各種の遊離脂肪酸 (飽和, 分枝, 不飽和) の逆相HPLCによる分析を紫外波長可変型検出器を用い, 196～220nmで行った。溶出液としては, 0.1%リン酸/H₂O-MeOH系を用いた。補正した保持容量の対数値vs.直鎖飽和脂肪酸の炭素数のプロットは良好な直線性を示した。この直線関係から分枝脂肪酸, 不飽和脂肪酸のC値 (測定した保持容量に相当する直鎖飽和脂肪酸の炭素数) を求めた。分枝脂肪酸及び若干の不飽和脂肪酸のC値は溶媒の水の含量に無関係であったが, 多不飽和脂肪酸の場合は水の含量が多い程C値が増大することが認められた。分枝脂肪酸や不飽和脂肪酸のC値はそれらの全炭素数よりも小さい値であった。すなわち, これらの酸は相当する直鎖飽和脂肪酸より極性が高い。不飽和脂肪酸の幾何異性体及び位置異性体の分離について試みた。cis体はtrans体よりも, 又, 二重結合が酸の極性基に近い方がより極性が高くなることがわかった。これらの事実は, 酸と逆相との相互作用から説明ができた。ラウリン酸 (12 : 0) に対する不飽和脂肪酸の相対感度について検討した。S (不飽和脂肪酸) /S (12 : 0) vs. Wt (不飽和脂肪酸)) /Wt (12 : 0) のプロットは良好な直線性を示した。このことは, 紫外低波長領域のみに吸収をもつ不飽和脂肪酸やその類縁化合物のHPLCによる定量分析において, 安定かつ安価で入手しやすい飽和脂肪酸が内部標準として使用できることを示している。12 : 0に対する不飽和脂肪酸の相対感度は検出波長が短い程大きな値を示した。12 : 0を内部標準として数種の植物油の不飽和脂肪酸の組成を調べたところ, GLCによる分析結果と良好な一致を示した。

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炭素数10-14のアルキルトリメチルアンモニウム=ブロミドのcmc値を蒸留水中で15, 20, 25, 30, 35, 40℃で測定した。次いでこれらの界面活性剤のミセル化に対する熱力学的パラメーターの値 (ΔGm : ミセル化の自由エネルギー, ΔHm : ミセル化のエンタルピー, ΔSm : ミセル化のエントロピー) を計算した。おのおのの界面活性剤に対しΔHmとΔSmとの間には直線関係が成立した。そしてこれらの直線は互いに平行であった。このことに対する主な原因は, ミセルを作るときに界面活性剤の炭化水素鎖のまわりの構造水が破壊される程度が, 炭化水素鎖の長さによって異なるということである。

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High resolution gas chromatography of fatty acid methyl esters prepared from ten samples of refined vegetable oils was carried out on glass capillary columns. Effective separations of the positional isomers of monounsaturated fatty acids, the trans-9, cis-12 isomer of linoleate, and the cis-9, cis-12, trans-15 and trans-9, cis-12, cis-15 isomers of linolenate were performed on a Silar-5 CP or SP 2300 column. Additionally, the cis-9, trans-12, isomer of linoleate was separated on a Silar-10c or SP 2340 column. The cis-9, trans-12, cis-15 isomer of linolenate has not been detected in this study. Conversion of linolenate to the trans isomers during the refining process was 1329%, and that of linoleate was about 10% of the conversion of linolenate to the trans isomer. The fatty acid composition of refined vegetable oils is presented in detail.

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Crude tall oils imported from five countries were analyzed by glass capillary gas chromatography. The 5-olefinic fatty acids they contained consisted of cis-5, cis-9-octadecadienoic acid (5, 9-18 : 2), 5, 9, 12-18 : 3, 5, 11-20 : 2, and 5, 11, 14-20 : 3; the proportions varied widely among the samples. For the effective separation of a specified 5-olefinic acid, it is important to select suitable crude tall oils as original material. The contents of the 5-olefinic acids in the total fatty acids increased with increasing contents of linoleic acid and with decreasing oleic acid in the samples analyzed.

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Reversed phase high performance liquid chromatography (HPLC) on methyl silica column was used for the separation of phospholipids including phosphatidyl choline (PC), phosphatidyl ethanolamine (PE), phosphatidyl inositol (PI) and phosphatidyl serine (PS) in naturally occurring samples.
Hexane/2-propanol/water (1 : 60 : 39) was one of the best eluents for the separation of these phospholipids which were detected at 210nm.
The molar extinction coefficient of each phospholipid is not yet known and it is very difficult to obtain an authentic sample, so that purified soybean phospholipids, quantitated by Reinecke's salt method for PC and by 2, 4-dinitro-1-fluorobenzene (DNFB) method for PE, were used as standard samples for the determination of PC and PE.
The calibration curves between the amount and the peak height in the HPLC were obtained with good linearity ranging from 3.7 to 74μg for PC and from 0.7 to 6.6μg for PE.
PC and PE in some phospholipids such as soybean, egg yolk, pig liver and dry yeast (Saccharomyces cerevisiae sp.) phospholipids were determined with reliable accuracy under the conditions employed.
The present method can be used for the routine quantitation of PC and PE in various phospholipids prepared from plant and animal sources.

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To compare the effects of various metals (periodic group VI) on the autoxidation of methyl oleate and the decomposition of methyl oleate hydroperoxide in methyl oleate, the substrates were kept with metal carbonyls [Mo (CO) ₆, Cr (CO) ₆ and W (CO) ₆] at 80°C.
The effects of the catalysts were investigated by observing the changes in peroxide value, iodine value, saponification value, refractive index, molecular weight, and trans isomer content. The identification of autoxidation products of methyl oleate and decomposition products of methyl oleate hydroperoxide were carried out by gas chromatography of trimethylsilyl ether derivatives.
Mo (CO) ₆ showed marked effect on the autoxidation of methyl oleate and the decomposition of methyl oleate hydroperoxide. The products were found as methyl cis-epoxyoctadecanoate and methyl hydroxyoctadecenoate, which were produced by intermolecular reaction among methyl oleate and methyl oleate hydroperoxide. Moreover, methyl hydroxyepoxyoctadecanoate was also produced by intramolecular reaction of methyl oleate hydroperoxide itself.
Cr (CO) ₆ showed more marked effect than Mo (CO) ₆. The autoxidized products of methyl oleate were identified as methyl trans-epoxyoctadecanoate, methyl cis-epoxyoctadecanoate, methyl hydroxyoctadecenoate and methyl oxooctadecenoate, but methyl hydroxyepoxyoctadecanoate was not produced. Methyl oxooctadecenoate and methyl hydroxyoctadecenoate were produced by decomposition of methyl oleate hydroperoxide in the presence of Cr (CO) ₆, but W (CO) ₆ showed almost no effects.

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The stabilities of 20% fluorocarbon (FC) /water emulsions containing 5% fluorinated nonionic surfactants were determined by measuring the variation of droplet diameter distribution with time (up to 10 months). For comparison of less effective emulsifiers, the rate of phase separation was also used.
O/W emulsions containing HCF₂ (CF₂) ₃CH₂O (C₂H₄O) _9.7H showed low stability, but those stabilized by HCF₂ (CF₂) ₇CH₂O (C₂H₄O) _10.5H showed excellent stability. Although emulsions containing HCF₂ (CF₂) ₅CH₂O (C₂H₂O) _10.3H separate a minor proportion of the aqueous phase in a relatively short time, the distribution of FC droplet diameter changed little over a long period.
In the present investigation, emulsions stabilized by CF₃ (CF₂) ₆CH₂O (C₂H₄O) _10.3H exhibited the highest stability, indicating the importance of a greater affinity of the terminal CF₃ group for FC.
The percentages of the aqueous phase formed 5h after preparation of emulsions containing various surfactants were as follows : HCF₂ (CF₂) ₇CH₂O (C₂H₄O) _10.5H (0%), CF₃ (CF₂) ₆CH₂O (C₂H₄O) _10.3H (00.3%), CF₃ (CF₂) ₅CH₂O (C₂H₄O) _10.3H (00.6%), HCF₂ (CF₂) ₃CH₂O (C₂H₄O) _9.7H (01%), HCF₂ (CF₂) ₅CH₂O (C₂H₄O) _10.3H (12.613.4%), CH₃ (CH₂) ₁₁O (C₂H₄O) ₈H (6670%).

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6, 10-Dimethyl-2-undecanone (10), a key intermediate for squalane and isophytol, was effectively synthesized from prenyl chloride (4a, b) via telomerization with isobutylene and hydroformylation with cobalt catalyst followed by aldol condensation with acetone.
Telomerization of (4a, b) with excess amount of isobutylene was carried out in the presence of zinc chloride catalyst to obtain 6-chloro-2, 6-dimethyl-2-heptene (5) in 63.5%. Dehydrochlorination of (5) was investigated under various conditions. A mixture of 2, 6-dimethyl-1-heptene (7a) and 2, 6-dimethyl-2-heptene (7b) was obtained from (5) by hydrogenation followed by dehydrochlorination. Hydroformylation of the mixed products (7a, b) with cobalt catalyst proceeded with migration of the double bond to yield 3, 7-dimethyloctanal (8) as the sole product which was converted to (10) by aldol condensation with acetone and by selective hydrogenation.

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Fluorination of various terpenic alcohols and fatty alcohols with N, N-diethyl-1, 1, 2, 3, 3, 3-hexafluoropropyl amine (PPDA) was carried out. A mixture of 2- (2'-fluoroethyl) -6, 6-dimethyl-bicyclo [3.1.1] hept-2-ene (2) and nopyl 2, 3, 3, 3-tetrafluoropropionate (3) was obtained from the reaction of nopol (1) with PPDA. Similar results were obtained from other terpenic alcohols and fatty alcohols.

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