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High throughput green reduction of tris(p-nitrophenyl)amine at ambient temperature over homogenous AgNPs as H-transfer catalyst

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Abstract

A green, facile, fast, and high throughput reusable catalytic reduction process was developed for the large-scale reduction of tris(p-nitrophenyl)amine to its corresponding amino-compound, tris(p-aminophenyl)amine (TAPA). The homogenous AgNPs and NaBH4 were used as the H-transfer catalyst and the H-donor compound, respectively. The successful reduction of TNPA was investigated by FT–IR, EDX, and XRD analysis, and its optical properties were checked by the UV–Visible and FL spectroscopies. Factors affecting the reduction yield including, temperature, reaction time, mmol of NaBH4, and catalyst volume, were optimized. Although the AgNPs are homogenous, both TNPA and TAPA are insoluble in water (AgNPs), hence the reduction process is heterogeneous. The importance of the heterogeneous reduction of TNPA was investigated, indicated that the reduction yield reached its maximum value when TNPA heterogeneously reduced on the surface of AgNPs. The reduction yield at optimal conditions was calculated at about 98.0% for the first and 72.0% after the 6th operational cycle, respectively. The mechanism of the reduction process was also established, indicated that the process works through a possible Langmuir–Hinshelwood mechanism. The easy recovery and excellent reusability of homogenous AgNPs along with high reaction yield reveal the power of the proposed method for the reduction of nitro-compounds.

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Synopsis A high throughput reusable catalytic reduction process has developed for the reduction of tris(p-nitrophenyl)amine to its corresponding amino-compound, tris(p-aminophenyl)amine (TAPA) using the homogenous AgNPs the H-transfer. As a significant advantage, the developed method works through a green chemistry approach.

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Acknowledgement

The authors wish to acknowledge the support of this work by Shiraz University Research Council.

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  1. Massoumi Laboratory, Department of Chemistry, College of Sciences, Shiraz University, Shiraz, 71454, Iran

    SAEED REZA HORMOZI JANGI & MORTEZA AKHOND

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  1. SAEED REZA HORMOZI JANGI
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  2. MORTEZA AKHOND
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Correspondence to SAEED REZA HORMOZI JANGI.

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HORMOZI JANGI, S.R., AKHOND, M. High throughput green reduction of tris(p-nitrophenyl)amine at ambient temperature over homogenous AgNPs as H-transfer catalyst. J Chem Sci 132, 110 (2020). https://doi.org/10.1007/s12039-020-01819-9

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  • DOI: https://doi.org/10.1007/s12039-020-01819-9

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