11/18/11 - Polymerization of Methyl-2-Cyanacrylate

    This reaction of the day was influenced by a graceful ballerina using a fast drying glue on her point shoes making me wonder what it is she is actually putting on there.  So I looked into what the 'Jet instant glue' was made up of and it was concluded that it was a cyanacrylate based glue (which also make up the ingredients in krazy glue and many other adhesives).  So the basis of this glue is the molecule methyl-2-Cyanacrylate (seen below) and it is activated once in the presence of moisture or other nucleophilic species.  In most cases the nucleophile exists as the water molecules in the air which attack the terminal alkene group, making a carboanion, which in turn attacks another methy-2-cyanacrylate group acting as the nucleophile, producing a long, polymerized chain.
 
Picture: Wikipedia