Methods for conversion of carbohydrates in ionic liquids to...

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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C549S489000

Reexamination Certificate

active

07939681

ABSTRACT:
Methods are described for converting carbohydrates including, e.g., monosaccharides, disaccharides, and polysaccharides in ionic liquids to value-added chemicals including furans, useful as chemical intermediates and/or feedstocks. Fructose is converted to 5-hydroxylmethylfurfural (HMF) in the presence of metal halide and acid catalysts. Glucose is effectively converted to HMF in the presence of chromium chloride catalysts. Yields of up to about 70% are achieved with low levels of impurities such as levulinic acid.

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patent: 6518440 (2003-02-01), Lightner
patent: 2006063220 (2006-06-01), None
Dortmund Database Aug. 31, 2005 online: “http://www.ddbst.de
ew/downloads/ListOflonicLiquidsInTheDDB2005-08-31.pdf” accessed May 12, 2010.
Murugesan et. al. “Ionic Liquids in Carbohydrate Chemistry—Current Trends and Future Directions” Current Organic Synthesis 2005, 2, 437-451.
Gelas, et. al. “A new method for the preparation of 5-hydroxymethyl-2-furaldehyde by the reaction of ammonium or immonium salts with mono-, oligo- and polysaccharides. Direct access to 5-halomethy1-2-furaldehydes.” Carbohydrate Research, 1983, 122(1), 59-68.(translation of pp. 65-66 experimental).
“Carbohydrate” IUPAC Goldbook 1997, online: “http://www.iupac.org/goldbook/C00820.pdf” accessed May 12, 2010.
Dieter, et al, Ionic Structure and Interactions in 1-Methyl-3 ethylimidazolium Chloride-A1C13 Molten Salts, J. Am. Chem Soc. 1988, 110, pp. 2722-2726.
Lansalot-Matras, et al., Dehydration of fructose into 5-hydroxymethylfurfural in the presence of ionic liquids, Catalysis Communications, vol. 4, (2003), pp. 517-520.
Moreau, et al., Dehydration of fructose and sucrose into 5-hydroxymethylfurfural in the presence of 1-H-3-methyl imidazolium chloride acting both as solvent and catayst, Journal of Molecular Catalysis A: Chemical 253 (2006) pp. 165-169.
Office Action (Mail Date Jun. 16, 2010) from U.S. Appl. No. 12/110,997, filed Apr. 28, 2008.

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