# US 8,785,667 B2 · Processes for preparing diacids, dialdehydes and polymers

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- Number: US 8,785,667 B2
- Document ID: US8785667B2
- Status: Granted
- Kind: B2
- Application number: 13/950,401
- Filed: 2013-07-25
- Published: 2013-11-21
- Granted: 2014-07-22
- Earliest claimed: 2000-03-27
- Assignees: E. I. Du Pont de Nemours and Company
- Applicants: E I du Pont de Nemours and Company
- Inventors: Vladimir Grushin; Leo Ernest Manzer; Walter Partenheimer
- Web page: https://patentgrep.com/patent/US8785667B2

## CPC

- C08G 65/002: {from unsaturated compounds (unsaturated oxiranes C08G65/14)}
- C07C 45/298: {with manganese derivatives}
- C07D 307/36: with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
- C07D 307/46: Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
- C07D 307/48: Furfural
- C07D 307/68: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C08G 6/00: Condensation polymers of aldehydes or ketones only
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Alcohols are catalytically oxidized to aldehydes, in particular to benzaldehyde and diformylfuran, which are useful as intermediates for a multiplicity of purposes. The invention also relates to the polymerization of the dialdehyde and to the decarbonylation of the dialdehyde to furan.

## Claims

### Claim 1

A process for the preparation of a diacid of the formula HOOC—R′—COOH from an alcohol/aldehyde of the formula HOH2C—R′—(C═O)H, wherein R′ is an optionally substituted furan ring, comprising the step of:
contacting the alcohol/aldehyde with an oxidant in the presence of a metal bromide catalyst and a solvent or a solvent mixture, thereby forming a mixture of an acid/aldehyde having the formula HOOC—R′—(C═O)H and the diacid, and optionally isolating at least one of the acid/aldehyde or the diacid,
wherein the oxidant is selected from the group consisting of oxygen, oxygen-containing gas and mixture thereof,
wherein the metal bromide catalyst comprises two or more transition metals, and
wherein the solvent or the solvent mixture comprises at least one aliphatic C2-C6 monocarboxylic acid compound.

### Claim 2 (depends on 1)

The process of claim 1 wherein the process is run in acetic acid.

### Claim 3 (depends on 1)

The process of claim 1 wherein the metal bromide catalyst comprises a source of bromine and at least one metal selected from the group consisting of Co and Mn.

### Claim 4 (depends on 3)

The process of claim 3 wherein the metal bromide catalyst further comprises Zr.

### Claim 5 (depends on 4)

The process of claim 4 wherein the catalyst comprises Co and Mn.

### Claim 6 (depends on 1)

The process of claim 1 wherein the diacid is furan-2,5-dicarboxylic acid and the alcohol/aldehyde is 5-(hydroxymethyl)furfural.