3-Oxo-butyric acid 2-(2-methylacryloyloxy)ethyl ester
[CAS# 21282-97-3]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Acid ester compound
• Name: 3-Oxo-butyric acid 2-(2-methylacryloyloxy)ethyl ester
• Synonyms: 2-[(2-Methyl-1-oxoallyl)oxy]ethyl acetoacetate
• Molecular Formula: C₁₀H₁₄O₅
• Molecular Weight: 214.21
• CAS Registry Number: 21282-97-3
• EC Number: 244-311-1
• SMILES: CC(=C)C(=O)OCCOC(=O)CC(=O)C

Properties

• Density: 1.122
• Boiling point: 100 ºC
• Refractive index: 1.456
• Flash point: 113 ºC

Safety Data

• Hazard Symbols: GHS07;GHS08 Danger
• Hazard Statements: H315-H317-H319-H334-H335-H412
• Precautionary Statements: P233-P260-P261-P264-P264+P265-P271-P272-P273-P280-P284-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P333+P317-P337+P317-P342+P316-P362+P364-P403-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Respiratory sensitization	Resp. Sens.	1	H334
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412

Discovory and Applicatios

3-Oxo-butyric acid 2-(2-methylacryloyloxy)ethyl ester, commonly known as acetoacetoxyethyl methacrylate (AAEM), is a versatile chemical compound widely used in the fields of polymer chemistry and material science. This ester serves as a reactive monomer in the production of various polymers and copolymers, offering unique properties that enhance the performance and functionality of coatings, adhesives, and sealants.

The discovery of AAEM was part of the broader efforts in the mid-20th century to develop monomers with enhanced reactivity and specific functional groups. Researchers were interested in creating materials that could provide tailored properties for industrial applications. AAEM was synthesized by esterifying acetoacetic acid with 2-hydroxyethyl methacrylate (HEMA), combining the keto functionality of acetoacetic acid with the methacrylate group of HEMA. This synthesis produced a monomer capable of participating in free-radical polymerization, while also offering the potential for further chemical modifications due to the presence of the acetoacetoxy group.

One of the primary applications of 3-oxo-butyric acid 2-(2-methylacryloyloxy)ethyl ester is in the formulation of coatings. When polymerized, AAEM imparts excellent adhesion properties, resistance to UV degradation, and improved flexibility to the resulting materials. These characteristics make it an ideal component in automotive coatings, protective finishes, and architectural paints. The acetoacetoxy group in AAEM allows for crosslinking with various other components, enhancing the durability and chemical resistance of the coatings.

In adhesives and sealants, AAEM plays a crucial role by providing enhanced bonding strength and flexibility. The reactive nature of the acetoacetoxy group allows it to participate in crosslinking reactions with different types of resins, leading to the formation of strong, resilient adhesive bonds. This makes AAEM-containing adhesives suitable for use in demanding applications such as in the automotive, aerospace, and electronics industries, where high-performance bonding is required.

Another significant application of AAEM is in the field of polymer modification. By copolymerizing AAEM with other monomers, researchers can create tailor-made polymers with specific properties. For instance, copolymers of AAEM and styrene or acrylates are often used to produce materials with improved toughness, impact resistance, and thermal stability. These copolymers find use in various industrial sectors, including packaging, construction, and electronics, where materials with customized mechanical and thermal properties are essential.

Additionally, AAEM is utilized in the synthesis of functional resins for inks and coatings. Its ability to undergo further chemical modifications, such as reactions with amines, enables the production of resins with specific functionalities, including enhanced adhesion to substrates, improved flow characteristics, and resistance to solvents and chemicals. These resins are particularly valuable in the formulation of high-performance inks, coatings for electronic components, and specialty finishes for consumer goods.

Despite its widespread use, the application of 3-oxo-butyric acid 2-(2-methylacryloyloxy)ethyl ester is not without challenges. The synthesis and handling of AAEM require careful control to avoid premature polymerization, which can lead to issues in storage and processing. Additionally, the environmental impact of AAEM and its derivatives is an area of ongoing research, particularly concerning their potential to release volatile organic compounds (VOCs) during application and curing processes. As a result, there is a growing interest in developing more sustainable alternatives and improving the environmental profile of AAEM-based materials.

In conclusion, 3-oxo-butyric acid 2-(2-methylacryloyloxy)ethyl ester is a valuable chemical compound in the realm of polymer chemistry, offering unique properties that enhance the performance of coatings, adhesives, and modified polymers. Its discovery has paved the way for the development of high-performance materials that meet the demands of various industrial applications. However, ongoing research is essential to address the environmental concerns associated with its use, ensuring that the benefits of AAEM can be realized in a more sustainable manner.

References

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2018. β-ketoester-functionalized magnetoactive electrospun polymer fibers as Eu(III) adsorbents. SN Applied Sciences, 1(1).
DOI: 10.1007/s42452-018-0034-7