Conversion of Furfural Derivatives to 1,4-Pentanediol and Cyclopentanol in Aqueous Medium Catalyzed by trans-[(2,9-Dipyridyl-1,10-phenanthroline)(CH3CN)2Ru](OTf)2Click to copy article linkArticle link copied!
- Maryanne K. StonesMaryanne K. StonesThe Guelph-Waterloo-Centre for Graduate Work in Chemistry (GWC)2, Department of Chemistry, University of Guelph, 50 Stone Road East, Guelph, Ontario N1G 2W1, CanadaMore by Maryanne K. Stones
- Elise M.-J. Banz ChungElise M.-J. Banz ChungThe Guelph-Waterloo-Centre for Graduate Work in Chemistry (GWC)2, Department of Chemistry, University of Guelph, 50 Stone Road East, Guelph, Ontario N1G 2W1, CanadaMore by Elise M.-J. Banz Chung
- Igor Tadeu da CunhaIgor Tadeu da CunhaThe Guelph-Waterloo-Centre for Graduate Work in Chemistry (GWC)2, Department of Chemistry, University of Guelph, 50 Stone Road East, Guelph, Ontario N1G 2W1, CanadaMore by Igor Tadeu da Cunha
- Ryan J. SullivanRyan J. SullivanThe Guelph-Waterloo-Centre for Graduate Work in Chemistry (GWC)2, Department of Chemistry, University of Guelph, 50 Stone Road East, Guelph, Ontario N1G 2W1, CanadaMore by Ryan J. Sullivan
- Parnian SoltanipanahParnian SoltanipanahThe Guelph-Waterloo-Centre for Graduate Work in Chemistry (GWC)2, Department of Chemistry, University of Guelph, 50 Stone Road East, Guelph, Ontario N1G 2W1, CanadaMore by Parnian Soltanipanah
- Megan MageeMegan MageeThe Guelph-Waterloo-Centre for Graduate Work in Chemistry (GWC)2, Department of Chemistry, University of Guelph, 50 Stone Road East, Guelph, Ontario N1G 2W1, CanadaMore by Megan Magee
- Gary J. UmphreyGary J. UmphreyDepartment of Mathematics and Statistics, University of Guelph, 50 Stone Road East, Guelph, Ontario N1G 2W1, CanadaMore by Gary J. Umphrey
- Cameron M. MooreCameron M. MooreChemistry Division, Los Alamos National Laboratory, MS J514, Los Alamos, New Mexico 87545, United StatesMore by Cameron M. Moore
- Andrew D. SuttonAndrew D. SuttonChemistry Division, Los Alamos National Laboratory, MS J514, Los Alamos, New Mexico 87545, United StatesMore by Andrew D. Sutton
- Marcel Schlaf*Marcel Schlaf*E-mail: [email protected]The Guelph-Waterloo-Centre for Graduate Work in Chemistry (GWC)2, Department of Chemistry, University of Guelph, 50 Stone Road East, Guelph, Ontario N1G 2W1, CanadaMore by Marcel Schlaf
Abstract
The complex trans-[(2,9-dipyridyl-1,10-phenanthroline)(CH3CN)2Ru](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 °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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