BISOMER 2HEA (2-HYDROXYETHYL ACRYLATE)
Bisomer 2HEA (2-Hydroxyethyl acrylate) is a multifunctional acrylic monomer containing both a highly reactive acrylate double bond and a polar hydroxyl group, providing dual reactivity in polymer systems.
This dual functionality makes Bisomer 2HEA (2-Hydroxyethyl acrylate) a versatile reactive diluent and building block in free-radical, UV-curing, and emulsion polymerization processes, enabling crosslinking, adhesion, and post-functionalization.
Bisomer 2HEA (2-Hydroxyethyl acrylate) is widely used in high-performance coatings, adhesives, sealants, inks, and specialty polymers, where it improves adhesion to polar substrates, flexibility, and overall formulation performance.
CAS Number: 818-61-1
EC Number: 212-454-9
Molecular Formula: C5H8O3
Molecular Weight: ~116.12 g/mol
Synonyms: 2-Propenoic acid, 2-hydroxyethyl ester, Ethylene glycol monoacrylate, Bisomer 2HEA (2-Hydroxyethyl acrylate), 2-(Acryloyloxy)ethanol, Ethylene glycol, acrylate, Acrylic acid, 2-hydroxyethyl ester, Ethylene glycol, monoacrylate, DTXSID2022123, 25GT92NY0C, beta-Bisomer 2HEA (2-Hydroxyethyl acrylate), DTXCID202123, RefChem:6744, 212-454-9, 2-hydroxyethyl prop-2-enoate, 2-hydroxyethylacrylate, Acrylic acid 2-hydroxyethyl ester, MFCD00002865, 2-Hydroxyethylester kyseliny akrylove, MFCD00081878, 26403-58-7, 2-Bisomer 2HEA (2-Hydroxyethyl acrylate) (stabilized with MEHQ), CAS-818-61-1, ROCRYL(TM) 420 (HEA) Monomer LA, Rocryl 420, Viscoat 220, Acrylic Acid, 2-hydroxyethyl ester, HEA, 2-Propenoic acid, 2-hydroxyethyl ester, acrylic acid, 2-hydroxyethyl ester, acrylic acid, monoester with ethyleneglycol, 2-( acryloyloxy)ethanol, ethylene glycol, monoacrylate, 2- hydroxyethyl prop-2-enoate, acrylate, stabilized / ethylene glycol, CCRIS 3431, HSDB 1123, EINECS 212-454-9, 2-Bisomer 2HEA (2-Hydroxyethyl acrylate)(7.56 cp(15.5 degrees c)), BRN 0969853, UNII-25GT92NY0C, 2-Hydroxyethylester kyseliny akrylove [Czech], hydroxyethylacrylate, hydroxylethyl acrylate, 2-hydroxylethylacrylate, 2-hydroxy-ethyl acrylate, EC 212-454-9, .beta.-Bisomer 2HEA (2-Hydroxyethyl acrylate), SCHEMBL14875, MLS002174257, SCHEMBL204415, SCHEMBL2512082, SCHEMBL7830905, SCHEMBL9115624, SCHEMBL9831446, CHEMBL1330518, 2-Bisomer 2HEA (2-Hydroxyethyl acrylate), Ethylene glycol monoacrylate, .beta.-Bisomer 2HEA (2-Hydroxyethyl acrylate), 2-(Acryloyloxy)ethanol, 2-Bisomer 2HEA (2-Hydroxyethyl acrylate), 2-Bisomer 2HEA (2-Hydroxyethyl acrylate), 2-Propenoic acid, 2-hydroxyethyl ester (9CI), Acrylic acid, 2-hydroxyethyl ester (6CI, 8CI), Bisomer 2HEA (2-Hydroxyethyl acrylate), Ethylene glycol monoacrylate, Light Ester HOA, ROCRYL(TM) 420 (HEA) Monomer
Bisomer 2HEA (2-Hydroxyethyl acrylate) is a high-purity, low-molecular-weight acrylic monomer widely used as a reactive diluent and functional building block in polymer and resin formulations.
Bisomer 2HEA (2-Hydroxyethyl acrylate) contains both an acrylate group and a hydroxyl functional group, which provide excellent reactivity and enable strong adhesion, crosslinking, and compatibility with a wide range of polymer systems.
Bisomer 2HEA (2-Hydroxyethyl acrylate) is commonly applied in coatings, adhesives, sealants, inks, and specialty polymers, where it improves flexibility, adhesion to polar substrates, and formulation versatility.
Bisomer 2HEA (2-Hydroxyethyl acrylate)'s good miscibility with water and many organic solvents, combined with controlled reactivity, makes it suitable for high-performance industrial and specialty applications.
Bisomer 2HEA (2-Hydroxyethyl acrylate) contains both a hydroxyl group and an unsaturated double bond.
When reacting with isocyanates, Bisomer 2HEA (2-Hydroxyethyl acrylate) exhibits moderate reactivity, resulting partly from the electron-donating effect of the hydrocarbon chains and partly from its greater availability for reaction.
This means that a hydroxy group on a long chain has much greater mobility and can thus more easily interact with an isocyanate group.
Bisomer 2HEA (2-Hydroxyethyl acrylate) is more reactive than hydroxypropyl acrylate and less reactive than 4-hydroxybutyl acrylate.
Bisomer 2HEA (2-Hydroxyethyl acrylate) is the organic compound with the formula CH2=CHCO2CH2CH2OH.
Bisomer 2HEA (2-Hydroxyethyl acrylate) is a colorless viscous liquid.
Bisomer 2HEA (2-Hydroxyethyl acrylate) has dual functionality: a polymerizable acrylic and a hydroxy group.
Bisomer 2HEA (2-Hydroxyethyl acrylate) appears as a clear colorless liquid.
Bisomer 2HEA (2-Hydroxyethyl acrylate) is less dense than water.
Bisomer 2HEA (2-Hydroxyethyl acrylate) is a clear, colorless liquid with a slight acrylic odor.
Bisomer 2HEA (2-Hydroxyethyl acrylate) comprises of a polymerizable acrylate functional group in one end and a reactive hydroxyl group at the other end.
Bisomer 2HEA (2-Hydroxyethyl acrylate) is readily miscible with water and with most organic solvents and has relatively low volatility.
Bisomer 2HEA (2-Hydroxyethyl acrylate) copolymerizes readily with a wide variety of monomers, and the added hydroxyl groups impart properties such as hydrophilicity, improved adhesion to substrates, chemical and scratch resistance, crosslinking sites, low VOCs, and weatherability.
Bisomer 2HEA (2-Hydroxyethyl acrylate) is a colorless hydrophilic liquid monomer.
Bisomer 2HEA (2-Hydroxyethyl acrylate) is a dual reactive acrylic monomer and possesses reactive sites for reaction.
Bisomer 2HEA (2-Hydroxyethyl acrylate) complies with TSCA regulation.
Bisomer 2HEA (2-Hydroxyethyl acrylate) is a hydrophilic monomer with the chemical formula C5H8O3.
Bisomer 2HEA (2-Hydroxyethyl acrylate) is a clear water white liquid.
Bisomer 2HEA (2-Hydroxyethyl acrylate) has a boiling point 82°C and a freezing point of below -70°C.
Bisomer 2HEA (2-Hydroxyethyl acrylate) is miscible with water.
Bisomer 2HEA (2-Hydroxyethyl acrylate) is a multifunctional acrylic monomer characterized by the presence of both a highly reactive acrylate double bond and a polar hydroxyl group within the same molecule.
This dual functionality makes Bisomer 2HEA (2-Hydroxyethyl acrylate) a versatile intermediate and reactive diluent in a wide range of polymerization systems, including free-radical, UV-curing, and emulsion polymerization processes.
The acrylate moiety provides rapid polymerization and copolymerization capability, while the hydroxyl group enhances polarity, hydrogen bonding, and chemical reactivity toward isocyanates, epoxies, and melamine resins.
Bisomer 2HEA (2-Hydroxyethyl acrylate) is widely used in the formulation of high-performance coatings, adhesives, sealants, inks, and specialty polymers, where it contributes to improved adhesion to polar substrates such as metals, glass, concrete, and plastics.
Bisomer 2HEA (2-Hydroxyethyl acrylate)'s incorporation into polymer backbones increases flexibility, toughness, and intercoat adhesion, while also enabling post-functionalization and crosslinking reactions.
In water-based and solvent-based systems, Bisomer 2HEA (2-Hydroxyethyl acrylate) offers good miscibility and formulation compatibility, supporting the development of tailored resin properties.
Due to its relatively low viscosity, Bisomer 2HEA (2-Hydroxyethyl acrylate) is often employed as a reactive diluent to reduce formulation viscosity without introducing non-reactive components, thereby maintaining final film performance.
Bisomer 2HEA (2-Hydroxyethyl acrylate) is particularly valued in UV-curable and radiation-curable systems for enhancing cure speed, surface wetting, and coating uniformity.
When properly stabilized and handled, Bisomer 2HEA (2-Hydroxyethyl acrylate) delivers consistent performance and plays a critical role in advanced polymer design for industrial, construction, and specialty chemical applications.
Uses of Bisomer 2HEA (2-Hydroxyethyl Acrylate):
Bisomer 2HEA (2-Hydroxyethyl acrylate) is used as a reactive diluent in acrylic, UV-curable, and radiation-curable resin systems to reduce viscosity while remaining part of the final polymer structure.
Bisomer 2HEA (2-Hydroxyethyl acrylate) is applied in industrial, architectural, and protective coatings to improve adhesion, flexibility, and intercoat bonding.
Bisomer 2HEA (2-Hydroxyethyl acrylate) is utilized in adhesives and sealants to enhance bonding strength to polar substrates such as metals, glass, concrete, and plastics.
Bisomer 2HEA (2-Hydroxyethyl acrylate) is employed in printing inks and overprint varnishes to improve wetting, film formation, and curing performance.
Bisomer 2HEA (2-Hydroxyethyl acrylate) is used in water-based and emulsion polymerization systems to introduce hydroxyl functionality and increase polymer polarity.
Bisomer 2HEA (2-Hydroxyethyl acrylate) is applied in crosslinkable resin systems where the hydroxyl group enables secondary chemical reactions.
Bisomer 2HEA (2-Hydroxyethyl acrylate) is incorporated into specialty polymers and copolymers to tailor mechanical properties, flexibility, and chemical reactivity.
Bisomer 2HEA (2-Hydroxyethyl acrylate) is used in the manufacture of thermosetting acrylic coatings, light curing acrylic coatings, photosensitive coatings, adhesives, textile processing agents, paper processing, water quality stabilizers and polymer materials.
Bisomer 2HEA (2-Hydroxyethyl acrylate) can be incorporated into binders, such as polyacrylates, via radical or ionic polymerization.
Since Bisomer 2HEA (2-Hydroxyethyl acrylate) has a free hydroxy group, it can be used to incorporate hydroxy groups into resins.
These groups are then available for curing reactions with isocyanates or urea resins.
Bisomer 2HEA (2-Hydroxyethyl acrylate) is generally used as a monomer for various classes of binders and polymers.
In addition to the possibility of incorporating Bisomer 2HEA (2-Hydroxyethyl acrylate) into resins via the double bond, it is also possible to do so via the hydroxy group.
An example of this would be the reaction of 3 moles of Bisomer 2HEA (2-Hydroxyethyl acrylate) and one mole of HDI isocyanurate.
This results in a urethane acrylate , which can be used as a reactive diluent in UV-curable coatings.
Bisomer 2HEA (2-Hydroxyethyl acrylate) is a hydroxy functional acrylic monomer which can be used in a variety of ways to produce resins that are useful in high performance coating applications.
Using typical methods for the polymerization of ethylenically unsaturated monomers, Bisomer 2HEA (2-Hydroxyethyl acrylate) can be used to attach hydroxy groups to an acrylic polymer backbone.
The pendant hydroxyl groups can then act as sites for reaction with a variety of cross-linking agents.
Bisomer 2HEA (2-Hydroxyethyl acrylate) allows faster curing cycles and/or reduced baking temperatures, compared with hydroxyalkyl methacrylates.
Additionally, Bisomer 2HEA (2-Hydroxyethyl acrylate) can be formulated at higher solids in coating applications.
Bisomer 2HEA (2-Hydroxyethyl acrylate) is also a key raw material for acrylic polyols.
Bisomer 2HEA (2-Hydroxyethyl acrylate) is used in the manufacture of acrylic resins, polyester-acrylate resins, and urethane-acrylate resins.
Bisomer 2HEA (2-Hydroxyethyl acrylate) is a monomer used to make emulsion polymers along with other monomers and the resultant resins are used in coatings, sealants, adhesives and elastomers and other applications.
Industry Uses:
Intermediates
Not Known or Reasonably Ascertainable
Other (specify)
Paint additives and coating additives not described by other categories
Monomers
Photosensitive agent
Consumer Uses:
Other (specify)
Dispersing agent
Not Known or Reasonably Ascertainable
Binder
Photosensitive agent
Paint additives and coating additives not described by other categories
Monomers
Features of Bisomer 2HEA (2-Hydroxyethyl Acrylate):
Bisomer 2HEA (2-Hydroxyethyl acrylate) contains both an acrylate double bond and a hydroxyl functional group, providing dual reactivity and high formulation versatility.
Bisomer 2HEA (2-Hydroxyethyl acrylate) exhibits high polymerization reactivity, making it suitable for free-radical, UV-curing, and radiation-curing systems.
Bisomer 2HEA (2-Hydroxyethyl acrylate) offers good miscibility with water and many organic solvents, supporting use in water-based and solvent-based formulations.
Bisomer 2HEA (2-Hydroxyethyl acrylate) contributes to excellent adhesion and intercoat bonding due to its polar hydroxyl functionality.
Bisomer 2HEA (2-Hydroxyethyl acrylate) enables post-crosslinking reactions with isocyanates, epoxies, and melamine resins.
Bisomer 2HEA (2-Hydroxyethyl acrylate) has low viscosity, allowing effective viscosity reduction without introducing non-reactive components.
Bisomer 2HEA (2-Hydroxyethyl acrylate) supports flexibility, toughness, and durability in finished polymer systems.
Production of Bisomer 2HEA (2-Hydroxyethyl Acrylate):
Bisomer 2HEA (2-Hydroxyethyl acrylate) is produced through the controlled esterification of acrylic acid with ethylene glycol–based intermediates, typically under acid-catalyzed conditions.
The process is carefully managed to achieve high purity and to prevent premature polymerization of the acrylate double bond, with inhibitors added as needed during manufacture.
Reaction temperature, residence time, and purification steps are tightly controlled to minimize by-product formation and ensure consistent product quality.
The resulting monomer is refined to meet stringent specifications required for use in coatings, adhesives, and polymer applications, where reliable reactivity and performance are critical.
Synthesis of Bisomer 2HEA (2-Hydroxyethyl Acrylate):
Bisomer 2HEA (2-Hydroxyethyl acrylate) is synthesized by the controlled esterification of acrylic acid with ethylene glycol or ethylene oxide–derived intermediates, most commonly via the reaction of acrylic acid with ethylene oxide to form 2-hydroxyethyl acrylate.
The synthesis is carried out under carefully regulated temperature and pressure conditions in the presence of acidic catalysts, while polymerization inhibitors are added to prevent premature free-radical polymerization of the acrylate double bond.
Process parameters such as reaction time, catalyst concentration, and inhibitor level are optimized to achieve high conversion and selectivity.
After completion of the reaction, the product is purified to remove unreacted raw materials and by-products, resulting in a high-purity monomer suitable for use in coatings, adhesives, inks, and specialty polymer formulations.
Stability and Reactivity of Bisomer 2HEA (2-Hydroxyethyl Acrylate):
Chemical stability:
Bisomer 2HEA (2-Hydroxyethyl acrylate) is chemically stable under recommended storage and handling conditions when adequately inhibited.
Reactivity:
Contains a reactive acrylate double bond and may undergo free-radical polymerization.
Conditions to avoid:
Heat, direct sunlight, sources of ignition, contamination with peroxides or initiators, and uncontrolled temperature rise.
Incompatible materials:
Strong oxidizing agents, strong acids and bases, peroxides, and free-radical initiators.
Hazardous decomposition products:
Thermal decomposition may produce carbon oxides (CO, CO₂) and irritating acrylate vapors.
Handling and Storage of Bisomer 2HEA (2-Hydroxyethyl Acrylate):
Handling:
Handle in accordance with good industrial hygiene and safety practices.
Avoid skin and eye contact and prevent inhalation of vapors or mists.
Use grounded equipment and avoid sources of ignition.
Storage:
Store in a cool, dry, well-ventilated area in tightly closed containers.
Storage conditions:
Protect from heat, light, and air exposure.
Maintain inhibitor content as supplied.
Packaging materials:
Use stainless steel or approved coated containers.
Shelf life:
Stable for extended periods when stored under recommended conditions with inhibitor present.
First Aid Measures of Bisomer 2HEA (2-Hydroxyethyl Acrylate):
Inhalation:
Remove the affected person to fresh air.
Keep at rest and seek medical attention if symptoms such as irritation or dizziness persist.
Skin contact:
Wash immediately with plenty of soap and water.
Remove contaminated clothing and wash before reuse.
Seek medical attention if irritation develops.
Eye contact:
Rinse cautiously with water for several minutes.
Remove contact lenses if present and easy to do.
Seek medical attention if irritation persists.
Ingestion:
Rinse mouth with water.
Do not induce vomiting.
Seek medical advice immediately.
Most important symptoms:
Skin and eye irritation, respiratory irritation, possible sensitization upon repeated exposure.
Firefighting Measures of Bisomer 2HEA (2-Hydroxyethyl Acrylate):
Suitable extinguishing media:
Alcohol-resistant foam, dry chemical powder, carbon dioxide (CO₂), or water spray.
Specific hazards:
Combustible liquid; vapors may form explosive mixtures with air.
Protective equipment for firefighters:
Self-contained breathing apparatus and full protective clothing.
Special precautions:
Cool exposed containers with water spray.
Prevent runoff from entering drains.
Accidental Release Measures of Bisomer 2HEA (2-Hydroxyethyl Acrylate):
Personal precautions:
Evacuate unnecessary personnel.
Avoid breathing vapors and prevent skin or eye contact.
Use appropriate personal protective equipment.
Environmental precautions:
Prevent entry into drains, surface water, or soil.
Methods for cleanup:
Absorb spill with inert material such as sand or vermiculite.
Collect in suitable containers for disposal according to local regulations.
Exposure Controls / Personal Protective Equipment of Bisomer 2HEA (2-Hydroxyethyl Acrylate):
Occupational exposure limits:
Not specifically established.
Engineering controls:
Use local exhaust ventilation or closed systems to minimize exposure.
Personal protective equipment (PPE):
Respiratory protection:
Organic vapor respirator recommended where ventilation is insufficient.
Hand protection:
Chemical-resistant gloves (e.g., nitrile).
Eye protection:
Safety goggles or face shield.
Skin protection:
Protective clothing to prevent prolonged or repeated contact.
Hygiene measures:
Wash hands thoroughly after handling.
Do not eat, drink, or smoke in work areas.
Identifiers of Bisomer 2HEA (2-Hydroxyethyl Acrylate):
CAS number: 818-61-1
EC / EINECS number: 212-454-9
Molecular formula: C₅H₈O₃
Molecular weight: 116.12 g/mol
Chemical family: Acrylate esters
Physical form: Clear, colorless to slightly yellow liquid
Odor: Mild, characteristic acrylate odor
SMILES: C=CC(=O)OCCO
InChI Key: OMIGHNLMNHATMP-UHFFFAOYSA-N
Reaxys Registry Number: 969853
PubChem Substance ID: 87562286
SDBS (AIST Spectral DB): 940
MDL Number: MFCD00002865
Linear Formula: CH2=CHCOOCH2CH2OH
CAS Number: 818-61-1
Molecular Weight: 116.12
Beilstein: 969853
EC Number: 212-454-9
MDL number: MFCD00002865
UNSPSC Code: 12162002
PubChem Substance ID: 24857612
NACRES: NA.23
Physical state: liquid
Color: colorless
Odor: sweetish, pungent
Properties of Bisomer 2HEA (2-Hydroxyethyl Acrylate):
Chemical formula: C5H8O3
Molar mass: 116.116 g•mol−1
Appearance: colorless liquid
Density: 1.106
Boiling point: 220 °C (428 °F; 493 K)
Molecular Weight: 116.11 g/mol
XLogP3: -0.2
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 3
Rotatable Bond Count: 4
Exact Mass: 116.047344113 Da
Monoisotopic Mass: 116.047344113 Da
Topological Polar Surface Area: 46.5 Ų
Heavy Atom Count: 8
Complexity: 87.7
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Food Chemicals Codex Listed: No
Specific Gravity: 1.10600 to 1.11000 @ 20.00°C
Pounds per Gallon - (est): 9.214 to 9.247
Refractive Index: 1.44700 to 1.45200 @ 20.00°C
Flash Point: 209.00°F TCC (98.33°C)
Soluble in: water, 1.00E+06 mg/L @ 25°C (exp)
Molar mass: 116.1 g mol−1
State of matter: fluid
Density: 1.106 g cm−3
Melting point: <−60°C
Boiling point: 200.3°C
Vapor pressure: 0.1 hPa (21.4°C)
Solubility: miscible with water
EC No: 212-454-9
CAS No: 818-61-1
HS Code: 29161290
KH Product Code: 100472
Formula: C5H8O3
CAS: 818-61-1,150-76-5
Molecular Weight (g/mol): 116.12
PubChem CID: 13165
Formula Weight: 116.12
Physical Form: Oily Liquid
Acidity: 4 mg KOH/g max.
CAS Max %: 100.0
Color: Yellow to Brown
Boiling Point: 210°C to 215°C
Infrared Spectrum: Authentic
Packaging: Glass bottle
Refractive Index: 1.4490 to 1.451
InChI Key: OMIGHNLMNHATMP-UHFFFAOYSA-N
IUPAC Name: 2-hydroxyethyl prop-2-enoate
Stabilizer: 200 to 450 ppm MEHQ
Viscosity: 9 mPa.s (20°C)
Percent Purity: 97%
Odor: Characteristic ester-like odor
Density: ~1.106 g/mL (at ~20–25 °C)
Melting point / freezing point: Approx. –60 °C (some sources: –60 °C)
Vapor pressure: < 0.1 mm Hg (at 20 °C)
Vapor density: > 1 (air = 1)
Refractive index: n₍₂₀, D₎ ≈ 1.45
Viscosity: ~7.56 cP (at ~15.5 °C)
Solubility: Miscible with water; soluble in many organic solvents
Flash point: ~209 °F (~98–99 °C) (closed cup) for some grades
pKa (predicted): ~13.85 ± 0.10
Specifications of Bisomer 2HEA (2-Hydroxyethyl Acrylate):
Infrared spectrum: Conforms
Stabilizer: 200 to 450 ppm MEHQ
Appearance (Form): Clear liquid
Color scale: =<30 APHA
GC: >=96.0 %
Refractive index: 1.4470 to 1.4520 (20°C, 589 nm)
