Journal of the American Oil Chemists’ Society

, Volume 73, Issue 10, pp 1311–1316 | Cite as

Catalytic hydrogenation of linoleic acid on nickel, copper, and palladium

  • Yoshie Kitayama
  • Masahiro Muraoka
  • Megumi Takahashi
  • Tatsuya Kodama
  • Hirofumi Itoh
  • Eriko Takahashi
  • Mutsuo Okamura


The catalytic activity and selectivity for hydrogenation of linoleic acid were studied on Ni, Cu, and Pd catalysts. A detailed analysis of the reaction product was performed by a gas-liquid chromatograph, equipped with a capillary column, and Fourier transform-infrared spectroscopy. Geometrical and positional isomerization of linoleic acid occurred during hydrogenation, and many kinds of linoleic acid isomers (trans-9,trans-12; trans-8,cis-12 orcis-9,trans-13; cis-9,trans-12; trans-9,cis-12 andcis-9,cis-12 18∶2) were contained in the reaction products. The monoenoic acids in the partial hydrogenation products contained eight kinds of isomers and showed different isomer distributions on Ni, Cu, and Pd catalysts, respectively. The positional isomers of monoenoic acid were produced by double-bond migration during hydrogenation. On Ni and Pd catalysts, the yield ofcis-12 andtrans-12 monoenoic acids was larger than that ofcis-9 andtrans-9 monoenoic acids. On the contrary, the yield ofcis-9 andtrans-9 monoenoic acids was larger than that ofcis-12 andtrans-12 monoenoic acids on Cu catalyst. From these results, it is concluded that the double bond closer to the methyl group (Δ12) and that to the carboxyl group (Δ9) show different reactivity for hydrogenation on Ni, Cu, and Pd catalysts. Monoenoic acid formation was more selective on Cu catalyst than on Ni and Pd catalysts.

Key Words

Catalytic hydrogenation Cu geometrical and positional isomers linoleic acid Ni Pd reaction mechanism 


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Copyright information

© AOCS Press 1996

Authors and Affiliations

  • Yoshie Kitayama
    • 3
  • Masahiro Muraoka
    • 3
  • Megumi Takahashi
    • 3
  • Tatsuya Kodama
    • 3
  • Hirofumi Itoh
    • 1
  • Eriko Takahashi
    • 1
  • Mutsuo Okamura
    • 2
  1. 1.Nikki Chemical Co. Ltd. Niitsu Plant OfficeNiitsu CityJapan
  2. 2.Department of Chemistry, Faculty of ScienceNiigata UniversityIkarashi NiigataJapan
  3. 3.Department of Chemistry and Chemical Engineering, Faculty of EngineeringNiigata UniversityNiigataJapan

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