THE STEREOCHEMISTRY EFFECT OF EUGENOL, CIS-ISOEUGENOL AND TRANS-ISOEUGENOL ON THEIR CATALYTIC HIDROGENATION

https://doi.org/10.22146/ijc.21861

M. Muchalal(1*)

(1) Chemistry Department, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Yogyakarta
(*) Corresponding Author

Abstract


The stereochemistry effect of eugenol, cis-isoeugenol and trans-isoeugenol on their catalytic hydrogenation by Ni/g-Al2O3 catalyst was investigated. In this investigation, the catalyst is prepared by impregnation of Nickel into solid of γ-Al2O3 in methanol as a solvent. The calcination process, which is followed by reduction, is performed on Muchalal reactor at 400 oC. After that, the catalytic hydrogenation is carried out under hydrogen gas atmosphere by mixing 10 mL sample and 0.5 g Ni/g-Al2O3 catalyst at 200 oC for 3 hours. The stereochemistry effect of reactants is evaluated by computer modelling using PM3 semiempirical methods. The mass spectrum of catalytic hydrogenation product from those compounds shows a molecular ion at m/z 164, which proves the existence of 2 -methoxy-4-propylphenol. The eugenol gives the highest conversion (99%), followed by cis-isoeugenol (81%) and trans-isoeugenol (67%). It was found that there is a correlation between the stereochemistry of those compounds and catalytic reactivity.


Keywords


stereochemistry effects; 2-methoxy-4-propylphenol

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References

[1] Kadarohman, A., 1994 Mempelajari Mekanisme dan Kontrol Reaksi Isomerisasi Eugenol Menjadi Isoeugenol, Tesis Program Pascasarjana UGM, Jogjakarta.

[2] Kadarohman, A., 2003 Mempelajari Mekanisme dan Kontrol Reaksi Isomerisasi Eugenol Menjadi Isoeugenol, Disertasi, Program Pascasarjana UGM, Jogjakarta.

[3] Muchalal, M. dan Swasono, R.T., 1999 Berkala Ilmia MIPA 1, IX, 48 – 56

[4] Santoso, A.H., 2004, Preparasi dan Karakterisasi Katalis Ni/g-Al2O3 untuk Hidrogenasi Trans-Isoeugenol, Skripsi FMIPA – UGM, Jogjakarta

[5] McLeod, A.S., and Gladden, L.F., 1997, Catal.Let., 43, 189-194

[6] Hjelmencrantz, A., and Berg, U., 2002, J.Org.Chem., 67, 3585-3594

[7] Alesso, R, 2003, Synthesis of 1-Ethyl-2-methyl-3-arylindanes. Stereochemistry of Five-Membered Ring Formation, Arkivoc

[8] Stromberg, J. , Swensson, A,. and Zetterberg P., 1997, Organometallics, 16, 3165-3168

[9] Gates, B.C., Katzer, J.R., Schuit, G.C.A., 1979, Chemistry of Catalytic Processes, First edition, Mc Graw-Hill Book Company, New York

[10] Campbell, I. M., 1988, Catalyses of Surfaces, Champman and Hall, London

[11] Panchenkov, G. M. and Lebedev, V.P., 1976, Chemical Kinetics and Catalysis, Edisi pertama, MIR Publisher, Moscow

[12] Buxton, S.R., and Roberts, S.M., 1996, Guide to Stereochemistry, Adison Wesley Longman Ltd., New York

[13] Smith, G. W. and Northeisz, F., 1999, Heterogeneous Catalysis in Organic Chemistry, Academic Press, San Diego

[14] Muchalal, M. dan Kadarohman, A. 1998, Penelitian Pendahuluan Reaksi Isomerisasi Eugenol Menjadi Isouegenol, Penelitian, FMIPA UGM, Jogjakarta

[15] Corma, A, 1995, Chem. Rev., 95, 570 – 579



DOI: https://doi.org/10.22146/ijc.21861

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