Biaril Bileşiklerinin Sentezi İçin Kitosan-Guar Sakizi Kompoziti İçeren Biyobozunur Mikrokapsüller Üzerine İmmobilize Edilmiş Oldukça Aktif ve Sağlam Paladyum Nanopartiküller

Year 2020, , 113 - 121, 05.03.2020

Talat Baran

https://doi.org/10.36306/konjes.698694

Cited By: 1

Abstract

Bu çalışmada, kitosan-guar sakızı kompozitinden (CS-GG) oluşan son derece kararlı biyobozunur mikro kapsüller, katalizör desteği olarak hazırlandı. Daha sonra, paladyum partikülleri, herhangi bir toksik indirgeyici madde kullanmadan tasarlanan destek üzerine başarıyla dekore edildi (Pd NP@CS-GG). CS-GG ve Pd NP@CS-GG’lerin yapısal karakterizasyonu farklı analitik tekniklerle yapıldı ve paladyum nanopartiküllerinin boyutunun 23-48 nm aralığında değiştiği tespit edildi. Daha sonra, Pd NP @ CS-GG'nin katalitik aktivitesi, mikrodalga ısıtma kullanılarak çözücüsüz ortam altında çeşitli biaril bileşiklerin üretiminde değerlendirildi. Pd NPs@CS-GG, çeşitli aril halojenürlerin iyi reaksiyon verimleriyle istenilen biaril bileşiklerine dönüştürülmesinde yüksek katalitik performans gösterdi. Ayrıca, Pd NPs@CS-GG'nin, en az yedi kez tekrar kullanımı nedeniyle uzun yaşam süresine sahip bir katalizör olduğu bulundu.

Keywords

Kitosan, Mikro Kapsül, Katalizör, Paladyum Nanopartikül

HIGHLY ACTIVE AND ROBUST PALLADIUM NANOPARTICLES IMMOBILIZED ON BIODEGRADABLE MICROCAPSULES CONTAINING CHITOSAN-GUAR GUM COMPOSITE FOR SYNTHESIS OF BIARYL COMPOUNDS

Abstract

In this study, highly stable biodegradable microcapsules, which are composed of chitosan-guar gum composite (CS-GG), were prepared as catalyst support. Then, palladium nanoparticles were successfully decorated on the designed support without using any toxic reducing agent (Pd NPs@CS-GG). Structural characterizations of CS-GG and Pd NPs@CS-GG were carried out by different analytical techniques and it was detected that the size of palladium nanoparticles changed in the range of 23-48 nm. Then, the catalytic activity of Pd NPs@CS-GG was evaluated in the fabrication of various biaryl compounds under solventless media using microwave heating. Pd NPs@CS-GG showed high catalytic performance in the conversion of various aryl halides to desired biaryl compounds with good reaction yields. Moreover, it was found that Pd NPs@CS-GG was a catalyst having long life time because of its reuse at least seven times.

Keywords

Chitosan, Microcapsule, Catalyst, Palladium Nanoparticle

References

• Atarod, M., Nasrollahzadeh, M., Sajadi, S. M., 2016, "Euphorbia heterophylla leaf extract mediated green synthesis of Ag/TiO2 nanocomposite and investigation of its excellent catalytic activity for reduction of variety of dyes in water", Journal of Colloid and Interface Science, 462, 272-279.
• Baran, T., 2017, "Practical, economical, and eco-friendly starch-supported palladium catalyst for Suzuki coupling reactions" Journal of colloid and interface science, 496, 446-455.
• Baran, T., Menteş, A., Arslan, H., 2015, "Synthesis and characterization of water soluble O-carboxymethyl chitosan Schiff bases and Cu(II) complexes", International Journal of Biological Macromolecules, 72, 94-103.
• Baran, T., Sargın, İ., Kaya, M., Mulerčikas, P., Kazlauskaitė, S., Menteş, A., 2018, "Production of magnetically recoverable, thermally stable, bio-based catalyst: Remarkable turnover frequency and reusability in Suzuki coupling reaction", Chemical Engineering Journal, 331, 102-113.
• Baskar, D., Kumar, T. S., 2009, "Effect of deacetylation time on the preparation, properties and swelling behavior of chitosan films", Carbohydrate Polymers, 78(4), 767-772.
• Chen, A., Ostrom, C., 2015, "Palladium-based nanomaterials: synthesis and electrochemical applications", Chemical Reviews, 115(21), 11999-12044.
• Cui, X., Li, H., Yuan, M., Yang, J., Xu, D., Li, Z., Dong, Z., 2017, "Facile preparation of fluffy N-doped carbon modified with Ag nanoparticles as a highly active and reusable catalyst for catalytic reduction of nitroarenes", Journal of Colloid and Interface Science, 506, 524-531.
• Daniel, M.-C., Astruc, D., 2004, "Gold nanoparticles: assembly, supramolecular chemistry, quantum-size-related properties, and applications toward biology, catalysis, and nanotechnology", Chemical Reviews, 104(1), 293-346.
• Gholinejad, M., Najera, C., Hamed, F., Seyedhamzeh, M., Bahrami, M., Kompany-Zareh, M., 2017, "Green synthesis of carbon quantum dots from vanillin for modification of magnetite nanoparticles and formation of palladium nanoparticles: Efficient catalyst for Suzuki reaction" Tetrahedron, 73(38), 5585-5592.
• Mudgil, D., Barak, S., Khatkar, B. S., 2014, "Guar gum: processing, properties and food applications—A Review", Journal of Food Science and Technology, 51(3), 409-418.
• Naghdi, S., Sajjadi, M., Nasrollahzadeh, M., Rhee, K. Y., Sajadi, S. M., Jaleh, B., 2018, "Cuscuta reflexa leaf extract mediated green synthesis of the Cu nanoparticles on graphene oxide/manganese dioxide nanocomposite and its catalytic activity toward reduction of nitroarenes and organic dyes", Journal of the Taiwan Institute of Chemical Engineers, 86, 158-173.
• Nasrollahzadeh, M., Azarian, A., Maham, M., Ehsani, A., 2015, "Synthesis of Au/Pd bimetallic nanoparticles and their application in the Suzuki coupling reaction", Journal of Industrial and Engineering Chemistry, 21, 746-748.
• Nasrollahzadeh, M., Issaabadi, Z., Sajadi, S. M., 2019, "Green synthesis of Cu/Al2O3 nanoparticles as efficient and recyclable catalyst for reduction of 2,4-dinitrophenylhydrazine, Methylene blue and Congo red", Composites Part B: Engineering, 166, 112-119.
• Nasrollahzadeh, M., Mehdipour, E., Maryami, M., 2018, "Efficient catalytic reduction of nitroarenes and organic dyes in water by synthesized Ag/diatomite nanocomposite using Alocasia macrorrhiza leaf extract", Journal of Materials Science: Materials in Electronics, 29(19), 17054-17066.
• Nasrollahzadeh, M., Sajadi, S. M., 2016, "Preparation of Pd/Fe3O4 nanoparticles by use of Euphorbia stracheyi Boiss root extract: A magnetically recoverable catalyst for one-pot reductive amination of aldehydes at room temperature", Journal of Colloid and Interface Science, 464, 147-152.
• Nasrollahzadeh, M., Sajadi, S. M., Rostami-Vartooni, A., Bagherzadeh, M., 2015, "Green synthesis of Pd/CuO nanoparticles by Theobroma cacao L. seeds extract and their catalytic performance for the reduction of 4-nitrophenol and phosphine-free Heck coupling reaction under aerobic conditions", Journal of Colloid and Interface Science, 448, 106-113.
• Nasrollahzadeh, M., Sajadi, S. M., Rostami-Vartooni, A., Bagherzadeh, M., Safari, R., 2015, "Immobilization of copper nanoparticles on perlite: Green synthesis, characterization and catalytic activity on aqueous reduction of 4-nitrophenol", Journal of Molecular Catalysis A: Chemical, 400, 22-30.
• Pal, S., Ghorai, S., Dash, M. K., Ghosh, S., Udayabhanu, G., 2011, "Flocculation properties of polyacrylamide grafted carboxymethyl guar gum (CMG-g-PAM) synthesised by conventional and microwave assisted method", Journal of Hazardous materials, 192(3), 1580-1588.
• Phan, T. T. V., Hoang, G., Nguyen, V. T., Nguyen, T. P., Kim, H. H., Mondal, S., Junghwan, O., 2019, "Chitosan as a stabilizer and size-control agent for synthesis of porous flower-shaped palladium nanoparticles and their applications on photo-based therapies", Carbohydrate Polymers, 205, 340-352.
• Rai, M., Yadav, A., Gade, A., 2009, "Silver nanoparticles as a new generation of antimicrobials", Biotechnology advances, 27(1), 76-83.
• Rajender Reddy, K., Kumar, N. S., Surendra Reddy, P., Sreedhar, B., Lakshmi Kantam, M., 2006, "Cellulose supported palladium(0) catalyst for Heck and Sonogashira coupling reactions", Journal of Molecular Catalysis A: Chemical, 252(1), 12-16.
• Rathi, A. K., Gawande, M. B., Pechousek, J., Tucek, J., Aparicio, C., Petr, M., Varma, R. S., 2016, "Maghemite decorated with ultra-small palladium nanoparticles (γ-Fe 2 O 3–Pd): applications in the Heck–Mizoroki olefination, Suzuki reaction and allylic oxidation of alkenes", Green Chemistry, 18(8), 2363-2373.
• Seeli, D. S., Prabaharan, M., 2016, "Guar gum succinate as a carrier for colon-specific drug delivery", International Journal of Biological Macromolecules, 84, 10-15.
• Seeli, D. S., Prabaharan, M., 2017, "Guar gum oleate-graft-poly(methacrylic acid) hydrogel as a colon-specific controlled drug delivery carrier", Carbohydrate Polymers, 158, 51-57.
• Sharma, G., Sharma, S., Kumar, A., Al-Muhtaseb, A. A. H., Naushad, M., Ghfar, A. A., Stadler, F. J., 2018, "Guar gum and its composites as potential materials for diverse applications: A review", Carbohydrate Polymers, 199, 534-545.
• Sudhakar, P., Soni, H., 2018, "Catalytic reduction of Nitrophenols using silver nanoparticles-supported activated carbon derived from agro-waste", Journal of environmental chemical engineering, 6(1), 28-36.
• Tajik, H., Moradi, M., Rohani, S., Erfani, A., Jalali, F., 2008, "Preparation of chitosan from brine shrimp (Artemia urmiana) cyst shells and effects of different chemical processing sequences on the physicochemical and functional properties of the product", Molecules, 13(6), 1263-1274.
• Thombare, N., Jha, U., Mishra, S., Siddiqui, M. Z., 2016, "Guar gum as a promising starting material for diverse applications: A review", International Journal of Biological Macromolecules, 88, 361-372.
• Veisi, H., Gholami, J., Ueda, H., Mohammadi, P., Noroozi, M., 2015, "Magnetically palladium catalyst stabilized by diaminoglyoxime-functionalized magnetic Fe3O4 nanoparticles as active and reusable catalyst for Suzuki coupling reactions", Journal of Molecular Catalysis A: Chemical, 396, 216-223.
• Wan Ngah, W. S., Teong, L. C., Hanafiah, M. A. K. M., 2011, "Adsorption of dyes and heavy metal ions by chitosan composites: A review", Carbohydrate Polymers, 83(4), 1446-1456.
• Xiang, R. Y., Lin, Y., Wai, C. M., 2003, "Decorating catalytic palladium nanoparticles on carbon nanotubes in supercritical carbon dioxide", Chemical Communications(5), 642-643.
• Xue, S., Jiang, H., Zhong, Z., Low, Z.-X., Chen, R., Xing, W., 2016, "Palladium nanoparticles supported on a two-dimensional layered zeolitic imidazolate framework-L as an efficient size-selective catalyst", Microporous and Mesoporous Materials, 221, 220-227.
• Zahed, B., Hosseini-Monfared, H., 2015, "A comparative study of silver-graphene oxide nanocomposites as a recyclable catalyst for the aerobic oxidation of benzyl alcohol: Support effect", Applied Surface Science, 328, 536-547.
• Zhang, L., Zeng, Y., Cheng, Z., 2016, "Removal of heavy metal ions using chitosan and modified chitosan: A review", Journal of Molecular Liquids, 214, 175-191.