Furfural
[CAS# 98-01-1]

Identification

• Classification: Organic raw materials >> Heterocyclic compound
• Name: Furfural
• Synonyms: Furfuraldehyde; Furfurol; 2-Furaldehyde; 2-Furancarboxaldehyde; Furan-2-carboxaldehyde
• Molecular Formula: C₅H₄O₂
• Molecular Weight: 96.08
• CAS Registry Number: 98-01-1
• EC Number: 202-627-7
• FEMA: 2489
• SMILES: C1=COC(=C1)C=O

Properties

• Density: 1.16
• Melting point: -36 °C
• Boiling point: 167 °C
• Refractive index: 1.525-1.527
• Flash point: 60 °C
• Water solubility: 8.3 g/100 mL

Safety Data

• Hazard Symbols: GHS06;GHS07;GHS08 Danger
• Risk Statements: H301-H312-H315-H319-H330-H331-H351
• Safety Statements: P203-P260-P261-P264-P264+P265-P270-P271-P280-P284-P301+P316-P302+P352-P304+P340-P305+P351+P338-P316-P317-P318-P319-P320-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H301
Carcinogenicity	Carc.	2	H351
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H312
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	2	H330
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Flammable liquids	Flam. Liq.	3	H226
Acute toxicity	Acute Tox.	1	H330
Flammable liquids	Flam. Liq.	2	H225
Skin sensitization	Skin Sens.	1	H317
Specific target organ toxicity - single exposure	STOT SE	2	H371
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	3	H311
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411

• Transport Information: UN 1199

Discovery and Applications

Furfural is an organic compound with the formula C₄H₄O, recognized for its distinctive aroma and versatile applications in various industries. It is a colorless liquid that can be synthesized from agricultural byproducts, particularly pentosan-containing materials such as corncobs, oat hulls, and sugarcane bagasse. The discovery of furfural dates back to the mid-19th century, specifically 1832, when it was first isolated by the chemist Hermann Kolbe from the fermentation of sugars.

The significant commercial production of furfural began in the early 20th century, driven by the increasing demand for solvents, flavoring agents, and chemical intermediates. Furfural is primarily produced through the acid-catalyzed hydrolysis of pentosans, which are polysaccharides found in various plant materials. The process involves treating the biomass with acids, leading to the breakdown of hemicellulose and the subsequent formation of furfural. This method not only provides a valuable chemical but also promotes the utilization of renewable resources, aligning with sustainable practices in the chemical industry.

Furfural's applications are diverse and impactful. One of its primary uses is as a solvent in the production of resins, plastics, and pharmaceuticals. Its ability to dissolve a wide range of organic compounds makes it a valuable reagent in laboratories and industrial settings. Additionally, furfural serves as a precursor to various chemicals, including furfuryl alcohol, which is utilized in the manufacture of foundry resins and adhesives. The conversion of furfural to furfuryl alcohol enhances its utility in the production of high-performance materials.

Another notable application of furfural is in the food industry, where it is employed as a flavoring agent and aroma compound. Its pleasant, almond-like odor is incorporated into food products, enhancing sensory attributes. Furthermore, furfural is used in the formulation of agrochemicals, such as herbicides and fungicides, demonstrating its relevance in agricultural practices.

In recent years, furfural has garnered attention as a platform chemical in the biorefinery sector. As the world shifts towards renewable feedstocks and green chemistry, furfural's role in converting biomass into valuable chemicals is increasingly recognized. Research is ongoing to explore its potential in the synthesis of biofuels and other renewable chemicals, contributing to sustainable development and reducing dependence on fossil fuels.

In conclusion, furfural is a vital chemical substance with a rich history and a broad range of applications. From its discovery in the 19th century to its current status as an essential compound in various industries, furfural exemplifies the integration of renewable resources into modern chemical production. Its versatility and potential for sustainable use position it as an important player in the transition towards greener chemical processes.

References

2024. Impact of a homogeneous hydrogen bond catalysis for the ethyl (hetero)arylidene cyanoacetate preparation in the presence of TMDP. Research on Chemical Intermediates, 50(12).
DOI: 10.1007/s11164-024-05434-y

2010. Methodology for the Synthesis of Substituted 1,3-Oxazoles. Synlett : accounts and rapid communications in synthetic organic chemistry, 2010(3).
DOI: 10.1055/s-0029-1219374

2008. Characterization of Fast Pyrolysis Bio-oils Produced from Pretreated Pine Wood. Applied Biochemistry and Biotechnology, 151(2-3).
DOI: 10.1007/s12010-008-8445-3