Abstract
Methycis-9-octadecenoate (methyl oleate;c9), methylcis-9,cis-13-octadecadienoate (c9,c13) and a 50∶50 mixture of this diene with methylcis-9,cis-12-octadecadienoate (methyl linoleate;c9,c12) have been hydrogenated on a nonmetallic palladium-onresin catalyst in acetone as a solvent at 40 C and atmospheric hydrogen pressure. The monoene is hydrogenated very slowly, butc9,c12 is reduced easily and quickly. The ethylene-interrupted diene reacts more slowly thanc9,c12, but considerably faster thanc9, because active methylene-interrupted dienes are intermediates by double-bond migration. This isomerization process also results in the formation of inactive polymethylene-interrupted dienes, which accumulate during hydrogenation. Alsoc9 isomerizes considerably during reduction. In the 50∶50 mixture,c9,c12 is hydrogenated about eight times faster thanc9,c13.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
van der Plank, P., H.J. van Oosten and C. van Dijk, 56: 45
Lam, C.H., and M.S.F. Lie Ken Jie, J. Chromatogr. 115:559 (1975).
Hinze, A.G., U.S. Patent 3,865,853 (1975).
van der Plank, P., JAOCS, 49:489 (1972).
van der Plank, P., Ibid. 49:327 (1972).
Author information
Authors and Affiliations
Additional information
The activity of the catalyst for thec9,c12 hydrogenation described previously (1) is considerably higher than that derived from the present data. The experiments described in this study were carried out about eight months later, so that we have to deal with an older catalyst. However, reproduction of the catalyst resulted in the same activity. Furthermore, we used a new batch ofc9,c12 for these experiments, which was purified in the same way as the previous one. The catalyst is probably sensitive to apolar compounds which may be present inc9,c12 and which are not removed by alumina. Small amounts of these compounds may have a drastic influence on the activity of the catalysts under investigation because the catalyst dosing is very low. We emphasize that, though the activity may vary to some extent (depending on substrate quality), the selectivity and the isomerization pattern do not change.
About this article
Cite this article
Van der Plank, P., Van Oosten, H.J. Hydrogenation of monounsaturated and ethylene- and methylene-interrupted diunsaturated fatty acid esters on nonmetallic palladium-on-resin II. J Am Oil Chem Soc 56, 50–53 (1979). https://doi.org/10.1007/BF02671760
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02671760