Ethyl cyanoacrylate
Encyclopedia
Ethyl cyanoacrylate a cyanoacrylate
Cyanoacrylate
Cyanoacrylate is the generic name for cyanoacrylate based fast-acting adhesives such as methyl 2-cyanoacrylate, ethyl-2-cyanoacrylate , and n-butyl cyanoacrylate...

 ester, is an ethyl
Ethyl group
In chemistry, an ethyl group is an alkyl substituent derived from ethane . It has the formula -C2H5 and is very often abbreviated -Et.Ethylation is the formation of a compound by introduction of the ethyl functional group, C2H5....

 ester
Ester
Esters are chemical compounds derived by reacting an oxoacid with a hydroxyl compound such as an alcohol or phenol. Esters are usually derived from an inorganic acid or organic acid in which at least one -OH group is replaced by an -O-alkyl group, and most commonly from carboxylic acids and...

 of 2-cyano-2-propenoic acid
Acrylic acid
Acrylic acid is an organic compound with the formula CH2=CHCO2H. 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,...

. It is a colorless liquid with low viscosity. It is the main component of cyanoacrylate glues and can be encountered under many trade name
Trade name
A trade name, also known as a trading name or a business name, is the name which a business trades under for commercial purposes, although its registered, legal name, used for contracts and other formal situations, may be another....

s. Super glue and Krazy glue are believed to be virtually 100% ECA.http://msds.chem.ox.ac.uk/ET/ethyl_cyanoacrylate.html It is soluble in acetone
Acetone
Acetone is the organic compound with the formula 2CO, a colorless, mobile, flammable liquid, the simplest example of the ketones.Acetone is miscible with water and serves as an important solvent in its own right, typically as the solvent of choice for cleaning purposes in the laboratory...

, methyl ethyl ketone, nitromethane
Nitromethane
Nitromethane is an organic compound with the chemical formula . It is the simplest organic nitro compound. It is a slightly viscous, highly polar liquid commonly used as a solvent in a variety of industrial applications such as in extractions, as a reaction medium, and as a cleaning solvent...

, and methylene chloride.http://www.palmlabsadhesives.com/technical_data.htm ECA polymerizes rapidly in presence of moisture.

Production

Ethyl cyanoacrylate is prepared by the condensation of formaldehyde
Formaldehyde
Formaldehyde is an organic compound with the formula CH2O. It is the simplest aldehyde, hence its systematic name methanal.Formaldehyde is a colorless gas with a characteristic pungent odor. It is an important precursor to many other chemical compounds, especially for polymers...

 with ethyl cyanoacetate:
CH2(CN)CO2Et + CH2O → CH2=C(CN)CO2Et + H2O

This exothermic reaction affords the polymer, which is subsequently sintered,thermally "cracked"
Cracking (chemistry)
In petroleum geology and chemistry, cracking is the process whereby complex organic molecules such as kerogens or heavy hydrocarbons are broken down into simpler molecules such as light hydrocarbons, by the breaking of carbon-carbon bonds in the precursors. The rate of cracking and the end products...

 to give the monomer. Alternatively, it can be prepared by the ethoxycarbonylation
Carbonylation
Carbonylation refers to reactions that introduce carbon monoxide into organic and inorganic substrates. Carbon monoxide is abundantly available and conveniently reactive, so it is widely used as a reactant in industrial chemistry.-Organic chemistry:...

 of cyanoacetylene
Cyanoacetylene
Cyanoacetylene is an organic compound with formula or H-C≡C-C≡N. It is the simplest cyanopolyyne. Cyanoacetylene has been detected by spectroscopic methods in interstellar clouds, in the coma of comet Hale–Bopp and in the atmosphere of Saturn's moon Titan....

.

Applications

Ethyl cyanoacrylate is used for gluing of various materials. It finds applications also in medicine, for liquid bandage
Liquid bandage
Liquid bandage is a topical skin treatment for minor cuts and sores that is sold by several companies. The products are mixtures of chemicals which create a polymeric layer which binds to the skin...

s and for suture-less surgery, but it is used less often than the less toxic n-butyl and octyl cyanoacrylates. Off-the-shelf non-medical-grade glues are unsuitable for medical applications, as they may contain solvents (e.g. methyl alcohol) and produce heat during polymerization. http://www.miracleglue.com/wounds.htm

After curing, the resulting resin softens at temperatures above 150 °C (300 °F). The service temperature of the joint is -54..+82 °C (-65..+180 °F) Its dielectric constant
Dielectric constant
The relative permittivity of a material under given conditions reflects the extent to which it concentrates electrostatic lines of flux. In technical terms, it is the ratio of the amount of electrical energy stored in a material by an applied voltage, relative to that stored in a vacuum...

 at 1 MHz is 3.33. http://www.palmlabsadhesives.com/technical_data.htm

Safety

In the U.S., the Threshold Limit Value
Threshold Limit Value
The threshold limit value of a chemical substance is a level to which it is believed a worker can be exposed day after day for a working lifetime without adverse health effects. Strictly speaking, TLV is a reserved term of the American Conference of Governmental Industrial Hygienists...

 for ECA is 2 ppm. Heating causes depolymerization of the cured polyECA, producing gaseous products strongly irritating to lungs and eyes.

See also

  • Cyanoacrylate
    Cyanoacrylate
    Cyanoacrylate is the generic name for cyanoacrylate based fast-acting adhesives such as methyl 2-cyanoacrylate, ethyl-2-cyanoacrylate , and n-butyl cyanoacrylate...

  • Methyl cyanoacrylate
    Methyl cyanoacrylate
    Methyl cyanoacrylate 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. It can be encountered under many trade names...

  • Butyl cyanoacrylate
    Butyl cyanoacrylate
    n-Butyl cyanoacrylate , a cyanoacrylate ester, is a butyl ester of 2-cyano-2-propenoic acid. It is a clear colorless liquid with a sharp, irritating odor. It is insoluble in water. Its chief use is as the main component of medical cyanoacrylate glues. It can be encountered under various trade...

  • Octyl cyanoacrylate
    Octyl cyanoacrylate
    Octyl cyanoacrylate , a cyanoacrylate ester, is an octyl ester of 2-cyano-2-propenoic acid. It is a clear colorless liquid with a sharp, irritating odor. Its chief use is as the main component of medical cyanoacrylate glues...

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