconomy Research programs
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The complex trans-[(2,9-dipyridyl-1,10-phenanthroline)(CH3CN)(2)Ru](OTf)(2) was synthesized and tested as a homogeneous hydrodeoxygenation catalyst for the conversion of biomass-derived furfuryl alcohol and furfuryl acetate to 1,4-pentanediol (as the primary target compound) and cyclopentanol (formed by the competing Piancatelli rearrangement) in aqueous reaction medium at elevated temperature (150-200 degrees C) and hydrogen pressure (800 psi = 5.12 MPa). Catalytic reactions using furfuryl alcohol as a substrate were limited by the formation of solid resins with the product yields showing a strong negative correlation with increasing substrate concentration and maximum yields of 1,4-pentanediol and cyclopentanol being 23 and 41%, respectively. A two-level full factorial design of experiments study with four independent input variables (temp., time, [cat.], [substrate]) and a center point was carried out for the conversion of furfuryl acetate, showing good reproducibility between replicates and no humin formation. This enabled a full statistical analysis of the input variable impact on product distribution and yield. The maximum yields of 1,4-pentanediol and cyclopentanol using furfuryl acetate as a substrate are 68 and 35%, respectively. The decreased self-reactivity of furfuryl acetate versus furfuryl alcohol dramatically increases the yields of target products but still shows a strong negative correlation of the yield of the desired products with increasing substrate concentration.
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