2-Ethylhexyl Acrylate CAS 103-11-7

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2-Ethylhexyl acrylate is an organic compound with molecular formula of c11h20o2, CAS 103-11-7, Colorless transparent liquid, insoluble in water. It is mainly used as a soft monomer for the manufacture of acrylate solvent type and lotion type pressure sensitive adhesives. It is also used as the main monomer for the production of microsphere pressure-sensitive adhesive for notebooks. It is also used to manufacture coatings, plastic modifiers, paper and leather processing aids, fabric finishing agents and other products. It is classified as a flammable liquid and is known to be stable but prone to polymerization, especially under the influence of light or heat. It is typically stabilized with inhibitors like hydroquinone monomethyl ether (MEHQ) to prevent spontaneous polymerization. This compound is insoluble in water but miscible with alcohols and ethers.

2-Ethylhexyl acrylate (2-EHA), with the chemical formula C11H20O2, is a colorless and transparent liquid with a slight fruity aroma and low volatility. As an important member of acrylic ester compounds, the long-chain alkyl groups in their molecular structure endow them with excellent flexibility, weather resistance, and chemical stability. Since the mid-20th century, isooctyl acrylate has become a core raw material in the fields of coatings, adhesives, plastic modification, and has shown great potential in emerging industries such as new energy and biomedicine.

The cornerstone application of traditional industrial fields

 

1. Coatings industry: builders of high-performance coatings
It is a key monomer for preparing high-performance coatings, especially in the fields of automotive, construction, and industrial protection. The ester groups and long-chain alkyl groups in its molecular structure can form a flexible polymer network, endowing the coating with the following characteristics:
Weather resistance: Fluorine or silicon monomer can be introduced through copolymerization to prepare ultraviolet resistant and anti-aging exterior wall coatings, and the service life of these coatings is more than 30% longer than that of traditional products.

 

Impact resistance: Adding 20% -30% 2-EHA to automotive varnish can increase the flexibility of the coating by 40% and effectively resist stone impact damage.

Environmental protection: the introduction of 2-EHA in water-based acrylic lotion can reduce VOC emissions, which meets the European Union REACH regulations and the domestic "double carbon" target requirements.
Case: BASF's water-based automotive coating based on 2-EHA has been applied to Tesla Model Y and other vehicles, achieving zero VOC emissions while maintaining high glossiness.

 

2. Adhesive field: the leap from pressure-sensitive adhesive to structural adhesive
As the core soft monomer of pressure-sensitive adhesive, it improves the flexibility of the adhesive layer through internal plasticization and is widely used in:
Memo paper and tape: As the main monomer of microsphere pressure-sensitive adhesive, 2-EHA endows the adhesive layer with repeatable peeling properties, with an annual global consumption of over 100000 tons.
Electronic packaging: Adding 2-EHA to conductive adhesive can reduce the modulus to the level of 10 ³ Pa, meeting the bending requirements of flexible display screens.

 

Medical patch: the hydrogel patch prepared by copolymerization with acrylic acid has a transdermal absorption rate 25% higher than that of traditional products.

Technical breakthrough: Japan Toray Company has developed medical tape with adhesive strength of 30N/25mm through nano 2-EHA lotion polymerization technology, which has passed FDA certification.

3. Plastic modification: from universal materials to high-end functionalization
As a modifier, it can significantly improve the properties of plastics:
PVC toughening: Adding 5% -8% 2-EHA can increase the impact strength of PVC pipes by 2 times and reduce the low-temperature brittleness temperature to -30 ℃.

 

TPE elastomer: a thermoplastic elastomer prepared by copolymerization with styrene, with a tensile strength of up to 20MPa, widely used in automotive sealing strips.
3D printing material: As a flexible component of photocurable resin, 2-EHA enables the fracture elongation of printed parts to exceed 150%, meeting the requirements of shoe mold manufacturing.
Market data: The global market size of 2-EHA for plastic modification will reach 870 million US dollars in 2024, with a compound annual growth rate of 6.2%.

Breakthrough applications in emerging technology fields

 

1. New energy batteries: innovation in electrolytes and binders
In the field of lithium-ion batteries, material system upgrades are being promoted:
Solid electrolyte: As a soft segment of the polymer matrix, 2-EHA can increase the ionic conductivity to 10 ⁻ S/cm, which is 2 orders of magnitude higher than the traditional PEO system.
Silicon based negative electrode binder: A binder prepared by copolymerization with polyacrylic acid, which can alleviate the volume expansion of silicon particles and increase the cycle life to over 500 times.

 

Sodium ion battery: Introducing 2-EHA into the hard carbon negative electrode binder increases the initial efficiency to 85%, approaching the level of lithium-ion batteries.
R&D News: In the solid-state battery patent announced by CATL in 2025, 2-EHA based polymer electrolyte becomes a key component, with an energy density exceeding 400Wh/kg.

2. Biomedical materials: from tissue engineering to drug delivery
Its biocompatibility makes it shine in the medical field:
Hydrogel scaffold: 3D printing scaffold prepared by copolymerization with methacrylic anhydride, with porosity of 90%, promotes osteoblast proliferation.

 

Microsphere controlled release system: 2-EHA based PLGA microspheres have a drug loading capacity of up to 20%, achieving 6-month sustained release of insulin.

Antibacterial coating: Modified 2-EHA with quaternary ammonium salt groups introduced, achieving a 99.9% inhibition rate against Staphylococcus aureus.
Clinical progress: The 2-ethylhexyl acrylate based joint lubricant developed by Johnson&Johnson has entered phase III clinical trials and can significantly alleviate pain in osteoarthritis.

3. Flexible electronics: the core material of wearable devices
In the field of flexible displays and sensors, isooctyl acrylate plays an irreplaceable role:

 

Transparent conductive film: As a plasticizer for PEDOT: PSS, 2-EHA reduces the square resistance to 50 Ω/□ and maintains a transmittance of over 90%.
Strain sensor: A flexible sensor prepared by composite with carbon nanotubes, with a detection range of 100% and a response time of<10ms.
Electronic skin: ion conductive hydrogel based on 2-EHA, with pressure sensitivity of 1.2kPa ⁻⁻, can monitor micro physiological signals.
Industrial application: Samsung's Galaxy Ring smart ring, released in 2025, features a pressure sensing layer made of 2-EHA based composite material.

Direct esterification involves the reaction between acrylic acid and 2-ethylhexanol in the presence of a catalyst. This method is commonly used for industrial production.

Procedure:

Preparation of Reactants: Acrylic acid and 2-ethylhexanol are mixed in a suitable ratio, typically with an excess of alcohol to ensure complete esterification.

Catalyst Addition: A strong acid, such as sulfuric acid, is added as a catalyst to facilitate the esterification reaction.

Reaction Conditions: The mixture is heated to a suitable temperature, usually in the range of 100-150°C, and stirred vigorously to ensure thorough mixing and reaction.

Work-up: After the completion of the reaction, the mixture is neutralized with a base (e.g., sodium bicarbonate) to remove excess acid and catalyst. The product is then separated from the aqueous phase, washed with water to remove impurities, and dried over a desiccant (e.g., anhydrous sodium sulfate).

Purification: The dried product is then purified through distillation to obtain high-purity 2 ethylhexyl acrylate.

Advantages: Simple process, widely used in industry.

Disadvantages: The use of strong acids as catalysts can lead to equipment corrosion and the formation of by-products that require careful handling and disposal.

Transesterification involves the reaction of acrylic esters with 2-ethylhexanol in the presence of a catalyst. This method offers an alternative route to 2-ethylhexyl acrylate production.

Procedure:

Reactant Selection: Acrylic esters, such as acrylic methyl ester, are chosen as starting materials.

Catalyst Addition: A suitable catalyst, such as titanium tetrachloride, is added to the reaction mixture to promote the transesterification reaction.

Reaction Conditions: The mixture is heated to a moderate temperature, and the reaction is allowed to proceed under stirring.

Work-up and Purification: Similar to direct esterification, the mixture is worked up and purified through neutralization, washing, drying, and distillation to obtain the desired product.

Advantages: Can utilize readily available acrylic esters as starting materials.

Disadvantages: The selection of an appropriate catalyst and optimization of reaction conditions are crucial for achieving high yields and purity.

Gas-phase ester exchange is a less common method but offers potential advantages in terms of reaction efficiency and product purity.

Procedure:

Reactant Vaporization: Acrylic esters and 2-ethylhexanol are vaporized and fed into a reactor.

Catalyst: A solid catalyst, such as titanium tetrachloride supported on silica gel, is used to promote the ester exchange reaction in the gas phase.

Reaction Conditions: The reaction is carried out at high temperatures, typically in the range of 200-300°C, to ensure efficient vaporization and reaction.

Product Recovery: The resulting product vapor is condensed and purified through distillation or other separation techniques.

Advantages: Potentially higher reaction rates and product purity due to the gas-phase nature of the reaction.

Disadvantages: More complex equipment and process control requirements compared to liquid-phase methods.

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