2-ETHYLHEXYL ACRYLATE
CAS number:103-11-7
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Molecular Formula:
C11H20O2 / CH2=CHCOOC8H17
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Molecular Weight:
184.27 g/mol
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Brief Introduction:
2-Ethylhexyl acrylate (EHA) is a clear, colorless liquid with a pleasant odor, commonly used in the production of paints and plastics. It is less dense than water, insoluble in water, and has a flash point of 180°F. However, it is classified as a potential carcinogen by California's Labor Code and the WHO's IARC. EHA is synthesized by esterifying acrylic acid with 2-ethylhexanol, and its copolymerization with other monomers, such as N-isopropylmethacrylamide, has been explored for applications in lubricating oils. Polymers created from EHA exhibit varying properties, including good viscosity-increasing, freezing-point-lowering, and anti-corrosion effects. Additionally, copolymerization of EHA with styrene and methacrylate in emulsion polymerization has been studied to produce stable latexes with controlled particle sizes and high conversions, showing potential for industrial-scale production.
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Properities:
Appearance Colorless liquid [1] Boiling Point 220-222 °C [1] Density 0.96 g/cm³ [1] Refractive Index 1.438 [1] Solubility in Water Insoluble [1] Solubility in Organic Solvents Soluble in ethanol, ether, chloroform [1] Stability Stable under normal conditions [1] Hazard Class Flammable liquid [1] Flash Point 85 °C [1] Viscosity Low viscosity liquid [1] Odor Characteristic acrid odor [1] Reactivity Reacts with acids, bases, and oxidizing agents [1] Polymerization Capable of polymerization in the presence of catalysts [1] Toxicity Low toxicity, but irritation to eyes and skin [1] Storage Conditions Store in a cool, dry, well-ventilated area [1] Applications Used in the production of copolymers for coatings, adhesives, printing inks, binders for paints, super absorbent polymers, flocculants, fibers, and plastics [1] Synthesis Method Fischer esterification of acrylic acid with 2-ethyl-1-hexanol using sulfuric acid as a homogeneous catalyst [1] Esterification Kinetics Forward reaction activation energy: 53.23 kJ/mol, Reverse reaction activation energy: 30.37 kJ/mol [1] Reusability DES [Im:2PTSA] can be recycled and reused with almost unchanged performance [1] Glass Transition Temperature (Tg) Varies with copolymer composition, e.g., -24 °C to 19 °C for S/EHA copolymers [3] Self-Healing Capability Exhibits facile autonomous self-healing over a broad composition range [3] Glass Transition Breadth Enhanced glass transition breadth compared to other acrylate copolymers [3] Interdigitation of Side Groups 2-ethylhexyl side groups can interdigitate, contributing to self-healing [3] Copolymer Composition Compositions from 45/55 mol% to 70/30 mol% exhibit self-healing [3] Self-Healing Time Complete self-healing in 3-30 hours for various compositions [3] Secondary Bonding Interactions Presence of substantial secondary bonding interactions [3] FTIR Characterization Peaks at 3447 cm-1 (OH group), 2955 cm-1 and 2873 cm-1 (CH3 and CH2 groups), 1792 cm-1 and 1654 cm-1 (C=O group), 1241 cm-1 and 1170 cm-1 (C-O-C group) [2] -
References:
[1]: Wang, R., Qin, H., Wang, J., Cheng, H., Chen, L., Qi, Z. (2021). Reactive extraction for intensifying 2-ethylhexyl acrylate synthesis using deep eutectic solvent [Im:2PTSA]. Green Energy & Environment, 6, 405-412.
[2]: Zhang, X., Deng, W., Wang, J. (2022). Preparation and Characteristic of Waterborne Acrylate Adhesive. Proceedings of the 2022 International Conference on Smart Manufacturing and Material Processing (SMMP2022).
[3]: Wang, T., Young, W. O., Suazo, M. J., Peera, A., Carter, M. C. D., Yeung, K., Li, L., Torkelson, J. M. (2024). Random Copolymers Based on 2-Ethylhexyl Acrylate Exhibit Unusual Glass Transition Breadth and Facile Autonomous Self-Healing over a Broad Composition Range. Macromolecular Rapid Communications, 45, 2400198.
Acrylic Esters
It is an ester of acrylic acid, classified within the broader category of acrylic esters.
Monomers
It is a key monomer used in the production of polymers and copolymers, especially for applications in coatings, adhesives, and sealants.
Aliphatic Compounds
Since 2-EHA is derived from aliphatic alcohol (2-ethylhexanol) and acrylic acid, it is also considered an aliphatic compound.
Solvents
It is used as a solvent in various formulations, especially in coatings and adhesives, due to its good solvency properties.
Reactive Chemicals
As a monomer, it is reactive and can undergo polymerization to form various types of polymers, especially in the production of flexible coatings, paints, and adhesives.
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