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2-ETHYLHEXYL ACRYLATE

2-Ethylhexyl acrylate is a colorless liquid acrylate with a pleasant odor, used in the making of paints, plastics and adhesives.
2-Ethylhexyl acrylate is an enoate ester.

2-Ethylhexyl Acrylate (2-EHA) is an ester of Acrylic acid and is used as a raw material component in the synthesis of polymers.
2-Ethylhexyl Acrylate (2-EHA) is a difunctional monomer with a characteristic high reactivity of methacrylates and a branched hydrophobic moiety.
Copolymers of 2-Ethylhexyl acrylate can be prepared with (meth)acrylic acid and its salts, amides, and esters, and with (meth)acrylates, acrylonitrile, maleic acid esters, vinyl acetate, vinyl chloride, vinylidene chloride, styrene, butadiene, unsaturated polyesters and drying oils, etc.

Product Type: Acrylate Monomer

CAS: 103-11-7
European Community (EC) Number: 203-080-7

Molecular Formula: C11H20O2
CH2=CHCOOC8H17
Molecular Weight: 184.27 g/mol
IUPAC Name: 2-ethylhexyl prop-2-enoate

2-Ethylhexyl Acrylate (2-EHA ) is a highly versatile building block that readily copolymerizes with a wide variety of other acrylic and vinyl monomers to tailor specific high molecular weight copolymer properties for a diverse range of non-rigid applications.

As a higher alkyl acrylate comonomer, 2 Exylhexyl Acrylate uses a range of factors to impart a glass transition temperature that is well below room temperature (homopolymer Tg is – 65°C), flexibility, elasticity, and hydrophobic qualities.
Unique features the compound contributes to copolymer compositions include low-temperature flexibility, water resistance, good weathering characteristics, and UV (sunlight) resistance.

Primary applications that take advantage of these characteristics include multiple adhesives, especially pressure-sensitive adhesives (PSA), paint & coatings, caulks & sealants, textile & paper finishes, and printing inks.

Because 2-Ethylhexyl acrylate contributes to clarity, toughness, and light, weather, and chemical resistance, manufacturers can use acrylic copolymers containing 2-Ethylhexyl acrylate in interior, exterior, basecoat, and topcoat paint & coating formulations, as well as other related products.

New areas of technical advancements for 2-Ethylhexyl Acrylate uses exist in the homopolymer, poly(2-ethylhexyl acrylate), as a plasticizer material for surface coatings, film, sheeting, and pressure-sensitive adhesives and tapes.
As a plasticizer incorporated into PSAs, it results in an increase in peel strength and tack.

At the same time, 2-Ethylhexyl acrylate improves removability, making it great in areas that may need to be regularly recoated.
2-Ethylhexyl acrylate is used in superabsorbent copolymers to produce fast-swelling, highly-porous hydrogels for diapers and hygiene products.

Chemical Properties:

Purity: min. 99.6%
Acid Value: max. 0.009%
Water content: max. 0.05%
Color APHA: max. 10

Physical Properties:

Appearance: clear, colorless
Physical form: liquid
Odor: sweet
Molecular weight: 184.3 g/mol
Density: 0.885 g/cm3 at 20 °C
Boiling Point: 91 °C at 13 mbar
Freezing Point: approx. – 90 °C
Viscosity: 1.7 mPa ∙ s at 20 °C
Vapor Point: 0.1 mbar at 20 °C

Features & Benefits:

- Chemical resistance
- Chemical crosslinking
- Scratch resistance
- Adhesion
- Low VOC
- Rheology modifier
- Weatherability

Applications areas:
2-Ethylhexyl Acrylate (2-EHA) is used in the preparation of solid polymers, dispersions, and polymer solutions, which are used as binders, film formers, adhesives , and sealants, coatings in various industries.
Particularly widespread use of 2-Ethylhexyl Acrylate (2-EHA) was in the production of pressure-sensitive adhesives and hydrophobic coatings and binders.

2-Ethylhexyl acrylate is applied in the production of:

- Automotive Coatings
- Industrial Coatings
- Adhesives
- Plastics
- UV Curables

2-Ethylhexyl Acrylate (2-EHA) is also a very useful feedstock for chemical syntheses because it readily undergoes addition reactions with a wide variety of organic and inorganic compounds.

2-ethylhexyl acrylate appears as a clear colorless liquid with a pleasant odor.
2-Ethylhexyl acrylate is less dense than water and insoluble in water.
Vapors heavier than air.
Flash point 180 °F.
2-Ethylhexyl acrylate is used in making of paints and plastics.

Preparation
Racemic 2-ethylhexyl acrylate can be prepared with a high yield by esterification of acrylic acid with racemic 2-ethylhexanol in the presence of hydroquinone as a polymerization inhibitor and a strong acid such as methanesulfonic acid by reactive distillation using toluene as an azeotroping agent.

Properties
2-Ethylhexyl acrylate polymerizes easily.
The polymerization can be initiated by light, peroxides, heat, or contaminants.
2-Ethylhexyl acrylate can react violently when combined with strong oxidants and can form explosive mixtures with air at temperatures above 82 °C (180 °F).
The chemical, physical, and toxicological properties, however, can be greatly modified by additives or stabilizers.

Use
2-Ethylhexyl acrylate and butyl acrylate are the major base monomers for the preparation of acrylate adhesives.
2-Ethylhexyl acrylate can react by free-radical polymerization to form macromolecules having a molecular weight of up to 200,000 g/mol. Other monomers such as vinyl acetate, methyl acrylate, and styrene may be copolymerized to modify the properties of the resulting polymer.

Because 2-EHA contributes to clarity, toughness, and light, weather, and chemical resistance, manufacturers can use acrylic copolymers containing 2-EHA in interior, exterior, basecoat, and topcoat paint & coating formulations, as well as other related products.

At the same time, 2-Ethylhexyl acrylate improves removability, making it great in areas that may need to be regularly recoated.
2-EHA is used in superabsorbent copolymers to produce fast-swelling, highly-porous hydrogels for diapers and hygiene products.

2-Ethylhexyl acrylate can undergo free radical solution polymerization to yield its polymer.
2-Ethylhexyl acrylate can form a series of copolymers via atom transfer radical copolymerization.
A study reports the emulsion terpolymerization of the product with styrene, methacrylic acid.
2-ethylhexyl acrylate (EHA) is one of the constituents of acrylic polymeric latex.
2-Ethylhexyl acrylate can undergo free-radical solution polymerization.
EHA is known to undergo free radical emulsion co- polymerization with methyl methacrylate (MMA) to form pressure-sensitive adhesives.
2-Ethylhexyl acrylate may also form copolymers with acrylonitrile and acrylamide.

Attributes of 2-Ethylhexyl acrylate as a comonomer include:
- A low Tg -65°C and low-temperature flexibility
- Facilitates design of softness and tackiness in copolymers
- Excellent copolymerization characteristics
- Entanglement of the C8 side chain facilitates macromolecular entanglement (Me)
- Improves water resistance and weathering
- Suitable for external applications.
- A low order of toxicity
- Availability and commodity economics

2-Ethylhexyl Acrylate uses include being a key monomer in a wide range of copolymer compositions.
Free-radical polymerization techniques afford high monomer conversions and very high macromolecule molecular weights (>200,000).
The ease of handling and co-polymerization of 2-EHA allow for use in emulsion, solvent, suspension, and bulk polymerization uses.

Acrylate esters in general, which include 2-EHA, BA, MMA and GAA, represent a versatile family of building blocks for thousands of copolymer compositions.
Copolymerization can lead to well-designed properties required in a broad range of end-use applications.

Styrene monomers and short-chain acrylic monomers such as methyl methacrylate produce harder, more brittle polymers, with high cohesion and strength characteristics.
Long-chain monomers such as 2-EHA and BA enable soft, flexible, tacky polymers with lower strength characteristics, increasing adhesion, elasticity, and flexibility.

By managing the comonomer ratios and the glass transition temperatures, the chemist can balance hardness and softness, tackiness and block resistance, adhesive and cohesive properties, low-temperature flexibility, strength, durability, and other key properties to facilitate end-use goals.

Functional monomers such as diacetone acrylamide, (meth)acrylic acid, glycidyl acrylates, and maleic anhydride can be incorporated as crosslinking agents and/or as cure accelerators.

Monomers including acrylonitrile and (meth)acrylamide can improve solvent and oil resistance.

2-ethyl hexyl acrylate is an acrylate monomor with a molecular formula of CH2=CHCOOC8H17.
2-Ethylhexyl acrylate is a clear liquid which is completely soluble in alcohols and ethers but not soluble in water.
2 ethylhexyl acrylate is not a very flammable liquid with a flashpoint between 75 – 90° C and has a characteristic acrylic odour.

2-Ethylhexyl acrylate is easily miscible with other organic solvents and is readily polymerized with monomer molecules to create polymer chains.
2-Ethylhexyl acrylate will react with oxidising agents such as alkalis and will polymerise with the application of heat.
Polymerisation is inhibited with methyl ether or hydroquinone.

How is it produced?
2-Ethylhexyl acrylate is commonly produced by combining 2-ethyl hexanol and an acrylic acid in a dehydraisation process that acts as the catalyst (sulphuric acid).
Using solid catalysts can help reduce the drawbacks of this process such as corrosion and spillage of the spent acid.

What is 2-Ethyl Hexyl Acrylate used for?
2-Ethylhexyl acrylate is used in the chemical manufacturing industry for the production of homopolymers and co-polymers which have further uses in creating aqueous polymers.
2-Ethylhexyl acrylate is used as a co-polymer for caulks, paint coatings, pressure sensitive adhesives, leather finishing, textiles and paper coatings.
Due to its low volatile nature and reactivity of double bonds, 2-Ethylhexyl acrylate is the perfect choice for plasticising many applications.
The primary end user market of 2-Ethylhexyl acrylate is the textiles, leather, adhesive, paints and coatings industry.

2-Ethylhexyl acrylate forms homopolymers and copolymers.
Copolymers of 2-Ethylhexyl acrylate can be prepared with acrylic acid and its salts, amides and esters, and with methacrylates, acrylonitrile, maleic acid esters, vinyl acetate, vinyl chloride, vinylidene chloride, styrene, butadiene, unsaturated polyesters and drying oils, etc.
2-Ethylhexyl acrylate is also a very useful feedstock for chemical syntheses, because it readily undergoes addition reactions with a wide variety of organic and inorganic compounds.

Uses
Acrylic esters are used in the production of polymers and copolymers with a wide range of applications.
As a plasticizing co-monomer, 2-ethylhexyl acrylate is used in the production of resins for pressure-sensitive adhesives, latex, paints, textile and leather finishes and coatings for paper.
2-Ethylhexyl acrylate can also be used as a co-monomer in solution polymers for industrial metal finishing.
The major current use of 2-ethylhexyl acrylate is in acrylic pressure-sensitive adhesives, of which it is a major component.
The typical composition of an adhesive for general-purpose tape is 75% 2-ethylhexyl acrylate, 20% vinyl acetate, 4% acrylic acid and 1% N-methylolacrylamide.

2-Ethylhexyl acrylate is also used in ultraviolet-curable coatings without solvents, which provide a glossy, abrasion-resistant finish, e.g. on book covers and record albums.
A typical ultraviolet-cured formulation might include 20% trimethylpropane triacrylate, 70% acrylated polyurethane oligomer, 10% 2-ethylhexyl acrylate diluent monomer and small amounts of photoinitiator.
A liquid coating or ink is spread on the surface of the substrate, and the coating is exposed to ultraviolet light for less than 1 sec and is completely cured.

Production
Direct, acid-catalysed esterification of acrylic acid with 2-ethylhexanol is the principal method for the manufacture of 2-ethylhexyl acrylate.
The commonest catalysts are sulfuric and para-toluenesulfonic acid and sulfonic acid functional cation-exchange resins.
The monomethyl ether of hydroquinone is added as a polymerization inhibitor, and the esters are used in this form in most industrial applications.

Occurrence

Natural occurrence
2-Ethylhexyl acrylate is not known to occur as a natural product.

Water
2-Ethylhexyl acrylate was detected at concentrations ranging from 0.6 to 11 ppb (µg/L) (mean, 4 ppb) in the effluent from the last stage of an on-site waste-treatment facility which received water from a large petrochemical plant on the US coast of the Gulf of Mexico.
The influent untreated wastewater contained 0.55-5.6 ppm (mg/L) (mean, 2.0 ppm).

2-Ethylhexyl acrylate (2-EHA) is an important bulk chemical used as precursor in the production of acrylic polymers.
Industrially, 2-EHA is produced batchwise by esterification of acrylic acid (AA) and 2-ethylhexanol (2-EH), with formation of water as byproduct.
The reaction takes place in presence of strong homogeneous catalysts as sulfuric acid.
To overcome corrosion, catalyst recovery from product and catalyst disposal problems, research based on solid catalysts received recently an increased attention.

Storage & Handling:
In order to prevent polymerization, 2-Ethylhexyl Acrylate (2-EHA) must always be stored under air, and never under inert gases.
The presence of oxygen is required for the stabilizer to function effectively.
It has to contain a stabilizer and the storage temperature must not exceed 35 °C.
For extended storage periods over 4 weeks, it is advisable to replenish the dissolved oxygen content.
Under these conditions, the storage stability of one year can be expected.
In order to minimize the likelihood of over storage, the storage procedure should strictly follow the “first-in-first-out” principle.
Storage tanks and pipes should be made of stainless steel or aluminum.
Although 2-Ethylhexyl Acrylate (2-EHA) does not corrode carbon steel, there is a risk of contamination if corrosion does occur.
Storage tanks, pumps, and pipes must be earthed.

SYNONYMS:

2-ETHYLHEXYL ACRYLATE
103-11-7
2-ethylhexyl prop-2-enoate
2-Ethylhexyl 2-propenoate
2-ETHYLHEXYLACRYLATE
2-Ethyl-1-hexyl acrylate
2-Propenoic acid, 2-ethylhexyl ester
Acrylic acid, 2-ethylhexyl ester
1-Hexanol, 2-ethyl-, acrylate
2-ethylexyl acrylate
Mono(2-ethylhexyl) acrylate
NSC 4803
CCRIS 3430
9003-77-4
HSDB 1121
2EHA
ethylhexylacrylate
UNII-HR49R9S6XG
EINECS 203-080-7
HR49R9S6XG
BRN 1765828
DTXSID9025297
AI3-03833
2-Ethylhexanol acrylate
JC BASE ACRYLATE
2-Ethylhexylester kyseliny akrylove
NORSOCRYL 2-EHA
NSC-4803
DTXCID405297
CHEBI:82465
EC 203-080-7
2EHA; EHA; JR 910; NSC 4803; Norsocryl 2-EHA
2-ETHYLHEXYL ACRYLATE (IARC)
2-ETHYLHEXYL ACRYLATE [IARC]
CAS-103-11-7
2-Ethylhexylester kyseliny akrylove [Czech]
acrylic acid 2-ethylhexyl ester
EINECS 215-330-2
1-Hexanol, acrylate
Octyl Acrylate Monomer
2-ethylhexyl propenoate
Acrylic Acid 2-Ethylhexyl Ester Monomer
2-ethylhexyl-2-propenoate
2-Ethylhexyl Acrylate Resin
SCHEMBL14869
2-Ethylhexyl Acrylate Monomer
Acrylic acid-2-ethylhexyl ester
CHEMBL1574328
Acrylic Acid Octyl Ester Monomer
NSC4803
ETHYLHEXYL ACRYLATE [INCI]
2-Ethylhexyl ester of acrylic acid
Tox21_202053
Tox21_303227
WLN: 4Y2 & 1OV1U1
MFCD00009495
MFCD00084372
AKOS015894409
(+/-)-Acrylic acid 2-ethylhexyl ester
NCGC00091115-01
NCGC00091115-02
NCGC00091115-03
NCGC00256960-01
NCGC00259602-01
2-Ethylhexyl acrylate, analytical standard
A0144
FT-0612226
2-Ethylhexyl Acrylate Monomer, stab. w/MEHQ
C19420
A896619
Q209383
Q-200277
2-Ethylhexyl Acrylate Monomer (stabilized with MEHQ)
2-Ethylhexyl acrylate, 98%, contains >=0.001-<=0.11% monomethyl ether hydroquinone as stabilizer