Furfuryl alcohol
[CAS# 98-00-0]

Identification

• Classification: Organic raw materials >> Amino compound >> Cycloalkylamines, aromatic monoamines, aromatic polyamines and derivatives and salts
• Name: Furfuryl alcohol
• Synonyms: 2-Furan methanol; 2-Furylmethanol; 2-Furylcarbinol; 2-Hydroxymethylfuran
• Molecular Formula: C₅H₆O₂
• Molecular Weight: 98.10
• CAS Registry Number: 98-00-0
• EC Number: 202-626-1
• FEMA: 2491
• SMILES: C1=COC(=C1)CO

Properties

• Density: 1.135 g/mL (Expl.)
• Melting point: -29 ºC (Expl.)
• Boiling point: 170 ºC (Expl.)
• Refractive index: 1.486 (Expl.)
• Flash point: 65 ºC (Expl.)
• Water solubility: MISCIBLE (Expl.)

Safety Data

• Hazard Symbols: GHS06;GHS07;GHS08 Danger
• Hazard Statements: H301-H302-H311-H312-H315-H319-H330-H335-H351-H373
• Precautionary Statements: P203-P260-P261-P262-P264-P264+P265-P270-P271-P280-P284-P301+P316-P301+P317-P302+P352-P304+P340-P305+P351+P338-P316-P317-P318-P319-P320-P321-P330-P332+P317-P337+P317-P361+P364-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Carcinogenicity	Carc.	2	H351
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	2	H330
Skin irritation	Skin Irrit.	2	H315
Germ cell mutagenicity	Muta.	2	H341
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Specific target organ toxicity - single exposure	STOT SE	3	H370
Acute toxicity	Acute Tox.	4	H332

• Transport Information: UN 2874

Discovory and Applicatios

Furfuryl alcohol, with the chemical formula C₆H₅CH₂OH, is a colorless to yellow liquid derived from furfural, an organic compound typically obtained from agricultural byproducts such as corncobs, oat hulls, and sawdust. It is a key building block in the production of various chemicals and materials, prized for its versatility and its applications in industries ranging from resin production to fuel additives. Furfuryl alcohol was first synthesized in the early 19th century, and its industrial relevance has grown significantly in the decades since.

The discovery of furfuryl alcohol dates back to 1867, when the French chemist Charles H. Bertholle first identified it by reducing furfural with hydrogen. Furfuryl alcohol itself is derived through a catalytic hydrogenation process of furfural, where the aldehyde group is reduced to a primary alcohol. This alcohol has been used extensively in the manufacturing of resins, particularly in the production of phenolic resins, and as a chemical intermediate in other synthetic processes.

Furfuryl alcohol is most commonly known for its role in the production of furfuryl alcohol resins, which are used in the creation of foundry sand binders. These resins are essential in the casting of metals, where they help to hold sand particles together while maintaining the ability to withstand high temperatures during metal casting. The use of furfuryl alcohol-based resins in metal casting dates back to the 1920s, and the material has since been a mainstay in industries where durable molds are essential.

One of the key characteristics of furfuryl alcohol is its reactivity, particularly in forming resins when combined with other chemicals such as phenols. These resins exhibit excellent thermal stability and resistance to chemicals, making them ideal for applications in high-temperature environments. Phenolic resins made from furfuryl alcohol are used in automotive parts, electronics, and various industrial applications, particularly where strength and heat resistance are important.

In addition to its role in resin production, furfuryl alcohol is used as a precursor in the synthesis of various fine chemicals and pharmaceutical intermediates. It is involved in the production of butanedione and tetrahydrofuran, both important chemicals in the manufacture of pharmaceuticals and plastics. Furfuryl alcohol is also used in the production of surfactants and agrochemicals.

Beyond industrial uses, furfuryl alcohol has been explored as a potential fuel additive due to its high energy content. Researchers have been studying its potential as an alternative fuel or as a fuel component in biodiesel formulations. Furfuryl alcohol’s high cetane number makes it a promising candidate for such applications, and it is being considered for use in renewable energy solutions, particularly in biofuels.

Furfuryl alcohol also has applications in the production of personal care products, including fragrances and flavors. Its distinctive, slightly sweet aroma is used in perfumes and as a flavoring agent in the food industry, particularly for the production of caramel and other flavorings.

In terms of environmental sustainability, furfuryl alcohol is being investigated for use in green chemistry processes. As a renewable product derived from biomass, its utilization helps reduce dependency on petroleum-based chemicals, aligning with efforts to develop more sustainable industrial processes. Additionally, studies have shown that furfuryl alcohol-based resins are biodegradable, offering potential environmental benefits over other synthetic resins.

While furfuryl alcohol is primarily used in industrial applications, handling it requires care. It is a flammable liquid with a low flash point, which means that safety precautions must be taken during storage and transportation to prevent accidents. The compound can also be irritating to the skin and eyes, and proper protective measures should be taken when working with it.

In conclusion, furfuryl alcohol is an important chemical with a broad range of applications across industries such as resin manufacturing, metal casting, pharmaceuticals, and renewable energy. Its discovery in the 19th century marked the beginning of its industrial use, and ongoing research continues to explore new applications in areas such as biofuels and sustainable chemistry.

References

2024. Recent advances in microenvironment engineering for electrocatalytic upgrading of biomass derivatives. Science China Chemistry, 67(12).
DOI: 10.1007/s11426-024-2372-1

2016. Catalytic Transfer Hydrogenation of Furfural to Furfuryl Alcohol over Nitrogen-Doped Carbon-Supported Iron Catalysts. ChemSusChem, 9(9).
DOI: 10.1002/cssc.201600089

2012. Characterization of the polymerization of furfuryl alcohol during roasting of coffee. Food & Function, 3(9).
DOI: 10.1039/c2fo30020f