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 - 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
UR - http://www.scopus.com/inward/record.url?scp=85015362043&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85015362043&partnerID=8YFLogxK
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 -