Preparation of sub-microspherical Fe3O4@PDA-Pd NPs catalyst and application in catalytic hydroreduction reaction of halogenated aromatic nitro compounds to prepare halogenated aromatic amines
Abstract Background The side reactions of dehalogenation or C–N coupling tend to occur when halogenated aromatic amines are prepared by catalytic hydrogenation reduction of halogenated aromatic nitro compounds. In this paper, we prepared the sub-microspherical Fe3O4@PDA-Pd NPs catalyst apply it effi...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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BMC
2019-11-01
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| Series: | BMC Chemistry |
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| Online Access: | http://link.springer.com/article/10.1186/s13065-019-0649-9 |
| _version_ | 1818329207487332352 |
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| author | Haichang Guo Renhua Zheng Huajiang Jiang Zhenyuan Xu Aibao Xia |
| author_facet | Haichang Guo Renhua Zheng Huajiang Jiang Zhenyuan Xu Aibao Xia |
| author_sort | Haichang Guo |
| collection | DOAJ |
| description | Abstract Background The side reactions of dehalogenation or C–N coupling tend to occur when halogenated aromatic amines are prepared by catalytic hydrogenation reduction of halogenated aromatic nitro compounds. In this paper, we prepared the sub-microspherical Fe3O4@PDA-Pd NPs catalyst apply it efficiently in the hydrogenation reduction of halogenated aromatic nitro compounds to prepare the halogenated aromatic amines under atmospheric pressure. The catalyst shows a high selectivity of greater than 96% and can effectively inhibit the occurrence of the side reactions of dehalogenation and C–N coupling. Results The optimum condition of the hydroreduction reaction is when tetrahydrofuran is used as solvent and the reaction happens at 50 °C for 5 h. The selectivity of the chlorinated aromatic amine and the fluorinated aromatic amine products exceed 99% and the yield exceeds 90%. Only a small amount of dehalogenated products and C–N coupling by-products were produced in the brominated aromatic compound and the iodinated aromatic compound. Conclusion We developed a promising method for preparing the superparamagnetic and strongly magnetic Fe3O4@PDA core–shell sub-microsphere-supported nano-palladium catalyst for catalyzing the hydrogenation reduction of halogenated aromatic nitro compounds. The halogenated aromatic amines were efficiently and highly selectively prepared under atmospheric pressure, with the side reactions of dehalogenation and C–N coupling effectively inhabited simultaneously. |
| first_indexed | 2024-12-13T12:44:23Z |
| format | Article |
| id | doaj.art-b603009eac5344ad954bb6bab429fa32 |
| institution | Directory Open Access Journal |
| issn | 2661-801X |
| language | English |
| last_indexed | 2024-12-13T12:44:23Z |
| publishDate | 2019-11-01 |
| publisher | BMC |
| record_format | Article |
| series | BMC Chemistry |
| spelling | doaj.art-b603009eac5344ad954bb6bab429fa322022-12-21T23:45:32ZengBMCBMC Chemistry2661-801X2019-11-011311710.1186/s13065-019-0649-9Preparation of sub-microspherical Fe3O4@PDA-Pd NPs catalyst and application in catalytic hydroreduction reaction of halogenated aromatic nitro compounds to prepare halogenated aromatic aminesHaichang Guo0Renhua Zheng1Huajiang Jiang2Zhenyuan Xu3Aibao Xia4School of Pharmaceutical and Material Engineering, Taizhou UniversitySchool of Pharmaceutical and Material Engineering, Taizhou UniversitySchool of Pharmaceutical and Material Engineering, Taizhou UniversityZhejiang Key Laboratory of Green Pesticides and Cleaner Production Technology, Catalytic Hydrogenation Research Center, Zhejiang University of TechnologyZhejiang Key Laboratory of Green Pesticides and Cleaner Production Technology, Catalytic Hydrogenation Research Center, Zhejiang University of TechnologyAbstract Background The side reactions of dehalogenation or C–N coupling tend to occur when halogenated aromatic amines are prepared by catalytic hydrogenation reduction of halogenated aromatic nitro compounds. In this paper, we prepared the sub-microspherical Fe3O4@PDA-Pd NPs catalyst apply it efficiently in the hydrogenation reduction of halogenated aromatic nitro compounds to prepare the halogenated aromatic amines under atmospheric pressure. The catalyst shows a high selectivity of greater than 96% and can effectively inhibit the occurrence of the side reactions of dehalogenation and C–N coupling. Results The optimum condition of the hydroreduction reaction is when tetrahydrofuran is used as solvent and the reaction happens at 50 °C for 5 h. The selectivity of the chlorinated aromatic amine and the fluorinated aromatic amine products exceed 99% and the yield exceeds 90%. Only a small amount of dehalogenated products and C–N coupling by-products were produced in the brominated aromatic compound and the iodinated aromatic compound. Conclusion We developed a promising method for preparing the superparamagnetic and strongly magnetic Fe3O4@PDA core–shell sub-microsphere-supported nano-palladium catalyst for catalyzing the hydrogenation reduction of halogenated aromatic nitro compounds. The halogenated aromatic amines were efficiently and highly selectively prepared under atmospheric pressure, with the side reactions of dehalogenation and C–N coupling effectively inhabited simultaneously.http://link.springer.com/article/10.1186/s13065-019-0649-9Catalytic hydrogenationDopamineFe3O4 sub-microsphere nano-palladiumHalogenated aromaticNano-palladium |
| spellingShingle | Haichang Guo Renhua Zheng Huajiang Jiang Zhenyuan Xu Aibao Xia Preparation of sub-microspherical Fe3O4@PDA-Pd NPs catalyst and application in catalytic hydroreduction reaction of halogenated aromatic nitro compounds to prepare halogenated aromatic amines BMC Chemistry Catalytic hydrogenation Dopamine Fe3O4 sub-microsphere nano-palladium Halogenated aromatic Nano-palladium |
| title | Preparation of sub-microspherical Fe3O4@PDA-Pd NPs catalyst and application in catalytic hydroreduction reaction of halogenated aromatic nitro compounds to prepare halogenated aromatic amines |
| title_full | Preparation of sub-microspherical Fe3O4@PDA-Pd NPs catalyst and application in catalytic hydroreduction reaction of halogenated aromatic nitro compounds to prepare halogenated aromatic amines |
| title_fullStr | Preparation of sub-microspherical Fe3O4@PDA-Pd NPs catalyst and application in catalytic hydroreduction reaction of halogenated aromatic nitro compounds to prepare halogenated aromatic amines |
| title_full_unstemmed | Preparation of sub-microspherical Fe3O4@PDA-Pd NPs catalyst and application in catalytic hydroreduction reaction of halogenated aromatic nitro compounds to prepare halogenated aromatic amines |
| title_short | Preparation of sub-microspherical Fe3O4@PDA-Pd NPs catalyst and application in catalytic hydroreduction reaction of halogenated aromatic nitro compounds to prepare halogenated aromatic amines |
| title_sort | preparation of sub microspherical fe3o4 pda pd nps catalyst and application in catalytic hydroreduction reaction of halogenated aromatic nitro compounds to prepare halogenated aromatic amines |
| topic | Catalytic hydrogenation Dopamine Fe3O4 sub-microsphere nano-palladium Halogenated aromatic Nano-palladium |
| url | http://link.springer.com/article/10.1186/s13065-019-0649-9 |
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