Immobilization of platinum nanoparticles on the functionalized chitosan particles: an efficient catalyst for reduction o
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ORIGINAL ARTICLE
Immobilization of platinum nanoparticles on the functionalized chitosan particles: an efficient catalyst for reduction of nitro compounds and tandem reductive Ugi reactions Seyedeh Fazileh Hamzavi1 · Shahla Jamili2 · Morteza Yousefzadi3 · Ali Mashinchian Moradi1 · Narges Amrollahi Biuki3 Received: 21 August 2019 / Accepted: 17 October 2019 © Springer Nature Switzerland AG 2019
Abstract In this work, we reported a facile synthesis of Pt nanoparticles (NPs) on proline-functionalized cross-linked chitosan particles to catalyze the reduction of R-NO2 to R-NH2 in aqueous medium using sodium borohydride. Chitosan was functionalized with (3-bromopropyl)proline and cross-linked with glutaraldehyde for the synthesis of chitosan NPs. The platinum NPs was prepared on the chitosan NPs. This catalyst showed the good selectivity and activity for reduction of nitro compound as well as for tandem reduction of nitro groups in Ugi reaction.
* Shahla Jamili [email protected] 1
Department of Natural Resources and Environment, Science and Research Branch, Islamic Azad University, Tehran, Iran
2
Iranian Fisheries Science Research Institute, Agricultural Research Education and Extension Organization, Tehran, Iran
3
Department of Marine Biology, Faculty of Marine Science and Technology, University of Hormozgan, Bandarabbas, Iran
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Vol.:(0123456789)
Molecular Diversity
Graphic abstract
Keywords Pt NPs · Chitosan · Proline functionalization · Nitro reduction · Tandem reactions
Introduction Primary amines especially aniline derivatives are an important class of compounds that used for the synthesis of numerous polymers, dyes, pharmaceutical and natural compounds [1–3]. The anilines compounds were produced more than a million tons per year [4]. The common ways for their synthesis are the reductive amination of alcohols and aldehydes and hydrogenation of nitro and nitrile compounds [5–8]. The hydrogenation of nitro compounds was carried out using various hydrogen source such as hydrazine hydrate, borohydride and aluminum hydride salts, ammonia borane, alcohols and hydrogen gas atmosphere [9, 10]. All
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of these methods were done in the presence of a noble metal and have some limitation consisting low reaction selectivity and yields, long reaction time, harsh reaction conditions and high costs. To great more green conditions, the using of the nanocatalyst systems with excellent properties such as high surface area and higher activities of their surface atoms of NPs was greatly used in the recent decades for the reduction of nitro compounds [11–14]. Among the various metals that used for redox reaction, Pt was the most used especially for the reduction of nitro compounds in industrial process, for example, Pt on activated charcoal [11, 15–17].
Molecular Diversity
Chitosan (CS) is a polysaccharide which is existed in living organisms. Chitosan is a natural polymer of glucosamine unites that partially acetylated in their amino groups and have basic and hydrophilic nature due to their amino
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