Bio-based building blocks from 5-hydroxymethylfurfural via 1-hydroxyhexane-2,5-dione as intermediate

Abstract

1-Hydroxy-2,5-hexanedione, obtained in good yield from renewable 5-hydroxymethylfurfural, is a versatile building block for a variety of new compounds.

Mechanistic understanding of humin formation in the conversion of glucose and fructose to 5-hydroxymethylfurfural in [BMIM]Cl ionic liquid

“…[1][2][3][4][5][6][7] Among products that can be obtained from cellulose, 5-hydroxymethylfurfural (5-HMF) has been recognized as a potentially versatile platform chemical. [8][9][10] 5-HMF and its derivatives offer the potential to replace an array of compounds derived from fossil fuels, enabling biomass to be a viable feedstock for the production of liquid fuels and chemicals. [11][12][13] Especially, 2,5furandicarboxylic acid, the oxidation product of 5-HMF, is an alternative of puried terephthalic acid (PTA) monomer.…”

Preparation of 1-Hydroxy-2,5-hexanedione from HMF by the Combination of Commercial Pd/C and Acetic Acid

“…G. Descotes et al gave the first report on this transformation with a yield of 60% of HHD using Pt/C and oxalic acid, in 1991 [48]. After that, there were several reports on the hydrogenation of HMF to HHD catalyzed by heterogeneous or homogeneous precious metal catalysts [48][49][50][51][52][53][54][55][56]. Ir or Ru is favored as a homogeneous catalyst and Pd or Au are effective as heterogeneous catalysts.…”

Direct Catalytic Conversion of Furfural to Furan‐derived Amines in the Presence of Ru‐based Catalyst

“…In the case of benzaldehyde, the byproduct formed was bis(1‐phenylethyl)amine. In the presence of hexanedione, a cyclization occurred to produce pyrrole as was reported by de Vries and co‐workers with the formation of 2‐(2‐(furan‐2‐yl)vinyl)‐5‐methyl‐1 H ‐pyrrole (28 %) and 2‐(2‐(furan‐2‐yl)ethyl)‐5‐methyl‐1 H ‐pyrrole (65 %). These results confirm that Ru/C enables a selective synthesis of biobased primary amines with the possibility to produce pyrrole.…”