Ethyl cyanoacrylate

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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
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-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.[2] It is soluble in acetone, methyl ethyl ketone, nitromethane, and methylene chloride.[3] ECA polymerizes rapidly in presence of moisture.

Production[edit]

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

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

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[edit]

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[4]

In forensics, cyanoacrylate ester has also been found to have 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 seek out 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.[5][6]

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.[7]

Safety[edit]

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[edit]

References[edit]

  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.
  3. ^ "Archived copy". palmlabsadhesives.com. Archived from the original on 3 June 2009. Retrieved 12 January 2022.{{cite web}}: CS1 maint: archived copy as title (link)
  4. ^ "Wounds and Miracle Glue".
  5. ^ 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.
  6. ^ 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.
  7. ^ "Archived copy". Archived from the original on 2008-12-08. Retrieved 2008-12-08.{{cite web}}: CS1 maint: archived copy as title (link)