Esters of 5-hydroxymethylfurfural and methods for their preparation
AssigneeBattelle Memorial Institute
InventorsHerman P. Benecke, Jerry L. King, II, Alex Walter Kawczak, Donald W. Zehnder, II, Erica E. Hirschl
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Abstract
Disclosed are compositions and methods for the production of mono-esters and di-esters from the reaction of HMF and a reactant selected from a diacid or a diacid derivative; typical reactants are PAN, phthaloyl dichloride, dimethyl phthalate, maleic acid, and maleic anhydride or mono-esters that can be prepared from HMF and MAN.
Claims21
A method for di-ester synthesis comprising:
- mixing 5-(hydroxymethyl)-2-furfuraldehyde and dimethyl phthalate with a suitable catalyst;
- and
- heating at about 80° C. to about 110° C. while stirring for about 2 to about 4 hours.
A method for di-ester synthesis comprising:
- melting 5-(hydroxymethyl)-2-furfuraldehyde:
- adding phthalic anhydride and an optional esterification catalyst to the molten 5-(hydroxymethyl)-2-furfuraldehyde while stirring;
- and
- reacting the mixture while stirring for about 16 to about 30 hours at a temperature between about 110° C. to about 140° C.
A method for di-ester synthesis comprising;
- mixing a mono-ester reaction product of 5-(hydroxymethyl)-2-furfuraldehyde and phthalic anhydride with a molar equivalent of a coupling reagent;
- adding 5-(hydroxymethyl)-2-furfuraldehyde to the mixture;
- cooling the mixture to between about −10° C. to about 10° C.;
- and
- reacting the cooled mixture for about 10 to 18 hours at the reduced temperature.
A method for producing a mono-ester and/or a di-ester comprising:
- a. contacting 5-(hydroxymethyl)-2-furfuraldehyde with a second reactant selected from maleic anhydride, maleic acid, fumaric acid, dimethylfumarate, phthalic anhydride, phthalic acid, phthalic acid diester, phthalic diacid chloride, isophthalic acid, isophthalic di-ester, isophthalic diacid chloride, terephthalic acid, terephthalic di-ester, terephthalic di-ester, or mixtures thereof in a reaction vessel;
- and
- b. reacting the contacting reactants to obtain the mono-ester and/or di-ester product.
A method for producing an ester of 5-hydroxymethylfurfural comprising:
- a. mixing 5-(hydroxymethyl)-2-furfuraldehyde and phthalic anhydride;
- and
- b. reacting at a temperature between about 75° C. and about 150° C. to obtain the product.
A method for producing a di-ester comprising:
- reacting 5-(hydroxymethyl)-2-furfuraldehyde and dimethyl phthalate at an elevated temperature in the presence of a catalyst,
- wherein the ratio of 5-(hydroxymethyl)-2-furfuraldehyde:dimethyl phthalate is about 2:1 to about 5:1.
Dependencies are inferred from the claim text.