The catalytic dimerization reaction of tall oil fatty acids by flow method was investigated. Tall oil fatty acids were found to be dimerized fairly good yield by continuously passing over a catalyst having phosphoric acid deposited on a high surface-area synthetic silica-alumina contained 70% of silica and 29% of alumina. From the long run experiment of dimerization of tall oil fatty acids, it is also seen that the activity of the catalyst is maintained even after the total amount of fatty acid reached 1.5l flow through the 25g catalyst bed. Moreover, the unsaponifiable matters in monomer fraction produced together with the dimerization reaction, were experimented in detail and noticed to be almost hydro-carbons such as parafines and olefines, and also to be straight-chain 2-ketone compounds and cyclic ketone compounds of the 5-and 6-membered ring.
Liquid crystal obtained from a mixed system of monopalmitin and water was examined for phase diagram, growth mechanism of liquid crystal and morphological changes during phase transition, using a polarizing microscope and DSC. 1) With concentration of monoglyceride in the range of 9973%, a reversed middle phase was formed, and it became a neat phase with 8030% concentration. At concentrations below 70%, a viscous isotropic phase appeared in the high temperature region and this transited to a neat phase with lowering of temperature. With monoglyceride concentration below 40%, the stable range of the neat phase and viscous isotropic phase transited gradually to a lower temperature side, and the liquid crystal disappeared at about 23% concentration of monoglyceride. 2) The reversed middle phase observed in the region of high concentration of monoglyceride grew by the crossed aggregation of a rod-like pattern. It was similar to the growth of usual smectic liquid crystal. On the other hand, the neat phase served in the low concentration range is considered to grow, as the nuclei was generated from the monomolecular film and micelle formed in the viscous isotropic phase.
Separations of cis, trans fatty acid isomers of C16C22 chain-lengths were successfully carried out by packed column gas chromatography (GC) using a cyanosiloxane liquid phase, OV-275. Peak separations of C18 : 1 and C22 : 1 isomers were examined at various column temperatures. The best separations of these isomers were obtained at 220°C and 240°C, respectively. No linear relationship between carbon numbers and logarithmic values of retention times of saturated esters was found. Therefore, the equivalent chain lengths (ECL) of unsaturated esters were calculated from the logarithmic retention times of neighboring saturated homologous pairs. The ECL values were significantly affected by column temperature, and selection of adequate column temperature permitted separations of critical pairs. For example, no separation of linoleate-arachidate pair was obtained at 210°C but baseline separation was obtained at 240°C. Δt ECL, an increase of ECL for one degree raising of column temperature, was calculated for some unsaturated esters. The Δt ECL increased with increasing of degree of unsaturation of methyl esters. The values of linoleate and linolenate on the OV-275 were approximately twice of that on SILAR 10C and three times of that on DEGS. The Δt ECL of cis isomers was smaller than that of the corresponding trans isomers. The packed column GC was first applied to determinations of trans fatty acids of beef tallows, partially hydrogenated pollach oil and commercial margarines containing partially hydrogenated fish oils. The analytical results fatty acid compositions were in good agreement with them obtained by DEGS column.
The formation of carvacrol from d-limonene-1, 2-epoxide  by platinum group metal catalysts was studied. It was found that carvacrol was formed from  in the presence of palladium catalyst at 170°C. The reaction mechanism of carvacrol from  was proposed on the basis of results under various reaction condition.
New cationic and amphoteric surfactants containing N-long alkylpyrazolidinone ring have been derived from alkylhydrazine. The antimicrobial activities of these surfactants were tested using Gram positive, Gram negative bacilli and fungi by Minimum Inhibition Concentration's method. The effects of the chain length of alkyl group in pyrazolidinone and also an introduction of propionic acid and acetic acid group into N-alkylpyrazolidinone were studied. Antimicrobial activities of these cationic surfactants, N-alkylpyrazolidinone, against microorganism were low or absent. But antimicrobial increasing effect of the introduction of acetic or propionic acid into the corresponding N-alkylpyrazolidinone was shown in some microorganisms. As for the alkyl group in N-alkylpyrazolidinone, dodecyl group was more potent than decyl group. And the N-alkylpyrazolidinoyl propionic acid was generally more active than the acetic acid derivative. Moreover, surface activities of aqueous solution of these surfactants were confirmed.
On the analysis of fatty acid compositions of vegetable oils such as rapeseed oil and peanut oil by GLC, the use of a packed column with SP-2300 thermostable liquid phase was effective as one of the solutions of the difficulty due to chain-length overlap between methyl linolenate and arachidate or eicosenoate. The retention time of methyl derivatives above C20 on SP-2300 column was much faster, because of high temperature operating, than that on polar polyester or organosilicone polyester phases used commonly in fatty acid analysis. For example, methyl linolenate, arachidate, eicosenoate and tetracosenoate were eluted in 8.0, 8.8, 9.4 and 18.7min, respectively, by a temperature programming from 180 to 240°C at a rate of 4°C/min on a stainless steel column (3mm×2.25m) packed with 5% SP-2300 on 6080mesh Chromosorb W AWDMCS or on 6080mesh Celite 545 SKDMCS. The quantitative analysis of a standard mixture of fatty acid methyl esters for GLC on the above two columns showed that the percentage of the peak area for each fatty acid ester except methyl linolenate agreed closely with that of weight of the corresponding fatty acid ester, and that no correction of detector response was needful even in long chain esters containing 20 or more carbon atoms for usual analyses.
The catalytic dimerization of castor fatty acids or their methyl esters by flow method was investigated. It is found that the synthetic silica-alumina composed of 70% SiO2 and 29% Al2O3 has high catalytic activity for the dimerization of castor fatty acid methyl esters and that the dimerization of castor fatty acids also easily proceeded over a phosphoric acid deposited on the silica-alumina support. Besides, it is observed that the dimerization process of ricinoleic acid, being main component of castor fatty acids, proceeded over the phosphoric acid catalyst and for its mechanism ricinoleic acid was dehydrated first and then octadecadienoic acid which was dehydrated products of ricinoleic acid, was dimerized.