香料として重要なdl-ムスコンの合成中間体の1つである2, 15-ヘキサデカンジオンを新しい方法で収率よく合成した。1, 6-ビス (p-トルエンスルホニル) ヘキサン (1) と4, 4- (エチレンジオキシ) 吉草酸エチルとのClaisen縮合により, 2, 2, 15, 15-ビス (エチレンジオキシ) -6, 11-ビス (p-トルエンスルホニル) -5, 12-ヘキサデカンジオン (2) を定量的収率で得た。 (2) のスルホニル基を還元除去したあと, Wolff-Kishner還元によってカルボニル基を除去, 続いてジアセタールを加水分解して2, 15-ヘキサデカンジオンを (1) からの全収率69%で得た。2, 15-ヘキサデカンジオンからdl-ムスコンへは, 古くは, Stollが, 最近では, 辻らが報告している。

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種々のフミン酸溶液の表面張力を測定した。相模湾, 駿河湾の海洋たい積物から0.5NNaOHで抽出した海洋フミン酸は, 市販の陸成フミン酸に比べて高い界面活性を示す。表面張力と海洋フミン酸濃度との関係から, 表面張力は濃度の対数とともに直線的に減少し, 濃度0.1%で約40dyn/cmの一定値に達する。この0.1%折れ曲り点は, イオン性界面活性剤のように塩の添加によって低濃度に移動する。折れ曲り点の存在と, それに対する塩の効果から, 海洋フミン酸の会合が示唆される。
海洋フミン酸を限外濾過によって分画し, それぞれ分画分の表面張力を測定した。その結果, 試料の75%を占める高分子量部分が高い界面活性を示し, 表面張力-濃度曲線には0.1%に折れ曲がり点がみられる。
3種類のゲルを用いてフミン酸の高速液体クロマトグラフ分析をすると, フミン酸は広い分子量分布をもった混合物であることが示される。クロマトグラフ的分子サイズの分布は限外炉過の結果と大体一致した。海洋フミン酸のクロマトグラムから, 高分子量成分の親水性が低く, この弱い親水性が高分子量成分に界面活性を与えていると思われる。

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The fatty acid composition of fourteen Japanese rice bran oils were determined. Gas liquid chromatography using ethylene glycol succinate analyzed eleven fatty acids, mainly palmitic (1718%), oleic (3442%), and linoleic (3542%) acids. The ethylene glycol succinate column was useful to separate linolenic (1.431.77%) and icosenoic (0.410.52%) acids.
Fatty acid composition of extracted oils from endosperms, germs and bran of a rice were also investigated. The rice was variety, “Kiyonishiki” which was harvested in Japan. The germs showed the highest oil content (25.98%) than bran (20.27%) and endosperms (0.61%). Linoleic acid content of germ oil was the highest value (42%) than those of the another oils.

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The biodegradation of linear alkylbenzene sulfonate (LAS), α-olefine sulfonate (AOS), and alcohol sulfate (AS) were examined under the low dissolved oxygen (DO) condition. Also the accumulation of LAS in sediments was determined.
It was showed that these surfactants were biodegraded enough under the condition of less 1 mg/l of DO concentration. Especially AOS and AS were biodegraded very easily. LAS is able to adsorb on sediments in rivers and lakes, but not accumulate so long time because of its biodegradability under the low DO condition.

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Multicycle JIS (K 3371) -test was investigated as a method for assessing the soil removal efficiency of laundry detergents. Each evaluation vas performed by visual judgment and quantitative determination of residual soil after each washing of the soiled test collar cloths.
Six detergents were used in this test, A : (the JIS index detergent, STPP 10% as P₂O₅) the standard detergent, B : (soap Powder), C : (STPP 0%), D : (STPP 5% as P₂O₅, Zeolite 8.5%), E and F : (no phosphate commercial synthetic detergents).
Four cycles of the “wear-wash” tests were repeated in accordance with JIS-test, and visual judgment was performed after each cycle. On the other hand residual soils of the test collar cloths after one and four cycles were determined by Iatroscan (TLC/FID) after extraction with benzene.
The results obtained are summarized as follows.
1) The visual differences of the soil removal efficiency were difficult to detect after once “wear-wash”, but became remarkable by multicycle JIS-test.
2) Evaluation by quantitative determination of residual soils agreed well with visual judgment, and could detect even small differences between each detergency which were difficult to discriminate by visual judgment.
3) The results of the comparison with A vs. C and A vs. D detergents in this test were extremely well correlative to those of bundle test and JIS-test in our previous reports.

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The solvent effect on the oxidation of N, N-diethylnerylamine (NA) by 60% H₂O₂ aq.solution was examined. In alcohols, unreacted NA was little and N, N-diethylnerylamineoxide (NAO) was obtained in high yield. In aprotic solvents, a large amount of O-linalyl-N, N-diethylhydroxylamine (LHA) was formed by the Meisenheimer rearrangement of NAO and much unreacted NA remained. The yield of (NAO+LHA) was low, therefore aprotic solvents were unsuitable for the practical use. Further, the behavior of LHA in alcohols was studied and it was found that LHA rearranged to NAO in alcohols and this was a reversible reaction.
From these results, the mechanism of solvent effect was discussed in connection with the function of the hydroxy group of solvents stabilizing NAO.

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The ring-opening reaction of 1, 2-epithiodecane with a mixture of t-butyl alcohol and ethanol in the presence of sulfuric acid gave a mixture of 1-ethoxy-2-decanethiol (1), 2-ethoxy-1-decanethiol (2), 1-ethoxy-2- (t-butylthio) decane (3), 2-ethoxy-1- (t-butylthio) decane (4), 1-mercapto-2-decanol (5), and 1-t-butylthio-2-decanol (6). The product distribution varied with reaction time, amounts of sulfuric acid, and molar ratio of t-butyl alcohol to ethanol, the ratio of (4) to total products increased with longer reaction time or larger amounts of sulfuric acid.
Among these products, it was proved that (5) and (6) were formed via the reaction of 1, 2-epithiodecane with t-butyl alcohol. The formation of (3), (4), and (6) are reasonably explained in terms of intermediacy of the episulfonium (7) which is formed by the attack of t-butyl cation to 1, 2-epithiodecane.
The reaction of 1, 2-epithiodecane with a mixture of t-butyl alcohol and methanol, 1-propanol or 2-propanol in the presence of sulfuric acid gave the products corresponding to (4), and the order of these yields was methanol>ethanol>1-propanol>2-propanol.

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Isomerization of α-pinene oxide (1) was studied in dimethyl sulfoxide (DMSO) without catalyst.
It was found that l-trans-carveol (7) was obtained as majior product accompanying α-pinene (2), p-cymene (3), campholene aldehyde (4), pinocamphone (5), and pinocarveol (6) as minor products.
When the conversion of (1) was 98.2%, (7) was found to be 70.6% of products by GLC analysis.
Isomerization of d-limonene-1, 2-oxide (A) and 3-carene-3, 4-oxide (B) in DMSO was also studied.

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Activity and selectivity of Cu-Cr-manganese oxide catalyst (KW catalyst) added polydimethylsiloxane (MPS) and free fatty acid (FFA) in hydrogenation of marineoils were studied.
It was observed that both activity and selectivity of KW catalyst were decreased by addition of MPS, while increment of selectivity of nickel catalyst had been observed by addition of it.
Influence of FFA was scarcely observed in case of lower FFA concentration (0.33 wt% or lower) but both activity and selectivity were also decreased in case of higher FFA concentration (0.99 wt%). Relation between reactivity or selectivity and hydrogenation conditions was also studied.

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