Synthesis, characterization and antimicrobial evaluation of quaternary ammonium compounds from natural oils

Abstract

Quaternary ammonium salts refer to any class of salt derived from ammonium in which the nitrogen atom is attached to four organic groups covalently, as in benzalkonium chloride (R4N+). Quaternary ammonium compounds were synthesized from Canola oil (Brasssicanapus) and Coconut oil (Cocos nucifera) extracts by reacting the oils with N,N-diethylethylenediamine in the presence of potassium tertiary butoxide as catalyst. Fourier Transform Infrared (FTIR) Spectrometric analyses of the starting materials, the intermediates and the final products were conducted, the results showed a disappearance of the carbonyl (C=O) stretch of an ester (the oil) at 1744cm-1 and appearance of N-H band of an amide at 3433cm-1, which resulted from the quaternization of benzyl chloride with the intermediates for both oils. Other functional groups such as C=C and C-H stretch of aromatic compound, C=O stretch of an amide were also observed.Mass spectrometric analysis of the final products were conducted and results showed the Molecular Ion peak (M+) which is the molecular weights of the products. Vital fragments such as base peaks were observed for both quats, other fragmented radical cations were observed.Antimicrobial activity of the synthesized Quaternary ammonium compounds (QACs) exhibited excellent anti-bacterial activity covering a diameter of 22 mm and 28 mm of E. coli for QACs from Cocos nucifera and Brassic anapus oils respectively as compared to the standard antibiotic (Ampillicin).