Dodecyl 2-methylacrylate
[CAS# 142-90-5]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Other ester compounds
• Name: Dodecyl 2-methylacrylate
• Synonyms: Lauryl methacrylate; 2-Methyl-2-propenoic acid dodecyl ester
• Molecular Formula: C₁₆H₃₀O₂
• Molecular Weight: 254.41
• CAS Registry Number: 142-90-5
• EC Number: 205-570-6
• SMILES: CCCCCCCCCCCCOC(=O)C(=C)C

Properties

• Density: 0.871
• Melting point: -7 °C
• Refractive index: 1.444-1.447
• Boiling point: 142 °C
• Flash point: 109 °C
• Water solubility: insoluble

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Risk Statements: H315-H319-H335-H400-H410
• Safety Statements: P261-P264-P264+P265-P271-P273-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Skin corrosion	Skin Corr.	1C	H314

Discovery and Applications

Dodecyl 2-methylacrylate is a chemical compound that has gained prominence in polymer chemistry and material science due to its unique properties and applications. This ester is characterized by a dodecyl group, a 12-carbon alkyl chain, attached to the 2-methylacrylate backbone. The long hydrocarbon chain imparts notable hydrophobic characteristics, making it a valuable component in various industrial processes.

The discovery of dodecyl 2-methylacrylate can be traced back to research focused on developing novel monomers for polymer synthesis. The aim was to create polymers with enhanced hydrophobicity and stability. The synthesis of dodecyl 2-methylacrylate involves the esterification of 2-methylacrylic acid with dodecanol. The resulting compound combines the reactive acrylate functionality with a long alkyl chain, offering unique attributes that are useful in several applications.

One of the primary applications of dodecyl 2-methylacrylate is in the production of specialty polymers and copolymers. The hydrophobic nature of the dodecyl group enhances the water resistance of the resulting polymers. This property is particularly useful in applications where water resistance is critical, such as in coatings, adhesives, and sealants. The compound's ability to improve the water repellency of materials makes it valuable in both consumer products and industrial applications.

Dodecyl 2-methylacrylate is also employed in the creation of surfactants and emulsifiers. In these applications, the compound's long hydrophobic chain helps to stabilize emulsions and foams, which are essential in various formulations, including personal care products and detergents. Its effectiveness in enhancing the stability of emulsions contributes to the performance and longevity of these products.

Furthermore, the compound's role in enhancing the performance of materials is not limited to water resistance. It also contributes to the flexibility and durability of polymers. This makes dodecyl 2-methylacrylate a valuable component in the production of flexible films and coatings that require both strength and elasticity.

Despite its advantages, there are considerations related to the environmental impact and safety of using dodecyl 2-methylacrylate. Research is ongoing to assess the potential effects of this compound on human health and the environment. Efforts are focused on ensuring safe handling practices and exploring alternatives with improved safety profiles.

Overall, dodecyl 2-methylacrylate is a significant chemical compound with applications in polymer chemistry, surfactant production, and material science. Its unique properties enhance the performance of various products, making it an important component in both industrial and consumer applications.

References

2024. Oil-soluble polymer brushes-functionalized nanoMOFs for highly efficient friction and wear reduction. Friction, 12(7).
DOI: 10.1007/s40544-023-0823-x

2024. Effect of polymethacrylate additive functionalization on low-temperature properties of diesel fuel. Journal of Thermal Analysis and Calorimetry, 149(12).
DOI: 10.1007/s10973-024-13271-9

2024. Synthesis of nonionic polyacrylate emulsions: coatings for digital inkjet printing. Journal of Coatings Technology and Research, 21(5).
DOI: 10.1007/s11998-024-00916-5