Studies of Structural Changes of Unsaturated Fatty Acid by Heating. III.

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  • TOTANI Nagao
    Department of Industrial Chemistry, College of Technology, Seikei University
  • MATSUO Noboru
    Department of Industrial Chemistry, College of Technology, Seikei University

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Other Title
  • 不飽和脂肪酸の加熱による構造変化に関する研究 (第3報)
  • フホウワ シボウサン ノ カネツ ニヨル コウゾウ ヘンカ ニカンスルケンキュ
  • Quantitative Analysis of Cyclopentadiene Compounds
  • シクロペンタジエン化合物の定量に関する研究

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Many papers have ever been reported about cyclic monomers (mostly 6-membered ring compounds) formed from unsaturated fatty acids or their triglycerides during thermal treatment or by catalytic cyclization. But, existance of 5-membered ring compounds in such cyclic monomers has not been proved chemically. Therefore qualitative and quantitative condition of the color reaction of cyclopentadiene in a mixture of 1, 3-cyclohexadiene, benzene, cyclohexene, cyclohexane, cyclopentene and cyclopentane, was examined using sulfuric acid and ethyl alcohol in reference to our previous papers. <BR>On the other hand, purified ethyl linoleate, ethyl linolenate and photo-isomerized Lung oil were respectively heated to cyclize with sodium hydroxide and ethylene glycol under the condition of 295°C, 15min. in a stainless autoclave, then acidified, esterified and purified by silica gel column, yThe cyclized ethyl linoleate, ethyl linolenate and photo-isomerized tong oil fatty acid ethyl ester were separated by urea adduct and column chromatography obtained ethyl linoleate cyclic monomer (11CM), ethyl linolenate cyclic monomer (1nCM) and photo-isomerized tung oil fatty acid ethyl ester cyclic monomer (βCM) were analyzed by GLC, IR, TLC and the above mentioned color reaction. <BR>It was concluded that cyclopentadiene compounds were formed from ethyl linolenate, but not from ethyl linoleate and eleostearic acid, since 1nCM, βCM and 11CM contained 4.1%, 0.08% and 0% of cyclopentadiene compounds respectively.

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