In order to reduce methyl linoleate selectively, catalytic hydrogen transfer from eleven steroids, six terpenes, and an alkaloid was investigated at 140°C. In the hydrogenation with cholesterol and D-limonene, RuH₂ (PPh₃)₄ was the most active catalyst and RhH (PPh₃)₄ was the next, but the latter showed higher selectivity to monoenes and less formation of isolated trans double bonds than the former. The catalytic activity of RuCl₂ (PPh₃)₃ was low and that of (NH₄)₂PdCl₄, PdCl₂, Pd-carbon, Pd-black, Pt-asbestos, and Pt-black was negligible. Most of the other natural products showed high hydrogen-donating ability in the presence of RuH₂ (PPh₃)₄ and RhH (PPh₃)₄. In the cholesterol-RhH (PPh₃) ₄ system, complete selectivity to monoenes and scarce formation of trans bonds were realized with high conversion. This system in which the reactions of other substrates were also carried out showed the following characteristics : (1) the reactivity of trans-9, trans-12-octadecadienoate was comparable to that of linoleate, and that of elaidate was comparable to that of oleate; (2) the reactivity of alkali conjugated octadecadienoates was much lower than that of the nonconjugated dienoates; (3) in the reactions of the dienoates, the selectivity to monoenoates was complete but oleate and elaidate were also reduced considerably, that is, monoenes were reduced in the absence of dienes but were not reduced in the presence of dienes; (4) the ratio of cis to trans in the isolated double bonds became nearly constant in the absence of conjugated dienes and it was about 3 : 1. in the cholesterol-RuH₂ (PPh₃)₄ system, the reactivity of the conjugated dienoates was comparable to that of the nonconjugated dienoates and the selectivity to monoenes was low. Also in this system, the ratio of cis to trans isomers became approximately constant and it was about 2 : 1.

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Citric acid was added into the deodorized soybean oil. Citric acid content in the oil was determined by GLC wtih 5% Silicone OV-17 and the effect of citric acid on the oxidative and flavor stability of the soybean oil was tested. Citric acid did not protect the oil against fluorescent light. On the other hand, citric acid markedly improved flavor and oxidative stability when the oils were deteriorated under spontaneous autoxidation conditions. However, its efficiency was independent of its concentration. Citric acid solubility in the soybean oil was measured. At least 50ppm citric acid could be dissolved in the oil after 4 weeks of storage.

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The reactions of di-n-alkylphosphine oxides (1) with halocarboxylic acids (2) and their esters (3) were carried out in boiling sodium ethoxide and methoxide solutions, respectively. The products were identified by P%, NV, and IR and MS spectra. Di-n-hexylphosphine oxide (1b) was reacted with haloacetic and 3-halopropionic acids X- (CH2) n-CO2H, (2) (X=Cl, Br; n=1, 2) to give di-n-hexylphosphinic and 3- (di-n-hexylphosphinyl) propionic acids ((4b) and (5b)), respectively. The yield increased with increasing the concentration of sodium ethoxide. Reactions of (1) with methyl bromoacetate and 3-bromopropionate ((3a) and (3b)), followed by alkaline (potassium hydroxide) hydrolysis, gave di-n-alkylphosphinic and 3- (di-n-alkylphosphinyl) propionic acids ((4) and (5)), respectively. In the case of (3a), the optimum condition was (1) : (3a) : [NaOMe] =1 : 1 : 1 (mol/mol/mol), but the yield of (5) increased with increasing concentration of sodium methoxide in the reaction with (3b). The reaction of di-n-heptylphosphine oxide (1c) with ethyl 2-bromobutyrate (1 : 1 : 1) gave 93% of di-n-heptylphosphinic acid (4c), but a trace of (4c) was obtained with ethyl acetate. An intermediate ester, methyl 3- (di-n-hexylphosphinyl) propionate (6b), was isolated in the reaction of (1b) with (3b) (1 : 1 : 2.2, t=5h) without the hydrolysis, and was easily hydrolyzed by potassium hydroxide. For the formation of (4) which is a new oxidation reaction of (1), a mechanism involving a nucleophilic attack of the reactive species R2P (O) Na (7) on the carbonyl carbon of (2) (n=1) or (3a) to give an intermediate enol phosphate analog (9) was proposed and discussed. For the formation of (5), a possible mechanism involving a nucleophilic addition of (7) to the activated olefin produced by the ordinary alkoxide promoted 1, 2-elimination of hydrogen halide from (2) (n=2) or (3b) was proposed and discussed.

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In order to discriminate effectively the presence of a substitute in cacao butter, the compositions of shea butter, Borneo tallow, and sal fat, used as substitute materials, were analyzed and the results were compared with that of cacao butter. Results obtained are as follows :
1) In fatty acid composition, contents of C₁₆ acid in shea butter and sal fat, and of C₂₀ acid in sal fat were greatly different from that in cacao butter. Also, C_{20 : 1}, not found in cacao butter, was found in both shea butter and sal fat, and C₂₂ was found in sal fat. Borneo tallow showed a composition similar to that of cacao butter, although a slight difference was seen in the content of C₁₆ and C₁₈ acids.
2) In triglyceride composition, a great difference from cacao butter was seen in C₅₀ of borneo tallow and sal fat, C₅₂ in shea butter and sal fat, and C₅₄ content in all three. Further, C₅₀ was not found in shea butter, while C₅₆ was found in all three fats, although it is hardly found in cacao butter. The latter was present especially in large amount in sal fat.
3) In sterol composition, the content of stigmasterol in borneo tallow and campesterol in sal fat was markedly different from that in cacao butter, and the content of campesterol was larger than that of stigmasterol in both fats in contrast to cacao butter. The main components in shea butter were α-spinasterol and Δ₇-stigmastenol, being entirely different from cacao butter.
4) In 7 indices for judgement of purity of cacao butter indicated previously, a great difference from cacao butter was found in the ratios of C₁₆/C₁₈ and C₅₂/C₁₈ in shea butter, sito/ (stigma) - (campe) and stigma/campe in Borneo tallow, and sito/stigma) - (campe) and C₁₆/C₁₈ in sal fat.

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The effect of urea on the interaction of polyvinyl alcohol (PVA) with sodium dodecyl sulfate (SDS) in aqueous solution was investigated by means of viscosity, electrophoresis, and dialysis equilibrium. In the absence of urea, the intrinsic viscosity [η], the electrophoretic mobility u, the number of effective charge Z (corresponding to the number of bound surfactant ion on PVA) of PVA-SDS complex, and the bound SDS on PVA changed depending on the SDS concentration (Cs) in solution and increased steeply from the vicinity of the first critical micelle concentration (cmc) of the surfactant. Then the first three reached maxima at the concentration corresponding to the second cmc. In the presence of urea, [η] Cs, uCs, ZCs curves and the bound SDS on PVA changed with the concentration of urea. At SDS concentrations higher than the first critical micelle concentration, the above three curves fell and the bound SDS decreased with increasing concentration of urea. These results suggest a release of the bound SDS from PVA and a contraction of the PVA-SDS complex molecule by the weakening of the electric repulsion between the surfactant ions bound on PVA.

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High-boiling fractions of China gum terpentine have been investigated. The following compounds were shown to be present; α-longipinene longicyclene, β-ylangene, longifolene, β-caryophyllene, α-humulene, β-humulene, δ-cadinene, γ-cadinene, calamenene, dihydrocaryophyllene-5-one, longi-β-fenchylalcohol, caryophylla-4 (12), 8 (13) -dien-5 α-ol, caryophylla-3, 8 (13) -dien-5 α-ol, and caryophylla-3, 8 (13) -dien-5 β-ol.

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Hydration of p-menthenes (1-p- (1) and 3-p- (2)) and p-menthadienes (1, 3-p- (3), 2, 4 (8) -p- (4), 1, 4 (8) -p- (5), and 1, 4-p- (6)) with an equimolar mono-, di-, and trichloroacetic acids afforded various p-menthanols and p-menthenols. Some of them were obtained with high conversion ratio and selectivity.

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Alkylation reactions of α, β-unsaturated cyclic ketones, such as 3-methyl-2-cyclopenten-1-one using crown ethers as catalysts were studied. The reactiones of α, β-unsaturated ketones with alkyl halides were carried out with powdered potassium hydroxide in the presence of a crown ether as a catalyst in 1, 4-dioxane (DOX) under an innert atomosphere below 30°C. The yield in the alkylation of 3-methyl-2-cyclopenten-1-one was about 40%.

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