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Ethyl cyanoacrylate

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.

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
  • 7085-85-0 Y
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL1564920
ChemSpider
  • 73564 Y
ECHA InfoCard 100.027.628
EC Number
  • 230-391-5
  • 81530
RTECS number
  • UD3330050
UNII
  • 2G95FOH7SF Y
UN number 1993
  • DTXSID1025279
  • InChI=1S/C6H7NO2/c1-3-9-6(8)5(2)4-7/h2-3H2,1H3 Y
    Key: FGBJXOREULPLGL-UHFFFAOYSA-N Y
  • 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]
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).
Y verify (what is YN ?)

Production Edit

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 Edit

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 Edit

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 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. ^ . 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.

ethyl, cyanoacrylate, cyanoacrylate, ester, ethyl, ester, cyano, acrylic, acid, colorless, liquid, with, viscosity, faint, sweet, smell, pure, form, main, component, cyanoacrylate, glues, encountered, under, many, trade, names, soluble, acetone, methyl, ethyl,. 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 Ethyl cyanoacrylate NamesPreferred IUPAC name Ethyl 2 cyanoprop 2 enoateOther 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 VeneerIdentifiersCAS Number 7085 85 0 Y3D model JSmol Interactive imageChEMBL ChEMBL1564920ChemSpider 73564 YECHA InfoCard 100 027 628EC Number 230 391 5PubChem CID 81530RTECS number UD3330050UNII 2G95FOH7SF YUN number 1993CompTox Dashboard EPA DTXSID1025279InChI InChI 1S C6H7NO2 c1 3 9 6 8 5 2 4 7 h2 3H2 1H3 YKey FGBJXOREULPLGL UHFFFAOYSA N YInChI 1 C6H7NO2 c1 3 9 6 8 5 2 4 7 h2 3H2 1H3Key FGBJXOREULPLGL UHFFFAOYAGSMILES N CC C C O OCCPropertiesChemical formula C 6H 7N O 2Molar mass 125 127 g mol 1Density 1 06 g mLMelting point 22 C 8 F 251 K Boiling point 54 to 56 C 129 to 133 F 327 to 329 K at 3 mmHgSolubility in water PolymerisesHazardsGHS labelling 1 PictogramsSignal word WarningHazard statements H315 H319 H335Precautionary statements P261 P305 P351 P338Flash point 83 C 181 F 356 K Threshold limit value TLV 0 2 ppmExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Contents 1 Production 2 Applications 3 Safety 4 See also 5 ReferencesProduction EditEthyl cyanoacrylate is prepared by the condensation of formaldehyde with ethyl cyanoacetate NCCH2CO2C2H5 CH2O H2C C CN CO2C2H5 H2OThis 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 EditEthyl 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 EditIn 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 EditCyanoacrylate Methyl cyanoacrylate Butyl cyanoacrylate Octyl cyanoacrylateReferences Edit GHS Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health a b Ohara Takashi Sato Takahisa Shimizu Noboru Prescher Gunter 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 Cyanoacrylate Technical Data palmlabsadhesives com Archived from the original on 3 June 2009 Retrieved 12 January 2022 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 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 Retrieved from https en wikipedia org w index php title Ethyl cyanoacrylate amp oldid 1176046249, wikipedia, wiki, book, books, library,

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