Green Chemicals: A Kinetic Study on the Conversion of Glucose to Levulinic Acid

Levulinic acid has been identified as a promising green, biomass derived platform chemical. A kinetic study on one of the key steps in the conversion of biomass to levulinic acid, i.e., the acid catalysed decomposition of glucose to levulinic acid has been performed. The experiments were performed in a broad temperature window (140–200°C), using sulphuric acid as the catalyst (0.05–1 M) and a initial glucose concentration between 0.1 and 1 M. A kinetic model of the reaction sequence was developed including the kinetics for the intermediate 5-hydroxymethyl-2-furaldehyde (HMF) and humins byproducts using a power-law approach. The yield of levulinic acid is favoured in dilute glucose solution at high acid concentration. On the basis of the kinetic results, continuous reactor configurations with a high extent of back-mixing are preferred to achieve high levulinic acid yields.

[1]  K. Heimlich,et al.  A Kinetic Study of Glucose Degradation in Acid Solution , 1960 .

[2]  F. Tanimoto,et al.  LEVULINIC ACID, A NEW CHEMICAL RAW MATERIAL. ITS CHEMISTRY AND USE , 1976 .

[3]  Jerome F. Saeman,et al.  Kinetics of Wood Saccharification - Hydrolysis of Cellulose and Decomposition of Sugars in Dilute Acid at High Temperature , 1945 .

[4]  Michael R Ladisch,et al.  Characterization of acid catalytic domains for cellulose hydrolysis and glucose degradation. , 2002, Biotechnology and bioengineering.

[5]  C. Knightes,et al.  Statistical analysis of nonlinear parameter estimation for Monod biodegradation kinetics using bivariate data. , 2000, Biotechnology and bioengineering.

[6]  M. Feather,et al.  Intramolecular carbon-2 .far. carbon-1 hydrogen transfer reactions during the conversion of aldoses to 2-furaldehydes , 1974 .

[7]  R. Helm,et al.  The reversion reactions of D-glucose during the hydrolysis of cellulose with dilute sulfuric acid , 1989 .

[8]  B. Kuster,et al.  5‐Hydroxymethylfurfural (HMF). A Review Focussing on its Manufacture , 1990 .

[9]  D. A. Palmer,et al.  Dissociation constant of bisulfate ion in aqueous sodium chloride solutions to 250 degree C , 1990 .

[10]  B. Kuster,et al.  The influence of the initial and catalyst concentrations on the dehydration of d-fructose , 1977 .

[11]  T. Brubaker,et al.  Nonlinear Parameter Estimation , 1979 .

[12]  M. Hanna,et al.  Industrial Applications for Levulinic Acid , 1997 .

[13]  M. Wolfrom,et al.  Acid Reversion Products from D-Glucose , 1954 .

[14]  P. McCarty,et al.  Thermochemical pretreatment of lignocellulose to enhance methane fermentation: I. Monosaccharide and furfurals hydrothermal decomposition and product formation rates , 1988, Biotechnology and bioengineering.

[15]  G. T. Tsao,et al.  CORRELATION OF GLUCOSE (DEXTROSE) DEGRADATION AT 90 TO 190°C IN 0.4 TO 20% ACID , 1987 .

[16]  R. H. Leonard.  Levulinic Acid as a Basic Chemical Raw Material , 1956 .

[17]  Andrew Porteous,et al.  Kinetics of the acid hydrolysis of cellulose found in paper refuse , 1971 .

[18]  Qian Xiang,et al.  Kinetics of glucose decomposition during dilute-acid hydrolysis of lignocellulosic biomass , 2004, Applied biochemistry and biotechnology.

[19]  M. Feather,et al.  Evidence for a C-2→C-1 intramolecular hydrogen-transfer during the acid-catalyzed isomerization of D-glucose to D-fructose ag]☆☆☆ , 1973 .

[20]  Yong Wang,et al.  Production of levulinic acid and use as a platform chemical for derived products , 2000 .

[21]  T. E. Edwards,et al.  114. Quantitative aspects of the acid reversion of glucose , 1958 .

[22]  B. V. Timokhin,et al.  Levulinic acid in organic synthesis , 1999 .

[23]  M. Feather,et al.  Mechanism of the interconversion of D-glucose, D-mannose, and D-fructose in acid solution , 1975 .

[24]  J. Horvat,et al.  Mechanism of levulinic acid formation , 1985 .

[25]  H. V. Bekkum,et al.  The Conversion of Fructose and Glucose in Acidic Media: Formation of Hydroxymethylfurfural , 1986 .

[26]  Gerard Avignon,et al.  Dehydration of fructose to 5-hydroxymethylfurfural over H-mordenites , 1996 .