水産動物内臓油利用に関する研究-IX

Abstract

From the viewpoint of opening the use of residual oil brought forth in preparing a concentrated product of vitamin A by molecular distillation, a few investigations were advanced into the technique of obtaining from molecular distillation residue of dogfish liver oil a concentrated preparation of glyceryl ether as well as into the surface-active properties of the preparation thus obtained. In the first part of the present work, a sample of dogfish liver oil as starting material was hydrolyzed by following the routine saponification procedure, unsaponifiable matters were separated and these matters were then collectively submitted to molecular distillation (see Table 1). From the sum of distillate fractions 2, 3 and 4, there was thus obtained through the trial of taking out glyceryl ether from said kind of residual oil in which the ether had been known to be present as resistive to molecular distillation a concentrated preparation of glyceryl ether containing selachyl alcohol as main constituent and having an acetyl value of 246-257.6 and an iodine value of 82.1-87.9 with an yield of 5.36% based upon the amount of starting material. Then, by hydrogenating the preparation of glyceryl ether and recrystallizing the hydrogenation product in ethyl ether, a refined preparation as fine crystals was obtained, which had a melting point of 67.5°C and was proved by elemental analysis to contain C of 73.28% and H of 12.71%. These data may be looked upon to be in a close approximation to those for batyl alcohol appearing in literature. In the second part of the present work, measuring the interfacial tension between a kerosene solution of the concentrated preparation of selachyl alcohol and water (see Table 6 and Figs. I and 2), said preparation obtained as above from a molecular distillation residue of dogfish liver oil was examined in its aspect of surface-activity (see Tables 2, 3, 4 and 5). As seen from the values thus obtained, the interfacil tension between kerosene and water is strongly minimized by adding the former with selachyl alcohol as said type of concentrated preparation in an amount of 0.25-1%. It was found also that, with kerosene solution containing said preparation in amounts not in excess of 1%, selachyl alcohol exerts the greater ability of lowering the interfacil tension between kerosene and water at the lower temperature, insofar as the temperature concerned is in the range of 20-60°C. Further, to estimate the emulsifying power of said concentrated preparation of selachyl alcohol, two similar series of samples were prepared, which consisted of refined coconut oil added with said selachyl alcohol preparation, on the one hand, and mono fatty acid glyceryl ester, on the other, up to various concentrations ranging from 0.5 to 4%, and these samples were compared with one another in respect of the emulsifying effect they developed in water. According to the result obtained (see Table 7), the two substances examined were both found to be fairly good in emulsifying power. As to the state of emulsion they produce, however, these substances used as emulsifyer were observed to behave somewhat differently from each other. Thus, when the breakdown of emulsion commences, while the emulsion prepared with mono fatty acid glyceryl ester begins to separate an aqueous layer, that prepared with the concentrated preparation of selachyl alcohol does so an oily layer.