From Lignocellulosic Biomass to Furans via 5-Acetoxymethylfurfural as an Alternative to 5-Hydroxymethylfurfural

• Published in: ChemSusChem 2015-04, Vol.8 (7), p.1179-1188
• Main Authors: Kang, Eun-Sil, Hong, Yeon-Woo, Chae, Da Won, Kim, Bora, Kim, Baekjin, Kim, Yong Jin, Cho, Jin Ku, Kim, Young Gyu
• Format: Article
• Language: English
• Subjects: Acetates - chemistry; Biomass; Furaldehyde - analogs & derivatives; Furaldehyde - chemical synthesis; Furaldehyde - chemistry; Furaldehyde - isolation & purification; furan derivatives; Hydrophobic and Hydrophilic Interactions; Lignin - chemistry; Lignocellulose; reaction mechanisms; renewable resources; synthesis design
• ISSN: 1864-5631; 1864-564X
• DOI: 10.1002/cssc.201403252

A facile pathway to furan derivatives from lignocellulosic biomass via 5‐acetoxymethylfurfural (AMF) was developed. AMF possesses advantageous properties due to its less‐hydrophilic acetoxymethyl group relative to the hydroxymethyl group of 5‐hydroxymethylfurfural (HMF). The hydrophobicity and chemical stability of AMF allowed practical isolation and purification to afford a highly pure product of up to 99.9 %. AMF was produced in good to excellent yields under mild conditions from 5‐chloromethylfurfural (CMF) and alkylammonium acetates, both of which could be obtained directly from lignocellulosic biomass. Heterogeneous reactions with polymer‐supported alkylammonium acetates were also established; this showed the feasibility of a continuous process for this pathway. AMF could be transformed into various promising furanic compounds, such as 2,5‐furandicarboxylic acid (FDCA), 2,5‐furandimethanol (FDM), and 5‐hydroxymethyl‐2‐furanoic acid (HFA), in high yields. Alternative routes: A facile pathway to furan derivatives from lignocellulosic biomass via 5‐acetoxymethylfurfural (AMF) is reported. AMF possesses advantageous properties to well‐known 5‐hydroxymethylfurfural (HMF) and can be transformed into various promising furanic compounds in high yields.