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Ethyl cyanoacrylate

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Ethyl cyanoacrylate
Structural formula of ethyl cyanoacrylate
Ball-and-stick model of the ethyl cyanoacrylate molecule
Names
IUPAC name
ethyl 2-cyanopropenoate
Other names
ethyl 2-cyanoacrylate, ECA, ethyl alpha-cyanoacrylate, 910EM, ace-ee, CN2, CN4, cemedine 3000rs, Krazy glue, permabond 105, permabond 200, super glue, pro grip 4000, TK 200, TK 201, cyanolite 201, Cyanacrine, Cyano-Veneer
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.027.628 Edit this at Wikidata
UNII
  • InChI=1S/C6H7NO2/c1-3-9-6(8)5(2)4-7/h2-3H2,1H3 checkY
    Key: FGBJXOREULPLGL-UHFFFAOYSA-N checkY
  • InChI=1/C6H7NO2/c1-3-9-6(8)5(2)4-7/h2-3H2,1H3
    Key: FGBJXOREULPLGL-UHFFFAOYAG
  • N#CC(=C)C(=O)OCC
Properties
C6H7NO2
Molar mass 125.13 g/mol
Density 1.06 g/mL
Melting point −22 °C (−8 °F; 251 K)
Boiling point 54 to 56 °C (129 to 133 °F; 327 to 329 K) at 3mm Hg
Hazards
Flash point 83 °C (181 °F; 356 K)
2 ppm
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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. Super glue is believed to be ECA. The makers of Krazy Glue state on their website, "The chemical name for Krazy Glue is ethyl cyanoacrylate."[1] Mercury Adhesives is an example of an American made ECA. [2] It is soluble in acetone, methyl ethyl ketone, nitromethane, and methylene chloride.[3] ECA polymerizes rapidly in presence of moisture.

Production

Ethyl cyanoacrylate is prepared by the condensation of formaldehyde with ethyl cyanoacetate:

CH2(CN)CO2Et + CH2O → CH2=C(CN)CO2Et + H2O

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.[4]

Applications

Ethyl cyanoacrylate is used for gluing of various materials. It finds applications also 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 non-medical-grade glues are unsuitable for medical applications, as they may contain solvents (e.g. methyl alcohol) and produce heat during polymerization.[5]

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 at 1 MHz is 3.33.[6]

Safety

In the U.S., the Threshold Limit Value for ECA is 0.2 ppm. Heating causes depolymerization of the cured polyECA, producing gaseous products strongly irritating to lungs and eyes.

See also

References

  1. ^ http://www.krazyglue.com/about-us
  2. ^ http://www.krazyglue.com/products/msds/mkg0583_a.htm
  3. ^ http://web.archive.org/web/20090603175358/http://palmlabsadhesives.com/technical_data.htm
  4. ^ Takashi Ohara, Takahisa Sato, Noboru Shimizu, Günter Prescher, Helmut Schwind, Otto Weiberg, Klaus Marten, Helmut Greim "Acrylic Acid and Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a01_161.pub2
  5. ^ http://www.miracleglue.com/wounds.htm
  6. ^ http://www.palmlabsadhesives.com/technical_data.htm
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