Oxidation process to produce 5 methyl 5-methylfuran-2-carboxylate (MMFC)

Patent metadata

Field	Value
Publication number	US-10544118-B2
Application number	US-201916430607-A
Country	US
Kind code	B2
Filing date	Jun 4, 2019
Priority date	Jun 25, 2018
Publication date	Jan 28, 2020
Grant date	Jan 28, 2020

Abstract

Disclosed herein is a very efficient method to make 5-(alkoxycarbonyl)furan-2-carboxylic acids (ACFC) from feedstocks comprised of furoates. When a feedstock comprised of methyl 5-methylfuran-2-carboxylate (MMFC) is used a product comprised of (5-(methoxycarbonyl)furan-2-carboxylic acid (MCFC) is obtained in high yield.

First claim

I claim:

1. A process to produce a carboxylic acid composition, said process comprising:
oxidizing in an oxidation zone at least one oxidizable compound in the presence of an oxidizing gas comprising oxygen and a solvent stream and a catalyst system to produce a carboxylic acid composition comprising 5-(methoxycarbonyl) furan-2-carboxylic acid (MCFC);
wherein said oxidation zone comprises at least one oxidation reactor;
wherein said oxidable compound comprises methyl 5-methylfuran-2-carboxylate (MMFC), methyl 5-(hydroxymethyl)furan-2-carboxylate, methyl 5-(methoxymethyl)furan-2-carboxylate, methyl 5-(ethoxymethyl)furan-2-carboxylate, methyl 5-((formyloxy)methyl)furan-2-carboxylate, methyl 5-(acetoxymethyl)furan-2-cayboxylate, methyl 5-((propionyloxy)methyl)furan-2-carboxylate, or combinations thereof; and
wherein said catalyst system comprises at least one selected from cobalt, bromine, manganese, zirconium, and nickel.

2. The process according to claim 1 where said oxidizable compound comprises at least one selected from the group consisting of methyl 5-methylfuran-2-carboxylate (MMFC), methyl 5-(hydroxymethyl)furan-2-carboxylate, methyl 5-(methoxymethyl)furan-2-carboxylate, and methyl 5-(ethoxymethyl)furan-2-carboxylate.

3. The process according to claim 1 wherein said catalyst system comprises cobalt, manganese, and bromine.

4. A process according to claim 1 wherein said catalyst system comprises cobalt in a range from 2 ppm by weight to 10,000 ppm by weight with respect to the weight of the liquid in the reaction medium, manganese in an amount ranging from 2 ppm by weight to 10,000 ppm by weight with respect to the weight of the liquid in the reaction medium, and bromine in an amount ranging from 2 ppm by weight to 10,000 ppm by weight with respect to the weight of the liquid in the reaction medium.

5. A process according to claim 1 wherein said MCFC is produced at a yield greater than 70%.

6. A process according to claim 1 wherein said MCFC is produced at a yield greater than 80%.

7. A process according to claim 1 wherein said MCFC is produced at a yield greater than 90%.

8. A process according to claim 1 wherein said carboxylic acid composition has a b* value of less than 20.

9. A process according to claim 1 wherein said carboxylic acid composition has a b* value of less than 10.

10. A process according to claim 1 wherein said carboxylic acid composition has a b* value of less than 5.

11. A process according to claim 1 wherein said carboxylic acid composition has a b* value of less than 3.

12. A process according to claim 1 wherein said carboxylic acid composition has a b* value of less than 1.

13. A process according to claim 1 wherein said oxidation reactor comprises a bubble column.

14. A process according to claim 1 wherein said catalyst comprises cobalt in a range from 100 ppm to 4500 ppm by weight with respect to the weight of the liquid in the oxidation zone, manganese in an amount ranging from 100 ppm by weight to 4500 ppm by weight with respect to the weight of the liquid in the oxidation zone, and bromine in an amount ranging from 100 ppm by weight to 4500 ppm by weight with respect to the weight of the liquid in the oxidation zone.

15. A process according to claim 1 wherein said carboxylic acid composition further comprises furan-2,5-dicarboxylic acid (FDCA).

16. A process according to claim 1 wherein said oxidizing is conducted at a temperature from 50° C. to 220° C.

17. A process according to claim 1 wherein said oxidizing is conducted at a temperature from 75° C. to 200° C.

18. A process according to claim 1 wherein said oxidizing is conducted at a temperature from 100° C. to 180° C.

19. A process according to claim 1 wherein said oxidizing is conducted at a temperature from 110° C. to 160° C.

20. A process according to claim 1 wherein said oxidizing is conducted at a pressure from 50 psig to 1000 psig.

Assignees

• Eastman Chem Co

Inventors

• Janka Mesfin Ejerssa

Classifications

• B01J27/128

  with iron group metals or platinum group metals · CPC title

• C07D307/68 Primary

  Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen · CPC title

• B01J35/12

  Operations & Transport · mapped topic

• B01J2231/70

  Oxidation reactions, e.g. epoxidation, (di)hydroxylation, dehydrogenation and analogues · CPC title

• B01J31/04

  containing carboxylic acids or their salts {(B01J31/0277 - B01J31/0298 take precedence; multi-metal carboxylate complexes like Pd (II) acetate, i.e. Pd3 (OAc) 6 or Cr(II)acetate, i.e. Cr2(OAc)4 B01J31/2226)} · CPC title