ONE-STEP CONVERSION OF EUGENOL TO METHYL ISOEUGENOL USING MICROWAVE IRRADIATION IN SOLVENT-FREE CONDITIONS

https://doi.org/10.22146/ijc.21734

Marcellino Rudyanto(1*), Lanny Hartanti(2)

(1) Research and Community Service Institute, Widya Mandala Catholic University, Jl. Dinoyo 42-44 Surabaya 60265
(2) Faculty of Pharmacy, Widya Mandala Catholic University, Jl. Dinoyo 42-44 Surabaya 60265
(*) Corresponding Author

Abstract


A research on conversion of eugenol to methyl isoeugenol via one-step reaction with microwave irradiation has been carried out. Mixtures containing eugenol, sodium or potassium carbonate as solid support, with or without sodium or potassium hydroxide as base, with or without tetrabutylammonium bromide as phase transfer catalyst, with dimethyl sulfate as the methylating agent were irradiated in a domestic microwave oven for 20 - 50 seconds. It was revealed that one-step methylation and isomerization required combinations of sodium or potassium hydroxide base and tetrabutylammonium bromide. Without combination of base and TBAB only one product, i.e. methyl eugenol, was formed.


Keywords


eugenol; methyl eugenol; methyl isoeugenol; microwave

Full Text:

Full Text Pdf


References

[1] Harian Kompas, 27 Maret 2003.

[2] Fitriany, R., Fahrurrozi, M., Sediawan, W. B., 2003, Peningkatan recovery isolasi eugenol dari minyak daun cengkeh dengan penggunaan NaOH berlebih dan solven organik n-hexane. Seminar nasional Teknik Kimia Indonesia, Yogyakarta, 16-17 September 2003.

[3] Nurdin, A., Mulyana, A., Suratno, H., 2001, Jurnal Sains dan Teknologi Indonesia, 3 (9), 58-62.

[4] Hong, T. K., 1991, Peranan ekoteknologi dan bahan semiokimia dalam pengurusan serangga perosak. Siri Syarahan Perlantikan Profesor, Universiti Sains Malaysia, Pulau Pinang.

[5] Anwar, C., 1994, The conversion of eugenol into more valuable substances, Doctoral dissertation, Gadjah Mada University, Yogyakarta.

[6] Payne, K. R., 1961, Indust. Chem., 523-527.

[7] Inokuchi, T., Kawafuchi, H., Torii, S., 1992, Synlett, 510-512.

[8] Marfu’ah, S., 1991, Sintesis Williamson metil dan benzil eugenil eter. Tesis S2. Institut Teknologi Bandung.

[9] Bogdal, D., Pielichowski, J., Boron, A., 1997, Synthesis of aromatic ethers under microwave iradiation in dry media. First International Electronic Conference in Synthetis Organic Chemistry (ECSOC-1) /www.mdpi.org/ecsoc, September 1-30,1997.

[10] Suwarso, W. P., Hasanah, S., Kurniawan, H., 2005, Microwave Chemistry: Semi-sintesis vanili dari eugenol dengan menggunakan gelombang mikro (microwave). Seminar Bersama ITB-UKM VI. http://www.chem.itb.ac.id/jschem/download/abstrak/ wahyudi_priyo_suwarso.pdf

[11] Kishore, D., Kannan, S., 2002, Green. Chem., 4, 607-610.

[12] Bram, G., Loupy, A., Villemia, D., 1992, Microwave activation of reactions on organic solid supports. In: Smith, K. (ed), Solid Supports and Catalysts in Organic Synthesis. Ellis Horwood, Chichester.



DOI: https://doi.org/10.22146/ijc.21734

Article Metrics

Abstract views : 2888 | views : 5527


Copyright (c) 2010 Indonesian Journal of Chemistry

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

 


Indonesian Journal of Chemistry (ISSN 1411-9420 /e-ISSN 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Web
Analytics View The Statistics of Indones. J. Chem.