An Easy and Promising Tool for the Determination of Iodine and Epoxy Values of Epoxidized Soybean Oil by 1H NMR Spectrometry
High-resolution 1 H nuclear magnetic resonance ( 1 H NMR ) was advanced to determine both epoxy value and iodine value ( IV ) of vegetable oils that occur during their epoxidation. For calibration, rather than using a series of diluted stock samples, epoxidized soybean oils with a range of IV and epoxy value synthesized using entrapped peroxophosphotungstate as the catalyst under different reaction conditions were used. During the epoxidation reaction, IV and epoxy value were tracked with respect to time using 1 H NMR and conventional volumetric methods. The integrated peak area of the olefinic hydrogens (5.3–5.5 ppm) was used to calculate the absolute number of double-bonded protons. By comparison of IV obtained by 1 H NMR and the traditional Wijs-cyclohexane methods, the correlation coefficient was R 2 = 0.9997 for the regression equation y = 1.1314 x + 1.0035, where x was the result given by 1 H NMR. The average integrated peak areas related to the hydrogens of the epoxide groups located at chemical shifts of 2.9 ppm (monoepoxide) and 3.1 ppm (diepoxide) were used to determine the epoxy value. The quantification of the number of epoxides was carried out by 1 H NMR and the values obtained were correlated with epoxide content determined by the hydrochloric acid/acetone method. As a consequence, the correlation coefficient was R 2 = 0.9991 for the regression equation y = 0.0052 x + 1.7258, where x was the average integrated peak areas related to the hydrogens of the epoxide groups by 1 H NMR. The novelty of our study lies in the simultaneous correlation between IV and epoxy value obtained from conventional titrations, the integrated peak area related to olefinic protons, and the average integrated peak area located at the hydrogen of epoxide group, calculated using 1 H NMR. This approach is used to monitor and optimize the epoxidation reaction.
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