TY - JOUR
T1 - Chemicals from Biomass
T2 - Combining Ring-Opening Tautomerization and Hydrogenation Reactions to Produce 1,5-Pentanediol from Furfural
AU - Brentzel, Zachary J.
AU - Barnett, Kevin J.
AU - Huang, Kefeng
AU - Maravelias, Christos T.
AU - Dumesic, James A.
AU - Huber, George W.
N1 - Funding Information:
This material is based upon work supported by the Department of Energy, Office of Energy Efficiency and Renewable Energy (EERE), under Award Number DE-EE0006878, and the National Science Foundation Engineering Research Center for Biorenewable Chemicals (CBiRC), under Award Number EEC-0813570. The authors would like to thank the Magnetic Resonance Facility in the Chemistry Department of the University of Wisconsin-Madison for use of the Bruker Advance III 500 gifted by Paul J. Bender. We thank William Banholzer for helpful discussions about α,ω-diols. Any opinions, findings, and conclusions or recommendations expressed in this material are those of the authors and do not necessarily reflect the views of the Department of Energy or National Science Foundation.
Publisher Copyright:
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2017/4/10
Y1 - 2017/4/10
N2 - A process for the synthesis of 1,5-pentanediol (1,5-PD) with 84 % yield from furfural is developed, utilizing dehydration/hydration, ring-opening tautomerization, and hydrogenation reactions. Although this process has more reaction steps than the traditional direct hydrogenolysis of tetrahydrofurfuryl alcohol (THFA), techno-economic analyses demonstrate that this process is the economically preferred route for the synthesis of biorenewable 1,5-PD. 2-Hydroxytetrahydropyran (2-HY-THP) is the key reaction pathway intermediate that allows for a decrease in the minimum selling price of 1,5-PD. The reactivity of 2-HY-THP is 80 times greater than that of THFA over a bimetallic hydrogenolysis catalyst. This enhanced reactivity is a result of the ring-opening tautomerization to 5-hydoxyvaleraldehyde and subsequent hydrogenation to 1,5-PD.
AB - A process for the synthesis of 1,5-pentanediol (1,5-PD) with 84 % yield from furfural is developed, utilizing dehydration/hydration, ring-opening tautomerization, and hydrogenation reactions. Although this process has more reaction steps than the traditional direct hydrogenolysis of tetrahydrofurfuryl alcohol (THFA), techno-economic analyses demonstrate that this process is the economically preferred route for the synthesis of biorenewable 1,5-PD. 2-Hydroxytetrahydropyran (2-HY-THP) is the key reaction pathway intermediate that allows for a decrease in the minimum selling price of 1,5-PD. The reactivity of 2-HY-THP is 80 times greater than that of THFA over a bimetallic hydrogenolysis catalyst. This enhanced reactivity is a result of the ring-opening tautomerization to 5-hydoxyvaleraldehyde and subsequent hydrogenation to 1,5-PD.
KW - biomass
KW - catalysis
KW - hydrogenation
KW - sustainable chemistry
KW - α,ω-diols
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U2 - 10.1002/cssc.201700178
DO - 10.1002/cssc.201700178
M3 - Article
C2 - 28277620
AN - SCOPUS:85015362043
SN - 1864-5631
VL - 10
SP - 1351
EP - 1355
JO - ChemSusChem
JF - ChemSusChem
IS - 7
ER -