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Ruthenium and Formic Acid Based Tandem Catalytic Transformation of Bioderived Furans to Levulinic Acid and Diketones in Water
Author(s) -
Dwivedi Ambikesh D.,
Gupta Kavita,
Tyagi Deepika,
Rai Rohit K.,
Mobin Shaikh M.,
Singh Sanjay K.
Publication year - 2015
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201501021
Subject(s) - levulinic acid , formic acid , chemistry , catalysis , ruthenium , furfural , organic chemistry
Efficient tandem catalytic transformations of bioderived furans, such as furfural, 5‐hydroxymethylfurfural (5‐HMF), and 5‐methylfurfural (5‐MF), to levulinic acid (LA) and diketones, 1‐hydroxyhexane‐2,5‐dione (1‐HHD), 3‐hydroxyhexane‐2,5‐dione (3‐HHD), and hexane‐2,5‐dione (2,5‐HD), was achieved by using water‐soluble arene–Ru II complexes, containing ethylenediamine‐based ligands, as catalysts in the presence of formic acid. The catalytic conversion of furans depends on the catalyst, ligand, formic acid concentration, reaction temperature, and time. Experimental evidence, including time‐resolved 1 H NMR spectral studies, indicate that the catalytic reaction proceeds first with formyl hydrogenation followed by hydrolytic ring opening of furans. The ruthenium–formic acid tandem catalytic transformation of fructose to diketones and LA was also achieved. Finally, the molecular structures of the four representative arene–Ru II catalysts were established by single‐crystal X‐ray diffraction studies.