Journal
POLYHEDRON
Volume 149, Issue -, Pages 153-162Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.poly.2018.03.035
Keywords
Glucose; 5-Hydroxymethylfurfural; Aluminum catalysts; Dehydration; Ionic liquids
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Funding
- Kentucky Science Foundation [KSEF-2428-RDE-014]
- US National Science Foundation [CBET 1604491]
- CRIF program of the US National Science Foundation [CHE-9974810]
- NSF [MRI CHE0319176, CHE1625732]
- Direct For Mathematical & Physical Scien [1625732] Funding Source: National Science Foundation
- Division Of Chemistry [1625732] Funding Source: National Science Foundation
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Air-stable dimethylaluminum complexes L(R)AIMe(2) that contain (aminomethyl)phenolate (L-R) ligands were prepared in high yield. NMR data and X-ray crystallographic characterization of the molecular structures of several of the complexes confirmed bidentate coordination of the (aminomethyl)phenolate ligand to aluminum. Efficient aluminum catalysts for glucose dehydration to HMF were generated via modification of the (aminomethyl)phenolate ligand. L(R)AIMe(2) complexes containing bidentate (aminomethyl)phenolate ligands with an aryl substituent on the amino moiety are efficient catalysts for glucose dehydration to HMF in ionic liquid solvents. In [EMIM]Br and [BMIM]Br, the reaction proceeds at 120 degrees C to very high conversion in 2 h to produce HMF with 60-63% selectivity and in 58-60% yield. Evidently, L(R)AIMe(2) complexes catalyze glucose isomerization to fructose at >= 120 degrees C while the HMF yield depends on the degree of competing HMF loss to humins formation. These results indicate that additional studies of ancillary ligand effects on aluminum-catalyzed glucose dehydration are needed to improve knowledge of structure-function relationships that are key to increasing the efficiency of aluminum catalysts for dehydration of glucose (and ultimately cellulose) to HMF. Published by Elsevier Ltd.
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