Ethyl cyanoacrylate

Last updated
Ethyl cyanoacrylate
Ethyl cyanoacrylate.svg
Ethyl cyanoacrylate 3D ball.png
Ethyl cyanoacrylate.jpg
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 230-391-5
PubChem CID
RTECS number
  • UD3330050
UNII
UN number 1993
  • InChI=1S/C6H7NO2/c1-3-9-6(8)5(2)4-7/h2-3H2,1H3 Yes check.svgY
    Key: FGBJXOREULPLGL-UHFFFAOYSA-N Yes check.svgY
  • 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]
GHS-pictogram-exclam.svg
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

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

Related Research Articles

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<span class="mw-page-title-main">Acrylic acid</span> Chemical compound

Acrylic acid (IUPAC: propenoic acid) is an organic compound with the formula CH2=CHCOOH. It is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus. This colorless liquid has a characteristic acrid or tart smell. It is miscible with water, alcohols, ethers, and chloroform. More than a million tons are produced annually.

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<span class="mw-page-title-main">Acrylate polymer</span> Group of polymers prepared from acrylate monomers

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<span class="mw-page-title-main">Methacrylic acid</span> Chemical compound

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<span class="mw-page-title-main">Lawsone</span> Chemical compound

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<span class="mw-page-title-main">Ethyl acrylate</span> Chemical compound

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<span class="mw-page-title-main">Butyl cyanoacrylate</span> Chemical compound

n-Butyl cyanoacrylate, a cyanoacrylate ester, is a butyl ester of 2-cyano-2-propenoic acid. It is a colorless liquid with a sharp, irritating odor. It is insoluble in water. Its chief use is as the main component of medical cyanoacrylate glues. It can be encountered under various trade names, e.g. Cutseal, MediBond, MediCryl, PeriAcryl, GluStitch, Xoin, Gesika, VetGlu, Vetbond, LiquiVet, Indermil, LiquiBand, Histoacryl, IFABond, CutisSeal and others. The generic international nonproprietary name (INN) for NBCA is enbucrilate.

<span class="mw-page-title-main">Octyl cyanoacrylate</span> Chemical compound

Octyl cyanoacrylate (OCA), a cyanoacrylate ester, is an octyl ester of 2-cyano-2-propenoic acid. It is a clear colorless liquid with a sharp, irritating odor. Its chief use is as the main component of medical cyanoacrylate glues.

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α,β-Unsaturated carbonyl compound Functional group of organic compounds

α,β-Unsaturated carbonyl compounds are organic compounds with the general structure (O=CR)−Cα=Cβ-R. Such compounds include enones and enals, but also carboxylic acids and the corresponding esters and amides. In these compounds the carbonyl group is conjugated with an alkene. Unlike the case for carbonyls without a flanking alkene group, α,β-unsaturated carbonyl compounds are susceptible to attack by nucleophiles at the β-carbon. This pattern of reactivity is called vinylogous. Examples of unsaturated carbonyls are acrolein (propenal), mesityl oxide, acrylic acid, and maleic acid. Unsaturated carbonyls can be prepared in the laboratory in an aldol reaction and in the Perkin reaction.

References

  1. GHS: Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. 1 2 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. "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.