Micropacked‐bed Reactor for Continuous Hydrogenation of Aromatic Dinitro Compounds

Yang, Shangjin; Liu, Song; Ming, Weixing; Wei, Wei; Lu, Jianjun; Zhang, Jianjun; An, Tingwang; Gong, Dangsheng; Zhao, Jianzhang; Meng, Qingwei; Yan, Dongmao

doi:10.1002/slct.202203577

Cited by 4 publications

(2 citation statements)

References 45 publications

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“…It is evident that the selectivity in μPBR is higher than that in batch reactors. As a result of the enhanced gas‐liquid mass transfer effect, [38] the residence time is shortened and side reactions occur less frequently, thus leading to a significant improvement in the space time yield (STY).…”

Section: Resultsmentioning

confidence: 99%

Continuous Hydrogenation of Nitriles to Primary Amines with High Selectivity in Flow by Using Raney Cobalt

Yu,

Ming,

Zhang

et al. 2024

ChemistrySelect

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Primary amines produced by selective catalytic hydrogenation of cyano compounds are widely used as basic chemicals, but due to the complexity of the hydrogenation mechanism and the inefficient mass transfer of the intermittent reaction, the process tends to produce secondary and tertiary amines as undesirable by‐products. In this research, a continuous hydrogenation system employing a micropacked‐bed reactor (μPBR) was established for the catalytic hydrogenation of 3‐ethylaminopropionitrile (3‐EAPN) to synthesize N‐ethyl‐1,3‐propanediamine (3‐EAPA). Under optimal experimental conditions using Raney cobalt as a catalyst, complete conversion of 3‐EAPN was achieved, and a high selectivity of 99.6 % for the primary amine (3‐EAPA) was obtained. On this basis, the system was extended with other cyano compounds of different structures as hydrogenation substrates, demonstrating the general applicability of this continuous hydrogenation system by using Raney cobalt as a catalyst in a μPBR for the hydrogenation of various nitriles.

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Section: Resultsmentioning

confidence: 99%

Continuous Hydrogenation of Nitriles to Primary Amines with High Selectivity in Flow by Using Raney Cobalt

Yu,

Ming,

Zhang

et al. 2024

ChemistrySelect

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“…TDA is produced industrially using catalysts by hydrogenation of dinitrotoluene isomers 9 . The catalysts used are mainly transition metals or their compounds on various usually carbon-based supports 10 – 14 .…”

Section: Introductionmentioning

confidence: 99%

Bentonite as eco-friendly natural mineral support for Pd/CoFe2O4 catalyst applied in toluene diamine synthesis

Hatvani-Nagy,

Hajdu,

Ilosvai

et al. 2024

Sci Rep

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Toluene diamine (TDA) is a major raw material in the polyurethane industry and thus, its production is highly important. TDA is obtained through the catalytic hydrogenation of 2,4-dinitrotoluene (2,4-DNT). In this study a special hydrogenation catalyst has been developed by decomposition cobalt ferrite nanoparticles onto a natural clay-oxide nanocomposite (bentonite) surface using a microwave-assisted solvothermal method. The catalyst particles were examined by TEM and X-ray diffraction. The palladium immobilized on the bentonite crystal surface was identified using an XRD and HRTEM device. The obtained catalyst possesses the advantageous property of being easily separable due to its magnetizability on a natural mineral support largely available and obtained through low carbon- and energy footprint methods. The catalyst demonstrated outstanding performance with a 2,4-DNT conversion rate exceeding 99% along with high yields and selectivity towards 2,4-TDA and all of this achieved within a short reaction time. Furthermore, the developed catalyst exhibited excellent stability, attributed to the strong interaction between the catalytically active metal and its support. Even after four cycles of reuse, the catalytic activity remained unaffected and the Pd content of the catalyst did not change, which indicates that the palladium component remained firmly attached to the magnetic support's surface.

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Study on Continuous-Flow Process for Direct Synthesis of p-Aminophenol from Nitrobenzene

Huang,

Zhou,

et al. 2024

Org. Process Res. Dev.

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p-Aminophenol (PAP) is an important organic chemical raw material and a pharmaceutical intermediate. Catalytic hydrogenation of nitrobenzene (NB) is an environmentally friendly and economical production method. However, the one-pot method in a traditional batch reactor often leads to a low reaction rate and low PAP yield at low hydrogen pressure. In this work, a continuous-flow process for direct synthesis of PAP by the hydrogenation−rearrangement of NB was established, which provides a safe, green, and efficient method for the synthesis of PAP. The effects of various reaction conditions were investigated. Under the optimal reaction conditions, a 94.5% yield of phenylhydroxylamine (PHA) was achieved in the hydrogenation process under atmospheric pressure. The catalyst activity remained good for 50 h of continuous operation. Solvent tetrahydrofuran (THF) and additive 4-dimethylaminopyridine (DMAP) are more conducive to the synthesis of PHA than other solvents. For different acid catalysts in the Bamberger rearrangement with an equivalent concentration of 2 N, stronger acidity led to greater conversion of PHA. The Bamberger rearrangement is solvent-sensitive, and aprotic solvents will reduce the conversion of PHA. The full continuous process for direct synthesis of PAP from NB was studied by mixing sulfuric acid solution and PHA/THF solution with a microfluidic chip. The conversion of PHA was 100% with a low H 2 SO 4 concentration of 1 wt % at a residence time of 13.6 min. The process was reduced from the hour level of the batch process to the minute level, and the H 2 SO 4 concentration was reduced.

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Micropacked‐bed Reactor for Continuous Hydrogenation of Aromatic Dinitro Compounds

Cited by 4 publications

References 45 publications

Continuous Hydrogenation of Nitriles to Primary Amines with High Selectivity in Flow by Using Raney Cobalt

Continuous Hydrogenation of Nitriles to Primary Amines with High Selectivity in Flow by Using Raney Cobalt

Bentonite as eco-friendly natural mineral support for Pd/CoFe2O4 catalyst applied in toluene diamine synthesis

Study on Continuous-Flow Process for Direct Synthesis of p-Aminophenol from Nitrobenzene

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