Tetrahydrofurfuryl methacrylate
[CAS# 2455-24-5]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Tetrahydrofurfuryl methacrylate
• Synonyms: Tetrahydrofuran-2-ylmethyl 2-methylprop-2-enoate
• Molecular Formula: C₉H₁₄O₃
• Molecular Weight: 170.21
• CAS Registry Number: 2455-24-5
• EC Number: 219-529-5
• SMILES: CC(=C)C(=O)OCC1CCCO1

Properties

• Density: 1.044
• Boiling point: 52 ºC (0.4 mmHg)
• Refractive index: 1.458
• Flash point: 91 ºC

Safety Data

• Hazard Symbols: GHS07;GHS08 Danger
• Hazard Statements: H315-H317-H319-H335-H360-H412
• Precautionary Statements: P203-P261-P264-P264+P265-P271-P272-P273-P280-P302+P352-P304+P340-P305+P351+P338-P318-P319-P321-P332+P317-P333+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Reproductive toxicity	Repr.	1B	H360
Skin sensitization	Skin Sens.	1A	H317
Skin sensitization	Skin Sens.	1	H317
Reproductive toxicity	Repr.	1B	H360D

Discovory and Applicatios

Tetrahydrofurfuryl methacrylate (THFMA) is a chemical compound derived from the reaction of tetrahydrofurfuryl alcohol and methacrylic acid. This compound is part of a broader class of methacrylate esters and has gained prominence due to its unique chemical properties and applications in various industrial and commercial fields.

The discovery of tetrahydrofurfuryl methacrylate can be traced back to advancements in polymer chemistry during the mid-20th century. Researchers sought to develop esters with enhanced properties for use in high-performance polymers and coatings. The incorporation of the tetrahydrofurfuryl group into the methacrylate structure provided a compound with distinctive characteristics, such as increased solubility and reactivity, which were beneficial for various applications.

Tetrahydrofurfuryl methacrylate is widely utilized in the production of polymeric materials, particularly in the field of coatings and adhesives. Its methacrylate functional group allows for polymerization, forming durable and versatile polymers with excellent chemical and mechanical properties. The tetrahydrofurfuryl group, on the other hand, enhances the solubility of the resulting polymers in organic solvents, making them suitable for a range of applications.

In the coatings industry, tetrahydrofurfuryl methacrylate is used to produce high-performance coatings that offer superior adhesion, flexibility, and resistance to environmental factors such as moisture and chemicals. These coatings are employed in various applications, including automotive finishes, industrial equipment, and protective coatings for metal and plastic surfaces. The unique properties imparted by THFMA contribute to the development of coatings with enhanced durability and aesthetic qualities.

In adhesives, tetrahydrofurfuryl methacrylate is valued for its ability to form strong and durable bonds. Its presence in adhesive formulations enhances the adhesion properties to various substrates, including metals, plastics, and ceramics. This makes THFMA-based adhesives suitable for use in structural bonding applications, such as in the automotive and aerospace industries, where high-strength and reliable bonding are essential.

The polymerization of tetrahydrofurfuryl methacrylate is also utilized in the production of specialty resins. These resins are used in the manufacture of composite materials, where they provide improved mechanical properties and resistance to environmental factors. The incorporation of THFMA into resin formulations allows for the creation of composites with enhanced performance characteristics, suitable for high-stress applications.

In addition to its use in coatings, adhesives, and resins, tetrahydrofurfuryl methacrylate finds application in the development of dental materials and medical devices. Its biocompatibility and ease of polymerization make it suitable for use in dental composites and prosthetics, where durability and resistance to degradation are crucial.

Overall, tetrahydrofurfuryl methacrylate is a versatile compound with a range of applications in industrial and commercial sectors. Its unique chemical properties contribute to the development of high-performance materials that meet the demands of various applications, from coatings and adhesives to specialty resins and dental materials.