Use of Mineral Water as a Co-Catalyst for the Conversion of Toxic Nitro Benzene Derivatives to Aryl Amine Derivatives
Year 2025,
Volume: 13 Issue: 3, 1422 - 1430, 31.07.2025
Haydar Göksu
,
Elif Aydınlı
Abstract
A series of toxic nitro compounds were converted to aryl amine derivatives at room temperature in the presence of a hydrogen source such as sodium borohydride and in commercially available mineral water without the need for an organic solvent. A commercial catalyst containing Pd (PdAlO(OH) NPs) was used as the supporting material in the study. However, the amount of catalyst used was reduced by 40% compared to the amounts used previously due to the effect of mineral water. Thanks to the developed environmentally friendly and practical method, 8 different nitro arene compounds were converted to aryl amine derivatives with yields over 95%. The most powerful aspect of the developed method is that it is economical and industrial.
Ethical Statement
This research was supported by Duzce University Research Fund.
Supporting Institution
Duzce University
Project Number
2023.26.07.1386
Thanks
We would like to thank Düzce University BAP unit.
References
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[27] V. I. Parvulescu, F. Epron, H. Garcia and P. Granger, "Recent progress and prospects in catalytic water treatment," Chemical Reviews, vol. 122, no. 3, pp. 2981-3121, 2021.
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[28] R. Pelalak, R. Alizadeh and E. Ghareshabani, "Enhanced heterogeneous catalytic ozonation of pharmaceutical pollutants using a novel nanostructure of iron-based mineral prepared via plasma technology: a comparative study," Journal of Hazardous Materials, vol. 392, 2020, Art. no. 122269.
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[30] H. Goksu and E. Orhan, "The local and natural sources in synthetic methods: the practical synthesis of aryl oximes from aryl aldehydes under catalyst-free conditions in mineral water," Journal of Chemical Sciences, vol. 133, pp. 1-5, 2021.
-
[31] B. Y. Kara, M. Yazici, B. Kilbas and H. Goksu, "A practical and highly efficient reductive dehalogenation of aryl halides using heterogeneous Pd/AlO (OH) nanoparticles and sodium borohydride," Tetrahedron, vol. 72, no. 39, pp. 5898-5902, 2016.
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[32] K. S. Egorova and V. P. Ananikov, "Which metals are green for catalysis? Comparison of the toxicities of Ni, Cu, Fe, Pd, Pt, Rh, and Au salts," Angewandte Chemie International Edition, vol. 55, no. 40, pp. 12150-12162, 2016.
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Toksik Nitro Benzen Türevlerinin Aril Amin Türevlerine Dönüştürülmesinde Yardımcı Katalizör Olarak Maden Suyunun Kullanımı
Year 2025,
Volume: 13 Issue: 3, 1422 - 1430, 31.07.2025
Haydar Göksu
,
Elif Aydınlı
Abstract
Bir dizi toksik nitro bileşiği, organik bir çözücüye ihtiyaç duyulmadan, sodyum borhidrür gibi bir hidrojen kaynağının varlığında ve ticari olarak temin edilebilen maden suyunda oda sıcaklığında aril amin türevlerine dönüştürülmüştür. Çalışmada destekleyici malzeme olarak Pd (PdAlO(OH) NPs) içeren ticari bir katalizör kullanılmıştır. Ancak, kullanılan katalizör miktarı, maden suyunun etkisi nedeniyle daha önce kullanılan miktarlara kıyasla %40 oranında azaltılmıştır. Geliştirilen çevre dostu ve pratik yöntem sayesinde, 8 farklı nitro aren bileşiği %95'in üzerinde verimlerle aril amin türevlerine dönüştürülmüştür. Geliştirilen yöntemin en güçlü yönü, ekonomik ve endüstriyel olmasıdır.
Project Number
2023.26.07.1386
References
-
[1] M. Kulkarni and A. Chaudhari, "Microbial remediation of nitro-aromatic compounds: an overview," Journal of Environmental Management, vol. 85, no. 2, pp. 496-512, 2007.
-
[2] M. Bilal, A. R. Bagheri, P. Bhatt and S. Chen, "Environmental occurrence, toxicity concerns, and remediation of recalcitrant nitroaromatic compounds," Journal of Environmental Management, vol. 291, 2021, Art. no. 112685.
-
[3] J. H. Weisburger, "Comments on the history and importance of aromatic and heterocyclic amines in public health," Mutation Research/Fundamental and Molecular Mechanisms of Mutagenesis, vol. 506, pp. 9-20, 2002.
-
[4] P. Vineis and R. Pirastu, "Aromatic amines and cancer," Cancer Causes & Control, vol. 8, pp. 346-355, 1997.
-
[5] M. D. Teli, "Softening finishes for textiles and clothing," in Functional Finishes For Textiles. Improving Comfort, Performance and Protection, R. Paul, Ed., 1st ed., Cambridge, UK: Woodhead Publishing, 2015, pp. 123-152.
-
[6] J. Qiu, B. Tang, B. Ju, Y. Xu and S. Zhang, "Stable diazonium salts of weakly basic amines-Convenient reagents for synthesis of disperse azo dyes," Dyes and Pigments, vol. 136, pp. 63-69, 2017.
-
[7] N. Querol, C. Barreneche and L. F. Cabeza, "Asphalt emulsion formulation: State of the art of formulation, properties and results of HIPR emulsions," Construction and Building Materials, vol. 212, pp. 19-26, 2019.
-
[8] F. Nakhaei and M. Irannajad, "Reagents types in flotation of iron oxide minerals: A review," Mineral Processing and Extractive Metallurgy Review, vol. 39, no. 2, pp. 89-124, 2018.
-
[9] C. M. C. Andrés, J. M. Pérez de la Lastra, E. B. Munguira, C. A. Juan and E. Pérez-Lebeña, "From psychoactivity to antimicrobial agents: Multifaceted applications of synthetic cathinones and catha edulis extracts," Molecules, vol. 29, no. 24, 2024, Art. no. 5918.
-
[10] I. A. Vamvakopoulou, K. A. Narine, I. Campbell, J. R. Dyck and D. J. Nutt, "Mescaline: the forgotten psychedelic," Neuropharmacology, vol. 222, 2023, Art. no. 109294.
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[11] F. Zamberlan, "On the quest for mescaline," Nature Chemical Biology, vol. 20, no. 7, pp. 796-796, 2024.
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[12] G. M. Shankar, "Potential drug-drug interactions with adefovir dipivoxil: Clinical implications and management strategies," Biosciences Biotechnology Research Asia, vol. 21, no. 2, 2024, Art. no. 509.
-
[13] R. Prabhukhot Prachi, M. Wagh Mahesh and C. Gangal Aneesh, "A review on solid state hydrogen storage material," Advances in Energy and Power, vol. 4, no. 11, pp. 11-22, 2016.
-
[14] H. A. Ousaleh, S. Mehmood, Y. F. Baba, I. Bürger, M. Linder and A. Faik, "An analytical review of recent advancements on solid-state hydrogen storage," International Journal of Hydrogen Energy, vol. 52, pp. 1182-1193, 2024.
-
[15] P. J. Megía, A. J. Vizcaíno, J. A. Calles and A. Carrero, "Hydrogen production technologies: from fossil fuels toward renewable sources. A mini review," Energy & Fuels, vol. 35, no. 20, pp. 16403-16415, 2021.
-
[16] Y. Bicer and F. Khalid, "Life cycle environmental impact comparison of solid oxide fuel cells fueled by natural gas, hydrogen, ammonia and methanol for combined heat and power generation," International Journal of Hydrogen Energy, vol. 45, no. 5, pp. 3670-3685, 2020.
-
[17] C. Tarhan and M. A. Çil, "A study on hydrogen, the clean energy of the future: Hydrogen storage methods," Journal of Energy Storage, vol. 40, 2021, Art. no. 102676.
-
[18] M. Fronczak, A. Kasprzak and M. Bystrzejewski, "Carbon-encapsulated iron nanoparticles with deposited Pd: a high-performance catalyst for hydrogenation of nitro compounds," Journal of Environmental Chemical Engineering, vol. 9, no. 1, 2021, Art. no. 104673.
-
[19] S. Chen, L.-L. Ling, S.-F. Jiang and H. Jiang, "Selective hydrogenation of nitroarenes under mild conditions by the optimization of active sites in a well defined Co@ NC catalyst," Green Chemistry, vol. 22, no. 17, pp. 5730-5741, 2020.
-
[20] R. Yun et al., "Fe single atoms and Fe2O3 clusters liberated from N-doped polyhedral carbon for chemoselective hydrogenation under mild conditions," ACS Applied Materials & Interfaces, vol. 12, no. 30, pp. 34122-34129, 2020.
-
[21] H. Liu et al., "Atomically dispersed Cu catalyst for efficient chemoselective hydrogenation reaction," Nano Letters, vol. 21, no. 24, pp. 10284-10291, 2021.
-
[22] X. Cui et al., "Intrinsic kinetics of catalytic hydrogenation of 2-nitro-4-acetylamino anisole to 2-amino-4-acetylamino anisole over Raney nickel catalyst," Chinese Journal of Chemical Engineering, vol. 64, pp. 1-8, 2023.
-
[23] W. Liu et al., "Highly-efficient RuNi single-atom alloy catalysts toward chemoselective hydrogenation of nitroarenes," Nature Communications, vol. 13, no. 1, 2022, Art. no. 3188.
-
[24] S. S. Satapathy and S. Si, "One-step chemical synthesis of Ag–Au alloy nanoparticles for modulating the catalytic hydrogenation reaction," Applied Nanoscience, vol. 10, no. 11, pp. 4139-4148, 2020.
-
[25] C. Han, L. Du, M. Konarova, D.-C. Qi, D. L. Phillips and J. Xu, "Beyond hydrogen evolution: solar-driven, water-donating transfer hydrogenation over platinum/carbon nitride," ACS Catalysis, vol. 10, no. 16, pp. 9227-9235, 2020.
-
[26] H. Göksu, "Recyclable aluminium oxy-hydroxide supported Pd nanoparticles for selective hydrogenation of nitro compounds via sodium borohydride hydrolysis," New Journal of Chemistry, vol. 39, no. 11, pp. 8498-8504, 2015.
-
[27] V. I. Parvulescu, F. Epron, H. Garcia and P. Granger, "Recent progress and prospects in catalytic water treatment," Chemical Reviews, vol. 122, no. 3, pp. 2981-3121, 2021.
-
[28] R. Pelalak, R. Alizadeh and E. Ghareshabani, "Enhanced heterogeneous catalytic ozonation of pharmaceutical pollutants using a novel nanostructure of iron-based mineral prepared via plasma technology: a comparative study," Journal of Hazardous Materials, vol. 392, 2020, Art. no. 122269.
-
[29] M. Haas, S. Lamour, S. B. Christ and O. Trapp, "Mineral-mediated carbohydrate synthesis by mechanical forces in a primordial geochemical setting," Communications Chemistry, vol. 3, no. 1, 2020, Art. no. 140.
-
[30] H. Goksu and E. Orhan, "The local and natural sources in synthetic methods: the practical synthesis of aryl oximes from aryl aldehydes under catalyst-free conditions in mineral water," Journal of Chemical Sciences, vol. 133, pp. 1-5, 2021.
-
[31] B. Y. Kara, M. Yazici, B. Kilbas and H. Goksu, "A practical and highly efficient reductive dehalogenation of aryl halides using heterogeneous Pd/AlO (OH) nanoparticles and sodium borohydride," Tetrahedron, vol. 72, no. 39, pp. 5898-5902, 2016.
-
[32] K. S. Egorova and V. P. Ananikov, "Which metals are green for catalysis? Comparison of the toxicities of Ni, Cu, Fe, Pd, Pt, Rh, and Au salts," Angewandte Chemie International Edition, vol. 55, no. 40, pp. 12150-12162, 2016.
-
[33] E. Herington and E. Rideal, "On the poisoning of metallic catalysts," Transactions of the Faraday Society, vol. 40, pp. 505-516, 1944.
-
[34] K. S. Egorova and V. P. Ananikov, "Toxicity of metal compounds: knowledge and myths," Organometallics, vol. 36, no. 21, pp. 4071-4090, 2017.
-
[35] J. Klausen, S. P. Troeber, S. B. Haderlein and R. P. Schwarzenbach, "Reduction of substituted nitrobenzenes by Fe (II) in aqueous mineral suspensions," Environmental Science & Technology, vol. 29, no. 9, pp. 2396-2404, 1995.
-
[36] M. Fomina and I. Skorochod, "Microbial interaction with clay minerals and its environmental and biotechnological implications," Minerals, vol. 10, no. 10, Art. no. 861.
-
[37] D. Colón, E. J. Weber and J. L. Anderson, "QSAR study of the reduction of nitroaromatics by Fe (II) species," Environmental Science & Technology, vol. 40, no. 16, pp. 4976-4982, 2006.
-
[38] Y. Ren, Y. Yang and M. Wei, "Recent advances on heterogeneous non-noble metal catalysts toward selective hydrogenation reactions," ACS Catalysis, vol. 13, no. 13, pp. 8902-8924, 2023.
-
[39] I. Harrison, R. U. Leader, J. J. Higgo and G. M. Williams, "A study of the degradation of phenoxyacid herbicides at different sites in a limestone aquifer," Chemosphere, vol. 36, no. 6, pp. 1211-1232, 1998.
-
[40] W. Lee and B. Batchelor, "Abiotic reductive dechlorination of chlorinated ethylenes by iron-bearing phyllosilicates," Chemosphere, vol. 56, no. 10, pp. 999-1009, 2004.