Method for producing 5-hydroxymethylfurfural in the presence of catalysts of the family of homogeneous sulfonic acids in the presence of at least one aprotic polar solvent
The invention relates to a novel process for the conversion of a feedstock comprising at least one sugar to 5-hydroxymethylfurfural, in which said feedstock is contacted with one or more catalysts of the family of the homogeneous sulphonic acids in the presence of at least one aprotic polar solvent, used alone or in a mixture, at a temperature comprised between 30° C. and 200° C., and at a pressure comprised between 0.1 MPa and 10 MPa in which said catalysts are selected from the compounds of general formula
1. A process comprising producing 5-hydroxymethylfurfural by contacting a feedstock comprising at least one sugar with one or more homogeneous sulphonic acid catalysts in the presence of at least one aprotic polar solvent having a dipole moment expressed in Debye (D) greater than 2.00, the aprotic polar solvent being pyridine, butan-2-one, acetone, acetic anhydride, N,N,N′,N′-tetramethylurea, benzonitrile, acetonitrile, methyl ethyl ketone, propionitrile, hexamethylphosphoramide, nitrobenzene, nitromethane, N,N-dimethylformamide, N,N-dimethylacetamide, sulpholane, N-methylpyrrolidone, dimethyl sulphoxide, propylene carbonate or γ-valerolactone, used alone or in a mixture, at a temperature of 30° C. to 200° C., and at a pressure of 0.1 MPa to 10 MPa in which said catalysts have formula
in which R is
halogen,
linear or branched, cyclic or non-cyclic alkyl, of 1 to 20 carbon atoms optionally substituted with at least one substituent that is:
an oxo group,
halogen or
an aryl group, optionally fused, optionally substituted by halogen and/or linear or branched, cyclic or non-cyclic alkyl groups of 1 to 20 carbon atoms,
aryl of 6 to 14 carbon atoms optionally substituted with at least one substituent that is:
linear or branched, cyclic or non-cyclic alkyl of 1 to 20 carbon atoms optionally substituted with at least one halogen or at least one nitro group,
halogen or
a nitro group.
2. The process according to claim 1 in which said sugar is an oligosaccharide or monosaccharide, alone or in a mixture.
3. The process according to claim 2 in which the monosaccharide is glucose, mannose or fructose, used alone or in a mixture.
4. The process according to claim 2 in which the oligosaccharide is saccharose, lactose, maltose, isomaltose, inulobiose, melibiose, gentiobiose, trehalose, cellobiose, cellotriose, cellotetraose or an oligosaccharide originating from hydrolysis of a polysaccharide originating from the hydrolysis of starch, inulin, cellulose or hemicellulose, used alone or in a mixture.
5. The process according to claim 1 , in which R is a linear alkyl group containing from 1 to 6 carbon atoms.
6. The process according to claim 5 , in which R is a methyl group and the homogeneous sulphonic catalyst is methanesulphonic acid.
7. The process according to claim 1 , in which R is a branched alkyl group containing 3 to 10 carbon atoms.
8. Process according to claim 1 , in which R is a substituted aryl group and the catalyst of the family of the sulphonic acids is p-toluenesulphonic acid.
9. The process according to claim 1 , in which the aprotic polar solvent is acetone, N,N-dimethylformamide, N,N-dimethylacetamide, sulpholane, N-methylpyrrolidone, dimethyl sulphoxide, propylene carbonate and γ-valerolactone alone or in a mixture.
10. The process according to claim 1 , in which the temperature is 50° C. to 200° C., and in which the pressure is 0.1 MPa to 8 MPa.
11. The process according to claim 1 , in which the feedstock is introduced at a solvent/feedstock mass ratio of 0.1 to 200.
12. The process according to claim 1 , in which the homogeneous sulphonic acid catalyst is introduced at a feedstock/organic catalyst(s) mass ratio of 1 to 1000.