A review on 119 original papers for the Japan Oil Chemist's Society Award is presented.
1) After heating the decrease of the oxidative stability by tocopherol (Toc) degradation was larger for olive, coconut and hardened oils than for soybean, corn, cottonseed, and rapeseed oils. Decomposition of Toc in oils was apparently promoted by the oxidative products (especially oxidized fatty acids: fatty substances insoluble in petroleum ether) and free fatty acids. The preventive effects of additive on the thermal decomposition of Toc in oils were in the order of gallic and thiodipropionic acids>cystine>homogentisic acid>tryptophan>soya lecithin>catechins.
2) Histidine (His) and Cu (II)-His complex inhibited the photosensitized of unsaturated fatty acid by quenching ¹O₂, and O₂^-, respectively. Gly-Gly-His inhibited both the outoxidation and the photosensitized oxidation in the presence of copper (II) ion.
3) Antioxidative activity of metabolic products of several amino acids was investigated. In the metabolites of tryptophan, proline, and phenylalanine, the 3-hydroxyanthranilic acid, 5-hydroxyproline and homogentisic acid showed great antioxidative activity on the autoxidation of lard, respectively.
4) The greatest anitioxidative activity was recognized with methanol extracted fraction of the smoke or tea and tea-grounds, and by the analysis, naphtol, isoamyl gallate and hydroquinone were detected in smoke. Epigallocatechin in tea showed the strongest antioxidative effect for oils.
5) Antioxidant was adsorbed on paper, and the antioxidant paper was packed with various foods in bag. Oxidative stability of Foods was considerably improved with indirect method of antioxidant NDGA and BHA.
6) BHA, NDGA, isoamyl gallate and hydroquinone showed a potent antiseptic and antimold action on the microbe or mold.
7) The decomposition of amino acids, vitamins, and chlorophyll was apparently promoted by oxidative products (oxidized fatty acids, peroxide and malonaldehyde etc.) of oil.
8) The rats fed oxidized oil showed growth depression, whereas better growth was observed those fed same oil with Toc, oryzanol, pyridoxine, and water extractum of animal liver or garlic, respectively.

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The reaction of 2(10)-pinene (1) with cerium (IV) ammonium nitrate (CAN) and methanol adsorbed on silica gel [CAN(MeOH)/SiO₂] reagent was studied in order to synthesize methyl α-terpinyl ether (4).
The CAN(MeOH)/SiO₂ reagent was easily prepared by the addition of a weighed amount of silica gel to a solution of CAN in methanol and the methanol was removed by 82% under reduced pressure.
CAN(MeOH)/SiO₂ was found to be an effective reagent for the etherification of (1).
(4) was obtained as the major product from (1) in an isolated yield of 58%.
(4) was also obtained from 2-pinene and d-limonene.
α-Terpineol was obtained by reaction of (1) with the CAN(H₂O)/SiO₂ reagent.

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Forming components were fractionated from a keratin hydrolysate with a molecular weight (F.M.W.) in the range of about 50, 000 by membrane ultrafiltration. Foam heights and stabilties of the fractions were measured. Ferrous salt FeSO₄·7H₂O or calcium salt CaCl₂·2H₂O was added at various concentrations to aqueous solutions of the keratin hydrolysate fractions.
The effects of added iron (II) or calcium on foam heigthts and stabilities and the amounts of sediment were studied. The maximum concentration of added iron (II) which could not form a precipitate was also determined.
The foam heights and stabilities of the keratin hydrolysate of the present F.M.W. and its fractions increased with the addition of iron (II) or calcium.
Based on foam heights, foam stabilities, formation of Fe (II)-hydrolyzed protein chelate and the amounts of precipitate and sediment formed by addition of iron (II) or calcium, the upper limit of molecular weight of keratin hydrolysate for use in a protein foam extinguisher was determined as 300, 000.

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Tri (long-chain alkyl) amines are very important fatty chemicals. For example, they are used as extraction agents to recover various acids such as acetic acid from water solutions and as reaction additives which accelerate the rate of reaction as in the hydrogenation of unsaturated fatty acids.
Recently many researchers have investigated catalysts by which these tri (long-chain alkyl) amines are synthesized directly from fatty alcohols having a long chain alkyl group. But most of them are not satisfactory for industrial use from the stand-point of catalytic activity, selectivity and cost involved. We already reported that the Cu-Ni catalyst gives very high activity and selectivity in the synthesis of aliphatic amines such as N, N-dimethyl (long-chain alkyl) amines and N, N-di (long-chain alkyl) methylamines.
Thus, in this work, catalytic activity and selectivity of Cu-Ni catalyst in tri (long-chain alkyl) amine synthesis, especially in tridodecylamine synthesis, especially in tridodecylamine synthesis from dodecyl alcohol and ammonia were studied.
Tridodecylamine was formed with high selectivity (95%) and high dodecyl alcohol conversion (99%). In this reaction, transformation from the secondary amine to tertiary amine is considered to be a rate determining step of the total reaction. The valency of copper and nickel atoms on the catalyst surface under the reaction conditions was determined by ESCA, and that of copper was clearly shown to be 0 or 1 while that of nickel 2. From the results of comparative experiments using Cu and NiO individually as catalysts of the same reaction, Cu and Ni atoms of Cu-Ni catalyst have special valency and further investigation should be conducted.

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For the general use of sulfur-33 NMR spectroscopy, measuring conditions for benzenesulfonic acid were examined. A 0.75M solution (deuterium oxide-water mixture in the ratio of 2: 1) adjusted to pH 6.5-10.5 gave a good signal with line width at half the peak height of 13.5Hz after 3h of data accumulation. The chemical shift [-11.5ppm relative to (NH₄)₂SO₄] did not vary with this pH range. Hardly any signal could be observed at a pH less than 3.6. Slight lowering of S/N ratio and minor line-broadening were caused by the addition of excess sodium hydroxide (pH>14). Thus possibly, tuning of the probe and use appropriate pulse conditions are essential for measuring sulfur-33 NMR, and the sample solution of sulfonic acids should be made neutral or alkaline.

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マレイシアパーム油の物理精製工程から出る廃白土から回収されるパーム油の糖脂質の定量分析を行った。回収パーム油の糖脂質含量は3.8%であり,パーム原油の糖脂質含量の10倍以上であった。また糖脂質の廃白土に対する回収率は0.86%であった。糖脂質の種類としては,アシルステロールグリコシド(ESG),モノガラクトシルジグリセリド,セレブロシド,ステロールグリコシド(SG),ジガラクトシルジグリセリド,さらに,モノガラクトシルモノグリセリドの存在が推定された。
糖脂質組成はパーム原油のそれとほぼ同じであった。
各糖脂質の脂肪酸組成では,飽和酸ではパルミチン酸が,また不飽和酸ではオレイン酸が主なものであった。
ESGとSGの4-デスメチルステロール組成は,シトステロール,カンペステロール,スチグマステロールコレステロール,7-スチグマステノール,アベナステロールの順であった。

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The hydrolysis of bis (perfluoroalkanoyl) peroxides such as bis (perfluoroacetyl) peroxide [(CF₃CO₂)₂] and bis (perfluorooctanoyl) peroxide [(C₇F₁₅CO₂)₂] was conducted. Kinetic studies showed the decomposition of bis (perfluoroacetyl) peroxide to be remarkably accelerated by the addition of water, whereas that of bis (perfluorooctanoyl) peroxide to be only slightly accelerated. There thus appears to be strong repulsion for water owing to the high surface-active property of long-chain perfluoroalkyl groups (perfluoroheptyl group).

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