リノール酸メチルの選択的水素添加を目的として, 11種のステロイド, 6種のテルペン, 及びアルカロイド1種を水素源とし, RhH (PPh₃) ₄及びRuH₂ (PPh₃) ₄等を触媒とした系の反応を検討した。多くの天然物に高い水素供与能が見いだされたが, 特にコレステロール-RhH (PPh₃) ₄系においては, リノール酸メチルの転化率が高く, 生成物はモノエンのみであり, トランス二重結合の生成は少ない, というすぐれた結果が得られた。
この反応系で, 他の基質の反応も行い, 次の様な結果を得た。 (1) trans-9, trans-12-オクタデカジエン酸メチルの反応性は, リノール酸メチルのそれとほぼ等しく, エライジン酸メチルの反応性もオレイン酸メチルのそれにほぼ等しい。 (2) アルカリ共役化で得た共役オクタデカジエン酸メチルの反応性は, 非共役ジエン類のそれと比べ著しく低い。 (3) 共役及び非共役ジエンの反応では, 飽和化合物は生成しないが, 一方オレイン酸メチル, エライジン酸メチルは水添を受ける。これはモノエンはジエンが共存しないときは水添を受けるが, ジエンが共存すると水添を受けないことを示している。 (4) 共役ジエンが共存しない場合, 孤立二重結合中のシス-トランス比は一定となり, その値は3 : 1である。

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大豆油を脱臭したときクエン酸を添加した。大豆油中のクエン酸含量を5%シリコーンOV-17 GLCにて定量し, また大豆油の風味及び酸化安定性に及ぼすクエン酸の影響について検討した。大豆油をけい光燈照射にて劣化させたとき, クエン酸は風味の劣化を防止することはできなかった。一方, 大豆油を自動酸化的に劣化させたとき, クエン酸は大豆油の酸化及び風味安定性を著しく改善した。しかしながら, その効果はクエン酸濃度には関係がなかった。大豆油へのクエン酸の溶解度を測定した。4週間の保存試験の結果から, 少なくとも50ppmのクエン酸が大豆油中に溶解できることがわかった。

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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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p-メンテン類 (1-p- (1) 及び3-p- (2)) 及びp-メンタジエン類 (1, 3-p- (3), 2, 4 (8) -p- (4), 1, 4 (8) -p- (5) 及び1, 4-p- (6) を等モルのモノ, ジ及びトリクロロ酢酸を用いて水和反応を行い, 種々のp-メンタノール類及びp-メンテノール類を得た。そのうち二, 三のものは, 高収率かつ選択的に得られた。

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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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