title: From lignocellulosic biomass to furans via 5-acetoxymethylfurfural as an alternative to 5-hydroxymethylfurfural.
abstract: 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.
authors.affiliation: Department of Chemical and Biological Engineering, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 151-742 (Korea).
authors.forename: Eun-Sil
authors.initials: ES
authors.lastname: Kang
authors.forename: Yeon-Woo
authors.initials: YW
authors.lastname: Hong
authors.forename: Da Won
authors.initials: da W
authors.lastname: Chae
authors.forename: Bora
authors.initials: B
authors.lastname: Kim
authors.forename: Baekjin
authors.initials: B
authors.lastname: Kim
authors.forename: Yong Jin
authors.initials: YJ
authors.lastname: Kim
authors.forename: Jin Ku
authors.initials: JK
authors.lastname: Cho
authors.forename: Young Gyu
authors.initials: YG
authors.lastname: Kim
mesh_terms: D000085:Acetates / Q000737:chemistry; D018533:Biomass; D005662:Furaldehyde / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification; D057927:Hydrophobic and Hydrophilic Interactions; D008031:Lignin / Q000737:chemistry*
chemical_list: C000603995:5-acetoxymethylfurfural; D000085:Acetates; C036909:lignocellulose; C008046:5-hydroxymethylfurfural; D008031:Lignin; D005662:Furaldehyde
keywords: biomass; furan derivatives; reaction mechanisms; renewable resources; synthesis design