Processes for the preparation and purification of hydroxymethylfuraldehyde and derivatives
AssigneeArcher Daniels Midland Company
InventorAlexandra Sanborn
Life of this patent
Estimating the term…
Abstract
A method for utilizing an industrially convenient fructose source for a dehydration reaction converting a carbohydrate to a furan derivative is provided. Recovery methods also are provided. Embodiments of the methods improve upon the known methods of producing furan derivatives.
Claims37
A method of preparing 2,5 -hydroxymethyl)furaldehyde comprising:
- i) combining a fructose source, a solvent selected from the group consisting of 1-methyl-2-pyrrolidinone, dimethylacetamide, dimethylformamide and combinations of thereof, with a catalyst to provide a reaction mixture;
- ii) heating said reaction mixture to a temperature and for a time sufficient to promote an acid-catalyzed dehydration reaction of fructose in said fructose source to form a product mixture;
- and
- iii) isolating 2,5-(hydroxymethyl)furaldehyde from said product mixture.
A method of preparing 2,5-(hydroxymethyl)furaldehyde comprising:
- i) combining a fructose source, an organic solvent, and an acid catalyst to provide a reaction mixture;
- ii) heating said reaction mixture to a temperature and for a time sufficient to promote a dehydration reaction of fructose in said fructose source to form a first product mixture;
- iii) neutralizing the pH of the first product mixture to a pH of about 7 to 9;
- iv) distilling the first product mixture after neutralizing the pH to remove said organic solvent remaining in the first product mixture;
- and
- v) purifying said product mixture to provide a second product mixture comprising greater than 60% by weight of 2,5-(hydroxymethyl)furaldehyde.
A method of preparing 2,5-(hydroxymethyl)furaldehyde comprising the steps of:
- i) combining a fructose source, an acid catalyst, a first organic solvent, and a second organic solvent that is non miscible with the first organic solvent to provide a reaction mixture, the first and second organic solvents being selected so that the second organic solvent preferentially dissolves 2,5-(hydroxymethyl)furaldehyde relative to the first organic solvent;
- ii) heating said reaction mixture to a temperature and for a time sufficient to promote a dehydration reaction of fructose in said fructose source to form a product mixture with a first immiscible phase and a second immiscible phase;
- and
- iii) isolating 2,5-(hydroxymethyl)furaldehyde from said second immiscible phase of said product mixture.
The method of claim 42 wherein said second organic solvent has a Log P value of from about 0.4 to about 3.4, and said first organic solvent has a Log P value of less than zero.
The method of claim 47 wherein said second organic solvent has a Log P value of from about 0.6 to about 2.7.
The method of claim 47 wherein said first organic solvent has a Log P value of from about −0.075 to about −1.95.
A method of preparing an R-oxymethylfurfural ether of hydroxylmethylfurfural of the formula:
- where R is selected from the group consisting of alkyl, cycloalkyl, allyl and aryl, comprising:
- (i) combining a fructose source, an R—OH solvent, and an acid catalyst to form a reaction mixture;
- (ii) heating said reaction mixture to a temperature and for a time sufficient to promote an acid-catalyzed dehydration reaction fructose in the fructose source and to form R-oxymethylfurfural in a product mixture;
- and
- (iii) Isolating the R-oxymethylfurfural from said product mixture.
A method of preparing levulinic acid comprising:
- (i) combining a fructose source, at least one of polyethylene glycol and end capped polyethylene glycol, and an acid catalyst to form a reaction mixture;
- (ii) heating said reaction mixture to a temperature and for a time sufficient to promote an acid-catalyzed dehydration reaction of fructose in the fructose source and to form levulinic acid in a product mixture;
- and
- (iii) isolating levulinic acid from said product mixture.
A method of preparing 2,5-bis-(hydroxymethyl)furan comprising:
- heating a reaction mixture comprising 2,5-(hydroxymethyl)furaldehyde, a solvent, and a catalyst system comprising nickel and zirconium at a temperature, for a time, and at a pressure sufficient to promote reduction of the 2,5-(hydroxymethyl)furaldehyde to 2,5-bis-(hydroxymethyl)furan to produce a product mixture comprising 2,5-bis-(hydroxymethyl)furan.
Dependencies are inferred from the claim text.