Preparation methods and application of 2-(2-Ethoxyethoxy)ethyl acrylate

2-(2-Ethoxyethoxy)ethyl acrylate is an unsaturated carboxylic acid ester compound that exists as a colorless transparent liquid under ambient temperature and pressure, characterized by a distinctive ester-like odor and a certain degree of volatility. It is insoluble in water but miscible with most organic solvents. The structure of 2-(2-ethoxyethoxy)ethyl acrylate contains a highly reactive unsaturated double bond unit, which makes it suitable for the structural modification and synthesis of polyvinyl-based polymeric materials. Additionally, this compound can be used as a component in coatings, adhesives, and inks, offering excellent adhesion and durability.

Figure1: Picture of 2-(2-Ethoxyethoxy)ethyl acrylate

Preparation Methods

This synthesis method belongs to the field of photocurable materials and relates to a clean production process for 2-(2-ethoxyethoxy)ethyl acrylate. The specific steps are as follows: (1) esterification and reflux dehydration of diethylene glycol monoethyl ether or ethylene glycol phenyl ether, acrylic acid, a catalyst, a solvent, a polymerization inhibitor, and an antioxidant; (2) neutralization by adding flake alkali and a small amount of water; (3) adsorption of salts generated during neutralization using a magnesium polysilicate adsorbent; (4) dehydration and solvent removal under reduced pressure; (5) pressure filtration to remove magnesium polysilicate and the adsorbed salts; (6) decolorization and removal of trace water and trace acids by adding alkaline calcium-based bentonite and calcium oxide; (7) pressure filtration; and (8) product quality testing. The invention provides a clean production method for 2-(2-ethoxyethoxy)ethyl acrylate with high yield, economic benefits, and environmental advantages, fundamentally addressing the issue of organic wastewater pollution during the production of 2-(2-ethoxyethoxy)ethyl acrylate. [1]

Application

Synthesis of UV-curable coatings

Patents have reported that 2-(2-ethoxyethoxy)ethyl acrylate can be used in the synthesis of UV-curable coatings, films, and graphite heat dissipation materials. The described UV-curable coating comprises: PUA oligomer (50–75%), reactive diluent (1) (0.5–20%), reactive diluent (2) (0.2–10%), reactive diluent (3) (0.05–10%), photoinitiator (1–10%), and additives (0.05–0.4%). Reactive diluent (1) includes 2-(2-ethoxyethoxy)ethyl acrylate, reactive diluent (2) includes ethylene glycol diacrylate derivatives, and reactive diluent (3) includes hydroxyl-functional acrylates and/or tetrahydrofurfuryl acrylate. The coating can be cured under ultraviolet light without the need for heating and without solvent emission. When applied to graphite sheet substrates and cured, the resulting film exhibits low shrinkage, excellent flex resistance, voltage breakdown resistance, abrasion resistance, and flexibility, along with strong adhesion to substrates such as graphite sheets, making it an environmentally friendly material. In this system, the incorporation of 2-(2-ethoxyethoxy)ethyl acrylate contributes significantly to the overall performance and sustainability of the coating formulation. [2]

Polymer Properties

In this study, a high-pressure variable-volume view cell was employed to investigate the phase behavior data of binary and ternary mixture systems composed of poly[2-(2-ethoxyethoxy)ethyl acrylate] with supercritical solvents and cosolvents over a wide range of temperatures and pressures. As the concentrations of DME and 2-(2-ethoxyethoxy)ethyl acrylate increased, the cloud-point behavior of the poly[2-(2-ethoxyethoxy)ethyl acrylate]–CO₂–cosolvent system shifted toward lower temperatures and pressures. Notably, when 65.0 wt% of 2-(2-ethoxyethoxy)ethyl acrylate was added to the poly[2-(2-ethoxyethoxy)ethyl acrylate]–CO₂ system, various phase behaviors such as fluid, liquid–liquid, liquid–vapor, and hypothetical liquid–liquid–vapor equilibria were observed. The CO₂–2-(2-ethoxyethoxy)ethyl acrylate system exhibited type‑I phase behavior and showed no three-phase coexistence at any of the five selected temperatures. The experimental data were compared with results calculated using the PR equation of state, in which the temperature-independent interaction parameters (kij and ηij) were obtained at T = 353.2 K, as well as with values calculated using adjustable optimized parameters derived at each temperature. Good agreement was observed between the experimental data and the calculated values from the PR equation at each temperature, with a root‑mean‑square deviation of 2.6% for the CO₂–2-(2-ethoxyethoxy)ethyl acrylate system across the five temperatures. [3]

Reference

[1] Hu Jianfei, Zhang Lili, Ma Huaixiang, et al. Clean production method for 2-(2-ethoxyethoxy)ethyl acrylate or 2-phenoxyethyl acrylate. Chinese Invention Patent, Patent No.: CN102633634A.

[2] Kuang Xuping, Cao Xing, Hou Yaru, et al. A UV-curable coating, film, and graphite heat dissipation material: CN201710450074.9 [P].

[3] Yoon S D, Phase behavior for the poly [2-(2-ethoxyethoxy) ethyl acrylate] and 2-(2-ethoxyethoxy) ethyl acrylate in supercritical solvents[J]. The Journal of Supercritical Fluids, 2014, 86: 41-48.