Ethyl methacrylate

Last updated
Ethyl methacrylate
Ethyl methacrylate.svg
Names
Preferred IUPAC name
Ethyl 2-methylprop-2-enoate
Other names
Ethyl 2-methylpropenoate, Acryester E, Acryester BMA
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.002.362 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-597-5
PubChem CID
RTECS number
  • OZ4550000
UNII
UN number 2277
  • InChI=1S/C6H10O2/c1-4-8-6(7)5(2)3/h2,4H2,1,3H3
    Key: SUPCQIBBMFXVTL-UHFFFAOYSA-N
  • CCOC(=O)C(=C)C
Properties
C6H10O2
Molar mass 114.144 g·mol−1
AppearanceColorless liquid
Density 0.9135 g/cm3
Boiling point 117 °C (243 °F; 390 K)
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg
Warning
H225, H315, H317, H319, H335
P210, P233, P240, P241, P242, P243, P261, P264, P271, P272, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazards (white): no code
2
3
2
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Ethyl methacrylate is the organic compound with the formula C2H5O2CC(CH3)=CH2. A colorless liquid, it is a common monomer for the preparation of acrylate polymers. [1] It is typically polymerized under free-radical conditions. [2]

Contents

Ethyl methacrylate was first obtained by treating ethyl 2-hydroxyisobutyrate with phosphorus pentachloride in a dehydration reaction. [3]

Environmental issues and health hazards

The related methyl and butyl methacrylates have respective acute LD50s of 10 and 20 g/kg (oral, rat); [1] a linear extrapolation suggests that ethyl methacrylate would have an LD50 of approximately 13 g/kg.

Acrylate esters irritate the eyes and can cause blindness. [1]

See also

Related Research Articles

<span class="mw-page-title-main">Poly(methyl methacrylate)</span> Transparent thermoplastic, commonly called acrylic

Poly(methyl methacrylate) (PMMA) is a synthetic polymer derived from methyl methacrylate. It is a transparent thermoplastic, used as an engineering plastic. PMMA is also known as acrylic, acrylic glass, as well as by the trade names and brands Crylux, Hesalite, Plexiglas, Acrylite, Lucite, and Perspex, among several others. This plastic is often used in sheet form as a lightweight or shatter-resistant alternative to glass. It can also be used as a casting resin, in inks and coatings, and for many other purposes.

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">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">Methyl methacrylate</span> Organic monomer

Methyl methacrylate (MMA) is an organic compound with the formula CH2=C(CH3)COOCH3. This colorless liquid, the methyl ester of methacrylic acid (MAA), is a monomer produced on a large scale for the production of poly(methyl methacrylate) (PMMA).

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

Poly(methyl acrylate) (PMA) is a family of organic polymers with the formula (CH2CHCO2CH3)n. It is a synthetic acrylate polymer derived from methyl acrylate monomer. The polymers are colorless. This homopolymer is far less important than copolymers derived from methyl acrylate and other monomers. PMA is softer than polymethyl methacrylate (PMMA), It is tough, leathery, and flexible.

<span class="mw-page-title-main">Acrylate polymer</span> Group of polymers prepared from acrylate monomers

An acrylate polymer is any of a group of polymers prepared from acrylate monomers. These plastics are noted for their transparency, resistance to breakage, and elasticity.

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

Methacrylic acid, abbreviated MAA, is an organic compound with the formula CH2=C(CH3)CO2H. This colorless, viscous liquid is a carboxylic acid with an acrid unpleasant odor. It is soluble in warm water and miscible with most organic solvents. Methacrylic acid is produced industrially on a large scale as a precursor to its esters, especially methyl methacrylate (MMA), and to poly(methyl methacrylate) (PMMA).

<span class="mw-page-title-main">Methacrylate</span> Index of articles associated with the same name

Methacrylates are derivatives of methacrylic acid. These derivatives are mainly used to make poly(methyl methacrylate) and related polymers.

<span class="mw-page-title-main">Acrylic resin</span> Thermoplastic or thermosetting plastic

An acrylic resin is a thermoplastic or thermosetting plastic substance typically derived from acrylic acid, methacrylic acid and acrylate monomers such as butyl acrylate and methacrylate monomers such as methyl methacrylate. Thermoplastic acrylics designate a group of acrylic resins typically containing both a high molecular weight and a high glass transition temperature which exhibit lacquer dry capability. Acrylic resins designed for use in two component systems for crosslinking with isocyanate are referred to as polyols and are made with the monomers previously mentioned as well as hydroxy monomers such as hydroxy ethyl methacrylate. Acrylic resins are produced in different liquid carriers such as a hydrocarbon solvent or water in which case they are referred to as emulsions or dispersions and they are also provided in 100% solids bead form.

<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.

In polymer chemistry, a comonomer refers to a polymerizable precursor to a copolymer aside from the principal monomer. In some cases, only small amounts of a comonomer are employed, in other cases substantial amounts of comonomers are used. Furthermore, in some cases, the comonomers are statistically incorporated within the polymer chain, whereas in other cases, they aggregate. The distribution of comonomers is referred to as the "blockiness" of a copolymer.

Catalytic chain transfer (CCT) is a process that can be incorporated into radical polymerization to obtain greater control over the resulting products.

<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">Butyl methacrylate</span> Chemical compound

Butyl methacrylate is the organic compound with the formula C4H9O2CC(CH3)=CH2. A colorless liquid, it is a common monomer for the preparation of methacrylate polymers. It is typically polymerized under free-radical conditions.

<span class="mw-page-title-main">2-Hydroxyisobutyric acid</span> Chemical compound

2-Hydroxyisobutyric acid is the organic compound with the formula (CH3)2C(OH)CO2H. A white solid, it is classified as an hydroxycarboxylic acid. It has been considered as a naturally occurring precursor to polyesters. It is closely related to lactic acid.

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

Poly(ethyl acrylate) (PEA) is a family of organic polymers with the formula (CH2CHCO2CH2CH3)n. It is a synthetic acrylate polymer derived from ethyl acrylate monomer. The polymers are colorless. This homopolymer is far less important than copolymers derived from ethyl acrylate and other monomers. It has a low glass-transition temperature about -8 °C (20 °C).

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

Poly(butyl acrylate) (PBA) is a family of organic polymers with the formula (CH2CHCO2CH2CH2CH2CH3)n. It is a synthetic acrylate polymer derived from butyl acrylate monomer. The polymers are colorless. This homopolymer is far less important than copolymers derived from methyl acrylate and other monomers. It has a low glass-transition temperature of about -43 °C (20 °C).

<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.

<i>tert</i>-Butyl methacrylate Chemical compound

tert-Butyl methacrylate is an organic compound with the formula (CH3)3CO2CC(CH3)=CH2. A colorless solid, it is a common monomer for the preparation of methacrylate polymers. It is employed in other kinds of polymerizations.

References

  1. 1 2 3 Bauer, Jr., William (2002). "Methacrylic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a16_441. ISBN   978-3527306732..
  2. ↑ Granel, C.; Dubois, Ph.; Jérôme, R.; Teyssié, Ph. (1996). "Controlled Radical Polymerization of Methacrylic Monomers in the Presence of a Bis(ortho-chelated) Arylnickel(II) Complex and Different Activated Alkyl Halides". Macromolecules. 29 (27): 8576–8582. Bibcode:1996MaMol..29.8576G. doi:10.1021/ma9608380.
  3. ↑ E. Frankland, B. F. Duppa (1865). "Untersuchungen über Säuren aus der Acrylsäure-Reihe; 1) Umwandlung der Säuren aus der Milchsäure-Reihe in die der Acrylsäure-Reihe". Justus Liebigs Annalen der Chemie. 136: 12. doi:10.1002/jlac.18651360102.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.