(205d) Influence of Water and Solvents on the Production of Levoglucosenone and 5-(Hydroxymethyl)Furfural from Cellulose

Authors: 
He, J., University of Wisconsin-Madison
Cao, F., Nanjing Tech University
Karanjkar, P. U., University of Wisconsin-Madison
Krishna, S. H., University of Wisconsin-Madison
Huang, K., University of Wisconsin-Madison
Maravelias, C. T., University of Wisconsin-Madison
Dumesic, J., University of Wisconsin-Madison
Huber, G. W., University of Wisconsin-Madison
Cellulose is the most abundant renewable source of carbon on the earth. 5-hydroxymethylfurfural (HMF) as a major decomposition product from cellulose hydrolysis is one of the most promising platform chemical. Anhydro-sugars could also be obtained from cellulose depolymerization via pyrolysis or dehydration under anhydrous conditions. Levoglucosenone (LGO) is an anhydro-sugars that has potential as a chiral building block, which was used for the synthesis of a wide variety of high value pharmaceuticals. Both HMF and LGO could be converted to 1,6-hexanediol, which could serve as a precusor in polymer industry. Water, which is ubiquitus in biomass feedstock and solvents both play very important role on the product selectivites during the formation of HMF and LGO from cellulose.

In the absence of water, cellulose is first dehydrated to form anhydro-sugar (Levoglucosan), which could be further dehydrated to LGO. The final product distribution could be controlled by the addition of water to the reaction system. Cellulose will be hydrolyzed to glucose, which could be further dehydrated to HMF. The selectivity to HMF will gradually increase with increasing water content in the solvent. A series of solvents have been screened for the production of HMF and LGO from cellulose, it has been shown that the use of polar, aprotic solvents is very promising.