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Eight new fat-splitting agents (acid type surface-active agents) which were superior to those usually used were prepared. On the mechanism of fat splitting, two theories which were inconsistent with each other had been presented; one : the hydrolysis of fats was a surface reaction and the other : a homogeneous reaction in oil phase. New mechanism that three stepwise reactions are performed in oil layer and interface; oil layer (on which the reaction less depends than in the former case) and interface; and water layer, respectively, was proposed. The mechanism was demonstrated theoretically and experimentally, and both theories mentioned above were able to be explained by this mechanism reasonably. Besides, several new superior detergents were prepared. [2] Autoxidation Reactions of Fats (Involving the papers on Atherosclerosis and Cancer) . 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It was first found that the DNA radicals were formed by the reaction of DNA with lipoperoxide. From the resemblance of such DNA radicals to the radicals in cancer tissues, it was suggested that cancer itself might be DNA radicals. The difference in the effect of antioxidants on the autoxidation of geometric and position isomers of lipids was first made clear. It was found that photosensitizing dyes, phenothiazine derivatives, ion exchange resins, and ethyleneimine polymers were useful antioxidants. Tocopherols as antioxidants were examined, and nucleic acids were first shown as effective synergists. Besides new quantitative methods for hydroperoxides by infrared spectroscopy and NMR shift reagent were reported. In the same composition systems the TBA test could be utilized to estimate the variation of lipoperoxides, but not in the different systems. Even in the latter case, the TBA test could be used to evaluate lipoperoxides as long as the special treatment takes place. 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Studies on the reaction of fats and oils : hydrolysis, autoxidation, hydrogenation, etc.
https://doi.org/10.18999/memfenu.30.2.200
https://doi.org/10.18999/memfenu.30.2.2004a9d859d-f790-4166-b99a-505262e93ea1
名前 / ファイル | ライセンス | アクション |
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30-2-02.pdf (4.7 MB)
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Item type | 紀要論文 / Departmental Bulletin Paper(1) | |||||
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公開日 | 2020-11-24 | |||||
タイトル | ||||||
タイトル | Studies on the reaction of fats and oils : hydrolysis, autoxidation, hydrogenation, etc. | |||||
言語 | en | |||||
著者 |
Fukuzumi, Kazuo
× Fukuzumi, Kazuo |
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アクセス権 | ||||||
アクセス権 | open access | |||||
アクセス権URI | http://purl.org/coar/access_right/c_abf2 | |||||
抄録 | ||||||
内容記述 | Studies of the reactions of fats and oils mentioned above consist of those on fat splitting, surface-active agents, autoxidation, hydrogenation, fatty acid derivatives, etc. [1] Fat-Splitting Reactions and Surface-Active Agents. Eight new fat-splitting agents (acid type surface-active agents) which were superior to those usually used were prepared. On the mechanism of fat splitting, two theories which were inconsistent with each other had been presented; one : the hydrolysis of fats was a surface reaction and the other : a homogeneous reaction in oil phase. New mechanism that three stepwise reactions are performed in oil layer and interface; oil layer (on which the reaction less depends than in the former case) and interface; and water layer, respectively, was proposed. The mechanism was demonstrated theoretically and experimentally, and both theories mentioned above were able to be explained by this mechanism reasonably. Besides, several new superior detergents were prepared. [2] Autoxidation Reactions of Fats (Involving the papers on Atherosclerosis and Cancer) . In the autoxidation of highly unsaturated fatty acid esters at low temperature (about 0℃), extremely high peroxide values (m.eq./kg.) which had been never reported in the field of fats, for example about 1×104, were estimated, and it was made clear that monomeric dihydroperoxides, which were separated in the concentrated state, could be formed. It was also first confirmed that at low temperature conjugated dienes were easily formed, but conjugated triene and so on scarcely. Trimers were first separated from the oxidized polymers of highly unsaturated fatty acid esters. The existence of trans, trans conjugated diene hydroperoxides (a kind of lipoperoxides) in atherosclerotic artery and the tissus of cancer was first shown. From the results of the studies and the other literature, so-called “lipoperoxide hypothesis” as the causes of the generation of atherosclerosis and cancer was first presented, by which many phenomena about these diseases were explained reasonably. It was first found that the DNA radicals were formed by the reaction of DNA with lipoperoxide. From the resemblance of such DNA radicals to the radicals in cancer tissues, it was suggested that cancer itself might be DNA radicals. The difference in the effect of antioxidants on the autoxidation of geometric and position isomers of lipids was first made clear. It was found that photosensitizing dyes, phenothiazine derivatives, ion exchange resins, and ethyleneimine polymers were useful antioxidants. Tocopherols as antioxidants were examined, and nucleic acids were first shown as effective synergists. Besides new quantitative methods for hydroperoxides by infrared spectroscopy and NMR shift reagent were reported. In the same composition systems the TBA test could be utilized to estimate the variation of lipoperoxides, but not in the different systems. Even in the latter case, the TBA test could be used to evaluate lipoperoxides as long as the special treatment takes place. [3] Hydrogenation Reactions of Fats and Some Other Compounds In the heterogeneous catalytic hydrogenation of highly unsaturated fatty acid esters, it was clarified that precise results were hardly obtained by ultraviolet spectroscopy and gas liquid chromatography. The hydrogenation of conjugated tetraenoate took place first, and conjugated triene and conjugated diene were not detected in the reaction mixture. Conjugated diene in polyenes was hydrogenated faster than nonconjugated polyenes. The reaction systems having the characteristic that selectivity was 100% and almost no trans isomers were formed were found by us, of which the discovery had been desired eagerly but it had been almost impossible. They were the new transfer hydrogenation systems using RuCl2(PPh3)3 and RuH2(PPh3)4 as homogeneous catalysts, methyl linoleate as a hydrogen acceptor, and 2-propanol and hydrocortizone as hydrogen donors, respectively. Almost no studies on the homogeneous transfer hydrogenation of simple olefins except for ours had been published. Especially such studies of ours on unsaturated fatty acid esters were the first in the world. Besides, by using general organic compounds as hydrogen acceptors, many new effective hydrogen donors such as indoline etc. were found, the reaction mechanism was first clarified, and many new informations were obtained. [4] Fatty Acid Derivatives and Others. Gas liquid chromatography for highly unsaturated fatty acid esters was reported almost earlist. Reactivity for the side chain of heterocyclic compounds containing nitrogen with carboxylic acids as catalysts was investigated. It was shown that eliminations from the compounds having quinolyl group as an electron-withdrawing group took place easily, whose mechanism was proposed. The elimination with carboxylic acid catalysts had never been reported. The olefin metathesis reactions catalyzed by the WCl6-cocatalyst system were performed. The metathesis of olehins with functional groups had not been studied in detail. That of methyl oleate, a kind of these olefins, was carried out, and good results were obtained. Besides new superior catalyst systems and solvents were found, and the reaction mechanism was made clear. | |||||
言語 | en | |||||
内容記述タイプ | Abstract | |||||
出版者 | ||||||
言語 | en | |||||
出版者 | Faculty of Engineering, Nagoya University | |||||
言語 | ||||||
言語 | eng | |||||
資源タイプ | ||||||
資源 | http://purl.org/coar/resource_type/c_6501 | |||||
タイプ | departmental bulletin paper | |||||
出版タイプ | ||||||
出版タイプ | VoR | |||||
出版タイプResource | http://purl.org/coar/version/c_970fb48d4fbd8a85 | |||||
ID登録 | ||||||
ID登録 | 10.18999/memfenu.30.2.200 | |||||
ID登録タイプ | JaLC | |||||
ISSN(print) | ||||||
収録物識別子タイプ | PISSN | |||||
収録物識別子 | 0027-7657 | |||||
書誌情報 |
en : Memoirs of the Faculty of Engineering, Nagoya University 巻 30, 号 2, p. 200-244, 発行日 1979-03-31 |
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著者版フラグ | ||||||
値 | publisher |