Oxygen → 5-Formyl-2-furancarboxylic Acid

HRID 1500258Notes

Reaction equation

[CH:1]1[CH:5]=[C:4]([CH:6]=[O:7])[O:3][C:2]=1[CH2:8][OH:9].[O:10]=O>>[CH:8]([C:2]1[O:3][C:4]([C:6]([OH:10])=[O:7])=[CH:5][CH:1]=1)=[O:9]

Participants

Reactant 2

HCID 977Oxygen

HCID 2373325-(Hydroxymethyl)furfural

Product 1

HCID 27937195-Formyl-2-furancarboxylic Acid

Procedure

5-HMF feed is oxidized with elemental O2 in a multi-step reaction to form FDCA with 5-formyl furan-2-carboxylic acid (FFCA) as a key intermediate eq 1. Oxidation of 5-(acetoxymethyl)furfural (5-AMF), which contains an oxidizable ester and aldehydes moieties, produces FDCA, FFCA, and acetic acid, eq 2. Similarly oxidation of 5-(ethoxymethyl)furfural (5-EMF) produces FDCA, FFCA, 5-(ethoxycarbonyl)furan-2-carboxylic acid (EFCA) and acetic acid, eq 3.

Sources & evidence

ORD record: ord-ecee9efdf98948479c2b0e1bedd49a76
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206149B2

Reaction notes

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