Acrylates
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Acrylates
Acrylates (IUPAC: prop-2-enoates) are the salts, esters, and conjugate bases of acrylic acid. The acrylate ion is the anion C H2=CHC OO−. 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. Modified acrylates are also numerous, some examples being methacrylates (CH2=C(CH3)CO2R) and cyanoacrylates (CH2=C(CN)CO2R). Acrylate can also refer to polyacrylates prepared through the polymerization of the vinyl groups of acrylate monomers. File:Acrylate-anion.svg, The acrylate anion File:Trimethylolpropane triacrylate.svg, Trimethylolpropane triacrylate (TMPTA), a trifunctional acrylate ester File:Methylacrylat.svg, Methyl acrylate, an acrylic ester File:Hexandioldiacrylat.svg, Hexandiol diacrylate, a bifunctional acrylate File:Methyl-meth ...
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Ethyl Acrylate
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. Production Ethyl acrylate is produced by acid-catalysed esterification of acrylic acid, which in turn is produced by oxidation of propylene. It may also be prepared from acetylene, carbon monoxide and ethanol by a Reppe reaction. Commercial preparations contain a polymerization inhibitor such as hydroquinone, phenothiazine, or hydroquinone ethyl ether. Reactions and uses Precursor to polymers and other monomers Ethyl acrylate is used in the production of polymers including resins, plastics, rubber, and denture material.Ethyl acrylate ...
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Methyl Methacrylate
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). Production and properties Given the scale of production, many methods have been developed starting from diverse two- to four-carbon precursors.. Two principal routes appear to be commonly practiced. Cyanohydrin route The compound is manufactured by several methods, the principal one being the acetone cyanohydrin (ACH) route. ACH is produced by condensation of acetone and hydrogen cyanide. The cyanohydrin is hydrolyzed in the presence of sulfuric acid to a sulfate ester of the methacrylamide. Methanolysis of this ester gives ammonium bisulfate and MMA. Although widely used, the ACH route coproduces substantial amounts of ammonium sulfate. :(CH3)2CO + HCN → (CH3)2C(OH)CN :(CH3)2C(OH)CN + H2SO4 → (CH3)2C(OSO3H)C(O)NH2. ...
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Methyl Methacrylate
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). Production and properties Given the scale of production, many methods have been developed starting from diverse two- to four-carbon precursors.. Two principal routes appear to be commonly practiced. Cyanohydrin route The compound is manufactured by several methods, the principal one being the acetone cyanohydrin (ACH) route. ACH is produced by condensation of acetone and hydrogen cyanide. The cyanohydrin is hydrolyzed in the presence of sulfuric acid to a sulfate ester of the methacrylamide. Methanolysis of this ester gives ammonium bisulfate and MMA. Although widely used, the ACH route coproduces substantial amounts of ammonium sulfate. :(CH3)2CO + HCN → (CH3)2C(OH)CN :(CH3)2C(OH)CN + H2SO4 → (CH3)2C(OSO3H)C(O)NH2. ...
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Pentaerythritol Tetraacrylate
Pentaerythritol tetraacrylate (PETA or sometimes PETTA,PETRA) is an organic compound. It is a tetrafunctional acrylate ester used as a monomer in the manufacture of polymers. As it is a polymerizable acrylate monomer it is nearly always supplied with a polymerisation inhibitor such as MEHQ (monomethyl ether hydroquinone) added. Uses PETA is part of a family of acrylates used in epoxy resin chemistry and ultraviolet cure of coatings. Similar monomers used are 1,6-hexanediol diacrylate and TMPTA trimethylol propane triacrylate. It is a derivative of pentaerythritol One of the key uses of the material is in polymeric synthesis where it can form micelles and block copolymers. The molecule's acrylate group functionality enables the molecule to do the Michael reaction with amines. It is therefore sometimes used in epoxy chemistry enabling a large reduction in cure time. As the molecule has 4 functional acrylate groups it confers high cross-link density. Ethoxylation maybe used to pr ...
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Acrylate Polymer
An acrylate polymer (also known as acrylic or polyacrylate) is any of a group of polymers prepared from acrylate monomers. These plastics are noted for their transparency, resistance to breakage, and elasticity. Acrylate polymer is commonly used in cosmetics, such as nail polish, as an adhesive. History The first synthesis of acrylic polymer was reported by G.W.A Kahlbaum in 1880. Acrylic elastomers Acrylic elastomer is a general term for a type of synthetic rubber whose primary component is acrylic acid alkylester ( ethyl or butyl ester). Acrylic elastomer possesses characteristics of heat and oil resistance, with the ability to withstand temperatures of 170–180 °C. It is used primarily for producing oil seals and packaging related to automobiles. Acrylic elastomer can generally be characterized as one of two types. "Old" types include ACM (copolymer of acrylic acid ester and 2-chloroethyl vinyl ether) containing chlorine and ANM (copolymer of acrylic acid este ...
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Methyl Acrylate
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. Production The standard industrial reaction for producing methyl acrylate is esterification with methanol under acid catalysis (sulfuric acid, p-toluenesulfonic acid or acidic ion exchangers.). The transesterification is facilitated because methanol and methyl acrylate form a low boiling azeotrope (boiling point 62–63 °C). The patent literature describes a one-pot route involving vapor-phase oxidation of propene or 2-propenal with oxygen in the presence of methanol. Other methods Methyl acrylate can be prepared by debromination of methyl 2,3-dibromopropanoate with zinc.F. Beilstein: ''Handbuch der organischen Chemie'', 3. Auflage, 1. Band. Verlag Leopold Voss ...
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(Hydroxyethyl)methacrylate
Hydroxyethylmethacrylate (also known as glycol methyacrylate) is the organic compound with the chemical formula . It is a colorless viscous liquid that readily polymerizes. Hydroxyethylmethacrylate is a monomer that is used to make various polymers. Synthesis Hydroxyethylmethacrylate was first synthesized around 1925. Common methods of synthesis are: * reaction of methacrylic acid with ethylene oxide; * esterification of methacrylic acid with a large excess of ethylene glycol. Both these methods give also some amount of ethylene dimethacrylate. During polymerization of hydroxyethylmethacrylate, it works as crosslinking agent. Properties Hydroxyethylmethacrylate is completely miscible with water and ethanol, but its polymer is practically insoluble in common solvents. Its viscosity is 0.0701 Pa⋅s at 20°C and 0.005 Pa⋅s at 30°C. During polymerization, it shrinks by approximately 6%. Applications Contact lenses In 1960, O. Wichterle and D. Lím described its use in synthes ...
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Methacrylate
Methacrylates are derivatives of methacrylic acid. * Methyl methacrylate * Ethyl methacrylate * Butyl methacrylate * Hydroxyethyl methacrylate * Glycidyl methacrylate 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 ... {{set index Carboxylate anions Monomers Methacrylate esters ...
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Ethyl Cyanoacrylate
Ethyl cyanoacrylate (ECA), a cyanoacrylate ester, is an ethyl ester of 2-cyano-2-propenoic acid. It is a colorless liquid with low viscosity and a faint sweet smell in pure form. It is the main component of cyanoacrylate glues and can be encountered under many trade names. It is soluble in acetone, methyl ethyl ketone, nitromethane, and methylene chloride. ECA polymerizes rapidly in presence of moisture. Production Ethyl cyanoacrylate is prepared by the condensation of formaldehyde with ethyl cyanoacetate: : + → + This exothermic reaction affords the polymer, which is subsequently sintered, thermally "cracked" to give the monomer. Alternatively, it can be prepared by the ethoxycarbonylation of cyanoacetylene. Applications Ethyl cyanoacrylate is used for gluing various materials. It is also used in medicine, for liquid bandages and for suture-less surgery, but it is used less often than the less toxic ''n''-butyl and octyl cyanoacrylates. Off-the-shelf consumer glu ...
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Methyl Acrylate
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. Production The standard industrial reaction for producing methyl acrylate is esterification with methanol under acid catalysis (sulfuric acid, p-toluenesulfonic acid or acidic ion exchangers.). The transesterification is facilitated because methanol and methyl acrylate form a low boiling azeotrope (boiling point 62–63 °C). The patent literature describes a one-pot route involving vapor-phase oxidation of propene or 2-propenal with oxygen in the presence of methanol. Other methods Methyl acrylate can be prepared by debromination of methyl 2,3-dibromopropanoate with zinc.F. Beilstein: ''Handbuch der organischen Chemie'', 3. Auflage, 1. Band. Verlag Leopold Voss ...
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Trimethylolpropane Triacrylate
Trimethylolpropane triacrylate (TMPTA) is a trifunctional acrylate ester monomer derived from trimethylolpropane, used in the manufacture of plastics, adhesives, acrylic glue, anaerobic sealants, and ink. It is useful for its low volatility and fast cure response. It has the properties of weather, chemical and water resistance, as well as good abrasion resistance. End products include alkyd coatings, compact discs, hardwood floors, concrete polymers, Dental composites, photolithography, letterpress, screen printing, elastomers, automobile headlamps, acrylics and plastic components for the medical industry. Other uses As the molecule has acrylic functionality, it is capable of doing the Michael reaction with an amine. This allows its use in epoxy chemistry where its use speeds up the cure time considerably See also *Pentaerythritol tetraacrylate * 1,6-Hexanediol diacrylate References {{reflistTRIMETHYLOLPROPANE TRIACRYLATEat chemicalland21.comat OSHA OSHA or Osha may refer to: ...
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IUPAC
The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations working for the advancement of the chemical sciences, especially by developing nomenclature and terminology. It is a member of the International Science Council (ISC). IUPAC is registered in Zürich, Switzerland, and the administrative office, known as the "IUPAC Secretariat", is in Research Triangle Park, North Carolina, United States. This administrative office is headed by IUPAC's executive director, currently Lynn Soby. IUPAC was established in 1919 as the successor of the International Congress of Applied Chemistry for the advancement of chemistry. Its members, the National Adhering Organizations, can be national chemistry societies, national academies of sciences, or other bodies representing chemists. There are fifty-four National Adhering Organizations and three Associate National Adhering Organizations. IUPAC's Inter-divisional Committee on ...
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