Conversion of Cyclohexanone to Adipic Acid Catalyzed by Heteropoly Compounds

https://doi.org/10.22146/ijc.21225

Aldes Lesbani(1*), Fitriliana Fitriliana(2), Risfidian Mohadi(3)

(1) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Sriwijaya University, Jl. Raya Palembang Prabumulih Km32, Ogan Ilir Sumatera Selatan 30662
(2) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Sriwijaya University, Jl. Raya Palembang Prabumulih Km32, Ogan Ilir Sumatera Selatan 30662
(3) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Sriwijaya University, Jl. Raya Palembang Prabumulih Km32, Ogan Ilir Sumatera Selatan 30662
(*) Corresponding Author

Abstract


Conversion of cyclohexanone to adipic acid using hydrogen peroxide as green oxidant catalyzed by heteropoly compounds i.e. H5[a-BW12O40] H4[a-SiW12O40] and H4[a-PVMo11O40] has been carried out systematically in one pot synthesis under mild condition. The product of adipic acid was characterized using GC-MS, FT-IR, 1H-NMR and 13C-NMR spectroscopy. The results show that cyclohexanone could be converted into adipic acid by using H5[a-BW12O40] H4[a-SiW12O40] as catalysts, whereas H4[a-PVMo11O40] did not shows catalytic activity in this reaction. The effect of reaction time gave adipic acid 41% for reaction time 7 h. The yield of adipic acid was 30% with melting point 149-151 °C. The oxidation temperature at 100 °C gave the highest adipic acid 48% was obtained. The FT-IR, 1H-NMR and 13C-NMR spectra of the product are well agreed to the adipic acid standard.

Keywords


cyclohexanone; adipic acid; heteropoly compounds

Full Text:

Full Text Pdf


References

[1] Thiemens, M.H., and Trogler, W.C., 1991, Science, 251(4996), 932–934.

[2] Vural-Gürsel, I., Wang, Q., Noël, T., Hessel, V., and Tinge, J.T., 2013, Ind. Eng. Chem. Res., 52(23), 7827–7835.

[3] Vafaeezadeh, M., and Hashemi, M.M., 2013, Chem. Eng. J., 221, 254–257.

[4] Sato, K., Aoki, M., and Noyori, R., 1998, Science, 281(2383), 1646–1647.

[5] Zhu, W., Li, H., He, X., Zhang, Q., Shu, H., and Yan, Y, 2008, Catal. Commun., 9(4), 551–555.

[6] Dutta, A., Pramanik, M., Patra, A.K., Nandi, M., Uyama, H., and Bhaumik, A., 2012, Chem. Commun., 48(53), 6738–6740.

[7] Knops-Gerrits, P.P., Thibault-Starzyk, F., and Jacobs, P.A., 1994, Stud. Surf. Sci. Catal., 84, 1411–1417.

[8] Blach, P., Böstrom, Z., Franceshi-Messant, S., Lattes, A., Perez, E., and Rico-Lattes, I., 2010, Tetrahedron, 66(35), 7124–7128.

[9] Pênate, I.Q., Lesage, G., Cognet, P., and Poux, M., 2012, Chem. Eng. J., 200-202, 357–364.

[10] Deng, Y., Ma, Z., Wang, K., and Chen, J., 1999, Green Chem., 1, 275–276.

[11] Lesbani, A., 2008, Jurnal Penelitian Sains, 11, 429–434.

[12] Mohadi, R., Hidayati, N., Lesbani, A, 2012, Majalah Ilmiah Sriwijaya, Lembaga Penelitian Universitas Sriwijaya, 8–16.

[13] Zhang, S-G., Jiang, H., Gong, H., and Sun, Z-L., 2003, Pet. Sci. Technol., 21(1), 275–282.

[14] Lesbani, A., and Mohadi, M., 2014, Bull. Chem. React. Eng. Catal., 9(2), 136–141.

[15] Shriver and Atkins, 2006, Inorganic Chemistry, 4th ed., Oxford University Press, Oxford.

[16] Lesbani, A., Mohadi, M., and Hidayati, N., 2012, Jurnal Penelitian Sains, 15, 145–147.

[17] Ren, S., Xie, Z., Cao, L., Xie, X., Qin, G., and Wang, J., 2009, Catal. Commun., 10(5), 464–467.

[18] Clayden, J., Greeves, N., Warren, S., and Wothers, P., 2008, Organic Chemistry, Oxford University Press, Oxford, UK.

[19] Jin, P., Zhao, Z., Dai, Z., Wei, D., Tang, M., and Wang, X., 2011, Catal. Today, 175(1), 619–624.



DOI: https://doi.org/10.22146/ijc.21225

Article Metrics

Abstract views : 2304 | views : 9860


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.