Butyl methacrylate

Last updated
Butyl methacrylate
Butylmethacrylaat.png
Names
Preferred IUPAC name
Butyl 2-methylprop-2-enoate
Other names
Butyl 2-methylpropenoate, Acryester B, Acryester BMA, n-butyl methacrylate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.002.378 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-615-1
PubChem CID
RTECS number
  • OZ3675000
UNII
UN number 2227
  • InChI=1S/C8H14O2/c1-4-5-6-10-8(9)7(2)3/h2,4-6H2,1,3H3
    Key: SOGAXMICEFXMKE-UHFFFAOYSA-N
  • CCCCOC(=O)C(=C)C
Properties
C8H14O2
Molar mass 142.198 g·mol−1
Appearancecolorless liquid
Density 0.8936 g/cm3
Melting point −25 °C (−13 °F; 248 K)
Boiling point 160 °C (320 °F; 433 K)
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg
Danger
H226, 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 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 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
1
2
2
Flash point 50 °C (122 °F; 323 K)
290 °C (554 °F; 563 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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. [1] It is typically polymerized under free-radical conditions. [2]

Contents

Health hazards

In terms of the acute toxicity of butyl methacrylate, the LD50 is 20 g/kg (oral, rat). It is an irritant to 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 the synthetic polymer derived from methyl methacrylate. It is used as an engineering plastic, and it is a transparent thermoplastic. 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.

In polymer chemistry, emulsion polymerization is a type of radical polymerization that usually starts with an emulsion incorporating water, monomers, and surfactants. The most common type of emulsion polymerization is an oil-in-water emulsion, in which droplets of monomer are emulsified in a continuous phase of water. Water-soluble polymers, such as certain polyvinyl alcohols or hydroxyethyl celluloses, can also be used to act as emulsifiers/stabilizers. The name "emulsion polymerization" is a misnomer that arises from a historical misconception. Rather than occurring in emulsion droplets, polymerization takes place in the latex/colloid particles that form spontaneously in the first few minutes of the process. These latex particles are typically 100 nm in size, and are made of many individual polymer chains. The particles are prevented from coagulating with each other because each particle is surrounded by the surfactant ('soap'); the charge on the surfactant repels other particles electrostatically. When water-soluble polymers are used as stabilizers instead of soap, the repulsion between particles arises because these water-soluble polymers form a 'hairy layer' around a particle that repels other particles, because pushing particles together would involve compressing these chains.

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">Methyl methacrylate</span> Chemical compound

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).

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Ethylene glycol dimethylacrylate (EGDMA) is a diester formed by condensation of two equivalents of methacrylic acid and one equivalent of ethylene glycol.

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<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)COOH. 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).

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

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<span class="mw-page-title-main">(Hydroxyethyl)methacrylate</span> Chemical compound

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<span class="mw-page-title-main">Glycidyl methacrylate</span> Chemical compound

Glycidyl methacrylate (GMA) is an ester of methacrylic acid and glycidol. Containing both an epoxide and an acrylate groups, the molecule is bifunctional. It is a common monomer used in the production of epoxy resins. While typical home epoxies contain diglycidyl ether of bisphenol A (DGEBA), glycidyl methacrylate is instead used to provide epoxy functionalization to polyolefins and other acrylate resins. Glycidyl methacrylate is produced by several companies worldwide, including Dow Chemical. It is used to prepare a range of composites.

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<span class="mw-page-title-main">Ethyl methacrylate</span> Organic compound

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. It is typically polymerized under free-radical conditions.

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

Hydroxyethyl acrylate is an organic chemical and a 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 Bauer, Jr., William (2002). "Methacrylic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a16_441..
  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.