Methods for production of aromatic dicarboxylic acids and derivatives thereof
AssigneeNovomer, Inc.
InventorsJay J Farmer, Sadesh H. Sookraj
Life of this patent
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Abstract
Provided are methods for the production of isophthalic acid (IP A) and derivatives thereof. The methods are based on the addition of beta propiolactone to furfural or a derivative thereof. Provided are cost effective routes to biobased IP A and derivatives thereof, including terephthalic acid.
Claims17
A method, comprising:
- continuously feeding a first reaction zone with furfural and a compound of formula:
- wherein Ry is independently hydrogen, or an optionally substituted moiety selected the group consisting of acyl;
- arylalkyl;
- 6- to l0-membered aryl;
- C1-20 aliphatic;
- C1-20 heteroaliphatic having 1-4 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur;
- 5- to 10 membered heteroaryl having 1-4 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur;
- 4- to 7-membered heterocyclic having 1-2 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur;
- and an oxygen protecting group, to provide a first product stream comprising a first product of formula:
- continuously feeding the first product stream to an oxidizing reaction zone where the first product is contacted with air to form a second product stream comprising a second product having formula:
- wherein each Rz is independently selected from the group consisting of —H, Ry, optionally substituted C1-20 aliphatic, and optionally substituted aryl;
- and continuously feeding the second product stream to a rearrangement reaction zone where the second product is converted to the compound of formula:
A method, comprising:
- continuously feeding a first reaction zone with furfural and beta propiolactone, and optionally an alcohol of formula HORy, to provide a first product stream comprising a first product having formula:
- where Ry is independently hydrogen, or an optionally substituted moiety selected the group consisting of acyl;
- arylalkyl;
- 6- to 10-membered aryl;
- C1-20 aliphatic;
- C1-20 heteroaliphatic having 1-4 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur;
- 5- to 10 membered heteroaryl having 1-4 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur;
- 4- to 7-membered heterocyclic having 1-2 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur;
- and an oxygen protecting group;
- and;
- continuously feeding the first product stream to an oxidizing reaction zone where the first product is contacted with air to form a second product stream comprising a second product having formula:
- wherein each Rz is independently selected from the group consisting of —H, Ry, optionally substituted C1-20 aliphatic, and optionally substituted aryl;
- and continuously feeding the second product stream to a rearrangement reaction zone where the second product is converted to the compound of formula:
An isophthalic acid composition produced via cycloaddition reaction of furfural with an alpha beta unsaturated carboxylic acid, wherein the isophthalic acid is at least partially derived from a biobased feedstock.
An isophthalic acid composition produced via reaction of furfural with beta propiolactone, wherein the isophthalic acid is at least partially derived from a biobased feedstock.
A method for the production of biobased terephthalic acid, comprising:
- a) reacting ethylene oxide with carbon monoxide to provide a product selected from beta propiolactone, acrylic acid and acrylate ester;
- b) reacting the product of step (a) with furfural to provide a Diels Alder adduct;
- c) oxidizing the Diels Alder adduct of step (b) to provide product selected from isophthalic acid and isophthalate ester;
- and
- d) treating the product of (c) to convert the isophthalic acid to terephthalic acid.
Dependencies are inferred from the claim text.