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-cyanoprop-2-enoate
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)
ChEMBL
ChemSpider
ECHA InfoCard 100.027.628 Edit this at Wikidata
EC Number
  • 230-391-5
RTECS number
  • UD3330050
UNII
UN number 1993
  • 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 125.127 g·mol−1
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 3 mmHg
Hazards
Flash point 83 °C (181 °F; 356 K)
0.2 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.[1] It is soluble in acetone, methyl ethyl ketone, nitromethane, and methylene chloride.[2] ECA polymerizes rapidly in presence of moisture.

Production

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

CH
2(C≡N)CO
2Et + CH
2O → H
2C
2Et + H
2O

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.[1]

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 glues are unsuitable for medical applications, as they are not medical-grade, which means their solvent and cyanoacrylate formulations have not been evaluated and optimized to reduce toxicity and prevent foreign body reactions, as would be the case with medical cyanoacrylates[3]

After curing, the resulting resin softens at temperatures above 150 °C (302 °F). The service temperature of the joint is −54 to 82 °C (−65 to 180 °F). Its dielectric constant at 1 megahertz is 3.33.[4]

Safety

In the U.S., the threshold limit value for ECA is 0.2 ppm. Heating causes depolymerization of the cured poly-ECA, producing gaseous products which are a strong irritant to the lungs and eyes.

See also

References

  1. ^ a b Ohara, Takashi; Sato, Takahisa; Shimizu, Noboru; Prescher, Günter; Schwind, Helmut; Weiberg, Otto; Marten, Klaus; Greim, Helmut; Shaffer (2020). "Acrylic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. pp. 1–21. doi:10.1002/14356007.a01_161.pub4. ISBN 978-3527306732.
  2. ^ https://web.archive.org/web/20090603175358/http://palmlabsadhesives.com/technical_data.htm
  3. ^ http://www.miracleglue.com/wounds.htm
  4. ^ "Archived copy". Archived from the original on 2008-12-08. Retrieved 2008-12-08.{{cite web}}: CS1 maint: archived copy as title (link)
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