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 encountered under many trade names. It is soluble in acetone, methyl ethyl ketone, nitromethane, and methylene chloride.[1] ECA polymerizes rapidly in presence of moisture.

Ethyl cyanoacrylate
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
EC Number
  • 230-391-5
RTECS number
  • UD3330050
UNII
UN number 1993
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 3mm Hg
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).
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Infobox references

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.[2]

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 −54–82 °C (−65–180 °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. https://web.archive.org/web/20090603175358/http://palmlabsadhesives.com/technical_data.htm
  2. Takashi Ohara, Takahisa Sato, Noboru Shimizu, Günter Prescher, Helmut Schwind, Otto Weiberg, Klaus Marten, Helmut Greim (2002). "Acrylic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_161.pub2.CS1 maint: uses authors parameter (link)
  3. http://www.miracleglue.com/wounds.htm
  4. "Archived copy". Archived from the original on 2008-12-08. Retrieved 2008-12-08.CS1 maint: archived copy as title (link)
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