An efficient catalytic dehydration of fructose and sucrose to 5-hydroxymethylfurfural with protic ionic liquids.
The renewable furan-based platform chemical, 5-hydroxymethylfurfural (HMF), has been efficiently synthesized from d-fructose and sucrose in the presence of a catalytic amount of protic ionic liquids. The 1-methylimidazolium-based and N-methylmorpholinium-based ionic liquids are employed. As a result, 74.8% and 47.5% yields of HMF are obtained from d-fructose and sucrose, respectively, at 90 degrees C for 2h under nitrogen atmosphere when N-methylmorpholinium methyl sulfonate ([NMM](+)[CH(3)SO(3)](-)) is used as the catalyst in an N,N-dimethylformamide-lithium bromide (DMF-LiBr) system. The acidities of ionic liquids are determined by the Hammett method, and the correlation between acidity and catalytic activity is discussed. Moreover, the effects of reaction temperature and time are investigated, and a plausible reaction mechanism for the dehydration of d-fructose is proposed.
Tong
Xinli
X
Tianjin Key Laboratory of Applied Catalysis Science and Technology and State Key Laboratory of Chemical Engineering, School of Chemical Engineering, Tianjin University, Tianjin 300072, China.
Ma
Yang
Y
Li
Yongdan
Y
D002384:Catalysis; D003681:Dehydration; D005632:Fructose / Q000737:chemistry*; D005662:Furaldehyde / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D052578:Ionic Liquids / Q000737:chemistry*; D015394:Molecular Structure; D011522:Protons; D013395:Sucrose / Q000737:chemistry*; D013696:Temperature
D052578:Ionic Liquids; D011522:Protons; D005632:Fructose; D013395:Sucrose; C008046:5-hydroxymethylfurfural; D005662:Furaldehyde