What molecule am I?
Ethyl 2-cyanoacrylate is a liquid that you鈥檝e 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 (Kingsport, TN), and colleague Fred Joyner 鈥渞ediscovered鈥� 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.聽
Ethyl 2-cyanoacrylate聽hazard information
| Hazard class* | Hazard statement | |
|---|---|---|
| Flammable liquids, category 4 | H227鈥擟ombustible liquid | |
| Skin corrosion/irritation, category 2 | H315鈥擟auses skin irritation |  |
| Serious eye damage/eye irritation, category 2A | H319鈥擟auses serious eye irritation聽 | |
| Specific target organ toxicity, single exposure, respiratory tract irritation, category 3 | H335鈥擬ay cause respiratory irritation | |
*Globally Harmonized System of Classification and Labeling of Chemicals.
Ethyl 2-cyanoacrylate聽
fast facts
| CAS Reg. No. | 7085-85-0 |
nomenclature | 2-Propenoic acid, 2-cyano-, ethyl ester |
| Empirical formula | C6H7NO2 |
| Molar mass | 125.13 g/mol |
| Appearance | Colorless liquid |
| Boiling point | 54鈥�56 潞C @ 3 torr |
| Water solubility | 笔辞濒测尘别谤颈锄别蝉听 |
MOTW update:
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) was formed to develop other cyanoacrylate esters that may be useful as engineering adhesives. The first step is to build a plant to make , a derivative that avoids ECA鈥檚 deficiencies for industrial use.
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