• Vol 8, No 8 (2017)
  • Chemical Engineering

Dimethyl 9-Octadecenedioate and 9-Oktadecene from Methyl Oleate Via a Ruthenium-Catalyzed Homo Olefin Metathesis Reaction

Robby Roswanda, Ilham Putra, Didin Mujahidin


Cite this article as:
Roswanda, R., Putra, I.A., Mujahidin, D., 2017. Dimethyl 9-Octadecenedioate and 9-Oktadecene from Methyl Oleate Via a Ruthenium-Catalyzed Homo Olefin Metathesis Reaction. International Journal of Technology. Volume 8(8), pp.1422-1428
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Robby Roswanda Institut Teknologi Bandung
Ilham Putra - Chemistry, ITB, Bandung and Indonesia
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Didin Mujahidin Inttitut Teknologi Bandung
Email to Corresponding Author

Abstract
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Oleic acid, one of the major components of palm oil, has attracted much interest in modern oleochemistry. The internal olefin group in oleic acid is a useful functional group in the transformation of a fatty acid to other functional chemicals and materials. In this paper, we discuss the application of the olefin metathesis reaction by preparing a long-chain dicarboxylic acid and alkene from the ester of oleic acid. The internal olefin metathesis reaction of methyl oleate produced dimethyl 9-oktadecendioate and 9-octadecene in the presence of a ruthenium Grubbs II (second generation) catalyst with a 51% yield. We also found that there was a higher amount of the E isomer products than the Z isomer products.

Dimethyl 9-oktadecenedioate; Methyl oleate; Olefin metathesis; 9-oktadecene

Conclusion

The homo olefin metathesis of methyl oleate was successfully carried out using a Grubbs II catalyst. The products were 9-octadecene and dimethyl 9-octadecendioate. Both products exist as a mixture of geometrical isomers, and the ratio of E/Z isomers is 8:2. The best yield was achieved by using only 1 mL of solvent and 1 mL of methyl oleate, which gave a 51% yield. It was also demonstrated that this homo olefin metathesis does not require much of the catalyst, since the decrease in yield that accompanies the decrease in the amount of catalyst was not very significant. This paper showed a promising start in developing the derivatization of palm-oil products in Indonesia.

Acknowledgement

The authors would like to thank Badan Pengelola Dana Perkebunan Kelapa Sawit (BPDPKS) for funding this research.

Supplementary Material
FilenameDescription
R1-CE-772-20171001202541.jpg Ratio product E/Z Homo olefin metathesis of methyl oleate
R1-CE-772-20171001202632.jpg Homo olefin metathesis of methyl oleate
R1-CE-772-20171001202722.jpg Catalysts for olefin metathesis reaction
R1-CE-772-20171001204837.jpg Esterification reaction of oleic acid
R1-CE-772-20171001205159.jpg Homo olefin metathesis of methyl oleate
R1-CE-772-20171001205333.jpg 1H NMR Spectra of oleic acid and methy
R1-CE-772-20171001210330.jpg 1H NMR Spectra of the products of homo olefin metathesis reaction and methyl oelate
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