Extensive N -methylation of chitosan: evaluating the effects of the reaction conditions by using response surface methodology

Abstract

The effects of reaction time, concentration of aqueous sodium hydroxide and molar ratio iodomethane/chitosan on the yield of the reaction of chitosan with iodomethane in N-methyl-2-pyrrolidone (NMP) at 25.0 ± 0.1 °C, as well as on the characteristics of the resulting N,N,N-trimethylchitosan (TMCh), were evaluated by using full-factorial 23 design analysis and response surface methodology. This study also aimed to determine the reaction conditions allowing the production of water-soluble TMCh presenting a high average degree of quaternization and intrinsic viscosity at high reaction yield. 1H NMR spectroscopy was employed for structural characterization, including the determination of average degrees of acetylation (DA‾) and quaternization (DQ‾), while capillary viscometry was used to determine intrinsic viscosity [η]. The results show that when the extensive N-methylation is carried out for 24 h in NMP/15% NaOH (w/v) employing a lower excess of iodomethane (CH3I/Ch = 9), water-soluble highly substituted (DQ‾ = 46.0%) TMCh ([η] = 213.0 mL g−1) can be produced in high yield (81.8%). The highly significant mathematical models resulting from this study describe the dependence of the experimental responses on the reaction conditions and allow the characteristics and properties of the resulting TMCh to be defined by properly choosing the reaction conditions. © 2015 Society of Chemical Industry