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Methyl cyanoacrylate (MCA; also sometimes referred to as α-cyanoacrylate or alpha-cyanoacrylate) [3] is an organic compound that contains several functional groups: a methyl ester, a nitrile, and an alkene. It is a colorless liquid with low viscosity. Its chief use is as the main component of cyanoacrylate glues.
Structure of the backbone of a cyanoacrylate polymer. Cyanoacrylates are a family of strong fast-acting adhesives with industrial, medical, and household uses. They are derived from ethyl cyanoacrylate and related esters. The cyanoacrylate group in the monomer rapidly polymerizes in the presence of water to form long, strong chains. [1]
Structure of the backbone of a cyanoacrylate polymer. In the same way that several variants of acrylic esters are known, so too are the corresponding polymers. Their properties strongly depends on the substituent. A large family of acrylate-like polymers are derived from methyl methacrylate and many related esters, especially polymethyl ...
Methyl acrylate can be prepared by debromination of methyl 2,3-dibromopropanoate with zinc. [10] Methyl acrylate is formed in good yield on pyrolysis of methyl lactate in the presence of ethenone (ketene). [11] Methyl lactate is a renewable "green chemical". Another patent [12] describes the dehydration of methyl lactate over zeolites.
Ethyl cyanoacrylate (ECA), a cyanoacrylate ester, is an ethyl ester of 2-cyano-acrylic 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 . [ 2 ]
NBCA in monomer form is soluble in acetone, methyl ethyl ketone, nitromethane, and methylene chloride. [4] It polymerizes rapidly in presence of ionic substances such as moisture, blood, or tissue fluids. NBCA has unique properties compared to other cyanoacrylates such as octyl cyanoacrylate or isoamyl cyanoacrylate.
Poly(methyl acrylate) (PMA) is a family of organic polymers with the formula (CH 2 CHCO 2 CH 3) 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.
When a lithium enolate is generated in diethyl ether or methyl t-butyl ether, treatment with Mander's reagent will selectively afford the C-acylation product. [1] Thus, for enolate acylation reactions in which C- vs. O-selectivity is a concern, methyl cyanoformate is often used in place of more common acylation reagent like methyl chloroformate.
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