4
$\begingroup$

I glued a sheet of paper to a cardboard package using superglue (labelled with ethyl 2-cyanoacrylate). To my surprise the paper became very warm. What kind of reaction is it?

$\endgroup$

1 Answer 1

10
$\begingroup$

I believe this is due to the fact that cyanoacrylates polymerize by anionic (or sufficiently strong neutral nucleophile) addition. In particular, they react with hydroxyl ($\ce{-OH}$) groups; paper, being primarily cellulose, is abundant in hydroxyls. The bond formation involved in the polymerization reaction is inherently exothermic (generating a $\ce{C-O}$ bond on initiation and many subsequent $\ce{C-C}$ bonds as the polymerization proceeds), and with a large surface area and many reactive groups, I could certainly imagine the reaction being surprisingly violent. The Wikipedia page on cyanoacrylates notes its reactivity with cotton fibers (again, being chiefly composed of cellulose), and the MSDSs for various similar compounds warn of exothermic reaction with paper and similar materials (q.v., 1, 2, 3).

$\endgroup$

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service and acknowledge you have read our privacy policy.

Not the answer you're looking for? Browse other questions tagged or ask your own question.