UTILIZATION OF EGGSHELL-DERIVED MATERIAL AS A SOLID BASE CATALYST FOR EFFICIENT SYNTHESIS OF SUBSTITUTED CHALCONES

Lina Mardiana, Bayu Ardiansah, Ridla Bakri, Antonius Herry Cahyana, Yulia Anita, Nuraini Pahlawati Aziza

Abstract


A simple preparation of sodium impregnated on activated chicken eggshells (Na-ACE) as a solid base material for substituted chalcones synthesis is presented. After characterization using FTIR, XRD, SEM, EDS and total basicity, the catalyst was applied in Aldol condensation to produce corresponding chalcones 3a-3j. Confirmation of products structure has been done by FTIR, UV-Vis and MS instruments. Reaction can be carried out in relative short time with ethanol as the best solvent and gave the highest yield of 95 %. This research presented a facile synthesis of chalcone derivatives, the prominent class of organic compounds with interesting biological activities. 


Keywords


Activated chicken eggshells, chalcones, Aldol condensation

Full Text:

PDF

References


El-Meligie, S., Taher, A. T., Kamal, A. M., and Youssef, A. 2017. Design, Synthesis and Cytotoxic Activity of Certain Novel Chalcone Analogous Compounds. European Journal of Medicinal Chemistry. 126: 52-60.

Leeza, S., Mittal, S., Rajala, M. S., Avecilla, F., Husain, M., and Azam, A. 2015. Synthesis, Characterization and Antiamoebic Activity of Chalcones Bearing N-substituted Ethanamine Tail. European Journal of Medicinal Chemistry. 98: 179-189.

Shakil, N. A., Singh, M. K., Sathiyendiran, M., Kumar, J., and Padaria, J. C. 2013. Microwave Synthesis, Characterization and Bio-efficacy Evaluation of Novel Chalcone Based 6-carbethoxy-2-cyclohexen-1-one and 2H-indazol-3-ol Derivatives. European Journal of Medicinal Chemistry. 59: 120-131.

Detsi, A., Majdalani, M., Kontogiorgis, C. A., Hadjipavlou-Litina, D. 2009. Natural and Synthetic 2-hydroxychalcones and Aurones: Synthesis, Characterization and Evaluation of the Antioxidant and Soybean Lipoxygenase Inhibitory Activity. Bioorganic and Medicinal Chemistry. 17: 8073-8085.

Madhavi, S., Sreenivasulu, R., Yazala, J. P., and Raju, R. R. 2016. Synthesis of Chalcone Incorporated Quinazoline Derivatives as Anticancer Agents. Saudi Pharmaceutical Journal. Article in Press. DOI: 10.1016/j.jsps.2016.06.005.

Azab, M. E., Youssef, M. M., and El-Bordany, E. A. 2013. Synthesis and Antibacterial Evaluation of Novel Heterocyclic Compounds Containing a Sulfonamido Moiety. Molecules. 18(1): 832-844.

Kaur, N. and Kishore, D. 2013. Application of Chalcones in Heterocycles Synthesis: Synthesis of 2-(isoxazolo, pyrazole and pyrimido) Substituted Analogues of 1,4-benzodiazepin-5-carboxamids Linked Through an Oxyphenyl Bridge. Journal of Chemical Science. 125(3): 555-560.

Fu, X., Feng, J., Dong, Z., Lin, L., Liu, X. and Feng, X. 2011. Enantioselective Synthesis of 2-substituted-1,5-benzodiazepines Through Domino Reaction of o-phenylenediamine and Chalcone Derivatives. European Journal of Organic Chemistry. 2011(27): 5233-5236.

Konstantinova, L. S., Berezin, A. A., Lysov, K. A. and Rakitin, O. A. 2007. Selective Synthesis of bis[1,2]dithiolo[1,4] thiazines from 4-isopropylamino-5-chloro-1,2-dithiole-3-ones. Tetrahedron Letters. 48(33): 5851-5854.

Bano, S., Javed, K., Ahmad, S., Rathish, I. G., Singh, S., Chaitanya, M., Arunasree, K. M. and Alam, M. S. 2013. Synthesis of Some Novel Chalcones, Flavanones and Flavones and Evaluation of Their Anti-inflammatory Activity. European Journal of Medicinal Chemistry. 65: 51-59.

Romanelli, G., Pasquale, G., Sathicq, Á., Thomas, H., Autino, J. and Vázquez, P. 2011. Synthesis of chalcones Catalyzed by Aminopropylated Silica Sol-Gel under Solvent-Free Condition. Journal of Molecular Catalysis A: Chemical. 340(1-2): 24-32.

Bahekar, S. P., Hande, S. V., Agrawal, N. R., Chandak, H. S., Bhoj, P. S., Goswami, K. and Reddy, M. V. R. 2016. Sulfonamide Chalcones: Synthesis and In Vitro Exploration for Therapeutic Potential against Brugia malayi. European Journal of Medicinal Chemistry. 124: 262-269.

Mitsutani, A. 2002. Future Possibilities of Recently Commercialized Acid/Base-Catalyzed Chemical Processes. Catalysis Today. 73: 57-63.

Sarojini, B. K., Narayana, B., Ashalatha, B. V., Indira, J. and Lobo, K. G. 2006. Synthesis, Crystal Growth and Studies on Non-linear Optical Property of New Chalcones. Journal of Crystal Growth. 295: 54-59.

Narender, T. and Reddy, K. P. 2007. A Simple and Highly Efficient Method for the Synthesis of Chalcones by Using Borontrifluoride-Etherate. Tetrahedron Letters. 48: 3177-3180.

Kalashnikov, V. V., Kalashnikova, I. P. ans Shestov, V. I. 2008. Synthesis of Chalcones on the Basis of Pyridin-2(1H)-one. Russian Journal of General Chemistry. 78(6): 1247-1252.

Winter, C., Caetano, J. N., Barros, A., Araújo, C., Chaves, A. R., Ostroski, I. C., Vaz, B. G., Pérez, C. N. and Alonso, C. G. 2016. Activated Carbon for Chalcones Production: Claisen-Schmidt Condensation Reaction. Chemical Engineering Journal. 303: 604-610.

Kunde, L. B., Gade, S. M., Kalyani, V. S. and Gupte, S. P. 2009. Catalytic Synthesis of Chalcone and Flavanone Using Zn-Al Hydrotalcite Adhere Ionic Liquid. Catalysis Communication. 10(14): 1881-1888.

Ballini, R., Bosica, G., Maggi, R., Ricciutelli, M., Chimiche, S., Agostino, V. S., Camerino, I. and Parma, I. 2001. Clay-catalysed Solventless Synthesis of Trans -chalcones Green Context. Green Chemistry. 3: 178-180.

Mardiana, L., Bakri, R., Septiarti, A. and Ardiansah, B. 2017. The Synthesis of 2-(5-(3-methoxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl)phenol Using Sodium Impregnated on Activated Chicken Eggshells Catalyst. IOP Conference Series: Materials Science and Engineering. 188: 012022 (Article ID). DOI: https://doi.org/10.1088/1757-899X/188/1/012022

Mosaddegh, E. 2013. Ultrasonic-assisted Preparation of Nano Eggshell Powder: A Novel Catalyst in Green and High Efficient Synthesis of 2-aminochromenes. Ultrasonics Sonochemistry. 20(6): 1436-1441.

Khemthong, P., Luadthong, C., Nualpaeng, W., Changsuwan, P., Tongprem, P. and Faungnawakij, K. 2012. Industrial Eggshell Wastes as the Heterogeneous Catalysts for Microwave-assisted Biodiesel Production. Catalysis Today. 190(1): 112-116.

Chakraborty, R., Bepari, S. and Banerjee, A. 2011. Application of Calcined Waste Fish (Labeo Rohita) Scale as Low-cost Heterogeneous Catalyst for Biodiesel Synthesis. Bioresource Technology. 102(3): 3610-3618.

Gao, Y. and Xu, C. 2012. Synthesis of Dimethyl Carbonate Over Waste Eggshell Catalyst. Catalysis Today. 190(1): 107-111.

Karoshi, G., Kolar, P., Shah, S.B., Gilleskie, G. and Das, L. 2015. Calcined Eggshell as an Inexpensive Catalyst for Partial Oxidation of Methane. Journal of Taiwan Institute of Chemical Engineering. 57: 123-128.

Patil, S., Jadhav, S. D. and Shinde, S. K. 2012. CES as an Efficient Natural Catalyst for Synthesis of Schiff Bases under Solvent-Free Conditions: An Innovative Green Approach. Organic Chemistry International Hindawi Publishing Corporation. Article ID 153159.

Kumar, D. and Ali, A. 2012. Nanocrystalline K-CaO for the Transesterification of a Variety of Feedstocks: Structure, Kinetics and Catalytic Properties. Biomass and Bioenergy. 46: 459-468.

Hu, K., Wang, H., Liu, Y. and Yang, C. 2015. KNO3/CaO as Cost-effective Heterogeneous Catalyst for the Synthesis of Glycerol Carbonate from Glycerol and Dimethyl Carbonate. Journal of Industrial and Engineering Chemistry. 28: 334-343.

Yan, B., Zhang, Y., Chen, G., Shan, R., Ma, W. and Liu, C. 2016. The Utilization of Hydroxyapatite-supported CaO-CeO2 Catalyst for Biodiesel Production. Energy Conversion and Management. 130: 156-164.

Tan, Y.H., Abdullah, M.O., Nolasco-hipolito, C. and Taufiq-yap, Y.H. 2015. Waste Ostrich- and Chicken-eggshells as Heterogeneous Base Catalyst for Biodiesel Production from Used Cooking Oil: Catalyst Characterization and Biodiesel Yield Performance. Applied Energy. 160: 58-70.

Eletta, O. A. A., Ajayi, O. A., Ogunleye, O. O. and Akpan, I. C. 2016. Adsorption of Cyanide from Aqueous Solution using Calcinated Eggshells: Equilibrium and Optimisation Studies. Journal of Environmental and and Chemical Engineering. 4(1): 1367-1375.

Maneerung, T., Kawi, S., Dai, Y. and Wang, C. 2016. Sustainable Biodiesel Production via Transesterification of Waste Cooking Oil by using CaO Catalysts Prepared from Chicken Manure. Energy Conversion and Management. 123: 487-497.

Mohammadi, M., Lahijani, P. and Rahman, A. 2014. Refractory Dopant-incorporated CaO from Waste Eggshell as Sustainable Sorbent for CO2 Capture: Experimental and Kinetic Studies. Chemical Engineering Journal. 243: 455-464.

Sathiyamoorthi, K., Mala, V., Sakthinathan, S. P., Kamalakkannan, D., Suresh, R., Vanangamudi, G. and Thirunarayanan, G. 2013. Solvent-free Synthesis, Spectral Correlations and Antimicrobial Aactivities of Some Aryl E 2-propen-1-ones. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 112: 245-256.

Zeng, D., Zhang, Q., Chen, S., Liu, S., Chen, Y., Tian, Y. and Wang, G. 2015. Preparation and Characterization of a Strong Solid Base from Waste Eggshell for Biodiesel Production. Journal of Environmental and Chemical Engineering. 3(1): 560-564.




DOI: http://dx.doi.org/10.11113/jt.v79.10220

Refbacks

  • There are currently no refbacks.


Copyright © 2012 Penerbit UTM Press, Universiti Teknologi Malaysia.
Disclaimer : This website has been updated to the best of our knowledge to be accurate. However, Universiti Teknologi Malaysia shall not be liable for any loss or damage caused by the usage of any information obtained from this web site.
Best viewed: Mozilla Firefox 4.0 & Google Chrome at 1024 × 768 resolution.