What molecule am I?
Ethyl 2-cyanoacrylate is a liquid that you’ve probably used around the house. Because of its conjugated unsaturated groups, it polymerizes easily. It is prepared by condensing ethyl 2-cyanoacetate with formaldehyde, followed by thermal decomposition of the resulting polymer.
Ethyl 2-cyanoacrylate and other less common 2-cyanoacrylate esters are the active ingredients in commercial superglues or instant glues. Some of these products contain additives such as fumed silica to make them more viscous or rubber to make them more impact resistant.
Cyanoacrylates were discovered serendipitously during World War II when scientists at B.F. Goodrich (located in Akron, OH at the time) sought suitable clear plastics for gun sights. Chemist Harry Coover Jr. and co-workers found that the esters auto-polymerized and stuck to everything in sight. Because of the wartime urgency for other materials, cyanoacrylates were abandoned until 1951, when Coover, then at Eastman Chemical (Eastport, TN), and colleague Fred Joyner “rediscovered” it. The first commercial glue appeared in 1958.
Ethyl 2-cyanoacrylate and its cousins polymerize instantly in water. The small amount of moisture in air is enough to initiate polymerization. The polymer forms within a matter of minutes, creating a bond that is often stronger than the materials it joins.
Despite its strength, the polymer can be removed by soaking it in acetone or mild acids. Household products such as nail polish remover or lemon juice will do the trick.
Ethyl 2-cyanoacrylate hazard information
|Hazard class*||Hazard statement|
|Flammable liquids, category 4||H227—Combustible liquid|
|Skin corrosion/irritation, category 2||H315—Causes skin irritation|
|Serious eye damage/eye irritation, category 2A||H319—Causes serious eye irritation|
|Specific target organ toxicity, single exposure, respiratory tract irritation, category 3||H335—May cause respiratory irritation|
|CAS Reg. No.||7085-85-0|
|2-Propenoic acid, 2-cyano-, ethyl ester|
|Molar mass||125.13 g/mol|
|Boiling point||54–56 ºC @ 3 torr|
April 5, 2021
Ethyl 2-cyanoacrylate (ECA) is the primary active ingredient in most superglues. Recently, a new joint venture between Arkema (Colombes, France) and Cartell Chemical (Minxiong Township, Taiwan, Province of China) was formed to develop other cyanoacrylate esters that may be useful as engineering adhesives. The first step is to build a plant to make 2-methoxyethyl 2-cyanoacrylate, a derivative that avoids ECA’s deficiencies for industrial use.
Learn more about this molecule from CAS, the most authoritative and comprehensive source for chemical information.
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