Methylation of Eugenol Using Dimethyl Carbonate and Bentonite as Catalyst

https://doi.org/10.22146/ijc.21193

Dina Asnawati(1*), I Made Sudarma(2), Emmy Yuanita(3), Baiq Fadila Arlina(4), Saprini Hamdiani(5), Siti Raudhatul Kamali(6)

(1) Department of Chemistry, Faculty of Science, Mataram University, Jl. Majapahit 62 Mataram 83125
(2) Natural Products, Synthesis and Transformation Research Groups, Mataram University, Jl. Majapahit 62 Mataram 83125
(3) Natural Products, Synthesis and Transformation Research Groups, Mataram University, Jl. Majapahit 62 Mataram 83125
(4) Natural Products, Synthesis and Transformation Research Groups, Mataram University, Jl. Majapahit 62 Mataram 83125
(5) Natural Products, Synthesis and Transformation Research Groups, Mataram University, Jl. Majapahit 62 Mataram 83125
(6) Natural Products, Synthesis and Transformation Research Groups, Mataram University, Jl. Majapahit 62 Mataram 83125
(*) Corresponding Author

Abstract


Eugenol is a compound with a variety of reactive functional groups such as allyl, hydroxy and methoxy. The presence of the functional groups brings eugenol possible to undertake the transformation into various derivative compounds with diverse activities. One of the simple and possible transformations is methylation or alkylation. Commonly, methyl halides and dimethyl sulphate are used as methylation agent. However, those kinds of methylation agents are toxic and carcinogenic. In this research dimethyl carbonate, an alternative methylation agent is used, because of its low toxicity, green, and economic. The synthesis has been carried out by using a catalyst. Bentonite was activated by heating to a temperature using 300 °C. Methylation was shown by the formation of a light yellow liquid (25.71% yield). The structures of products were characterized by GC-MS and obtained a compound, namely bis eugenol (4-allyl-2-methoxyphenoxy) methane (2.37% yield).

Keywords


methyl eugenol; bentonite; dimethyl carbonate

Full Text:

Full Text Pdf


References

[1] Hee, A.K.W., and Tan, K.H., 2006, Comp. Biochem. Physiol. C: Toxicol. Pharmacol., 143 (4), 422–428.

[2] Ngadiwiyana and Ismiyarto, 2004, Sintesis Metil Eugenol dan Benzil Eugenol dari Minyak Daun Cengkeh, FMIPA UNDIP, Semarang.

[3] Haq, I., Vreysen, M.J.B., Cacéres, C., Shelly, T.E., and Hendrichs, J., 2014, J. Insect Physiol., 68, 1–6.

[4] Rudyanto, M., and Hartanti, L., 2006, Indones. J. Chem., 6 (3), 292–296.

[5] Sohilait, H.J., Sastrohamidjojo, H., Matsjeh, S., and Grossert, J.S., 2005, Indones. J. Chem., 5 (3), 198–202.

[6] Bar, F.M.A., Khanfar, M.A., Elnagar, A.Y., Badria, F.A., Zaghloul, A.M., Ahmad, K.F., Sylvester, P.W., and El Sayed, K.A., 2010, Bioorg. Med. Chem., 18 (2), 496–507.

[7] Xu, H.X., Zheng, X.S., Yang, Y.J., Tian, J.C., Lu, Y.H., Tan, K.H., Heong, K.L.,and Lu, Z.X., 2015, Crop Prot., 72, 144–149.

[8] Sohilait, H.J., 2003, SIGMA, 6(2), 193–196.

[9] Tundo, P., and Selva, M., 2002, Acc. Chem. Res., 35 (9), 706–716.

[10] Supeno, Minto. 2007, Bentonit Alam Terpilar sebagai Material Katalis/Co-Katalis Pembuatan Gas Hidrogen dan Oksigen dari Air, Dissertation, Sumatra Utara University, Medan.

[11] Soetaredjo, F.E., 2014, Pembuatan dan Karakterisasi Katalis dari Bentonit Pacitan untuk Aplikasi Pembuatan Bahan Bakar Sintesis dari Sampah Plastik, Chemical Engineering Study Program, Widya Mandala Catholic University, Surabaya.

[12] Tanjaya, A., Sudono, Indraswati, N., and Ismadji, S., 2006, J. Teknik Kimia, 5(2), 429–434.

[13] Fessenden, R.J., and Fessenden, J.S., 2010, Dasar-Dasar Kimia Organik, translated by Maun, S., Binarupa Aksara Publisher, Jakarta.

[14] Sudarma, I.M., 2010, Uji Fitokimia, Ekstraksi, Isolasi dan Transformasi Senyawa Bahan Alam, Mataram University, Mataram.

[15] Supratman, U., 2010, Elusidasi Struktur Senyawa Organik, Widya Padjajaran, Bandung.

[16] Sitorus, M., 2009, Spektroskopi: Eludasi Struktur Molekul Organik, Graha Ilmu, Jogyakarta.



DOI: https://doi.org/10.22146/ijc.21193

Article Metrics

Abstract views : 3041 | views : 5662


Copyright (c) 2015 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.