2,5-Furandicarboxylic acid Property

Melting point:

>300 °C

Boiling point:

240.29°C (rough estimate)

Density 

1.7400

refractive index 

1.6400 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly Sonicated)

form 

Solid

pka

2.28±0.10(Predicted)

color 

White to Dark Brown

Water Solubility 

1g/L(18 ºC)

Stability:

Light Sensitive, Very Hygroscopic

InChIKey

CHTHALBTIRVDBM-UHFFFAOYSA-N

LogP

-1.43 at 20℃

CAS DataBase Reference

3238-40-2(CAS DataBase Reference)

NIST Chemistry Reference

Furan-2,5-dicarboxylic acid(3238-40-2)

EPA Substance Registry System

2,5-Furandicarboxylic acid (3238-40-2)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38-36

Safety Statements 

26-36/37/39-36/37

WGK Germany 

1

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29321900

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H319Causes serious eye irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P337+P313IF eye irritation persists: Get medical advice/attention.

2,5-Furandicarboxylic acid Chemical Properties,Usage,Production

Description

2,5-Furandicarboxylic acid (FDCA) is an organic chemical compound consisting of two carboxylic acid groups attached to a central furan ring. It was first reported as dehydromucic acid by Rudolph Fittig and Heinzelmann in 1876, who produced it via the action of concentrated hydrobromic acid upon mucic acid. It can be produced from certain carbohydrates and as such is a renewable resource, it was identified by the US Department of Energy as one of 12 priority chemicals for establishing the “green” chemistry industry of the future.Furan-2,5-dicarboxylic acid (FDCA) has been suggested as an important renewable building block because it can substitute for terephthalic acid (PTA) in the production of polyesters and other current polymers containing an aromatic moiety.
wikipedia

Chemical Properties

2,5-Furandicarboxylic acid is a chemical intermediate with high sensitivity and good stability. It is soluble in water under alkaline conditions and is a white powder solid under acidic conditions, and is an important monomer for the preparation of corrosion-resistant plastics. It is irritating to eyes, respiratory tract and skin.

History

2,5-Furandicarboxylic acid, also known as dehydromucic acid, is a furan derivative. This organic compound was first obtained by Fittig and Heinzelmann in 1876. More than 125 years later, FDCA was identified by the US Department of Energy as one of 12 priority chemicals for establishing the "green" chemistry industry of the future. On a laboratory scale, it is often synthesized from 5- hydroxymethylfurfural (HMF), which in turn can be obtained from carbohydrate-containing sources such as glucose, fructose, sucrose, and starch. From fructose and glucose, HMF is obtained by acidic eliminating three moles of water.

Uses

Interest in renewable based polymers has led to 2,5-furandicarboxylic acid being proposed as a green, sustainable alternative to the widely used petroleum-based terephthalic acid in the synthesis of polyesters. 2,5-Furandicarboxylic acid is produced from oxidation of 5-hydroxymethylfurfural (HMF) which is obtained from the dehydration of bio-based sugars such as fructose.

Uses

2,5-Furandicarboxylic acid (FDCA) is a renewable, greener substitute for terephthalate in the production of polyesters. It is widely used as a precursor for the synthesis of bio-based polyesters and various other polymers.

Applications of FDCA in the synthesis of several metal-organic frameworks (MOFs) have also been reported.

Preparation

2,5-Furandicarboxylic acid (FDCA) can be produced from biomass or its derived sugars or platform chemicals, and has demonstrated to be a very promising substitute for petroleum-derived polymer products.
Chapter 5 - Advances in the synthesis and application of 2,5-furandicarboxylic acid

Definition

ChEBI: A member of the class of furans carrying two carboxy substituents at positions 2 and 5.

Application

2,5-Furandicarboxylic acid (FDCA) is a renewable, greener substitute for terephthalate in the production of polyesters. It is widely used as a precursor for the synthesis of bio-based polyesters and various other polymers.
Applications of FDCA in the synthesis of several metal-organic frameworks (MOFs) have also been reported.

Synthesis Reference(s)

Tetrahedron Letters, 26, p. 1777, 1985 DOI: 10.1016/S0040-4039(00)98336-9

Flammability and Explosibility

Not classified

Solubility in organics

2,5-Furandicarboxylic acid (FDCA) serves as a monomer in various polyesters and is often obtained through the oxidation of 5-hydroxymethylfurfural. In pure solvents and binary mixtures, the solubility of FDCA increased with the increasing temperature. The order from largest to smallest solubility in pure solvents was as follows: methanol, 1-butanol, isobutanol, acetic acid, water, MIBK, ethyl acetate, and acetonitrile.
https://doi.org/10.1021/acs.jced.7b00927