3,4-Epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate
[CAS# 2386-87-0]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Butyl ester compound
• Name: 3,4-Epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate
• Synonyms: 7-Oxabicyclo[4.1.0]hept-3-ylmethyl 7-oxabicyclo[4.1.0]heptane-3-carboxylate
• Molecular Formula: C₁₄H₂₀O₄
• Molecular Weight: 252.31
• CAS Registry Number: 2386-87-0
• EC Number: 219-207-4
• SMILES: C1CC2C(O2)CC1COC(=O)C3CCC4C(C3)O4

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*, 1.17 g/cm³
• Index of Refraction: 1.539, Calc.^*, 1.498
• Boiling Point: 363.4±17.0 °C (760 mmHg), Calc.^*
• Flash Point: 160.5±21.0 °C, Calc.^*, 245 °F

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H317-H412
• Safety Statements: P261-P272-P273-P280-P302+P352-P321-P333+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin sensitization	Skin Sens.	1B	H317
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Germ cell mutagenicity	Muta.	2	H341
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

3,4-Epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate is a distinctive chemical compound recognized for its role in the synthesis of advanced polymers and resins. This substance plays a crucial role in polymer chemistry and material science, with applications spanning from high-performance coatings to specialty adhesives.

The discovery of 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate emerged from research aimed at developing new epoxy resins with enhanced properties. The compound is a member of the epoxy resin family, characterized by the presence of epoxy groups in its structure. These groups are reactive and can participate in crosslinking reactions, which are central to the formation of durable and resilient polymer networks.

The synthesis of 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate involves the reaction of 3,4-epoxycyclohexylmethyl alcohol with 3,4-epoxycyclohexanecarboxylic acid. The resulting product features two epoxy groups that are critical for its function as a resin. The unique structure of this compound includes a cyclohexyl ring with epoxy substituents, which imparts distinctive properties to the resulting polymers.

One of the primary applications of 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate is in the formulation of epoxy resins used for high-performance coatings. These coatings are valued for their excellent adhesion, chemical resistance, and mechanical strength. The compound's ability to form strong crosslinked networks makes it ideal for applications requiring durable and resistant coatings. These properties are particularly beneficial in industrial settings where materials are exposed to harsh environments and mechanical stresses.

In addition to coatings, 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate is used in the production of specialty adhesives. The epoxy resins derived from this compound exhibit superior bonding strength and resistance to various environmental factors, including moisture and temperature fluctuations. This makes them suitable for use in applications ranging from construction to automotive industries, where reliable adhesive performance is essential.

The compound also finds applications in the manufacture of composite materials. Epoxy resins incorporating 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate are used to create composites with enhanced mechanical properties and stability. These composites are employed in aerospace, automotive, and sporting goods industries, where the combination of strength and light weight is crucial.

Furthermore, 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate contributes to the development of advanced electronic materials. Epoxy resins are widely used in the electronics industry for encapsulating electronic components and ensuring their protection from environmental damage. The unique properties of this compound help in producing resins that offer high dielectric strength and thermal stability, essential for reliable electronic performance.

Despite its advantages, handling 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate requires caution. The epoxy groups in the compound are highly reactive and can cause skin and respiratory irritation. Proper safety measures should be implemented during its use and processing to mitigate potential health risks.

In conclusion, 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate is an important chemical substance with diverse applications in polymer chemistry and material science. Its role in enhancing the properties of epoxy resins has significant implications for various industries, from coatings and adhesives to composites and electronics.

References

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DOI: 10.1038/s41893-024-01349-z

2022. NIR spectroscopy for reaction monitoring and reaction mixture identification of cycloaliphatic epoxides. *Journal of Polymer Research*, 29(5).
DOI: 10.1007/s10965-022-03038-x

2017. Preparation and characterization of UV-curable urethane acrylate oligomers modified with cycloaliphatic epoxide resin. *Journal of Coatings Technology and Research*, 14(6).
DOI: 10.1007/s11998-017-9994-6