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)2

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...

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Published inACS catalysis Vol. 10; no. 4; pp. 2667 - 2683
Main Authors Stones, Maryanne K, Banz Chung, Elise M.-J, da Cunha, Igor Tadeu, Sullivan, Ryan J, Soltanipanah, Parnian, Magee, Megan, Umphrey, Gary J, Moore, Cameron M, Sutton, Andrew D, Schlaf, Marcel
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LanguageEnglish
Published American Chemical Society 21.02.2020
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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.
AbstractList 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.
Author Sullivan, Ryan J
Umphrey, Gary J
Magee, Megan
Schlaf, Marcel
Stones, Maryanne K
Sutton, Andrew D
Moore, Cameron M
da Cunha, Igor Tadeu
Soltanipanah, Parnian
Banz Chung, Elise M.-J
AuthorAffiliation Department of Chemistry
The Guelph-Waterloo-Centre for Graduate Work in Chemistry (GWC)
Department of Mathematics and Statistics
Chemistry Division
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Keywords hydrodeoxygenation
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Piancatelli rearrangement
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Snippet The complex trans-[(2,9-dipyridyl-1,10-phenanthroline)­(CH3CN)2Ru]­(OTf)2 was synthesized and tested as a homogeneous hydrodeoxygenation catalyst for the...
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Title 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)2
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