Methyl cyanoacrylate (MCA) (also sometimes referred to as α-cyanoacrylate or alpha-cyanoacrylate) is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

that contains several

functional group In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest ...

s: a

methyl In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula . In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in many ...

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ar ...

, a

nitrile In organic chemistry, a nitrile is any organic compound that has a functional group. The prefix ''cyano-'' is used interchangeably with the term ''nitrile'' in industrial literature. Nitriles are found in many useful compounds, including met ...

, and an

alkene In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, an ...

. It is a colorless liquid with low

viscosity The viscosity of a fluid is a measure of its resistance to deformation at a given rate. For liquids, it corresponds to the informal concept of "thickness": for example, syrup has a higher viscosity than water. Viscosity quantifies the inte ...

. Its chief use is as the main component of cyanoacrylate glues. It can be encountered under many

trade name A trade name, trading name, or business name, is a pseudonym used by companies that do not operate under their registered company name. The term for this type of alternative name is a "fictitious" business name. Registering the fictitious name w ...

s. Methyl cyanoacrylate is less commonly encountered than

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 encount ...

. It is soluble in

acetone Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour. Acetone is miscib ...

methyl ethyl ketone Butanone, also known as methyl ethyl ketone (MEK), is an organic compound with the formula CH3C(O)CH2CH3. This colourless liquid ketone has a sharp, sweet odor reminiscent of acetone. It is produced industrially on a large scale, but occurs in nat ...

nitromethane Nitromethane, sometimes shortened to simply "nitro", is an organic compound with the chemical formula . It is the simplest organic nitro compound. It is a polar liquid commonly used as a solvent in a variety of industrial applications such as in ...

, and

dichloromethane Dichloromethane (DCM or methylene chloride, methylene bichloride) is an organochlorine compound with the formula . This colorless, volatile liquid with a chloroform-like, sweet odour is widely used as a solvent. Although it is not miscible with ...

. MCA

polymerizes In polymer chemistry, polymerization (American English), or polymerisation (British English), is a process of reacting monomer molecules together in a chemical reaction to form polymer chains or three-dimensional networks. There are many for ...

rapidly in presence of

moisture Moisture is the presence of a liquid, especially water, often in trace amounts. Small amounts of water may be found, for example, in the air (humidity), in foods, and in some commercial products. Moisture also refers to the amount of water vapo ...

Safety

Heating the polymer causes

depolymerization Depolymerization (or depolymerisation) is the process of converting a polymer into a monomer or a mixture of monomers. This process is driven by an increase in entropy. Ceiling temperature The tendency of polymers to depolymerize is indicated by ...

of the cured MCA, producing gaseous products which are a strong irritant to the

lungs The lungs are the primary organs of the respiratory system in humans and most other animals, including some snails and a small number of fish. In mammals and most other vertebrates, two lungs are located near the backbone on either side of th ...

and

eyes Eyes are organs of the visual system. They provide living organisms with vision, the ability to receive and process visual detail, as well as enabling several photo response functions that are independent of vision. Eyes detect light and conve ...

. With regards to occupational exposure to MCA, the

National Institute for Occupational Safety and Health The National Institute for Occupational Safety and Health (NIOSH, ) is the United States federal agency responsible for conducting research and making recommendations for the prevention of work-related injury and illness. NIOSH is part of the C ...

recommends workers do not exceed exposures over 2 ppm (8 mg/m³) over an eight-hour workshift, or over 4ppm (16 mg/m³) over a short-term exposure.CDC - NIOSH Pocket Guide to Chemical Hazards
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References

{{Chemical agents Methyl esters Cyanoacrylate esters Monomers Lachrymatory agents