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

Yıl 2020, Cilt: 8 Sayı: 1, 113 - 121, 05.03.2020
https://doi.org/10.36306/konjes.698694

Öz

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.

Kaynakça

  • 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.

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

Yıl 2020, Cilt: 8 Sayı: 1, 113 - 121, 05.03.2020
https://doi.org/10.36306/konjes.698694

Öz

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.

Kaynakça

  • 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.
Toplam 34 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Mühendislik
Bölüm Araştırma Makalesi
Yazarlar

Talat Baran Bu kişi benim 0000-0003-0206-3841

Yayımlanma Tarihi 5 Mart 2020
Gönderilme Tarihi 26 Mart 2019
Kabul Tarihi 3 Temmuz 2019
Yayımlandığı Sayı Yıl 2020 Cilt: 8 Sayı: 1

Kaynak Göster

IEEE T. Baran, “HIGHLY ACTIVE AND ROBUST PALLADIUM NANOPARTICLES IMMOBILIZED ON BIODEGRADABLE MICROCAPSULES CONTAINING CHITOSAN-GUAR GUM COMPOSITE FOR SYNTHESIS OF BIARYL COMPOUNDS”, KONJES, c. 8, sy. 1, ss. 113–121, 2020, doi: 10.36306/konjes.698694.