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From Furfural to Fuel: Synthesis of Furoins by Organocatalysis and their Hydrodeoxygenation by Cascade Catalysis
Author(s) -
Wegenhart Benjamin L.,
Yang Linan,
Kwan Soon Cheong,
Harris Remi,
Kenttämaa Hilkka I.,
AbuOmar Mahdi M.
Publication year - 2014
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201402056
Subject(s) - hydrodeoxygenation , furfural , chemistry , catalysis , organocatalysis , organic chemistry , selectivity , yield (engineering) , carbene , enantioselective synthesis , materials science , metallurgy
The synthesis of furoins from biomass‐derived furfural and 2‐methylfurfural is demonstrated in high yields in green and renewable solvents using N‐heterocyclic carbene organocatalysts. The resulting furoin molecules are used as precursors for fuels using cascade catalysis, first by using Pd/C with acidic co‐catalysts under very mild conditions to yield oxygenated C 12 molecules. Two main products were formed, which we identified as 1,2‐bis(5‐methyltetrahydrofuran‐2‐yl)ethane and 1‐(5‐methyltetrahydrofuran‐2‐yl)heptanol. The use of a Pd/Zeolite‐β catalyst under more extreme conditions resulted in the complete hydrodeoxygenation of 5,5′‐dimethylfuroin to dodecanes in high yields (76 %) and exceptional selectivity (94 %) for n ‐dodecane.