The author reports in the present paper the separation and tentative identification of non-ureacomplex-forming multibranched-chain fatty acids as well as urea-complex-forming branched-chain ones of the iso, anteiso and of other series. Blue whale bone oil was deacidified with a 20%-potassium hydroxide solution in n-hexane, followed by purification through a silicic acid column. The methyl esters, obtained by alkali-catalyzed methanolysis of the refined oil, were separated by silicic acid column chromatography and ureacomplex fractionation. Each fraction was then analyzed by gas-liquid chromatography (GLC) on a polyester (PEGA) column before and after hydrogenation. In order to separate the urea-complex-forming branched-chain fatty acids, some urea-complex-forming fractions separated as mentioned above were converted into isopropyl esters by a BF3isopropyl alcohol reagent. The purified isopropyl esters and their hydrogenated products were separated by urea-complex fractionation. These fractions were analyzed by thin-layer, GLC and infrared spectrometry. Isopropyl esters of the branched-chain fatty acid concentrated in the non-urea-complex-forming fractions were saponified to the free acids. The infrared absorption spectrum of thus fractionated fatty acids suggested the existence of an isopropyl group as a doublet at near 1380 cm-1, and consequently the presence of branched-chain fatty acids was corroborated. The branched-chain fatty acids having “fractional carbon numbers (FCN)” of 0.2, 0.4, 0.6 and 0.8 on the PEGA column were found in the isopropyl ester of nonurea-complex-forming fraction. The last two were tentatively identified to be iso and anteiso acids, respectively, according to the published data. In addition, the component of ECL value 17.5 in the multibranched-chain fatty acid fraction was presumed as phytanic acid (3, 7, 11, 15-tetramethylhexadecanoic acid) after comparison with dihydrophytol acetate synthesized from phytol.
Cardiolipin was prepared from the frozen heart muscle of fin whale according to Pangborn's method. Every step in the course purification was pursued by T.L.C., and the sample after the last step showed only single spot corresponding to cardiolipin on T.L.C. From chemical analysis it's characteristics were as follows : P (%) -4.2%, N (%) -<O.1, I.V.-107. There was no difference between the pattern of IR apectrum of ox cardiolipin and that of fin whale cardiolipin. The composition of fatty acid calculated from the pattern of G.L.C. was as follows : Palmitic acid-23.5%, palmitoleic acid-4.5%, Oleic acid-44.5%, Linoleic acid-25.0%, Linolenic acid-1.4%, but the observed IV value did not coincide with that calculated from the composition of fatty acid based on G.L.C. In comparison with ox cardiolipin, cardiolipin of fin whale was found adaptable to the antigen for the routin test for syphilis.
Mono higher alkyl tertiary amine was prepared by a new one-step process from fatty acid ester : RCOOR' + R3'N H2→ RCH2NR2'+2 R'OH Ethyl laurate and triethyl amine were reacted at the condition of hydrogenolysis in an autoclave. Good yield (83%) of diethyl lauryl amine was obtained at 200250 kg/cm2, 300°C for 3 hrs using 1520% of Cu-Cr-O catalyst to raw ethyl laurate, and 57 mols of triethyl amine to 1 mol of raw ester.
N-alkyl-N'-gluconoylethylenediamine was synthesized almost quantatively by the reaction of δ-gluconolactone with N-alkylethylenediamine. As they were expected to have surface activity, the authors measured the lowering ability of surface and interfacial tension and the foaming power of the water solution of the N-alkyl-N'-gluconoylethylenediamines and their hydrochlorides that have C8C18 carbon atoms in the alkyl chain. Authors found that the surface active properties of N-octyl, N-decyl and N-dodecyl-N'-gluconoylethylendiamine and their hydrochlorides were satisfactory, and the lowering ability of the surface tention of N-dodecyl derivative was good for wide range of pH.
Authors investigated the determination of small amounts of iron in several samples of rice bran oil and rape seed oil by spectrophotometry. The maximum absorption of aqueous of Fe2+-2, 4, 6-tripyridyl-sym-triazine complex is 595 mμ, and optical density of the solution at 595 mμ conforms to Beer's low. Oil samples were obtained at each of the unit operations in the refinery. It was found that the range of content of iron in the several samples of rice bran oil and rape seed oil was 0.370.97 ppm and 0.290.98 ppm respectively, and the standard deviation of measured values was below 0.06. “Native” content of iron in rape seed oil was approximately 0.29 ppm. 47.3% of iron in refined rice bran oil was adsorbed by amberlite IR 120 resin column.