2-Ethylhexyl acrylate

Last updated
2-Ethylhexyl acrylate
2-ethylhexyl acrylate.svg
Names
Preferred IUPAC name
2-Ethylhexyl prop-2-enoate
Other names
2-Ethylhexyl acrylate
2-EHA
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.002.801 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-080-7
KEGG
PubChem CID
UNII
  • InChI=1S/C11H20O2/c1-4-7-8-10(5-2)9-13-11(12)6-3/h6,10H,3-5,7-9H2,1-2H3
    Key: GOXQRTZXKQZDDN-UHFFFAOYSA-N
  • CCCCC(CC)COC(=O)C=C
Properties
C11H20O2
Molar mass 184.279 g·mol−1
Appearancecolorless liquid
Density 0.885 g/mL
Melting point −90 °C (−130 °F; 183 K)
Boiling point 215–219 °C (419–426 °F; 488–492 K)
organic solvents
Hazards
GHS labelling:
GHS-pictogram-exclam.svg [1]
Warning
H315, H317, H335, H412 [1]
P273, P280, P304+P340+P312, P333+P313 [1]
Flash point 82 °C; 180 °F; 355 K
258 °C; 496 °F; 531 K
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2-Ethylhexyl acrylate is a colorless liquid acrylate used in the making of paints, [2] plastics [3] and adhesives. [4] It has an odor that has been variously described as pleasant [5] or acrid and musty. [6]

Contents

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. [7]

Properties

2-Ethylhexyl acrylate polymerizes easily. The polymerization can be initiated by light, peroxides, heat, or contaminants. It can react violently when combined with strong oxidants and can form explosive mixtures with air at temperatures above 82 °C (180 °F). [2] 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. [8]

Related Research Articles

A monomer is a molecule that can react together with other monomer molecules to form a larger polymer chain or three-dimensional network in a process called polymerization.

<span class="mw-page-title-main">Polyethylene</span> Most common thermoplastic polymer

Polyethylene or polythene (abbreviated PE; IUPAC name polyethene or poly(methylene)) is the most commonly produced plastic. It is a polymer, primarily used for packaging (plastic bags, plastic films, geomembranes and containers including bottles, cups, jars, etc.). As of 2017, over 100 million tonnes of polyethylene resins are being produced annually, accounting for 34% of the total plastics market.

Acrylates are the salts, esters, and conjugate bases of acrylic acid. The acrylate ion is the anion CH2=CHCO−2. Often, acrylate refers to esters of acrylic acid, the most common member being methyl acrylate. These acrylates contain vinyl groups. These compounds are of interest because they are bifunctional: the vinyl group is susceptible to polymerization and the carboxylate group carries myriad functionalities.

<span class="mw-page-title-main">Copolymer</span> Polymer derived from more than one species of monomer

In polymer chemistry, a copolymer is a polymer derived from more than one species of monomer. The polymerization of monomers into copolymers is called copolymerization. Copolymers obtained from the copolymerization of two monomer species are sometimes called bipolymers. Those obtained from three and four monomers are called terpolymers and quaterpolymers, respectively. Copolymers can be characterized by a variety of techniques such as NMR spectroscopy and size-exclusion chromatography to determine the molecular size, weight, properties, and composition of the material.

<span class="mw-page-title-main">Acrylic acid</span> Chemical compound

Acrylic acid (IUPAC: prop-2-enoic acid) is an organic compound with the formula CH2=CHCOOH. It is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus. This colorless liquid has a characteristic acrid or tart smell. It is miscible with water, alcohols, ethers, and chloroform. More than a million tons are produced annually.

<span class="mw-page-title-main">Reversible addition−fragmentation chain-transfer polymerization</span> Chemical reaction that produces polymers

Reversible addition−fragmentation chain-transfer or RAFT polymerization is one of several kinds of reversible-deactivation radical polymerization. It makes use of a chain-transfer agent (CTA) in the form of a thiocarbonylthio compound to afford control over the generated molecular weight and polydispersity during a free-radical polymerization. Discovered at the Commonwealth Scientific and Industrial Research Organisation (CSIRO) of Australia in 1998, RAFT polymerization is one of several living or controlled radical polymerization techniques, others being atom transfer radical polymerization (ATRP) and nitroxide-mediated polymerization (NMP), etc. RAFT polymerization uses thiocarbonylthio compounds, such as dithioesters, thiocarbamates, and xanthates, to mediate the polymerization via a reversible chain-transfer process. As with other controlled radical polymerization techniques, RAFT polymerizations can be performed under conditions that favor low dispersity and a pre-chosen molecular weight. RAFT polymerization can be used to design polymers of complex architectures, such as linear block copolymers, comb-like, star, brush polymers, dendrimers and cross-linked networks.

<span class="mw-page-title-main">Photopolymer</span>

A photopolymer or light-activated resin is a polymer that changes its properties when exposed to light, often in the ultraviolet or visible region of the electromagnetic spectrum. These changes are often manifested structurally, for example hardening of the material occurs as a result of cross-linking when exposed to light. An example is shown below depicting a mixture of monomers, oligomers, and photoinitiators that conform into a hardened polymeric material through a process called curing.

<span class="mw-page-title-main">Ethyl acrylate</span> Chemical compound

Ethyl acrylate is an organic compound with the formula CH2CHCO2CH2CH3. It is the ethyl ester of acrylic acid. It is a colourless liquid with a characteristic acrid odor. It is mainly produced for paints, textiles, and non-woven fibers. It is also a reagent in the synthesis of various pharmaceutical intermediates.

<span class="mw-page-title-main">Methyl acrylate</span> Chemical compound

Methyl acrylate is an organic compound, more accurately the methyl ester of acrylic acid. It is a colourless liquid with a characteristic acrid odor. It is mainly produced to make acrylate fiber, which is used to weave synthetic carpets. It is also a reagent in the synthesis of various pharmaceutical intermediates. Owing to the tendency of methyl acrylate to polymerize, samples typically contain an inhibitor such as hydroquinone.

<span class="mw-page-title-main">Polyacrylic acid</span> Anionic polyelectrolyte polymer

Poly(acrylic acid) (PAA; trade name Carbomer) is a polymer with the formula (CH2-CHCO2H)n. It is a derivative of acrylic acid (CH2=CHCO2H). In addition to the homopolymers, a variety of copolymers and crosslinked polymers, and partially deprotonated derivatives thereof are known and of commercial value. In a water solution at neutral pH, PAA is an anionic polymer, i.e., many of the side chains of PAA lose their protons and acquire a negative charge. Partially or wholly deprotonated PAAs are polyelectrolytes, with the ability to absorb and retain water and swell to many times their original volume. These properties – acid-base and water-attracting – are the bases of many applications.

Cobalt based catalysts, when used in radical polymerization, have several main advantages especially in slowing down the reaction rate, allowing for the synthesis of polymers with peculiar properties. As starting the reaction does need a real radical initiator, the cobalt species is not the only used catalyst, it is a mediator. For this reason this type of reaction is referred to as cobalt mediated radical polymerization.

<span class="mw-page-title-main">Poly(methacrylic acid)</span> Chemical compound

Poly(methacrylic acid) (PMAA) is a polymer made from methacrylic acid (preferred IUPAC name, 2-methylprop-2-enoic acid), which is a carboxylic acid. It is often available as its sodium salt, poly(methacrylic acid) sodium salt. The monomer is a viscous liquid with a pungent odour. The first polymeric form of methacrylic acid was described in 1880 by Engelhorn and Fittig. The use of high purity monomers is required for proper polymerization conditions and therefore it is necessary to remove any inhibitors by extraction (phenolic inhibitors) or via distillation. To prevent inhibition by dissolved oxygen, monomers should be carefully degassed prior to the start of the polymerization.

<span class="mw-page-title-main">Graft polymer</span> Polymer with a backbone of one composite and random branches of another composite

In polymer chemistry, graft polymers are segmented copolymers with a linear backbone of one composite and randomly distributed branches of another composite. The picture labeled "graft polymer" shows how grafted chains of species B are covalently bonded to polymer species A. Although the side chains are structurally distinct from the main chain, the individual grafted chains may be homopolymers or copolymers. Graft polymers have been synthesized for many decades and are especially used as impact resistant materials, thermoplastic elastomers, compatibilizers, or emulsifiers for the preparation of stable blends or alloys. One of the better-known examples of a graft polymer is a component used in high impact polystyrene, consisting of a polystyrene backbone with polybutadiene grafted chains.

<span class="mw-page-title-main">Allyl glycidyl ether</span> Chemical compound

Allyl glycidyl ether is an organic compound used in adhesives and sealants and as a monomer for polymerization reactions. It is formally the condensation product of allyl alcohol and glycidol via an ether linkage. Because it contains both an alkene and an epoxide group, either group can be reacted selectively to yield a product where the other functional group remains intact for future reactions.

Butyl acrylate is an organic compound with the formula C4H9O2CCH=CH2. A colorless liquid, it is the butyl ester of acrylic acid. It is used commercially on a large scale as a precursor to poly(butyl acrylate). Especially as copolymers, such materials are used in paints, sealants, coatings, adhesives, fuel, textiles, plastics, and caulk.

1-Vinylimidazole is a water-soluble basic monomer that forms quaternizable homopolymers by free-radical polymerization with a variety of vinyl and acrylic monomers. The products are functional copolymers, which are used as oil field chemicals and as cosmetic auxiliaries. 1-Vinylimidazole acts as a reactive diluent in UV lacquers, inks, and adhesives.

Dimethylaminoethyl acrylate or DMAEA is an unsaturated carboxylic acid ester having a tertiary amino group. It is a colorless to yellowish, water-miscible liquid with a pungent, amine-like odor. DMAEA is an important acrylic monomer that gives basic properties to copolymers.

1,6-Hexanediol diacrylate is a difunctional acrylate ester monomer used in the manufacture of polymers. It is particularly useful for use in ultraviolet light cure applications. Furthermore, it is also used in adhesives, sealants, alkyd coatings, elastomers, photopolymers, and inks for improved adhesion, hardness, abrasion and heat resistance. Like other acrylate monomers it is usually supplied with a radical inhibitor such as hydroquinone added.

Waterborne resins are sometimes called water-based resins. They are resins or polymeric resins that use water as the carrying medium as opposed to solvent or solvent-less. Resins are used in the production of coatings, adhesives, sealants, elastomers and composite materials. When the phrase waterborne resin is used, it usually describes all resins which have water as the main carrying solvent. The resin could be water-soluble, water reducible or water dispersed.

<span class="mw-page-title-main">Hydroxyethyl acrylate</span> Organic chemical-monomer

Hydroxyethyl acrylate is an organic chemical and an aliphatic compound. It has the formula C5H8O3 and the CAS Registry Number 818–61–1. It is REACH registered with an EU number of 212–454–9. It has dual functionality containing a polymerizable acrylic group and a terminal hydroxy group. It is used to make emulsion polymers along with other monomers and the resultant resins are used in coatings, sealants, adhesives and elastomers and other applications.

References

  1. 1 2 3 Record of 2-Ethylhexyl acrylate in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 11 March 2020.
  2. 1 2 "2-ETHYLHEXYL ACRYLATE". CAMEO Chemicals. Retrieved April 22, 2024.
  3. "2-Ethylhexyl acrylate (compound)". PubChem . National Center for Biotechnology Information.
  4. Heatley, Frank; Lovell, Peter A.; Yamashita, Tsuyoshi (2001-10-01). "Chain Transfer to Polymer in Free-Radical Solution Polymerization of 2-Ethylhexyl Acrylate Studied by NMR Spectroscopy". Macromolecules. 34 (22): 7636–7641. doi:10.1021/ma0101299. ISSN   0024-9297.
  5. "2-Ethylhexyl acrylate". PubChem. Retrieved April 22, 2024.
  6. Shah, Yogi (January 1995). "2-Ethylhexyl acrylate" (PDF). Occupational Safety and Health Administration .
  7. US 2917538,R.L. Carlyle,"Process for the production of acrylic acid esters",published 1959-12-15, assigned to The Dow Chemical Co.
  8. Bodo Müller, Walter Rath: Formulierung von Kleb- und Dichtstoffen 1. Auflage. Vincentz Network, Hannover 2004, ISBN   3878707916, S. 235 ( , p. 235, at Google Books)