2-HYDROXYETHYL ACRYLATE (2-HEA)
2-Hydroxyethyl acrylate (2-HEA) is a bifunctional acrylic ester derived from acrylic acid that contains both acrylate and hydroxyl functional groups, enabling it to form homopolymers and a wide range of copolymers.
2-Hydroxyethyl acrylate (2-HEA)'s low viscosity and high reactivity allow efficient copolymerization with monomers such as acrylic acid, acrylates, methacrylates, styrene, vinyl acetate, and butadiene, as well as secondary reactions with isocyanates, anhydrides, and epoxides.
Polymers and intermediates based on 2-Hydroxyethyl acrylate are widely applied in automotive and architectural coatings, photocurable resins, and adhesive systems where durability, adhesion, and surface performance are critical.
CAS Number: 818-61-1
EC Number: 212-454-9
Chemical Formula: C5H8O3
Molar Mass: 116.116 g·mol−1
Synonyms: Acrylic acid 2-hydroxyethyl ester, Acrylic acid, 2-hydroxyethyl ester, Acrylic acid hydroxyethyl ester, 2-Propenoic acid, 2-hydroxyethyl ester, 2-propenoic acid 2-hydroxyethyl ester, 2-Hydroxyethyl prop-2-enoate, 2-Hydroxyethyl-2-propenoate, 2-(Acryloyloxy)ethanol, Ethylene glycol monoacrylate, Ethylene glycol acrylate, Ethylene glycol, monoacrylate, Ethandiol-1,2-monoacrylate, 2-HYDROXYETHYL ACRYLATE [HSDB], CCRIS 3431, HSDB 1123, UNII-25GT92NY0C, BRN 0969853, MFCD00081878, MFCD00002865, DTXSID2022123, DTXCID202123, CHEMBL1330518, SCHEMBL14875, MLS002174257, AKOS015856805, Q27253959, Tox21_201430, Tox21_302968, CS-W013616, HAI (CHRIS Code), SMR001253953, A0743, FT-0626326, D78194, A840207, J-521472, NCGC00090958-01, NCGC00090958-02, NCGC00256462-01, beta-Hydroxyethyl acrylate, .beta.-Hydroxyethyl acrylate, hydroxyethylacrylate, hydroxylethyl acrylate, 2-hydroxyethylacrylate, 2-hydroxylethylacrylate, Bisomer 2HEA, HEA, Borica HEA, HYDROXYETHYL ACRYLATE [INCI]
2-Hydroxyethyl acrylate (2-HEA) is a reactive acrylic monomer characterized by the presence of both a polymerizable acrylate double bond and a hydrophilic hydroxyl group, which gives it high reactivity and functional versatility.
2-Hydroxyethyl acrylate (2-HEA) has the molecular formula C5H8O3 and typically appears as a clear, colorless to slightly yellow liquid with a characteristic acrylate odor.
The acrylate group readily participates in free-radical polymerization, while the hydroxyl functionality enables hydrogen bonding and further chemical modification such as esterification, urethane formation, or crosslinking.
This dual functionality allows 2-Hydroxyethyl acrylate (2-HEA) to improve adhesion, flexibility, and hydrophilicity in polymer systems.
Consequently, 2-Hydroxyethyl acrylate (2-HEA) is widely used as a monomer or comonomer in the production of coatings, adhesives, resins, inks, hydrogels, and UV-curable formulations where controlled surface properties and enhanced performance are required.
2-Hydroxyethyl acrylate (2-HEA) is an ester of Acrylic Acid and is used as a raw material in the synthesis of polymers.
2-Hydroxyethyl acrylate (2-HEA) is a methacrylate monomer with characteristic high reactivity and a branched hydrophobic part.
2-Hydroxyethyl acrylate (2-HEA) forms homo-polymers and copolymers.
Copolymers of 2-Hydroxyethyl acrylate (2-HEA) can be prepared with (meth) acrylic acid and its salts, amides, and esters, along with methacrylate, acrylonitrile, maleic esters, butadiene, and other monomers.
2-Hydroxyethyl acrylate (2-HEA) forms homopolymers and copolymers.
2-Hydroxyethyl acrylate (2-HEA) is used mainly either as a co-monomer in the manufacture of polymers or as a chemical reactant in the manufacture of chemical intermediates.
In the manufacture of polymers, 2-Hydroxyethyl acrylate (2-HEA) can be co-polymerized with acrylic acid, acrylates, methacrylates, vinyl acetate, vinyl chloride, vinylidene chloride, styrene, butadiene, and the like.
Co-reactants with 2-Hydroxyethyl acrylate (2-HEA) include aromatic and aliphatic isocyanates, anhydrides, and epoxides.
The polymers and chemical intermediates made with 2-Hydroxyethyl acrylate (2-HEA) find applications in automotive top coatings, architectural coatings, photocure resins, and adhesives.
Globally about half of the 2-Hydroxyethyl acrylate (2-HEA) produced is used in the production of acrylic enamels for the automotive industry, where a clear topcoat is applied to a pigmented base coat to increase corrosion protection and durability.
2-Hydroxyethyl acrylate (2-HEA) is a bifunctional monomer that contains both hydroxyl and acrylate functional groups, making it highly reactive in various polymerization processes.
2-Hydroxyethyl acrylate (2-HEA) appears as a clear, colorless liquid with a distinct acrylic odor and has a relatively low viscosity, allowing for easy incorporation into different formulations.
Due to its hydroxyl functionality, 2-Hydroxyethyl acrylate (2-HEA) is widely used in applications requiring strong adhesion, flexibility, and enhanced chemical resistance.
2-Hydroxyethyl acrylate (2-HEA) serves as a crucial component in the formulation of coatings, adhesives, sealants, resins, and specialty polymers.
2-Hydroxyethyl acrylate (2-HEA) is a multifunctional acrylic ester that plays an important role in modern polymer and materials chemistry due to its combination of high polymerization activity and chemical reactivity.
Structurally, 2-Hydroxyethyl acrylate (2-HEA) consists of an acrylate moiety linked to a two-carbon alcohol chain, providing both a vinyl group capable of rapid free-radical polymerization and a terminal hydroxyl group that enables secondary reactions and intermolecular interactions.
Physically, 2-Hydroxyethyl acrylate (2-HEA) is typically a clear, colorless to pale yellow liquid with a sharp acrylate odor and good miscibility with water and many polar organic solvents.
In polymer systems, the acrylate double bond ensures fast curing and efficient copolymerization, while the hydroxyl group enhances adhesion to substrates, increases hydrophilicity, and allows post-polymerization modifications such as crosslinking, esterification, or urethane formation.
Because of this dual functionality, 2-Hydroxyethyl acrylate (2-HEA) is extensively used as a reactive monomer or comonomer in coatings, adhesives, hydrogels, pressure-sensitive materials, inks, resins, and radiation-curable formulations, particularly in applications requiring strong adhesion, flexibility, and controlled surface and mechanical properties.
Uses of 2-Hydroxyethyl Acrylate (2-HEA):
2-Hydroxyethyl acrylate (2-HEA) is widely used as a reactive monomer and comonomer in polymer systems due to its combined acrylate and hydroxyl functionality.
2-Hydroxyethyl acrylate (2-HEA) is incorporated into coatings and paints to enhance adhesion, flexibility, hydrophilicity, and film durability, particularly on polar substrates.
In adhesive and sealant formulations, 2-Hydroxyethyl acrylate (2-HEA) improves bonding strength and compatibility with metals, glass, wood, and plastics.
2-Hydroxyethyl acrylate (2-HEA) is also employed in polymer and copolymer synthesis to introduce hydroxyl groups that allow further chemical modification and crosslinking.
Additionally, 2-Hydroxyethyl acrylate (2-HEA) is extensively used in the production of hydrogels and in UV- and radiation-curable systems such as inks, varnishes, and resins, where fast curing, strong adhesion, and controlled surface properties are required.
Coatings and Paints:
2-Hydroxyethyl acrylate (2-HEA) is used to improve adhesion, flexibility, hydrophilicity, and durability in water-based and solvent-based coating systems.
Adhesives and Sealants:
2-Hydroxyethyl acrylate (2-HEA) enhances bonding strength to polar substrates such as metals, glass, wood, and plastics.
Polymer and Copolymer Synthesis:
2-Hydroxyethyl acrylate (2-HEA) is incorporated to introduce hydroxyl functionality, enabling further chemical modification and crosslinking.
Hydrogels:
2-Hydroxyethyl acrylate (2-HEA) is widely used in hydrogel production for biomedical applications, including wound dressings, contact lenses, and drug delivery systems.
UV- and Radiation-Curable Systems:
2-Hydroxyethyl acrylate (2-HEA) is applied in UV- and electron-beam-curable inks, varnishes, and resins to achieve rapid curing and high conversion.
Inks and Printing Materials:
2-Hydroxyethyl acrylate (2-HEA) improves film formation, flexibility, and substrate adhesion in printing inks and overprint varnishes.
Textile and Paper Treatments:
2-Hydroxyethyl acrylate (2-HEA) is used to modify surface properties and enhance durability in textile and paper finishing applications.
Specialty and Functional Polymers:
2-Hydroxyethyl acrylate (2-HEA) serves as a key building block in functional polymers requiring controlled surface energy, reactivity, and mechanical performance.
Industry Uses:
Intermediates
Not Known or Reasonably Ascertainable
Other (specify)
Paint additives and coating additives not described by other categories
Monomers
Photosensitive agent
Uses at industrial sites:
2-Hydroxyethyl acrylate (2-HEA) is used in the following products: polymers.
2-Hydroxyethyl acrylate (2-HEA) has an industrial use resulting in manufacture of another substance (use of intermediates).
2-Hydroxyethyl acrylate (2-HEA) is used in the following areas: scientific research and development.
2-Hydroxyethyl acrylate (2-HEA) is used for the manufacture of: chemicals and plastic products.
Release to the environment of 2-Hydroxyethyl acrylate (2-HEA) can occur from industrial use: for thermoplastic manufacture, as an intermediate step in further manufacturing of another substance (use of intermediates) and as processing aid.
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
Production of 2-Hydroxyethyl Acrylate (2-HEA):
2-Hydroxyethyl acrylate (2-HEA) is primarily produced by the esterification of acrylic acid with ethylene oxide or by transesterification routes using suitable hydroxyethyl intermediates under controlled conditions.
The reaction is typically carried out in the presence of acid catalysts, while polymerization inhibitors such as MEHQ or hydroquinone are added to prevent premature polymerization of the acrylate double bond.
Temperature, pressure, and reaction time are carefully regulated to achieve high conversion and selectivity.
After completion, the crude product is purified by neutralization and vacuum distillation to remove unreacted raw materials, catalysts, and low-boiling impurities.
Industrial production is conducted in closed systems with strict control of oxygen, heat, and inhibitor levels to ensure product stability and consistent quality for use in coatings, adhesives, hydrogels, and specialty polymer applications.
Synthesis of 2-Hydroxyethyl Acrylate (2-HEA):
2-Hydroxyethyl acrylate (2-HEA) is synthesized mainly by the controlled esterification of acrylic acid with ethylene oxide or, alternatively, by transesterification routes using hydroxyethyl intermediates.
The process is carried out under carefully regulated conditions in the presence of acidic catalysts, while polymerization inhibitors such as MEHQ or hydroquinone are added to suppress premature free-radical polymerization of the acrylate group.
Reaction temperature, pressure, and residence time are closely controlled to achieve high yield and selectivity.
After completion, the reaction mixture is neutralized and purified, typically by vacuum distillation, to remove unreacted materials, catalysts, and volatile impurities.
Industrial synthesis is performed in closed systems with strict control of oxygen, heat, and inhibitor concentration to ensure product stability and consistent quality.
Stability and Reactivity of 2-Hydroxyethyl Acrylate (2-HEA):
Chemical Stability:
2-Hydroxyethyl acrylate (2-HEA) is chemically stable under normal ambient temperatures and recommended storage conditions when properly stabilized with polymerization inhibitors.
Without inhibitors or under unfavorable conditions, the material may undergo uncontrolled polymerization.
Reactivity:
2-Hydroxyethyl acrylate (2-HEA) is a highly reactive acrylate monomer and readily participates in free-radical polymerization reactions.
2-Hydroxyethyl acrylate (2-HEA) can react exothermically in the presence of heat, light, peroxides, or other radical initiators.
Conditions to Avoid:
Avoid excessive heat, direct sunlight, sparks, open flames, static discharge, oxygen exposure, and depletion of polymerization inhibitors.
Avoid prolonged storage at elevated temperatures.
Incompatible Materials:
Strong oxidizing agents, strong acids and bases, peroxides, amines, metal salts, and radical initiators should be avoided, as they may trigger polymerization or decomposition.
Hazardous Decomposition Products:
Under fire or extreme thermal conditions, decomposition may produce carbon monoxide, carbon dioxide, acrylate vapors, and irritating organic fumes.
Handling and Storage of 2-Hydroxyethyl Acrylate (2-HEA):
Safe Handling:
Handle 2-Hydroxyethyl acrylate (2-HEA) in well-ventilated areas using closed or controlled systems where possible.
Avoid skin contact, eye contact, and inhalation of vapors.
Prevent contamination with inhibitors-depleting materials.
Ground and bond containers during transfer to avoid static discharge.
Hygiene Measures:
Wash hands and exposed skin thoroughly after handling.
Do not eat, drink, or smoke in handling areas.
Remove contaminated clothing and wash before reuse.
Storage Requirements:
Store in tightly closed containers in a cool, dry, and well-ventilated location away from heat and ignition sources.
Maintain inhibitor concentration and protect from light and air.
Packaging Integrity:
Use stainless steel, aluminum, or approved polymer containers.
Keep containers sealed when not in use.
Shelf Stability:
Shelf life is limited and dependent on temperature, inhibitor content, and storage conditions.
Elevated temperatures or oxygen exposure may significantly reduce stability.
First Aid Measures of 2-Hydroxyethyl Acrylate (2-HEA):
Inhalation:
Move the exposed person to fresh air immediately.
Keep at rest and monitor breathing.
If irritation, coughing, or breathing difficulty persists, seek medical attention.
Skin Contact:
Remove contaminated clothing immediately.
Wash skin thoroughly with soap and plenty of water.
Seek medical attention if redness, irritation, or sensitization develops.
Eye Contact:
Rinse cautiously with clean water for several minutes while holding eyelids open.
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 immediate medical advice.
Notes for Physician:
Treat symptomatically.
Acrylates may cause irritation or sensitization; no specific antidote is available.
Firefighting Measures of 2-Hydroxyethyl Acrylate (2-HEA):
Flammability:
2-Hydroxyethyl acrylate (2-HEA) is a flammable liquid and may form flammable vapor–air mixtures.
Suitable Extinguishing Media:
Alcohol-resistant foam, dry chemical powder, carbon dioxide (CO₂), or water spray.
Hazardous Combustion Products:
Carbon oxides, acrylate vapors, and irritating organic fumes may be released during combustion.
Special Protective Equipment for Firefighters:
Wear self-contained breathing apparatus and full protective clothing.
Specific Hazards:
Containers may rupture due to pressure buildup under fire conditions.
Cool exposed containers with water spray.
Accidental Release Measures of 2-Hydroxyethyl Acrylate (2-HEA):
Personal Precautions:
Evacuate unnecessary personnel.
Avoid breathing vapors and prevent skin or eye contact.
Wear appropriate personal protective equipment.
Environmental Precautions:
Prevent release into drains, surface water, or soil.
Contain spills to avoid environmental contamination.
Cleanup Methods:
Absorb with inert materials such as sand, vermiculite, or absorbent pads.
Collect into suitable containers for disposal.
Do not use materials that may initiate polymerization.
Additional Advice:
Ventilate area thoroughly after cleanup.
Dispose of waste in accordance with local regulations.
Exposure Controls and Personal Protective Equipment of 2-Hydroxyethyl Acrylate (2-HEA):
Engineering Controls:
Use local exhaust ventilation, enclosed transfer systems, and explosion-proof equipment to minimize vapor exposure.
Respiratory Protection:
Use organic vapor respirators when ventilation is inadequate or during spill response.
Hand Protection:
Wear chemical-resistant gloves such as nitrile, neoprene, or butyl rubber.
Eye Protection:
Wear safety goggles or a face shield to prevent splashes.
Skin and Body Protection:
Wear protective clothing to prevent skin contact.
Environmental Exposure Controls:
Implement vapor containment and ventilation systems to limit atmospheric release.
Identifiers of 2-Hydroxyethyl Acrylate (2-HEA):
CAS Registry Number: 818-61-1
EC (EINECS) Number: 212-454-9
Molecular formula: C5H8O3
Molecular weight: 116.11 g/mol
Chemical class: Acrylic ester; hydroxyl-functional monomer
Structural formula: CH2=CH–COO–CH2–CH2–OH
InChI: InChI=1S/C5H8O3/c1-2-5(7)8-4-3-6/h2,6H,1,3-4H2
SMILES: C=CC(=O)OCCO
CAS Number: 818-61-1
ChEMBL: ChEMBL1330518
ChemSpider: 12612
ECHA InfoCard: 100.011.322
EC Number: 212-454-9
PubChem CID: 13165
RTECS number: AT1750000
UNII: 25GT92NY0C
UN number: 2927 1760
CompTox Dashboard (EPA): DTXSID20891159 DTXSID2022123, DTXSID20891159
InChI: InChI=1S/C5H8O3/c1-2-5(7)8-4-3-6/h2,6H,1,3-4H2
Key: OMIGHNLMNHATMP-UHFFFAOYSA-N
SMILES: C=CC(=O)OCCO
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
Properties of 2-Hydroxyethyl Acrylate (2-HEA):
vapor density: >1 (vs air)
Quality Level: 100
vapor pressure: <0.1 mmHg ( 20 °C)
Assay: 96%
form: solid
contains: 200-650 ppm monomethyl ether hydroquinone as inhibitor
refractive index: n20/D 1.45 (lit.)
bp: 90-92 °C/12 mmHg (lit.)
density: 1.011 g/mL at 25 °C (lit.)
storage temp.: 2-8°C
SMILES string: OCCOC(=O)C=C
InChI: 1S/C5H8O3/c1-2-5(7)8-4-3-6/h2,6H,1,3-4H2
InChI key: OMIGHNLMNHATMP-UHFFFAOYSA-N
Physical state: Clear, colorless to pale yellow liquid
Chemical class: Acrylic ester monomer
Molecular formula: C5H8O3
Molecular weight: 116.11 g/mol
Odor: Pungent, characteristic acrylate odor
Density (20 °C): ~1.12 g/cm3
Boiling point: ~213–215 °C
Melting point: Below 0 °C
Viscosity (20 °C): Low to moderate
Solubility: Miscible with water; soluble in most polar organic solvents
Volatility: Moderate
Hydrophilicity: High due to hydroxyl group
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
Specifications of 2-Hydroxyethyl Acrylate (2-HEA):
Acidity: 4mg KOH/g max.
CAS Min %: 96.0
Melting Point: -60°C
Density: 1.1060g/mL
Flash Point: 99°C
Assay Percent Range: 96% min. (GC)
Refractive Index: 1.4490 to 1.451
Specific Gravity: 1.106
Solubility in water: soluble in water
SMILES: C=CC(=O)OCCO
Stabilizer: 200 to 450ppm MEHQ
PubChem CID: 13165
Formula Weight: 116.12
Physical Form: Oily Liquid
Names of 2-Hydroxyethyl Acrylate (2-HEA):
Regulatory process names:
2-(Acryloyloxy)ethanol
2-hydroxyethyl acrylate
2-Hydroxyethyl acrylate
2-hydroxyethyl acrylate
2-Hydroxyethylester kyseliny akrylove
2-Propenoic acid, 2-hydroxyethyl ester
Acrylic acid 2-hydroxyethyl ester
acrylic acid, monoester with ethyleneglycol
Bisomer 2HEA
Ethylene glycol, acrylate
Ethylene glycol, monoacrylate
HEA
Hydroxyethyl acrylate
Translated names:
(2-hydroxyetyl)-akrylát (sk)
2-hidroksietil akrilat (sl)
2-hidroksietil-akrilat (hr)
2-hidroksietilakrilatas (lt)
2-hidroksietilakrilāts (lv)
2-hidroxietil acrilat (ro)
2-hidroxietil-akrilát (hu)
2-hydroksietyyliakrylaatti (fi)
2-hydroksyetylakrylat (no)
2-hydroxietylakrylat (sv)
2-hydroxyethyl-akrylát (cs)
2-hydroxyethylacrylaat (nl)
2-hydroxyethylacrylat (da)
2-Hydroxyethylacrylat (de)
2-hüdroksüetüülakrülaat (et)
2-хидроксиетил акрилат (bg)
acrilato de 2-hidroxietilo (es)
acrilato de 2-hidroxietilo (pt)
acrilato di 2-idrossietile (it)
acrylate de 2-hydroxyéthyle (fr)
akrylan 2-hydroksyetylu ester 2-hydroksyetylowy kwasu akrylowego (pl)
ακρυλικό 2-υδροξυαιθύλιο (el)
IUPAC names:
2-HYDROXYETHYL ACRYLATE
2-Hydroxyethyl acrylate
2-hydroxyethyl acrylate
2-Hydroxyethyl acrylate
2-hydroxyethyl acrylate
2-Hydroxyethyl Acrylate (stabilized with MEHQ)
2-Hydroxyethyl acrylate2-HEA
2-Hydroxyethyl ester propenoic acid
2-hydroxyethyl prop-2-enoate
2-hydroxyethylprop-2-enoate
2-Propenoic acid, 2-hydroxyethyl ester
2-propenoic acid, 2-hydroxyethyl ester
2HEA
HEA
Hydroxyethyl Acrylate
Hydroxyethyl acrylate
Trade names:
2-(Acryloyloxy)ethanol
2-HYDROXYETHYL ACRYLATE
2-Hydroxyethyl acrylate
2-Propenoic acid, 2-hydroxyethyl ester (9CI)
Acrylic acid, 2-hydroxyethyl ester (6CI, 8CI)
Bisomer 2HEA
Ethylene glycol monoacrylate
HEA
Light Ester HOA
Rocryl 420
ROCRYL(TM) 420 (HEA) Monomer
ROCRYL(TM) 420 (HEA) Monomer LA
urethane acrylate blend
Viscoat 220
β-Hydroxyethyl acrylate
Other identifiers:
139642-59-4
1637456-67-7
607-072-00-8
77210-89-0
818-61-1
