Document Type : Research Paper

Authors

Department of Wood and Paper Science and Technology, Faculty of Natural Resources and Environment, Science and Research Branch, Islamic Azad University, Tehran, Iran

Abstract

Abstract
In this study, acidified Luffa (AHS@L), by sulfonic acid, as an effective and biodegradable solid acid catalyst was produced. The synthesized catalyst was characterized by TGA, SEM, XRD and FTIR, and the results indicated that modified Luffa flour had an intense acidic property. The FT-IR analyze show a broad peak at 3400cm-1 that improve the acidification of the Luffa surface. Also the XRD analyze clearly show the change in the morphology of Luffa after acidification. The TGA analyze show us the heat resistance of the catalyst up to 245 ° C and the SEM images clearly showed that the catalyst surface was hydrated as a result of acidification. The synthesized catalyst was used to protect the amines in the N-tert butyl carbamate reaction under solvent-free conditions at room temperature. Different types of aliphatic and aromatic amines have been produced as related monocarbamates with excellent yields and short reaction times. This method was mild and selective and has advantages such as heterogeneous catalysis, low cost and catalyst recovery capability.

Keywords

-Atghia, V. and Beigbaghlou, S., 2013. Nanocrystalline titania-based sulfonic acid (TiO2-Pr-SO3H) as a new, highly efficient and recyclable solid acid catalyst for the N-Boc protection of amines at room temperature. Journal of Organometallic Chemistry, 745-746, 42-49.
-Akbari, J., Heydari, A., Ma’mani, L. and Hosseini, S., 2010. Protic ionic liquid [Tmg][Ac] as an efficient, homogeneous and recyclable catalyst for boc protection of amines. H. C. R. Chim. 13, 544-547.
-Bartoli, G., Bosco, M., Locatelli, M., Marcantoni, E., Massaccesi, M., Melchiorre, P., Sambri, L., 2004. A Lewis Acid-Mediated Protocol for the Protection of Aryl Amines as their Boc-Derivatives. Synlett 2004(10): 1794-1798.
-Chakraborti, A. K. and Chankeshwara, S.V., 2006. HClO4-SiO2 as a new, highly efficient, inexpensive and reusable catalyst for N-tert-butoxycarbonylation of amines. Org. Biomol. Chem. 2006(4): 2769-2771.
-Dai, Y., Chen, K., Wang, Y. and Chen, C., 2014. Application of Peanut Husk Ash as a Low-Cost Solid Catalyst for Biodiesel Production. International Journal of Chemical Engineering and Applications, 5(3): 276-280.
-Das, B., Venkateswarlu, K., Krishnaiah, M. and Holla, H., 2006. An efficient, rapid and regioselective nuclear bromination of aromatics and heteroaromatics with NBS using sulfonic-acid-functionalized silica as a heterogeneous recyclable catalyst. Tetrahedron Lett., 47(49): 8693-8697.
-Julian R.H., 2011. Ross, Heterogeneous Catalysis: Fundamentals and Applications 1st Edition, Kindle Edition, Elsevier, p. 232.
-Khaksar, S., Heydari, A., Tajbakhsh, M. and Vahdat, S.M., 2008. Hydrogen bond catalyzed chemoselective N-tert-butoxycarbonylation of amines. Tetrahedron Lett., 49(21): 3527-3529.
-Sun, M., Li, T., Zhang, Z., Wang, N., Xie, A., Lv, X., Wang, Y., Wu, F. and Wang, M., 2015. Natural biological template for ZnO nanoparticle growth and photocatalytic dye degradation under visible light. RSC Adv. 2015(5): 84406-84409.
-Mirjalili, B.F. and Zare, R. 2015. BF3/nano-sawdust as a green, biodegradable and inexpensive catalyst for the synthesis of highly substituted dihydro-2-oxopyrroles. RSC Advances, 2015(5): 15571-15566.
-Pandey, R.K., Ragade, S.P., Upadhyay, R.K., Dongare, M.K. and Kumar, P., 2002. A facile procedure for tert-butoxycarbonylation of amines promoted by yttria-zirconia based strong Lewis acid catalyst (SK-388EP). Arkivoc 2002.VII, 28-33.
-Qiao, Y., Teng, J., Wang, S. and Ma, H., 2018. Amine-Functionalized Sugarcane Bagasse: A Renewable Catalyst for Efficient Continuous Flow Knoevenagel Condensation Reaction at Room Temperature. Molecules, 23(1): 1-13.
-Sadeghi, B. and Zarepour, I. 2015. Nano-sawdust–BF3 as a new, cheap, and effective nano catalyst for one-pot synthesis of 2-amino benzo[h]chromene derivatives. J Nanostruct Chem., 5, 305-311.
-Shirini, F., Akbari-Dadamahaleh, S., Mohammad-Khah, A., Aliakbar, A., 2013. Rice husk: a mild, efficient, green and recyclable catalyst for the synthesis of 12-Aryl-8, 9, 10, 12-tetrahydro [a] xanthene-11-ones and quinoxaline derivatives. Comptes Rendus Chimie, 16(3): 207-216.