Ethyl cyanoacrylate
Structural formula of ethyl cyanoacrylate
Ball-and-stick model of the ethyl cyanoacrylate molecule
Pure ethyl cyanoacrylate
Names
Preferred 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
Polymerises
Hazards
GHS labelling:[1]
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P305+P351+P338
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-acrylic 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.[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:

NCCH2CO2C2H5 + CH2O → H2C=C(CN)CO2C2H5 + 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.[2]

Applications

Ethyl cyanoacrylate is used for gluing.

In forensics, cyanoacrylate ester has excellent non-destructive impressioning abilities, which are especially important when lifting fingerprints from delicate evidence items, or when the prints could not be lifted using traditional means such as fingerprinting powder. The procedure involves heating the acrylate in a sealed chamber. Its fumes then react with deposited proteins that form into a white, stable, and clear print outlines. The resulting prints could be used 'as is' or enhanced further by staining them with darker pigments.[4][5] Liquid bandage systems use the less toxic n-butyl and octyl cyanoacrylates.

Safety

In the U.S., the threshold limit value for ECA is 0.2 ppm. It is a strong irritant to the lungs and eyes.

See also

References

  1. ^ GHS: Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. ^ 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.
  3. ^ "Cyanoacrylate Technical Data". palmlabsadhesives.com. Archived from the original on 3 June 2009. Retrieved 12 January 2022.
  4. ^ Bumbrah, Gurvinder Singh (2017). "Cyanoacrylate fuming method for detection of latent fingermarks: a review". Egyptian Journal of Forensic Sciences. 7 (1): 4. doi:10.1186/s41935-017-0009-7. PMC 5514188. PMID 28781896.
  5. ^ Mutter, Nicole; Deacon, Paul; Farrugia, Kevin J. (2018-11-30). "The effect of cyanoacrylate fuming on subsequent protein stain enhancement of fingermarks in blood". Journal of Forensic Identification. 68 (4): 545–556. S2CID 104335657.
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