Esters of 5-hydroxymethylfurfural and methods for their preparation
First Claim
Patent Images
1. 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.
0 Assignments
0 Petitions
Accused Products
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.
-
Citations
21 Claims
-
1. 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.
-
-
2. 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.
-
-
3. 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.; andreacting the cooled mixture for about 10 to 18 hours at the reduced temperature. - View Dependent Claims (4)
-
-
5. 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. - View Dependent Claims (6, 7, 8, 9, 10, 11)
-
-
12. 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. - View Dependent Claims (13, 14, 15, 16, 17, 18, 19)
-
-
20. 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. - View Dependent Claims (21)
-
Specification