Synthesis and Characterization of 1-octyl 2-cyano Acrylate for Wound Healing Applications

Abstract

Cyanoacrylate glues are quick setting materials which rapidly cure to hard, clear glassy resins. Its synthesis too has not been reported in the open literature so far. Synthetic methods, which engage esterification of cyanoacetic acid with a preferred alcohol, polymerization by knoevenagel condensation and successive depolymerization, are applied to the synthesis of lower membered alkyl cyanoacryaltes in which the alkyl groups carry less than 8 carbons. We have synthesized 1-octyl cyanoacetate by a traditional method involving p-toluene sulphonic acid as the catalyst. In the second step, we have attempted the preparation of poly (n-octyl cyanoacrylate) by the reaction of formaldehyde with n-octyl-2-cyanoacetate in the presence of both piperidine and potassium carbonate in the absence of any solvents. Its FTIR spectrum confirmed its functional groups: Its –OH stretching yielded a broad band around 3400 cm-1. The polymer was depolymerized using poly phosphoric acid catalyst under vacuum to obtain the monomer. A simple method of obtaining monomer was also attempted by the reaction of 1-octyl- 2-cyano acetate and diiodomethane in the presence of potassium carbonate. This process directly yields the monomer. The second method looks better than the others, and it can be applied to any type of alcohols.