5-Hydroxymethylfurfural
[CAS# 67-47-0]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Aldehyde fragrance >> Acyclic aliphatic aldehyde
• Name: 5-Hydroxymethylfurfural
• Synonyms: 5-(Hydroxymethyl)-2-furaldehyde
• Molecular Formula: C₆H₆O₃
• Molecular Weight: 126.11
• CAS Registry Number: 67-47-0
• EC Number: 200-654-9
• SMILES: C1=C(OC(=C1)C=O)CO

Properties

• Density: 1.243 g/mL
• Melting point: 30-34 °C
• Boiling point: 114-116 °C (1 torr)
• Refractive index: 1.5627
• Flash point: 79 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335-H412
• Safety Statements: P261-P264-P264+P265-P271-P273-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin sensitization	Skin Sens.	1A	H317
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	1	H300

Discovery and Applications

5-Hydroxymethylfurfural (HMF) is a significant organic compound derived from the dehydration of hexoses like glucose and fructose. This compound, which contains both an aldehyde and a furan ring structure, plays a crucial role in various chemical and industrial processes. Its discovery and application have garnered attention due to its potential uses in renewable resource technology, materials science, and chemical synthesis.

The discovery of 5-hydroxymethylfurfural dates back to the early 20th century, but its relevance has increased with the growing focus on sustainable and green chemistry. Initially, HMF was identified as an intermediate in the degradation of sugars during heating. Over time, researchers recognized its potential as a valuable building block for various chemical transformations.

In the field of renewable chemicals, HMF has emerged as a promising platform molecule. It is primarily derived from biomass sources, making it an attractive alternative to petrochemical-derived products. The conversion of HMF into valuable chemicals and fuels has become a key area of research. For instance, HMF can be transformed into 2,5-furandicarboxylic acid (FDCA), a precursor to biobased plastics such as polyethylene furanoate (PEF). This conversion process involves oxidation and has significant implications for developing sustainable materials with improved properties compared to traditional plastics.

Another important application of HMF is in the synthesis of various fine chemicals and pharmaceuticals. The compound's reactivity allows for the production of a range of derivatives, including hydroxymethylfurfural esters and ethers, which are useful in the synthesis of agrochemicals and pharmaceuticals. For example, HMF can be used to produce 5-hydroxymethyl-2-furfuralic acid, which is utilized in the manufacture of flavorings and fragrances. Its role as an intermediate in the synthesis of these compounds highlights its versatility in chemical manufacturing.

HMF also finds applications in the field of materials science. It is employed in the production of advanced materials such as resins and adhesives. The compound's ability to form cross-linked networks makes it valuable in developing high-performance resins with enhanced mechanical properties. These resins are used in coatings, composites, and various industrial applications, where they provide durability and resistance to environmental factors.

In addition to its industrial applications, 5-hydroxymethylfurfural has garnered interest in environmental science due to its role in the degradation of organic matter. It is formed as a byproduct in the thermal degradation of biomass and can be used as a marker for tracking the degradation process. This property makes it useful in assessing the efficiency of biomass conversion processes and monitoring environmental impacts.

The ongoing research and development in the field of 5-hydroxymethylfurfural aim to enhance its production, optimize its conversion processes, and explore new applications. Efforts are focused on improving the efficiency of HMF production from renewable sources, developing more sustainable processes, and expanding its use in various industrial and commercial applications.

In summary, 5-hydroxymethylfurfural is a versatile compound with significant applications in renewable chemicals, fine chemical synthesis, materials science, and environmental monitoring. Its discovery has paved the way for advancements in sustainable chemistry and the development of high-performance materials and products.

References

2024. Immobilization of Heteropolyacids on Zeolite Surface for Catalytic Conversion of Glucose to 5-Hydroxymethyl Furfural (5-HMF). Topics in Catalysis, 67(17-18).
DOI: 10.1007/s11244-024-02017-4

2012. Conversion of fructose into 5-hydroxymethylfurfural (HMF) and its derivatives promoted by inorganic salt in alcohol. Carbohydrate Research, 349.
DOI: 10.1016/j.carres.2011.12.006

2010. Fast Transformation of Glucose and Di-/Polysaccharides into 5-Hydroxymethylfurfural by Microwave Heating in an Ionic Liquid/Catalyst System. ChemSusChem, 3(7).
DOI: 10.1002/cssc.201000124