2, 15-Hexadecanedione (5), a key intermediate for the synthesis of dl-muscone, was prepared from alkyl sulfone. The Claisen condensation of 1, 6-bis (p-toluenesulfonyl) hexane (1) and ethyl 4, 4- (ethylenedioxy) valerate afforded 2, 2, 15, 15-bis (ethylenedioxy) -6, 11-bis (p-toluenesulfonyl) -5, 12-hexadecanedione (2) in quantitative yield. The reductive elimination of the sulfonyl groups, the Wolff-Kishner reduction, and hydrolysis of the diacetal gave 2, 15-hexadecanedione (5) in good yield.

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The surface tension of various humic acid solutions was measured. The marine humic acids extracted with 0.5N NaOH from the marine sediments sampled from Suruga Bay and Sagami Bay show high surface activity compared to the commercially available terrestrial humic acids. From the relation between surface tension and marine humic acid concentration, the surface tension decreases linearly with the logarithmic concentration and becomes constant value of about 40 dyn/cm at the concentration of 0.1%. This bending point at 0.1% is removed to the lower concentration by addition of salts like an ionic surfactant. The presence of a bending point and salt effect to it may suggest the association of marine humic acids.
The marine humic acids were fractionated by ultrafiltration and the surface tension of each fraction was measured. The results show that the higher molecular weight fractions, which occupy 75% of the sample, exhibit high surface activity : bending points are also observed for their surface tension-concentration curves at 0.1%.
The high performance liquid chromatographic analysis of humic acids by use of three kinds of gel indicates that the humic acid is a mixture of compounds molecular weight of which are widely ranged. The chromatographic results of molecular size distribution agreed on the whole with those of fractionation by ultrafiltration. From chromatograms of marine humic acids, the higher molecular weight fraction seems to be less hydrophilic and this weak hydrophilic character may cause the surface activity of them.

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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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