Back to results
US 2019/0233360 A1Published application
Methods for Production of Aromatic Dicarboxylic Acids and Derivatives Thereof
AssigneeNovomer, Inc.
InventorsJay J. Farmer, Sadesh H. Sookraj
Life of this patent
Estimating the term…
Abstract
Provided are methods for the production of phthalic acid (PA), isophthalic acid (IP A), terephthalic acid (TP 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.
Claims33
A method for the production of a compound of formula:
- the method comprising the step of oxidizing a compound of formula:
- wherein each Rz is selected from the group consisting of:
- —H, Ry, optionally substituted C1-20 aliphatic, and optionally substituted aryl;
- and Ry is 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 selected from the group consisting of nitrogen, oxygen, and sulfur;
- 5- to 10-membered heteroaryl having 1-4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur;
- 4- to 7-membered heterocyclic having 1-2 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur;
- and an oxygen protecting group.
8 more elements
A method for the production of a compound of formula:
- the method comprising the steps of reacting furfural with beta propiolactone and oxidizing the resulting adduct, where each Rz is selected from the group consisting of:
- 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 selected from the group consisting of nitrogen, oxygen, and sulfur;
- 5- to 10-membered heteroaryl having 1-4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur;
- 4- to 7-membered heterocyclic having 1-2 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur;
- and an oxygen protecting group.
6 more elements
A method for the production of a compound of formula:
- the method comprising the steps of reacting furfural with beta propiolactone and oxidizing the resulting adduct, where each Rz is selected from the group consisting of:
- 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 selected from the group consisting of nitrogen, oxygen, and sulfur;
- 5- to 10-membered heteroaryl having 1-4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur;
- 4- to 7-membered heterocyclic having 1-2 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur;
- and an oxygen protecting group.
6 more elements
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 phthalic acid or an ester thereof, 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;
- and
- c. oxidizing the Diels Alder adduct of step (b) to provide a product selected from phthalic acid and phthalate ester.
1 more element
A method for the production of biobased isophthalic acid or an ester thereof, 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;
- and
- c. oxidizing the Diels Alder adduct of step (b) to provide a product selected from isophthalic acid and isophthalate ester.
1 more element
A method, comprising:
- feeding a first reaction zone with furfural and a compound of formula:
- wherein Ry is hydrogen, or an optionally substituted moiety selected from the group consisting of acyl;
- arylalkyl;
- 6- to 10-membered aryl;
- C1-20 aliphatic;
- C1-20 heteroaliphatic having 1-4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur;
- 5- to 10-membered heteroaryl having 1-4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur;
- 4- to 7-membered heterocyclic having 1-2 heteroatoms 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:
- 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 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 a compound of formula:
9 more elements
A method, comprising:
- feeding a first reaction zone with furfural and beta propiolactone, and an alcohol of formula HORy, to provide a first product stream comprising a first product having formula:
- wherein Ry is hydrogen, or an optionally substituted moiety selected from the group consisting of acyl;
- arylalkyl;
- 6- to 10-membered aryl;
- C1-20 aliphatic;
- C1-20 heteroaliphatic having 1-4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur;
- 5- to 10-membered heteroaryl having 1-4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur;
- 4- to 7-membered heterocyclic having 1-2 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur;
- and an oxygen protecting group;
- and;
- 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 selected from the group consisting of —H, Ry, optionally substituted C1-20 aliphatic, and optionally substituted aryl;
- and feeding the second product stream to a rearrangement reaction zone where the second product is converted to a compound of formula:
10 more elements
Dependencies are inferred from the claim text.