5-Hydroxymethylfurfural (HMF), an important versatile sugar derivative has been synthesized from glucose using catalytic amounts of CrCl2 in 1-ethyl-3-methylimidizolium chloride. Glycerol and glyceraldehyde were tested as sugar model compounds. Glycerol is unreactive and does not interfere with glucose conversion. Glyceraldehyde is reactive and does interfere with glucose conversion in competitive experiments. MnCl2 or FeCl2 catalyze dehydration of glyceraldehyde dimer to form compound I, a cyclic hemiacetal with an exocyclic double bond. Upon aqueous work-up I forms pyruvaldehyde. CrCl2 or VCl3 further catalyze a hydride transfer of I to form lactide. Upon aqueous work-up lactide is converted to lactic acid.
Revised: June 2, 2010 |
Published: April 3, 2008
Citation
Holladay J.E., H.M. Brown, A.M. Appel, and Z.C. Zhang. 2008.Novel Hydride Transfer Catalysis for Carbohydrate Conversions. In Proceedings of the 22nd Conference on Catalysis of Organic Reactions, edited by ML Prunier, 123, 411-418. Boca Raton, Florida:CRC Press.PNNL-SA-58413.