Influence of Different Catalysts and Solvents on the General Base Catalytical Esterification of Polyoxyethylene Sorbitan Trioleate with Maleic Anhydride and Styrene-Co-Maleic Anhydride

Abstract

The general base catalitycal esterification of Polyoxyethylene sorbitane Trioleate with maleic anhydride (Ma) and styrene-co-maleic anhydride (Sma) using pyridine as catalyst is described. We investigated the effect of different factors on the yield of reaction product. The analysis of the effect of different factors on the process of catalytical esterification showed that the catalysts and solvents can be arranged by their activity in the following order: sulfuric acid > toluene sulfonic acid > triethylamine > pyridine > without a catalyst and dimethylsulfoxide (DMSO) > O-xylene > dimethylformamide (DMF), respectively. It should be noted that pyridine to its activity is not significantly inferior to the traditional catalysts and with DMSO using the yield of product is increasing. It is concluded that the reaction proceeds by 2nd order. It was found that decreasing the temperature of reaction to a lower temperature, where there is an intensive incubation period, leads to decreasing of yield of polyesters. The rate constant and activation energy were calculated. It was found that the process occurred on 98% at 130 °С and 80 minutes for PoesTo/Ma and on 88% at 150 °С and 40 minutes for PoesTo/Sma. For preparation of reaction product to analysis new methods were developed. It was shown, that on 1H and 13C spectra an overlap of the individual peaks or their close concentration in one area is observed, which makes it not possible to complete the analysis of the spectra. 1H and 13C spectra give a preliminary idea of the structure of the reaction products. It is concluded that 2-D NMR measurements more useful for further confirming of structure of PoesTo/Ma and PoesTo/Sma. HLB shown that we obtained two different surfactants where by catalytical esterification the hydrophilic part of Tween in PoesTo/Ma and the lipophilic part in PoesTo/Sma was increased.