Abstract
The kinetic curves of levulinic acid accumulation in the process of saccharide dehydration at 80-98oC are compared. The structural features of the substrates and 5-hydroxymethylfurfural, which is the intermediate of the process, explain the observed difference in the rates of fructose and glucose conversion. Sulfuric acid can be effectively used under moderate conditions to synthesize levulinic acid with yields exceeding 35 mol % for glucose and 50% for sucrose at 98oC.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
B.V. Timokhin, V.A. Baransky, G.D. Eliseeva: Russian Chemical Reviews, 1, 80 (1999).
F.W. Lichtenthaler: Carbohydrate Res., 313 (1998).
B.I. Tokarev, V.I. Sharkov: Study of Hydroxymethylfurfural Formation in the Process of Cellulose Hydrolysis. Sb. tr. LLTA, Leningrad. Vol. 102, 153 (1963).
B.M. Levitin: Levulinic Acid. Properties, Production and Applications. Moscow 1978.
J. Horvat, B. Klaic, B. Metelko, V. Sunjic: Tetrahedron Lett., 26, 2111 (1985).
B.F.M. Kuster, H.S. van der Baan: Carbohydrate Res., 54, 165 (1977).
B.F.M. Kuster, H.M.G. Temmink: Carbohydrate Res., 54, 185 (1977).
S.K. Tyrlika, D. Szerszen, M. Olejnik, W. Danikiewicz: Carbohydrate Res., 315, 268 (1999).
W.A. Farone, J.E. Cuzens: US Pat. 6,054,611, 2000.
G.G. Pervishina, A.A. Efremov, B.N. Kuznetsov: J. Plant Raw Materials (Russia), 1, 11 (1998); http://www.dcn-asu.ru/chemwood.
L.F. Fieser, M. Fieser: Reagents for Organic Synthesis, New-York-London-Sydney 1968.
V.I. Sharkov: Hydrolysis of Wood. Leningrad 1936.
Comprehensive Organic Chemistry, E. Haslam (Ed.), Pergamon Press, Vol. 11, 1979.
H.E. van Dam, A.P.G. Kieboom, H. van Bekkum: Starch/Staerke, 38, 95 (1986).
M.S. Feather, J.F. Harris: Adv. Carbohyd. Chem. Biochem., 28, 161 (1973).
A.J. Gordon, R.A. Ford: A Handbook of Practical Data, Techniques and References. New York, London, Sydney, Toronto 1972.
D.W. Harris, M.S. Feather: J. Am. Chem. Soc., 97, 178 (1975).
B.D. Berezin, D.B. Berezin: Handbook of Modern Organic Chemistry, p. 640. Vysshaya Shkola, Moscow 1999.
K. Lourvanij, G.L. Rorrer: Ind. Eng. Chem. Res., 32, 11 (1993).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Tarabanko, V., Chernyak, M., Aralova, S. et al. Kinetics of levulinic acid formation from carbohydrates at moderate temperatures. Reaction Kinetics and Catalysis Letters 75, 117–126 (2002). https://doi.org/10.1023/A:1014857703817
Issue Date:
DOI: https://doi.org/10.1023/A:1014857703817