TY - JOUR
T1 - Catalytic strategy for conversion of fructose to organic dyes, polymers, and liquid fuels
AU - Chang, Hochan
AU - Bajaj, Ishan
AU - Huber, George W.
AU - Maravelias, Christos T.
AU - Dumesic, James A.
N1 - Funding Information:
This material is based upon work supported in part by the Great Lakes Bioenergy Research Center, U.S. Department of Energy, Office of Science, Office of Biological and Environmental Research under Award Number DE-SC0018409 and in part by U.S. Department of Energy under Award Number DE-EE0008353. We thank the Mass Spectrometry and NMR facilities that are funded by: Thermo Q ExactiveTM Plus by NIH 1S10 OD020022-1; Bruker Quazar APEX2 and Bruker Avance-500 by a generous gift from Paul J. and Margaret M. Bender; Bruker Avance-600 by NIH S10 OK012245; Bruker Avance-400 by NSF CHE-414 1048642 and the University of Wisconsin-Madison. We thank Minsoo Ju for help in NMR analysis of HAH dimer.
Publisher Copyright:
© The Royal Society of Chemistry.
PY - 2020/8/21
Y1 - 2020/8/21
N2 - We report a process to produce a versatile platform chemical from biomass-derived fructose for organic dye, polymer, and liquid fuel industries. An aldol-condensed chemical (HAH) is synthesized as a platform chemical from fructose by catalytic reactions in acetone/water solvent with non-noble metal catalysts (e.g., HCl, NaOH). Then, selective reactions (e.g., etherification, reduction, dimerization) of the functional groups, such as enone and hydroxyl groups, in the HAH molecule enable applications in organic dyes and polyether precursors. High yields of target products, such as 5-(hydroxymethyl) furfural (HMF) (85.9% from fructose) and HAH (86.3% from HMF) are achieved by sequential dehydration and aldol-condensation with a simple purification process (>99% HAH purity). The use of non-noble metal catalysts, the high yield of each reaction, and the simple purification of the target product allow for beneficial economics of the process. Techno-economic analysis indicates that the process produces HAH at minimum selling price (MSP) of $1958 per ton. The MSP of HAH product allows the economic viability of applications in organic dye and polyether markets by replacing its counterparts, such as anthraquinone ($3200-$3900 per ton) and bisphenol-A ($1360-$1720 per ton).
AB - We report a process to produce a versatile platform chemical from biomass-derived fructose for organic dye, polymer, and liquid fuel industries. An aldol-condensed chemical (HAH) is synthesized as a platform chemical from fructose by catalytic reactions in acetone/water solvent with non-noble metal catalysts (e.g., HCl, NaOH). Then, selective reactions (e.g., etherification, reduction, dimerization) of the functional groups, such as enone and hydroxyl groups, in the HAH molecule enable applications in organic dyes and polyether precursors. High yields of target products, such as 5-(hydroxymethyl) furfural (HMF) (85.9% from fructose) and HAH (86.3% from HMF) are achieved by sequential dehydration and aldol-condensation with a simple purification process (>99% HAH purity). The use of non-noble metal catalysts, the high yield of each reaction, and the simple purification of the target product allow for beneficial economics of the process. Techno-economic analysis indicates that the process produces HAH at minimum selling price (MSP) of $1958 per ton. The MSP of HAH product allows the economic viability of applications in organic dye and polyether markets by replacing its counterparts, such as anthraquinone ($3200-$3900 per ton) and bisphenol-A ($1360-$1720 per ton).
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U2 - 10.1039/d0gc01576h
DO - 10.1039/d0gc01576h
M3 - Article
C2 - 34703386
AN - SCOPUS:85091166504
SN - 1463-9262
VL - 22
SP - 5285
EP - 5295
JO - Green Chemistry
JF - Green Chemistry
IS - 16
ER -