Octyl cyanoacrylate

Last updated
Octyl cyanoacrylate
Octyl-cyanoacrylate-2D-skeletal.svg
Octyl cyanoacrylate 3D spacefill.png
Names
Preferred IUPAC name
Octyl 2-cyanoprop-2-enoate
Other names
Octyl 2-cyanopropenoate
Octyl 2-cyanoacrylate
Ocrylate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.027.045 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C12H19NO2/c1-3-4-5-6-7-8-9-15-12(14)11(2)10-13/h2-9H2,1H3 Yes check.svgY
    Key: RPQUGMLCZLGZTG-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C12H19NO2/c1-3-4-5-6-7-8-9-15-12(14)11(2)10-13/h2-9H2,1H3
    Key: RPQUGMLCZLGZTG-UHFFFAOYAE
  • N#CC(C(OCCCCCCCC)=O)=C
Properties
C12H19NO2
Molar mass 209.289 g·mol−1
AppearanceColorless liquid
Density 1.0±0.1 g/cm3
Boiling point 297.6±23.0 °C
Reacts
Hazards
Flash point 137.2±9.4 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.

In medical and veterinary applications, OCA, n-butyl cyanoacrylate (n-BCA) and isobutyl cyanoacrylate (ICA) are commonly used. They provide rapid wound closure, [1] are bacteriostatic, and their use is usually painless.[ citation needed ] Butyl esters provide a stronger bond, but the glue is rigid. The octyl ester, while providing weaker bond, is more flexible. Blends of OCA and n-BCA are available which offer both flexibility and a strong bond.

It polymerizes rapidly in presence of moisture.

Heating to higher temperatures causes pyrolysis and depolymerization of the cured glue, producing gaseous products strongly irritating to the lungs and eyes.

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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.

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Isobutyl cyanoacrylate is an isomer of butyl cyanoacrylate. It is used in medical procedures either to close incisions and lacerations without the use of sutures, or as an adjunct to strengthen the suturing. This use is possible because it is a bactericidal liquid monomer which, in the presence of small amounts of moisture, rapidly polymerizes to form a strong adhesive.

<span class="mw-page-title-main">2-Octyl cyanoacrylate</span> Chemical compound

2-Octyl cyanoacrylate is a cyanoacrylate ester typically used as a wound closure adhesive. It is closely related to octyl cyanoacrylate. The use of 2-octyl cyanoacrylate was approved in 1998; offered as an alternative to stitches, sutures, and or adhesive strips.

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References

  1. Singer, A. J.; McClain, S. A.; Katz, A. (2004). "A porcine epistaxis model: hemostatic effects of octylcyanoacrylate". Otolaryngology–Head and Neck Surgery. 130 (5): 553–557. doi:10.1016/j.otohns.2003.09.035. PMID   15138419.

See also