Ethyl 2-cyanoacrylate

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Structural formula
Structural formula of ethyl 2-cyanoacrylate
General
Surname Ethyl 2-cyanoacrylate
other names
  • Ethyl cyanoacrylate
  • ECA
  • Ethyl 2-cyano-2-propenoate
Molecular formula C 6 H 7 NO 2
Brief description

colorless liquid with a pungent odor

External identifiers / databases
CAS number 7085-85-0
EC number 230-391-5
ECHA InfoCard 100,027,628
PubChem 81530
Wikidata Q209366
properties
Molar mass 125.13 g · mol -1
Physical state

liquid

density

1.04 g cm −3

Melting point

−25 to −20 ° C

boiling point

60 ° C at 3.99 hPa

Vapor pressure

<2.7 hPa at 20 ° C

solubility
  • polymerizes rapidly on contact with water
  • miscible and dissolvable with acetone
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
07 - Warning

Caution

H and P phrases H: 315-319-335
P: 261-305 + 351 + 338
MAK

2 ppm, 9 mg m −3 (Austria)

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Ethyl 2-cyanoacrylate , also known as ethyl cyanoacrylate , is a nitrile derivative of the ethyl ester of acrylic acid . It belongs to the group of acrylates , more precisely cyanoacrylates .

Extraction and presentation

Ethyl 2-cyanoacrylate can be obtained by reaction of an alkyl cyanoacetate ( ethyl cyanoacetate ) with formaldehyde and subsequent depolymerization.

CH 2 (CN) CO 2 Et + CH 2 O → CH 2 = C (CN) CO 2 Et + H 2 O

Chemical properties

Ethyl 2-cyanoacrylate is a colorless liquid with a characteristic, pungent odor, which polymerizes very quickly in an exothermic reaction on contact with moisture, amines , alkaline substances and ethanol .

use

2-ethyl cyanoacrylate is mainly used as superglue used and cured most often in less than a minute. In addition to household use, it is also used in medicine for sutures without thread. It is also used in forensics to visualize fingerprints with the help of cyanoacrylate fumes. The homologous methyl cyanoacrylate was first investigated by researchers from Eastman Kodak in the 1930-40s and patented in 1956.

Individual evidence

  1. ↑ a b c d e f g h Entry on ethyl-2-cyanoacrylate in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
  2. ↑ a b c MSDS (mercareo) ( Memento from February 2, 2016 in the Internet Archive ) (PDF; 27 kB).
  3. ↑ Technical data sheet UHU superglue (PDF; 27 kB)
  4. ↑ Entry on Ethyl 2-cyanoacrylate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
  5. ^ Concise International Chemical Assessment Document (CICAD) for Methyl cyanoacrylate and ethyl cyanoacrylate , accessed December 9, 2014.
  6. ↑ www.reciprocalnet.org

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